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95-45-4

Basic Information
CAS No.: 95-45-4
Name: Dimethylglyoxime
Article Data: 52
Molecular Structure:
Molecular Structure of 95-45-4 (Dimethylglyoxime)
Formula: C4H8N2O2
Molecular Weight: 116.12
Synonyms: 2,3-Butanedione,dioxime (8CI,9CI);2,3-Diisonitrosobutane;Biacetyl dioxime;Chugaev's reagent;2,3-Butanedione,2,3-dioxime;NSC 9;Reagents, Chugaev's;Diacetyl dioxime;
EINECS: 202-420-1
Density: 1.17 g/cm3
Melting Point: 240-241 °C(lit.)
Boiling Point: 271.529 °C at 760 mmHg
Flash Point: 158.376 °C
Solubility: insoluble in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 22-20/21/22
Safety: 22-24/25-36
PSA: 65.18000
LogP: 0.68660
Synthetic route
7647-01-0

hydrogenchloride

triphenylantimony dimethylglyoximate

A

594-31-0, 34716-91-1, 20265-29-6

triphenylantimony dichloride

B

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
In hydrogenchloride react. antimony compd. with concd. HCl;A 99%
B n/a
431-03-8

dimethylglyoxal

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In methanol for 1h; Reflux;95%
With pyridine; hydroxylamine hydrochloride In methanol for 1h; Inert atmosphere; Reflux;92%
135636-66-7

butane-2,3-dione mono-oxime

A

89356-40-1

2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide

B

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With ammonium carbonate In ethanol; water for 72h; Heating;A 35%
B 9.0 g

nickel(II) bis(dimethylglyoximate)

A

95-45-4

butane-2,3-dione dioxime

B

nickel(II) nitrate

Conditions
ConditionsYield
With nitric acid In not givenA 32%
B n/a
With HNO3 In not givenA 32%
B n/a
151-50-8

potassium cyanide

135636-66-7

butane-2,3-dione mono-oxime

A

89356-40-1

2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide

B

95-45-4

butane-2,3-dione dioxime

89356-41-2

1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid

89356-38-7

(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione

Conditions
ConditionsYield
With ammonium carbonate; water In ethanol at 70℃; for 4h; Product distribution; Mechanism;A 0.5 g
B 0.07 g
C 3%
D 26.5%
With ammonium carbonate; water In ethanol at 70℃; for 4h;A 0.5 g
B 0.07 g
C 3%
D 26.5%
151-50-8

potassium cyanide

135636-66-7

butane-2,3-dione mono-oxime

89356-43-4

(3aRS,6aSR)-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethyl-5H-pyrrolo<3,4-d>imidazole-2,4,6-trione

B

95-45-4

butane-2,3-dione dioxime

89356-41-2

1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid

89356-38-7

(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione

Conditions
ConditionsYield
With ammonium carbonate; water In ethanol at 70℃; for 4h;A 0.4 g
B 0.07 g
C 3%
D 26.5%
609-14-3

2-acetylpropanoic acid ethyl ester

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With sodium hydroxide; water; sodium nitrite ueber mehrere Stufen;
With sodium hydroxide dann versetzt mit Natriumnitrit und leitet Schwefeldioxyd ein;
29027-51-8

diacetyldioxime monomethylether

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride
29027-51-8

diacetyldioxime monomethylether

A

617-32-3

butane-2,3-dione-2-methoxime

B

95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride at 60℃;
17235-39-1

2,3-dinitro-butane

95-45-4

butane-2,3-dione dioxime

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Chemistry

IUPAC Name: N-[(Z)-3-nitrosobut-2-en-2-yl]hydroxylamine
Molecular formula: C4H8N2O2
Molar mass: 116.12 g/mol
Appearance: White/Off White Powder 
Index of Refraction: 1.487
Molar Refractivity: 28.417 cm3
Molar Volume: 98.819 cm3
Polarizability: 11.265× 10-24cm3
Surface Tension: 37.538 dyne/cm
Density: 1.175 g/cm3
Flash Point: 158.376 °C
Enthalpy of Vaporization: 59.186 kJ/mol 
Melting point: 240 - 241 °C
Boiling Point: 271.529 °C at 760 mmHg
Vapour Pressure: 0.001 mmHg at 25°C
Storage temp.: 2-8°C
Solubility in water: low
Stability: Stable. Incompatible with strong oxidizing agents. 
Other names: Dimethylglyoxime,Diacetyl dioxime,Chugaev's Reagent 2,3-diisonitrosobutane
The Structure of Diacetyl dioxime (95-45-4):

 

Uses

 Diacetyl dioxime (95-45-4) is used in the analysis of palladium or nickel.
 Diacetyl dioxime (95-45-4) is used as a chelating agent in the gravimetric analysis of nickel.

Production

 Diacetyl dioxime (95-45-4) can be prepared from butanone first by reaction with ethylnitrite followed by conversion of the biacetyl monoxime using sodium hydroxylamine monosulfonate:
             

 

Toxicity Data With Reference

1.    

otr-ham:emb 100 µg/L

    FCTXAV    Food and Cosmetics Toxicology. 18 (1980),289.
2.    

orl-rat LDLo:250 mg/kg

    NCNSA6    National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),26.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xn
Risk Statements: 22-20/21/22
22:  Harmful if swallowed 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
Safety Statements: 22-24/25-36
22:  Do not breathe dust 
24/25:  Avoid contact with skin and eyes 
36:  Wear suitable protective clothing 
WGK Germany: 3
RTECS: EK2975000
F: 10: Keep under argon.
Hazard Note: Harmful
HS Code: 29280090

Specification

1. First Aid Measures
Ingestion:
Induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:
Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Eyes:
Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage:
Keep away from heat and flame. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.

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