Product Name

  • Name

    Dichloroglyoxime

  • EINECS
  • CAS No. 2038-44-0
  • Article Data39
  • CAS DataBase
  • Density 1.8 g/cm3
  • Solubility
  • Melting Point 213°C (dec.)
  • Formula C2H2Cl2N2O2
  • Boiling Point 334.6 °C at 760 mmHg
  • Molecular Weight 156.956
  • Flash Point 156.1 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 2038-44-0 (Dichloroglyoxime)
  • Hazard Symbols
  • Synonyms Ethanediimidoyldichloride, dihydroxy- (9CI);Glyoxime, dichloro- (6CI,7CI);Oxalohydroximoylchloride (8CI);1,2-Dichloroglyoxime;Ethanedioyldichloride, dioxime;NSC 528431;Oxalyl chloride, dioxime;
  • PSA 65.18000
  • LogP 1.03940

Synthetic route

diaminoglyoxime
2580-79-2

diaminoglyoxime

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 20℃; for 22h; Cooling with ice;96%
glyoxime
557-30-2

glyoxime

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With N-chloro-succinimide In N,N-dimethyl-formamide at 0 - 50℃; for 3h;94%
With hydrogenchloride; Oxone In water; N,N-dimethyl-formamide at 20℃; for 2h; Reagent/catalyst; Solvent; Temperature;94%
With 2-(2-methoxyethoxy)ethyl alcohol; chlorine In water at 5℃; Solvent; Temperature; Large scale;92.2%
3-amino-3-hydroximinopropane hydroxamic acid
56366-92-8

3-amino-3-hydroximinopropane hydroxamic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 0 - 5℃; for 1h;26%
(E,E)-monochloroglyoxime
4732-58-5, 17019-15-7, 17019-20-4

(E,E)-monochloroglyoxime

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride; chlorine unter Kuehlung;
(1Z,2E)-N-hydroxy-2-(hydroxyimino)-acetimidoyl chloride
17019-15-7

(1Z,2E)-N-hydroxy-2-(hydroxyimino)-acetimidoyl chloride

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride; chlorine unter Kuehlung;
3-Brom-3,3-dinitro-propionitril
1944-92-9

3-Brom-3,3-dinitro-propionitril

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride In water
furoxanecarboxylic acid

furoxanecarboxylic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With sodium hydroxide Ansaeuern mit Schwefelsaeure und Einleiten von Chlor;
With water at 70 - 80℃; Abkuehlen und Einleiten von Chlor;
sodium salt of/the/ labile <=a>-glyoximecarboxylic acid

sodium salt of/the/ labile <=a>-glyoximecarboxylic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With water; chlorine
(ONCCNO)(n) n:5-8;

(ONCCNO)(n) n:5-8;

dichloroglyoxime
2038-44-0

dichloroglyoxime

Conditions
ConditionsYield
With hydrogenchloride
2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate
85102-68-7

2-N-piperidino-5-methyl-1,3-dithiolium-4-thiolate

dichloroglyoxime
2038-44-0

dichloroglyoxime

C20H28N4O2S6(2+)*2Cl(1-)

C20H28N4O2S6(2+)*2Cl(1-)

Conditions
ConditionsYield
In acetone100%
dichloroglyoxime
2038-44-0

dichloroglyoxime

oxalohydroximoyl diazide
4732-61-0

oxalohydroximoyl diazide

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide for 0.5h; Heating;97%
With sodium azide In ethanol; water Cooling with ice;92%
With sodium azide In N,N-dimethyl-formamide Solvent; Cooling with ice;89.2%
4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

dichloroglyoxime
2038-44-0

dichloroglyoxime

6,7-dimethyl-2,3-bis-1,2,3,4-tetrahydroquinoxaline
134021-61-7

6,7-dimethyl-2,3-bis-1,2,3,4-tetrahydroquinoxaline

Conditions
ConditionsYield
With sodium carbonate In water95%
With sodium carbonate In dichloromethane at 0 - 5℃;
In dichloromethane; water at 0 - 5℃; for 0.5h;
N,N-diethylaniline
93-05-0

N,N-diethylaniline

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1,N2-bis(4-(diethylamino)phenyl)-N1’,N 2’-dihydroxyoxalamidine

N1,N2-bis(4-(diethylamino)phenyl)-N1’,N 2’-dihydroxyoxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;95%
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1’,N2’-dihydroxy-N1,N2-bis(2-methoxyphenyl)oxalamidine
1093112-37-8, 60035-43-0

N1’,N2’-dihydroxy-N1,N2-bis(2-methoxyphenyl)oxalamidine

Conditions
ConditionsYield
With sodium carbonate In isopropyl alcohol at 10 - 20℃; for 5h;94%
With triethylamine In ethanol at -10 - 20℃;76%
1-ethynyl-2-methylbenzene
766-47-2

1-ethynyl-2-methylbenzene

dichloroglyoxime
2038-44-0

dichloroglyoxime

5,5'-di-(2-methylphenyl)-3,3'-bisisoxazole
1446102-62-0

5,5'-di-(2-methylphenyl)-3,3'-bisisoxazole

Conditions
ConditionsYield
With potassium hydrogencarbonate In water; tert-butyl alcohol at 20℃; for 3.25h;94%
phenylacetylene
536-74-3

phenylacetylene

dichloroglyoxime
2038-44-0

dichloroglyoxime

5,5'-diphenyl-3,3'-bisisoxazole
6667-11-4

5,5'-diphenyl-3,3'-bisisoxazole

Conditions
ConditionsYield
With potassium hydrogencarbonate In water; tert-butyl alcohol at 0 - 20℃; for 3.75h;93%
N,N'-di-tert-butylethylenediamine
4062-60-6

N,N'-di-tert-butylethylenediamine

dichloroglyoxime
2038-44-0

dichloroglyoxime

1,4-Di-tert-butyl-piperazine-2,3-dione dioxime

1,4-Di-tert-butyl-piperazine-2,3-dione dioxime

Conditions
ConditionsYield
In methanol at -40 - 20℃;92%
3-Hexin-1,6-dicarbonsaeure-dimethylester
874008-12-5

3-Hexin-1,6-dicarbonsaeure-dimethylester

dichloroglyoxime
2038-44-0

dichloroglyoxime

4,4',5,5'-tetramethoxycarbonyl-3,3'-bisisoxazole
4328-82-9

4,4',5,5'-tetramethoxycarbonyl-3,3'-bisisoxazole

Conditions
ConditionsYield
With potassium hydrogencarbonate In water; tert-butyl alcohol at 20℃; for 3.25h;91%
para-butoxyaniline
4344-55-2

para-butoxyaniline

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1,N2-bis(4-butoxyphenyl)-N1’,N2’-dihydroxyoxalamidine

N1,N2-bis(4-butoxyphenyl)-N1’,N2’-dihydroxyoxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;91%
triphenylboroxine
3262-89-3

triphenylboroxine

[Fe(CH3CN)4Cl2]
227027-67-0

[Fe(CH3CN)4Cl2]

dichloroglyoxime
2038-44-0

dichloroglyoxime

Fe(dichloroglyoxime)3(B(C6H5))2

Fe(dichloroglyoxime)3(B(C6H5))2

Conditions
ConditionsYield
In nitromethane dichloroglyoxime and B-complex were dissolved in MeNO2, Fe-complex was added, stirred under Ar; solvent was distilled off, cooled to room temp., filtered, washed with HCl, EtOH, Et2O, hexane, dried in vacuo;90%
dichloroglyoxime
2038-44-0

dichloroglyoxime

disodium 5,5′-bistetrazole-1,1′-diolate

disodium 5,5′-bistetrazole-1,1′-diolate

Conditions
ConditionsYield
Stage #1: dichloroglyoxime With sodium azide In 1-methyl-pyrrolidin-2-one at 0℃; for 0.666667h;
Stage #2: With hydrogenchloride In 1-methyl-pyrrolidin-2-one; diethyl ether at 0℃;
90%
4-n-methylphenylacetylene
766-97-2

4-n-methylphenylacetylene

dichloroglyoxime
2038-44-0

dichloroglyoxime

5,5'-di-(4-methylphenyl)-3,3'-bisisoxazole
102006-96-2

5,5'-di-(4-methylphenyl)-3,3'-bisisoxazole

Conditions
ConditionsYield
With potassium hydrogencarbonate In water; tert-butyl alcohol at 0 - 20℃; for 3.75h;86%
iron(II) chloride tetrahydrate

iron(II) chloride tetrahydrate

pentafluorophenylboronic acid
1582-24-7

pentafluorophenylboronic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

Fe(dichloroglyoxime)3(B-pentafluorophenyl)2

Fe(dichloroglyoxime)3(B-pentafluorophenyl)2

Conditions
ConditionsYield
In trifluoroacetic acid for 0.833333h; Inert atmosphere; Reflux;86%
benzo[1,3]dioxolo-5-ylamine
14268-66-7

benzo[1,3]dioxolo-5-ylamine

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1,N2-di(benzo[d][1,3]dioxol-5-yl)-N1’,N2’-dihydroxyoxalamidine

N1,N2-di(benzo[d][1,3]dioxol-5-yl)-N1’,N2’-dihydroxyoxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;86%
dichloroglyoxime
2038-44-0

dichloroglyoxime

bis(tetraethylammonium)bis(2H-1,3-dithiol-2-thione-4,5-zincdithiolate)

bis(tetraethylammonium)bis(2H-1,3-dithiol-2-thione-4,5-zincdithiolate)

2-Thioxo-[1,3]dithiolo[4,5-b][1,4]dithiine-5,6-dione dioxime

2-Thioxo-[1,3]dithiolo[4,5-b][1,4]dithiine-5,6-dione dioxime

Conditions
ConditionsYield
In acetone for 2h; Heating;85%
4-Chloro-1,2-phenylenediamine
95-83-0

4-Chloro-1,2-phenylenediamine

dichloroglyoxime
2038-44-0

dichloroglyoxime

2,3-bis-6-chloro-1,2,3,4-tetrahydroquinoxaline
126448-31-5

2,3-bis-6-chloro-1,2,3,4-tetrahydroquinoxaline

Conditions
ConditionsYield
With sodium carbonate In dichloromethane for 0.5h;84%
With sodium carbonate In dichloromethane at 0 - 5℃;
In dichloromethane; water at 0 - 5℃; for 0.5h;
iron(II) chloride tetrahydrate

iron(II) chloride tetrahydrate

4-pyridylboronic acid
1692-15-5

4-pyridylboronic acid

trifluoroacetic acid
76-05-1

trifluoroacetic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

C16H10B2Cl6FeN8O6(2+)*2C2F3O2(1-)

C16H10B2Cl6FeN8O6(2+)*2C2F3O2(1-)

Conditions
ConditionsYield
for 1.5h; Inert atmosphere; Heating;81%
4-Ethoxyaniline
156-43-4

4-Ethoxyaniline

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1,N2-bis(4-ethoxyphenyl)-N1’,N2’-dihydroxyoxalamidine

N1,N2-bis(4-ethoxyphenyl)-N1’,N2’-dihydroxyoxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;81%
1-ethynyl-4-fluorobenzene
766-98-3

1-ethynyl-4-fluorobenzene

dichloroglyoxime
2038-44-0

dichloroglyoxime

5,5'-di-(4-fluorophenyl)-3,3'-bisisoxazole
1446102-61-9

5,5'-di-(4-fluorophenyl)-3,3'-bisisoxazole

Conditions
ConditionsYield
With potassium hydrogencarbonate In water; tert-butyl alcohol at 0 - 20℃; for 3.75h;80%
iron(II) chloride tetrahydrate

iron(II) chloride tetrahydrate

3-Formylphenylboronic acid
87199-16-4

3-Formylphenylboronic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

C20H10B2Cl6FeN6O8

C20H10B2Cl6FeN6O8

Conditions
ConditionsYield
In nitromethane Inert atmosphere;80%
iron(II) chloride tetrahydrate

iron(II) chloride tetrahydrate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

dichloroglyoxime
2038-44-0

dichloroglyoxime

C16H8B2Cl6FeN8O6

C16H8B2Cl6FeN8O6

Conditions
ConditionsYield
With trifluoroacetic acid for 1.5h; Inert atmosphere; Reflux;80%
2,4-Dimethoxyaniline
2735-04-8

2,4-Dimethoxyaniline

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1’,N2’-dihydroxy-N1,N2-bis(2,4-dimethoxyphenyl)oxalamidine

N1’,N2’-dihydroxy-N1,N2-bis(2,4-dimethoxyphenyl)oxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;80%
diphenyl diselenide
1666-13-3

diphenyl diselenide

dichloroglyoxime
2038-44-0

dichloroglyoxime

bis(phenylselanyl)glyoxime
1335030-64-2

bis(phenylselanyl)glyoxime

Conditions
ConditionsYield
Stage #1: diphenyl diselenide With sodium tetrahydroborate; sodium carbonate In ethanol; water Inert atmosphere;
Stage #2: dichloroglyoxime In ethanol; water for 12h; Inert atmosphere;
79%
dichloroglyoxime
2038-44-0

dichloroglyoxime

dihydroxylammonium 5,5'-bistetrazole-1,1'-diolate

dihydroxylammonium 5,5'-bistetrazole-1,1'-diolate

Conditions
ConditionsYield
With sodium azide In 1-methyl-pyrrolidin-2-one79%
4-Isopropylaniline
99-88-7

4-Isopropylaniline

dichloroglyoxime
2038-44-0

dichloroglyoxime

N1’,N2’-dihydroxy-N1,N2-bis(4-isopropylphenyl)oxalamidine

N1’,N2’-dihydroxy-N1,N2-bis(4-isopropylphenyl)oxalamidine

Conditions
ConditionsYield
With triethylamine In ethanol at -10 - 20℃;79%
dichloroglyoxime
2038-44-0

dichloroglyoxime

3,4-dichloro-1,2,5-oxadiazole-N-oxide
34698-60-7

3,4-dichloro-1,2,5-oxadiazole-N-oxide

Conditions
ConditionsYield
With nitric acid at 0 - 20℃; for 2.5h; Inert atmosphere; Schlenk technique;78%
With nitric acid; Nitrogen dioxide
dichloroglyoxime
2038-44-0

dichloroglyoxime

3,4-dichloro-1,2,5-thiadiazole
5728-20-1

3,4-dichloro-1,2,5-thiadiazole

Conditions
ConditionsYield
With pyridine; disulfur dichloride In acetonitrile at -25℃; for 5h; Inert atmosphere; Reflux;78%
With sulfur dichloride In N,N-dimethyl-formamide

Dichloroglyoxime Specification

The Dichloroglyoxime, with the CAS registry number 2038-44-0, is also known as Oxalohydroximoyl chloride. This chemical's molecular formula is C2H2Cl2N2O2 and molecular weight is 156.96. What's more, its IUPAC name is N-[(E)-1,2-Dichloro-2-nitrosoethenyl]hydroxylamine and systematic name is called N,N'-Dihydroxyoxalimidoyl chloride.

Physical properties about Dichloroglyoxime are: (1) ACD/LogP: 2.00; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): 2; (4) ACD/LogD (pH 7.4): 2; (5) ACD/BCF (pH 5.5): 19.59; (6) ACD/BCF (pH 7.4): 19.39; (7) ACD/KOC (pH 5.5): 292.7; (8) ACD/KOC (pH 7.4): 289.77; (9) #H bond acceptors: 4; (10) #H bond donors: 2; (11) #Freely Rotating Bonds: 3; (12) Polar Surface Area: 65.18 Å2; (13) Index of Refraction: 1.575; (14) Molar Refractivity: 28.77 cm3; (15) Molar Volume: 87 cm3;(16) Surface Tension: 58 dyne/cm; (17) Density: 1.8 g/cm3; (18) Flash Point: 156.1 °C; (19) Enthalpy of Vaporization: 66.91 kJ/mol; (20) Boiling Point: 334.6 °C at 760 mmHg; (21) Vapour Pressure: 8.92E-06 mmHg at 25 °C; (22) Melting Point: 213 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: C(=NO)(C(=NO)Cl)Cl
(2) InChI: InChI=1/C2H2Cl2N2O2/c3-1(5-7)2(4)6-8/h7-8H
(3) InChIKey: KTQVJAPIQPIIPF-UHFFFAOYAQ

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