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Jesse J. Sabatini

Jesse J. Sabatini
Army Research Laboratory, Aberdeen Proving Ground, MD, USA · Department of Defense

Doctor of Philosophy

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82
Publications
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Citations

Publications

Publications (82)
Preprint
Despite their favorable properties, azetidines are often overlooked as lead compounds across multiple industries. This is often attributed to the challenging synthesis of densely functionalized azetidines in an efficient manner. In this work, we report the scalable synthesis and characterization of seven azetidines with varying regio- and stereoche...
Article
The synthesis of 3‐(nitratoethyl‐N‐nitramino)‐5‐(nitratomethyl) isoxazole (C6H7N5O9, 1) is presented, and its energetic properties were ascertained and analyzed for energetic applications potential. 1 was found to be a solid without melting behavior, begins to decompose at 140 °C, and has a thermal onset decomposition temperature of 171.5 °C. 1 was...
Article
The synthesis of 3‐(1,2,4‐oxadiazolyl)‐5‐nitratomethyl isoxazole (C6H4N4O5), its physical properties, and its theoretical performances are described. This energetic material was found to have a melting point range of 76.6–79.2 °C, and a thermal onset decomposition temperature of 184.5 °C. These thermal features put this material into the standalone...
Article
Full-text available
A review of energetic materials based on the nitric ester functionality is presented. Examined are materials that are classified as primary explosives, pressable secondary explosives, melt-castable secondary explosives, and rocket- and gun-propellant materials. Disclosed are the molecular structures, physical properties, performances, and sensitivi...
Article
The first compound containing both a tetrazole and an azasydnone ring, a unique energetic material, is reported. Several energetic salts of the tetrazole azasydnone were synthesized and characterized, leading to the creation of new secondary and primary explosives. Molecular structures are confirmed by 1H and 13C NMR, IR spectroscopy, and X‐ray cry...
Article
Full-text available
We report the first compound containing both a tetrazole and an azasydnone ring, a unique energetic material. Several energetic salts of the tetrazole azasydnone were synthesized and characterized, leading to the creation of new secondary and primary explosives. Molecular structures are confirmed by 1 H and 13 C NMR, IR spectroscopy, and X‐ray crys...
Article
The synthesis and crystal structure of the heterocyclic explosive bis(nitroxymethylisoxazolyl) furoxan, C10H6N6O10, are described. In addition, we report its physical properties and theoretical performance. This material was found to exhibit standalone melt‐castable explosive properties, with a melting point of 89.8 °C and an onset decomposition te...
Article
The synthesis, physical properties and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials is described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By altering the stereo- and regiochemistry, complete tunabilit...
Preprint
The synthesis, physical properties and calculated performances of six stereo- and regioisomeric cyclobutane nitric ester materials is described. While the calculated performances of these isomers, as expected, were similar, their physical properties were found to be extremely different. By altering the stereo- and regiochemistry, complete tunabilit...
Article
A safer, convenient, cost-effective, and scalable synthesis for 3,4-dicyanofuroxan (C4N4O2) is described. Dropwise treatment of a well-stirred suspension of cyanoacetic acid in dichloromethane with concentrated mixed acid (HNO3/H2SO4) affords dicyanofuroxan in 72% yield and in 84% purity after liquid chromatography analysis. Single crystal X-ray di...
Article
The cover feature shows bis(1,2,4)‐oxadiazolyl furoxan, a potential melt‐castable explosive eutectic ingredient. This material is very insensitive to impact, friction, and electrostatic discharge, has a high heat of formation and density, and a calculated detonation pressure 20% higher than that of TNT. Details are given in the Communication by J....
Article
The syntheses and characterizations of two new energetic compounds based on a bis‐isoxazole scaffold are presented. The syntheses employ a metal‐free [3+2] cycloaddition of an alkyne and a nitrile oxide. In addition, we report the molecular structure of these compounds as determined by single crystal x‐ray diffractometry. Both materials have favour...
Article
A scalable synthesis of bis(1,2,4‐oxadiazoyl) furoxan, C6H2N6O4, its physical properties, and its theoretical performance values are described. Previous attempts to synthesize this compound required expensive reagents, and/or time‐consuming synthesis processes and low overall yields. In addition to disclosing a streamlined synthesis of bis(1,2,4‐ox...
Article
This study presents the synthesis of ethyl 5‐((nitrooxy)methyl) isoxazole‐3‐carboxylate (EEIN) and isoxazole‐3,5‐diylbis(methylene) dinitrate (IDN). These compounds, each derived from 5‐(hydroxymethyl)isoxazole‐3‐carboxylate, were fully characterized and explosive sensitivity properties were determined. EEIN was isolated as a solid material with a...
Article
Discussed herein is the synthesis of bis(1,2,4-oxadiazole)bis(methylene) dinitrate, determination of its crystal structure by X-ray diffractometry, calculations of its explosive performance, and sensitivity measurements. Steps taken to optimize the synthesis process and to improve yields of the dinitrate are also discussed. Bis(1,2,4-oxadiazole)bis...
Article
The cover pictures shows several explosive molecules of interest to the energetic materials community that can be synthesized from trinitrotoluene (TNT). The background is a picture of TNT in flaked form following purification and sulphitation. More details can be found in the Review by Mateusz Szala and Jesse J. Sabatini on page 262 ff.
Article
Full-text available
The molecular structure of 5,5′-bis(hydroxymethyl)-3,3′-biisoxazole, C 8 H 8 N 2 O 4 ( 1 ), is composed of two trans planar isoxazole rings [r.m.s deviation = 0.006 (1) Å], each connected with a methyl hydroxyl group. Similarly, the structure of 4,4′,5,5′-tetrakis(hydroxymethyl)-3,3′-biisoxazole, C 10 H 12 N 2 O 6 ( 2 ), is composed of two planar i...
Article
The inside backcover picture shows a red-light-emitting formulation at mid-burn (top-left), a green-light-emitting formulation at mid-burn (top-middle), a yellow/white-light-emitting 5-star cluster at mid-burn, yellow-light-emitting signaling illuminants at night (bottom-left) and a hand-held signaling parachute (bottom-right). The formulations are...
Article
This review presents a history, properties, and environmental fate of 2,4,6-trinitrotoluene (TNT). Industrial methods of TNT production are discussed, as are several energetic derivatives of TNT. The performances and applications of these TNT derivatives are also described.
Article
The development of a red, chlorine-/heavy metal-free pyrotechnic composition which serves as either strobe or flare is reported. The observed strobing behaviour of a red-light emitting composition of Mg/LiNO3/hexamine/binder was...
Article
A new procedure for the synthesis and isolation of diaminoglyoxime (DAG) is described. A previous procedure involved treating glyoxal with 2 equiv each of hydroxylammonium chloride and sodium hydroxide to form glyoxime, followed by further treatment of this intermediate with two additional equivalents of hydroxylammonium chloride and sodium hydroxi...
Article
The need to develop a red-light-emitting pyrotechnic illuminant has garnered interest from the pyrotechnics community due to potential Environmental Protection Agency (EPA) regulations of strontium and chlorinated organic materials. To address these environmental regulatory concerns, the development of lithium-based red-light-emitting pyrotechnic c...
Article
The need to develop a red-light-emitting pyrotechnic illuminant has garnered interest from the pyrotechnics community due to potential Environmental Protection Agency (EPA) regulations of strontium and chlorinated organic materials. To address these environmental regulatory concerns, the development of lithium-based red-light-emitting pyrotechnic c...
Article
This review article consists of efforts focused on the development of illuminating pyrotechnics. Examined will be the methods of generating red-, green-, yellow- and blue-light-emitting illuminating pyrotechnics. Ways to improve luminosity, spectral purity, and burn rate will be discussed. Recently developed formulations concerning the development...
Article
A new procedure for the synthesis and isolation of methyl nitroacetate is described. The previously published method required drying the explosive dipotassium salt of nitroacetic acid in a vacuum desiccator, followed by grinding this material into a fine powder with a mortar and pestle prior to esterification. To obtain the desired product, benzene...
Article
The efficient and scalable synthesis of 3,3′-biisoxazole-4,4′,5,5′-tetrakis(methyl nitrate) and its energetic properties are described. The synthesis features a metal-free [3+2] cycloaddition of an electron-rich internal alkyne and a nitrile oxide by simple heating, without using halogenated solvents. The material has favorable sensitivity properti...
Article
Full-text available
The molecular structure of the title energetic compound, C 8 H 6 N 4 O 8 , is composed of two planar isoxazole rings and two near planar alkyl-nitrate groups (r.m.s deviation = 0.006 Å). In the crystal, the molecule sits on an inversion center, thus Z ′ = 0.5. The dihedral angle between the isoxazole ring and the nitrate group is 69.58 (8)°. van de...
Article
The efficient and scalable synthesis of 3,3′-bis-isoxazole-5,5′-bis-methylene dinitrate and its energetic properties are described. The material has favorable sensitivity properties; energetic properties point toward its potential as both a melt-castable secondary explosive and as a propellant plasticizer.
Article
A new procedure for the synthesis and isolation of dichloroglyoxime is discussed. This material has historically been synthesized from glyoxime and elemental chlorine gas. Chlorine gas is difficult to handle and control in the laboratory and has a high toxicity profile. Our method for making dichloroglyoxime in high purity uses glyoxime and N-chlor...
Article
This optimized and cost-efficient synthesis in aqueous medium is an improvement over previously reported synthetic methods.
Article
The efficient method for the cycloaminomethylation of glycoluril to yield 2,6-ditert-butylhexahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dione is described. The material is synthesized employing water as the solvent, and is isolated by filtration. This is an improvement over the previous reported synthetic method, which relied o...
Article
Full-text available
This review discusses the recent advances in the syntheses of high explosive energetic materials. Syntheses of some relevant modern primary explosives and secondary high explosives, and the sensitivities and properties of these molecules are provided. In addition to the synthesis of such materials, processing improvement and formulating aspects usi...
Article
Full-text available
The development of a red, chlorine-free pyrotechnic illuminant of high luminosity and spectral purity was investigated. Red-light emission based solely on transient SrOH(g) has been achieved by using either 5-amino-1H-tetrazole or hexamine to deoxidize the combustion flame of a Mg/Sr(NO3 )2 /Epon-binder composition and reduce the amount of both con...
Article
Dieser Beitrag behandelt die Entwicklung eines roten, chlorfreien pyrotechnischen Leuchtsatzes hoher Lichtstärke und Farbsättigung. Sätze auf der Grundlage von Mg/Sr(NO3)2/Epon-Binder werden durch Zusatz von 5-Amino-1H-tetrazol oder Hexamethylentetramin desoxidiert, wodurch die Bildung von rot-orange emittierendem SrO(g) unterdrückt und die Entsteh...
Article
We report here on the development of novel yellow-emitting pyrotechnic flares based on ground magnesium, sodium nitrate (NaNO3), and a two-part epoxy thermoset. This work was aimed to eliminate the chemical exposure risk posed by the toxic and solvent-based polyester thermoset specified for two of the U.S. Army's 40 mm yellow illuminant flares, the...
Conference Paper
State of the art pyrotechnic formulations for red, green and blue flares require the use of PVC, barium and perchlorates. All these materials are under increased scrutiny due to their immediate adverse effects or the effects of their combustion products on both human health and the environment. Therefore current research is focused on finding benig...
Article
Die Erzeugung blauen Lichtes in pyrotechnischen Formulierungen wurde ohne den Einsatz von chlorhaltigen Verbindungen erreicht, wobei sich Kupfer(I)-iodid als geeigneter molekularer Emitter blauen Lichtes herausgestellt hat. Im Vergleich zu chlorhaltigen Formulierungen wurden durch die beste blau brennende Formulierung auf Basis von Kupfer(I)-iodid...
Article
The generation of blue-light-emitting pyrotechnic formulations without the use of chlorine-containing compounds is reported. Suitable blue-light emission has been achieved through the generation of molecular emitting copper(I) iodide. The most optimal copper(I) iodide based blue-light-emitting formulation was found to have performances exceeding th...
Article
Full-text available
Green-light-emitting pyrotechnic compositions based on tris(2,2,2-trinitroethyl)borate (TNEB) and boron carbide have been investigated. The best performing formulations were found to be insensitive to various ignition stimuli, and exhibited very high spectral purities and luminosities compared to previously reported green-light-emitting formulation...
Article
The development of perchlorate-free M662 40 mm illuminating pyrotechnic compositions is described. On the bases of cost, performance, and sensitivity, potassium periodate was determined to be most effective potassium perchlorate replacement in the compositions tested. The optimal periodate-based composition exceeded the performance of the perchlora...
Article
A novel yellow smoke formulation, based on the environmentally benign dye Solvent Yellow 33, has been validated as a replacement for the current formulation specified for the M194 yellow smoke hand-held signal. Sieve testing has revealed a fine granulation for the candidate mixture, centered at 53 μm. In addition, compressive strain testing has sho...
Article
The development of handheld signal cluster and 40-mm parachute green light–emitting pyrotechnic compositions is described. Of the new compositions evaluated, one was found to exceed the military requirements in burn time, luminous intensity, dominant wavelength, and spectral purity in both the cluster and parachute configurations. The new illuminan...
Article
Full-text available
The reaction of the lead-free primary explosive copper(I) 5-nitrotetrazolate (DBX-1) with sodium m-periodate yields a green precipitate of copper(II) iodate. The energetic properties of the copper(I) nitrotetrazolate starting material are lost since the nitrotetrazolate is removed into the aqueous phase during rinsing, leaving only non-explosive co...
Chapter
Mainly spurred by the United States Department of Defense, as a result of increasing federal and state regulations and the need to improve human health and to minimize collateral damage, the area of “green” pyrotechnics is a continuously evolving field. Described are some success stories and ongoing efforts in the environmentally friendly developme...
Patent
Full-text available
The present invention is a flare illuminant composition, useful in hand-held signals, which composition is environmentally friendly and economical, containing a commercially available, aromatic, high energy, amine-based organic compound, 5-aminotetrazole, in place of the conventional and toxic KClO4, or, for the known alternative to KClO4, expensiv...
Article
The development and prove-out of yellow-light-emitting pyrotechnic illuminants based on recover, recycle, and reuse (R3) technology is described. Magnesium used in this investigation was recovered from four different illuminating pyrotechnic munitions by means of an environmentally friendly demilitarization process. Despite significant differences...
Article
Prototype testing of perchlorate-free hand-held signal illuminants for the US Army's M126 A1 red-star and M195 green-star parachute illuminants are described. Although previous perchlorate-free variants for these items have been developed based on high-nitrogen compounds that are not readily available, the new formulations consist of anhydrous 5-am...
Article
We report herein the development of an environmentally benign yellow smoke formulation aimed to replace the environmentally hazardous mixture currently specified for the U.S. Army’s M194 yellow smoke hand-held signal. Static ignition test measurements have identified a replacement candidate that generates a robust fountain of yellow smoke, burning...
Article
Full-text available
A comparison of green light emission from both barium- and amorphous boron–based pyrotechnics is described. Emission spectra are shown for both the U.S. Army in-service M125A1 green star cluster formulation and an amorphous boron–potassium nitrate–binder formulation. The main peaks of the emission spectra, average dominant wavelength, and average s...
Article
The development of barium-free pyrotechnic illuminants is described. Heavy metal barium nitrate oxidizer and strontium nitrate oxidizer were replaced with sodium nitrate to adequately address environmental concerns while providing the brightest possible illuminant. The new formulations further address environmental concerns and mitigate single-poin...
Conference Paper
Nanoscale and nanostructured energetic materials are enabling technologies for a wide variety of defense applications. Many current and future requirements cannot be achieved by using more conventional materials only as they fall short in terms of performance, strength, sensitivity, or for environmental reasons. By exploiting the “tunable” nature o...
Conference Paper
Thermodynamic codes play a valuable role in the downselection of the constituents of energetic systems. This is particularly true for thermite and other systems in which the ratio of fuel to oxidizer can be greatly varied and are not contained within the same molecule. If the correct code is used properly, it becomes a very important tool in identi...
Article
AbstractA replacement for the M127A1 hand‐held signal illuminant was developed to alleviate concerns associated with single‐point‐of‐failure. In addressing single‐point‐of‐failure, Laminac 4116/Lupersol binder system were replaced with Epon 813/Versamid 140 binder system. Powdered sodium nitrate was replaced with prilled sodium nitrate in the discl...
Article
In a flash: pyrotechnic incendiary formulations with good stabilities toward various ignition stimuli have been developed without the need for barium or perchlorate oxidizers. KIO(4) and NaIO(4) were introduced as pyrotechnic oxidizers and exhibited excellent pyrotechnic performance. The periodate salts may garner widespread use in military and civ...
Article
The development of perchlorate-free hand-held signal illuminants for the US Army's M195 green star parachute is described. Compared with the perchlorate-containing control, the optimized perchlorate-free illuminants were less sensitive toward various ignition stimuli while offering comparable burn times and visible-light outputs. The results were a...
Article
Full-text available
Fluorous mixture synthesis minimizes the effort to synthesize small-molecule libraries by labelling the molecules rather than the reaction vessels. Reactants are labelled with fluorinated tags and products can later be demixed based on the fluorine content. A limit in the number of available tags can be overcome by using binary encoding so that a t...
Article
Full-text available
Fluorous mixture synthesis minimizes the effort to synthesize small-molecule libraries by labelling the molecules rather than the reaction vessels. Reactants are labelled with fluorinated tags and products can later be demixed based on the fluorine content. A limit in the number of available tags can be overcome by using binary encoding so that a t...
Article
The full-up prototype testing of perchlorate-free, hand-held, signal illuminants for the US Army's M126A1 red star parachute hand-held signal is described. Compared to the perchlorate-containing control, the disclosed illuminants yielded excellent stabilities toward various ignition stimuli while offering superior pyrotechnic performance. Militaril...
Article
Full-text available
The effect of using crystalline boron in green-colored handheld signal formulations is described. Due to its chemically inert nature, crystalline boron served to reduce the burn rates of the formulations. By adjusting crystalline boron percentages in the formulations, the pyrotechnic system could be tuned to meet burn time specifications.
Article
Perchlorate-free hand-held signal illuminant formulations for the M126A1 red star parachute have been developed. The formulations exhibited longer burn times and higher luminous intensities compared to the US Army in-service M126A1 formulation. The perchlorate-free formulations derive their enhanced performance from the inclusion of strontium bis-(...
Article
Grünes Feuerwerk für militärische wie zivile Zwecke muss nicht Barium und Chlorverbindungen enthalten: In Gegenwart von Kaliumnitrat als Oxidationsmittel und einem Epoxybinder verbrennt Borcarbid mit einer grünen Flamme. Diese umweltschonende Formulierung ist beständig gegen Stoß, Reibung und elektrostatische Entladungen und überdies thermisch sehr...
Article
The examination of Laminac 4116/Lupersol and Epon 813/Versamid 140 binder systems, and their influences on burn rates of pyrotechnic formulations is described. Laminac 4116/Lupersol-based formulations had shorter burn times and larger heat of explosion values compared to their Epon 813/Versamid 140 counterparts. An understanding of the chemical str...
Article
Side-chain analogs of Annonaceous acetogenins with a threo, trans, threo, trans, threo-bis-tetrahydrofuran core unit have been prepared and tested for cytotoxicity against HCT-116 human colon cancer cells.
Article
[reaction: see text] A synthesis of the Annonaceous acetogenin asimicin and a side-chain analogue has been achieved by a highly convergent route in which Grubbs cross-metathesis plays a key role.
Article
[reaction: see text] In an effort to develop a more concise route to differentially substituted pyrroles (such as that found in the lamellarins), a completely regioselective one-pot double Suzuki coupling has been discovered. The key feature is the use of a ligand-free palladium catalyst under optimized conditions, which results only in coupling of...
Article
[reaction: see text] Dihydroxylation of delta- and epsilon-mesyloxy alpha,beta-unsaturated esters proceeds with in situ cyclization to afford 2,5-disubstituted and 2,3,5-trisubstituted tetrahydrofurans.
Article
A method for the introduction of carbamate protecting groups on the ring nitrogen of electron-deficient pyrroles has been developed using the commercially available chloroformates and stoichiometric tetrabutylammonium iodide. The method is postulated to generate the more reactive iodoformates in situ to facilitate these protection reactions.
Article
Full-text available
Public reporting burden for the collection of information is estimated to average 1 hour per response, including the time for reviewing instructions, searching existing data sources, gathering and maintaining the data needed, and completing and reviewing the collection of information. Send comments regarding this burden estimate or any other aspect...
Article
Smokes are used on the battlefield for signaling, for marking targets, and for screening troop movements. Many high-performance compositions are toxic or hazardous, while non-toxic alternatives offer sub-par performance. The environmentally benign compositions described herein use boron carbide as a pyrotechnic fuel to produce thick clouds of white...

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