The Synthesis of 5-Aminotetrazole Derivatives

Herbst, Robert; Roberts, Carleton W.; Harvill, Edward J.

doi:10.1021/jo01141a021

Cited by 38 publications

(21 citation statements)

References 6 publications

(14 reference statements)

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“…The methylated aminotetrazoles were synthesized by methylation of 5-amino-1H-tetrazole using Me 2 SO 4 or MeI according to the literature procedures [48]. An alternative synthesis proceeds via cyclization reactions according to the literature [49].…”

Section: Experimental Partmentioning

confidence: 99%

Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials

Klapötke

Stierstorfer

2007

Helvetica Chimica Acta

126

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The nitration of 5-amino-1H-tetrazole (1), 5-amino-1-methyl-1H-tetrazole (3), and 5-amino-2-methyl-2H-tetrazole (4) with HNO 3 (100%) was undertaken, and the corresponding products 5-(nitrimino)-1H-tetrazole (2), 1-methyl-5-(nitrimino)-1H-tetrazole (5), and 2-methyl-5-(nitramino)-2H-tetrazole (6) were characterized comprehensively using vibrational (IR and Raman) spectroscopy, multinuclear ( 1 H, 13C, 14 N, and 15 N) NMR spectroscopy, mass spectrometry, and elemental analysis. The molecular structures in the crystalline state were determined by single-crystal X-ray diffraction. The thermodynamic properties and thermal behavior were investigated by using differential scanning calorimetry (DSC), and the heats of formation were determined by bomb calorimetric measurements. Compounds 2, 5, and 6 were all found to be endothermic compounds. The thermal decompositions were investigated by gas-phase IR spectroscopy as well as DSC experiments. The heats of explosion, the detonation pressures, and velocities were calculated with the software EXPLO5, whereby the calculated values are similar to those of common explosives such as TNT and RDX. In addition, the sensitivities were tested by BAM methods (drophammer and friction) and correlated to the calculated electrostatic potentials. The explosion performance of 5 was investigated by Koenen steel sleeve test, whereby a higher explosion power compared to RDX was reached. Finally, the long-term stabilities at higher temperatures were tested by thermal safety calorimetry (FlexyTSC). X-Ray crystallography of monoclinic 2 and 6, and orthorhombic 5 was performed.

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Section: Experimental Partmentioning

confidence: 99%

Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials

Klapötke

Stierstorfer

2007

Helvetica Chimica Acta

126

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“…The 1-alkyl-and 1-aryl-5-aminotetrazoles were characterized by analysis and comparison with samples obtained by the von Braun technique (10). Excepting p-nitrophenylcyanamide which could be isolated in pure form, an ethereal solution of the cyanamide was prepared by adding cyanogen bromide to the appropriate primary amine dissolved in ether.…”

Section: Rxhc-xhmentioning

confidence: 99%

The synthesis of certain 5-aminotetrazole derivatives. II. The action of hydrazoic acid on monoalkylcyanamides

Garbrecht¹,

Herbst²

1953

J. Org. Chem.

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In a previous communication the formation of 5-dialkylaminotetrazoles by the interaction of dialkylcyanamides and hydrazoic acid vas described (1). Since Hantzsch and Vagt had shown that cyanamide and hydrazoic acid react readily to form 5-aminotetrazole ( 2 ) , it was of interest to investigate the behavior of the monosubstituted cyanamides toward hydrazoic acid.1 Based on a thesis submitted to the School of Graduate Studies a t Michigan State College in 1952 by William L. Garbrecht in partial fulfillment of the requirements for the degree of Doctor of Philosophy.

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“…Compound 2 was observed as the main product (85 % yield), whereas 3 was obtained when the mother liquor was allowed to stand for a few days. Compound 4 was synthesized by the nitration of 1-methyl-5-aminotetrazole [21,22] by using fuming HNO 3 .…”

Section: Introductionmentioning

confidence: 99%

Copper Bis(1‐methyl‐5‐nitriminotetrazolate): A Promising New Primary Explosive

2007

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Copper bis(1‐methyl‐5‐nitriminotetrazolate) (1) was synthesized and investigated as a new primary explosive. Compound 1 was obtained by dehydration of diaquabis(1‐methylnitriminotetrazolato)copper(II) dihydrate (2) or diaquabis(1‐methylnitriminotetrazolato)copper(II) (3) at 120 °C. Complexes 2 and 3 are easily formed by the reaction of 1‐methyl‐5‐nitrimino‐1,2,3,4‐tetrazole (4) with copper(II) nitrate in aqueous solution in high yields. Single crystals of 1 were obtained by recrystallization from dry methanol, whereas wet methanol favors the yield of diaquabis(1‐methyl‐nitriminotetrazolato)copper(II) dimethanolate (5). Compound 1 was characterized by using single‐crystal X‐ray diffraction, IR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC). The sensitivities were investigated by using the BAM drophammer and friction tests, and the heat of formation was calculated on the basis of electronic energies at the B3LYP/SDD level of theory. Compound 1 shows an impact sensitivity that is five times higher and a friction sensitivity that is ten times lower than that of lead azide, which is appropriate. In addition, the long‐term stability of 1 at higher temperatures was tested by using isothermal safety calorimetry (TSC). Compounds 2 and 3 were characterized by single‐crystal X‐ray diffraction, IR spectroscopy, elemental analysis, DSC, bomb calorimetry, and BAM sensitivity tests. In addition, compound 5 was characterized by single‐crystal X‐ray diffraction and elemental analysis. The dehydration of 2 was determined by using thermal gravimetry (TG) to occur by the loss of crystal water in one discrete step. (© WILEY‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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The Synthesis of 5-Aminotetrazole Derivatives

Cited by 38 publications

References 6 publications

Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials

Nitration Products of 5‐Amino‐1H‐tetrazole and Methyl‐5‐amino‐1H‐tetrazoles – Structures and Properties of Promising Energetic Materials

The synthesis of certain 5-aminotetrazole derivatives. II. The action of hydrazoic acid on monoalkylcyanamides

Copper Bis(1‐methyl‐5‐nitriminotetrazolate): A Promising New Primary Explosive

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