2580-79-2

Basic information

• Product Name: DIAMINOGLYOXIME
• Synonyms: OXALAMIDE DIOXIME;DIAMINOGLYOXIM;DIAMINOGLYOXIME;2,6-Dibromo-4-tolylhydrazine hydrochloride;N,N-Dihydroxyoxalamidine;1,2-Diamino-1,2-ethanedione dioxime;N,N''-Dihydroxyethanediimidamide;Oxamide dioxime
• CAS NO: 2580-79-2
• Molecular Formula: C₂H₆N₄O₂
• Molecular Weight: 118.09
• Mol File: 2580-79-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 200-204 °C
• Boiling Point: 238.1°Cat760mmHg
• Flash Point: 97.8°C
• Appearance: /
• Density: 1.9g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.68
• PKA: 10.24±0.69(Predicted)
• CAS DataBase Reference: DIAMINOGLYOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: DIAMINOGLYOXIME(2580-79-2)
• EPA Substance Registry System: DIAMINOGLYOXIME(2580-79-2)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 2580-79-2(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C2H6N4O2/c3-1(5-7)2(4)6-8/h7-8H,(H2,3,5)(H2,4,6)

Synthetic route

Glyoxal (131543-46-9) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With hydroxylamine In water at 95℃;	80%
With hydroxylamine In water at 95℃; for 96h;	80%
With hydroxylamine In water for 72h; Reflux;	80%

glyoxime (557-30-2) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With sodium hydroxide; hydroxylamine hydrochloride at 90℃; for 6h;	60%
With sodium hydroxide; hydroxylamine hydrochloride for 0.05h; microwave irradiation;	60%
With hydroxylamine hydrochloride; sodium hydroxide at 90℃;

3,4-dibromo-1,2,5-oxadiazole 2-oxide (70134-71-3) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With ethanol; ammonia at 60 - 100℃; im Einschlussrohr;

ethanedinitrile (460-19-5) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With potassium hydroxide; hydroxylamine hydrochloride; water man filtriert von sich ausscheidenden Krystallen ab und behandelt das Filtrat von neuem mit Dicyan, bis ein amorpher Niederschlag auftritt;
With hydroxylamine
With sodium hydroxide; hydroxylamine hydrochloride at 0℃;

Cyan-imidoameisensaeureethylester (13369-04-5) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With diethyl ether; hydroxylamine hydrochloride; water unter Kuehlung;

1,2-Bisethan-1,2-diamin (157368-88-2) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

1,2-Bisethan-1,2-diamin (157368-88-2) → diaminoglyoxime (2580-79-2) + N-p-tolyl-oxalamide oxime

Conditions	Yield
With ethanol; hydroxylamine hydrochloride man filtriert nach dem Erkalten vom ausgeschiedenen Oxalsaeurediamidoxim ab, neutralisiert das Filtrat mit Soda und destilliert im Dampfstrome; den Rueckstand verdampft man zur Trockne und extrahiert ihn mit Alkohol;

N,N''-dibenzyl-oxalamidine (97496-74-7) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

dithiooxamide (79-40-3) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With ethanol; hydroxylamine hydrochloride; sodium carbonate

dichloroglyoxime (2038-44-0) → diaminoglyoxime (2580-79-2)

Conditions	Yield
(i) aq. Na2CO3, CH2Cl2, (ii) NH3, EtOH; Multistep reaction;

C6F6N4O4(4-)*4Na(1+) (131547-91-6) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With water few days;

3,4-dibromo-1,2,5-oxadiazole 2-oxide (70134-71-3) + ammonia (7664-41-7) → diaminoglyoxime (2580-79-2)

Conditions	Yield
at 60℃; im Rohr; Erhitzen des Reaktionsprodukts auf 100grad;

dithiooxamide (79-40-3) + hydroxylamine hydrochloride → diaminoglyoxime (2580-79-2)

Conditions	Yield
in sodaalkalischer Loesung;

diacetoxy-oxalodiimidoyl chloride (89715-76-4) + ammonia (7664-41-7) + ethyl acetate (141-78-6) → diaminoglyoxime (2580-79-2)

diacetate of oxalic acid bis- → diaminoglyoxime (2580-79-2)

Conditions	Yield
With acetic acid ester; ammonia

N,N''-diphenyl-oxalamidine (33420-38-1) → diaminoglyoxime (2580-79-2) + oxalic acid monophenyldiamide oxime

Conditions	Yield
With ethanol; hydroxylamine hydrochloride

1,2-Bisethan-1,2-diamin (157368-88-2) + hydroxylamine hydrochloride → diaminoglyoxime (2580-79-2) + N-hydroxy-N''-p-tolyl-oxalamidine + N-p-tolyl-oxalamide oxime

ethanol (64-17-5) + N-hydroxy-N''-p-tolyl-oxalamidine + hydroxylamine hydrochloride → diaminoglyoxime (2580-79-2) + p-toluidine (106-49-0)

ethanedinitrile (460-19-5) + hydroxylamine (7803-49-8) → diaminoglyoxime (2580-79-2)

Conditions	Yield
In not given introducing of cold C2N2 in NH2OH soln.;
In not given introducing of cold C2N2 in NH2OH soln.;

oxalic acid diureide dioxime (580-52-9) + nickel(II) → Ni(2+)*2H2NC(NO)C(NO)NH2(2-)*2H(1+)*2H2O={Ni(C2H5N4O2)2}*2H2O + diaminoglyoxime (2580-79-2)

Conditions	Yield
byproducts: carbamide;	A n/a B 0%

cyanogen di-N-oxide (4331-98-0) → diaminoglyoxime (2580-79-2)

Conditions	Yield
With ammonia little yield; polymeric products formed;

diaminoglyoxime (2580-79-2) + 3,4-dihydroxybenzaldehyde (139-85-5) → C9H10N4O4

Conditions	Yield
With tungstate phosphoric acid In ethanol at 60℃;	97%

diaminoglyoxime (2580-79-2) → dichloroglyoxime (2038-44-0)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 20℃; for 22h; Cooling with ice;	96%

diaminoglyoxime (2580-79-2) + trichloroacetic acid anhydride (4124-31-6) → 5,5'-bis(trichloromethyl)-3,3'-bi(1,2,4-oxadiazole) (4491-00-3)

Conditions	Yield
at 140℃;	95%

diaminoglyoxime (2580-79-2) + 4-Nitroanthranilic acid (619-17-0) → N'-hydroxy-7-nitro-4-oxo-3,4-dihydroquinazoline-2-carboximidamide (1446556-87-1)

Conditions	Yield
With acetic acid for 0.5h; Reflux;	95%

diaminoglyoxime (2580-79-2) + 2-amino-4,6-dichlorobenzoic acid (20776-63-0) → 5,7-dichloro-N'-hydroxy-4-oxo-3,4-dihydroquinazoline-2-carboximidamide (1446556-88-2)

Conditions	Yield
With acetic acid for 0.5h; Reflux;	95%

diaminoglyoxime (2580-79-2) + 4-methyl-benzaldehyde (104-87-0) → 4-amino-5-(hydroxyimino)-2-(4-methylphenyl)-2,5-dihydro-1H-imidazole-3-oxide

Conditions	Yield
With tungstate phosphoric acid In ethanol at 60℃; for 1h; Reagent/catalyst; Solvent;	95%
With zinc(II) oxide In water at 20℃; for 0.75h; Green chemistry;	92%

diaminoglyoxime (2580-79-2) + 4-methoxy-benzaldehyde (123-11-5) → C10H12N4O3

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 0.666667h; Green chemistry;	95%
With tungstate phosphoric acid In ethanol at 60℃;	78%

diaminoglyoxime (2580-79-2) + cyclohexanone (108-94-1) → C8H14N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1h; Green chemistry;	94%

diaminoglyoxime (2580-79-2) + benzaldehyde (100-52-7) → C9H10N4O2

Conditions	Yield
With zinc(II) oxide In water at 50℃; for 0.833333h; Time; Reagent/catalyst; Solvent; Green chemistry;	94%

diaminoglyoxime (2580-79-2) + Triethyl orthoacetate (78-39-7) → N'-hydroxy-5-methyl-1,2,4-oxadiazole-3-carboximidamide (162969-65-5)

Conditions	Yield
With boron trifluoride diethyl etherate	93%
With boron trifluoride diethyl etherate at 70 - 80℃; for 0.166667h;	92%

2-Amino-5-methylbenzoic acid (2941-78-8) + diaminoglyoxime (2580-79-2) → N'-hydroxy-6-methyl-4-oxo-3,4-dihydroquinazoline-2-carboximidamide (1446556-86-0)

Conditions	Yield
With acetic acid for 0.666667h; Reflux;	93%

diaminoglyoxime (2580-79-2) + 4-tercbutyl-cyclohexanone (98-53-3) → C12H22N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1.08333h; Green chemistry;	92%

diaminoglyoxime (2580-79-2) + acetone (67-64-1) → C5H10N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1h; Green chemistry;	91%

diaminoglyoxime (2580-79-2) + Triethyl orthoacetate (78-39-7) → 5,5'-dimethyl-3,3'-bi(1,2,4-oxadiazole) (89580-17-6)

Conditions	Yield
With boron trifluoride diethyl etherate at 80 - 100℃; for 1h;	90%

cobalt(II) sulphate heptahydrate + diaminoglyoxime (2580-79-2) → [(oxamide dioximemonoximium)][Co(oxamide dioxime)3](SO4)2*2H2O

Conditions	Yield
With H2SO4 In water CoSO4*7H2O dissolved in H2O at room temp. acidified with H2SO4, filteredinto aq. soln. of ligand, stirred for 1.5 h at room temp.; filtered, concd. by evapn. at 50°C, slowly evapd. at room temp. for 1 wk, filtered, recrystd. from H2O, evapd. to dryness, 2 d at room temp.; elem. anal.;	90%

diaminoglyoxime (2580-79-2) + cycloheptanone (502-42-1) → C9H16N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1.25h; Green chemistry;	90%

diaminoglyoxime (2580-79-2) + 5-bromosalicyclaldehyde (1761-61-1) → C9H9BrN4O3

Conditions	Yield
With tungstate phosphoric acid In ethanol at 60℃;	90%

diaminoglyoxime (2580-79-2) + butanone (78-93-3) → C6H12N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1h; Green chemistry;	89%

diaminoglyoxime (2580-79-2) + ortho-anisaldehyde (135-02-4) → C10H12N4O3

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1.08333h; Green chemistry;	89%

diaminoglyoxime (2580-79-2) + 6-(4-bromophenyl)-2,2-dimethyl-1,3-dioxin-4-one (98157-47-2) → 3-(4-Bromo-phenyl)-N-{2-[3-(4-bromo-phenyl)-3-oxo-propionylamino]-1,2-bis-[(E)-hydroxyimino]-ethyl}-3-oxo-propionamide (140836-10-8)

Conditions	Yield
at 145 - 150℃; for 0.166667h;	88%

diaminoglyoxime (2580-79-2) + 4-chlorobenzaldehyde (104-88-1) → C9H9ClN4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 0.833333h; Green chemistry;	88%

diaminoglyoxime (2580-79-2) + salicylaldehyde (90-02-8) → C9H10N4O3

Conditions	Yield
With tungstate phosphoric acid In ethanol at 60℃;	88%

diaminoglyoxime (2580-79-2) + orthoformic acid triethyl ester (122-51-0) → bis(1,2,4-oxadiazol-3-yl) (17098-88-3)

Conditions	Yield
With boron trifluoride diethyl etherate at 70 - 80℃; for 0.5h;	87%

diaminoglyoxime (2580-79-2) + cobalt(II) iodide → tris(oxamide oxime-N1,N2)cobalt(III) triiodide

Conditions	Yield
With aq. HI In water acidification of soln. of CoI2 with aq. HI, addn. of org. compd. with stirring (room temp.), stirring (2 h); filtration, slow evapn. (room temp., 3 weeks), filtration, further product on concn. of mother liquor, recrystn. (concd. aq. soln. acidified with aq. HI, room temp.);	87%

diaminoglyoxime (2580-79-2) + cyclopentanone (120-92-3) → C7H12N4O2

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 1.33333h; Green chemistry;	87%

diaminoglyoxime (2580-79-2) + 2-chloro-benzaldehyde (89-98-5) → C9H9ClN4O2

Conditions	Yield
With tungstate phosphoric acid In ethanol at 60℃;	87%
With zinc(II) oxide In water at 20℃; for 1.16667h; Green chemistry;	86%

2-Amino-5-methylbenzoic acid (2941-78-8) + diaminoglyoxime (2580-79-2) + acetic anhydride (108-24-7) → 6-methyl-2-(5-methyl-1,2,4-oxadiazol-3-yl)quinazolin-4(3H)-one (1446556-90-6)

Conditions	Yield
Stage #1: 2-Amino-5-methylbenzoic acid; diaminoglyoxime With acetic acid at 100℃; for 1h; Stage #2: acetic anhydride at 100℃; for 2h;	86%

diaminoglyoxime (2580-79-2) + 3-methoxy-benzaldehyde (591-31-1) → C10H12N4O3

Conditions	Yield
With zinc(II) oxide In water at 20℃; for 0.666667h; Green chemistry;	86%

diaminoglyoxime (2580-79-2) + salicylaldehyde (90-02-8) → (Z)-4-amino-5-(hydroxyimino)-2-(2-hydroxyphenyl)-2,5-dihydro-1H-imidazole 3-oxide (1058645-25-2)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 55 - 65℃; for 3h;	85%

diaminoglyoxime (2580-79-2) + 5-Bromo-2-aminobenzoic acid (5794-88-7) → 6-bromo-N'-hydroxy-4-oxo-3,4-dihydroquinazoline-2-carboximidamide (1446556-85-9)

Conditions	Yield
With acetic acid for 1.25h; Reflux;	85%

Upstream product

• 70134-71-3 3,4-dibromo-1,2,5-oxadiazole 2-oxide 
• 557-30-2 glyoxime 
• 79-40-3 dithiooxamide 
• 4331-98-0 cyanogen di-N-oxide 
• 580-52-9 oxalic acid diureide dioxime 
• 14701-22-5 nickel(II) 
• 460-19-5 ethanedinitrile 
• 7803-49-8 hydroxylamine 
• 64-17-5 ethanol 
• 157368-88-2 1,2-Bisethan-1,2-diamin 
• 33420-38-1 N,N''-diphenyl-oxalamidine 
• 89715-76-4 diacetoxy-oxalodiimidoyl chloride 
• 7664-41-7 ammonia 
• 141-78-6 ethyl acetate 

Downstream Products

• 7664-41-7 ammonia 
• 7803-49-8 hydroxylamine 
• 144-62-7 oxalic acid 
• 39512-81-7 1,2,4-oxadiazole-3-carboxamidoxime 
• 17098-88-3 bis(1,2,4-oxadiazol-3-yl) 
• 128452-48-2 1,2,4-oxadiazole-3-carboxyhydroxamic chloride 
• 2038-44-0 dichloroglyoxime 
• 1058093-90-5 (Z)-4-amino-5-(hydroxyimino)-2-phenyl-2,5-dihydro-1H-imidazole 3-oxide 

Relevant articles and documents

?-ADDUCTS IN THE 1,2,4-OXADIAZOLE SERIES

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Bis(1,2,4-oxadiazole)bis(methylene) Dinitrate: A High-Energy Melt-Castable Explosive and Energetic Propellant Plasticizing Ingredient

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(methylene) dinitrate has a calculated detonation pressure 50% higher than that of TNT. The dinitrate compound exhibits a relatively high decomposition temperature that is rarely observed for nitrate-based compounds. The dinitrate was found to have lower sensitivities to impact and friction compared with RDX. It is believed that intramolecular hydrogen bonding observed in the crystal lattice assists in the relatively high thermal stability and relatively low sensitivity of the material.

Synthesis and Characterization of the Potential Melt-Castable Explosive 3-(1,2,4-Oxadiazolyl)-5-Nitratomethyl Isoxazole

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 melt-castable explosive class. The material was found to have TNT performance, and was found to be insensitive to impact, friction, and electrostatic discharge, despite having a nitric ester functionality. A critical reaction in making this molecule was the desymmetrization of diaminoglyoxime. The optimization of this transformation is described. Previous reports of this desymmetrization were found to be inaccurate, as the desymmetrization reaction produces a co-crystal of mono- and bi-1,2,4-oxadiazole products.

METHOD FOR PREPARING DIHYDROXYLAMMONIUM 5,5'-BISTETRAZOLE-1,1'-DIOLATE

The present invention relates to a method for manufacturing dihydroxylammonium 5,5andprime;-bistetrazole-1,1andprime;-diolate. More specifically, the present invention relates to the method for manufacturing dihydroxylammonium 5,5andprime;-bistetrazole-1,1andprime;-diolate using a diaminoglyoxime intermediate. The present invention can provide a safe and convenient method for manufacturing TKX-50.(AA) ^(13)C-NMR spectrum of TKX-50COPYRIGHT KIPO 2019