Product Name

  • Name

    Dimethylglyoxime

  • EINECS 202-420-1
  • CAS No. 95-45-4
  • Article Data52
  • CAS DataBase
  • Density 1.17 g/cm3
  • Solubility insoluble in water
  • Melting Point 240-241 °C(lit.)
  • Formula C4H8N2O2
  • Boiling Point 271.529 °C at 760 mmHg
  • Molecular Weight 116.12
  • Flash Point 158.376 °C
  • Transport Information
  • Appearance white crystalline powder
  • Safety 22-24/25-36
  • Risk Codes 22-20/21/22
  • Molecular Structure Molecular Structure of 95-45-4 (Dimethylglyoxime)
  • Hazard Symbols HarmfulXn
  • 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;
  • PSA 65.18000
  • LogP 0.68660

Synthetic route

hydrogenchloride
7647-01-0

hydrogenchloride

triphenylantimony dimethylglyoximate

triphenylantimony dimethylglyoximate

A

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

triphenylantimony dichloride

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

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

dimethylglyoxal

butane-2,3-dione dioxime
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%
butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

A

2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide
89356-40-1

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

B

butane-2,3-dione dioxime
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)

nickel(II) bis(dimethylglyoximate)

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

nickel(II) nitrate

nickel(II) nitrate

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

potassium cyanide

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

A

2-(1-hydroxyiminoethyl)-2,4,5-trimethyl-2H-imidazole 1-oxide
89356-40-1

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

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid
89356-41-2

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

(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione
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%
potassium cyanide
151-50-8

potassium cyanide

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

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

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

1-hydroxytetrahydro-4,5-dimethyl-2-oxoimidazole-4,5-dicarboxylic acid
89356-41-2

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

(3aRS,6aSR)-6-amino-1,3,3a,6a-tetrahydro-1-hydroxy-3a,6a-dimethylpyrrolo<3,4-d>imidazole-2,4-dione
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%
2-acetylpropanoic acid ethyl ester
609-14-3

2-acetylpropanoic acid ethyl ester

butane-2,3-dione dioxime
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;
diacetyldioxime monomethylether
29027-51-8

diacetyldioxime monomethylether

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride
diacetyldioxime monomethylether
29027-51-8

diacetyldioxime monomethylether

A

butane-2,3-dione-2-methoxime
617-32-3

butane-2,3-dione-2-methoxime

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride at 60℃;
2,3-dinitro-butane
17235-39-1

2,3-dinitro-butane

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

ethyl methyl ketone oxime
96-29-7

ethyl methyl ketone oxime

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With sulfuric acid at 40℃;
butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

urea
57-13-6

urea

A

tetrahydro-3a,6a-dimethylimidazo<4,5-d>imidazole-2,5-(1H,3H)-dione
28115-25-5

tetrahydro-3a,6a-dimethylimidazo<4,5-d>imidazole-2,5-(1H,3H)-dione

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With ethanol; sulfuric acid
butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydroxylamine
With acid solution; sodium hydroxylamine-O-sulfonate at 70℃;
butanone
78-93-3

butanone

isopentyl nitrite
110-46-3

isopentyl nitrite

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydrogenchloride at 40 - 50℃; ueber mehrere Stufen;
butanone
78-93-3

butanone

isopentyl nitrite
110-46-3

isopentyl nitrite

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

dimethylglyoxal
431-03-8

dimethylglyoxal

Conditions
ConditionsYield
With hydrogenchloride
butanone
78-93-3

butanone

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
Darstellung;
2,3-butane diamine
563-86-0

2,3-butane diamine

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With titanium(IV) sulfate; titanium(III) sulphate; sulfuric acid at 32.85℃; Equilibrium constant; Reduction;
6,7-dimethylquinoline
20668-33-1

6,7-dimethylquinoline

chloroform
67-66-3

chloroform

A

pyrrolo[3,4-b]pyridine-5,7-dione dioxime
860716-16-1

pyrrolo[3,4-b]pyridine-5,7-dione dioxime

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
at -30℃; Beh. des Rktgem. mit Hydroxylamin-hydrochlorid und wss. Natriumcarbonat;
2,3-dimethylquinoline
1721-89-7

2,3-dimethylquinoline

chloroform
67-66-3

chloroform

A

glyoxime
557-30-2

glyoxime

B

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

C

5,6-dimethyl-pyrrolo<3,4-b>pyridine-1,3-dione dioxime

5,6-dimethyl-pyrrolo<3,4-b>pyridine-1,3-dione dioxime

Conditions
ConditionsYield
at -40℃; anschl. mit Hydroxylamin-hydrochlorid und wss. Natriumcarbonat;
3.3-dichlorobutanone

3.3-dichlorobutanone

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With hydroxylamine
dimethylfuroxane

dimethylfuroxane

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With acetic acid; zinc
dimethylglyoxal
431-03-8

dimethylglyoxal

hydroxylamine hydrochloride

hydroxylamine hydrochloride

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Conditions
ConditionsYield
With sodium carbonate
butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

hydroxylamine hydrochloride

hydroxylamine hydrochloride

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

hydrogenchloride
7647-01-0

hydrogenchloride

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

urea
57-13-6

urea

concentrated alcohol

concentrated alcohol

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

dimethylacetylene-diurein

dimethylacetylene-diurein

sulfuric acid
7664-93-9

sulfuric acid

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

urea
57-13-6

urea

concentrated alcohol

concentrated alcohol

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

dimethylacetylene-diurein

dimethylacetylene-diurein

hydrogenchloride
7647-01-0

hydrogenchloride

ethanol
64-17-5

ethanol

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

urea
57-13-6

urea

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

dimethylacetylenediurein

dimethylacetylenediurein

ethanol
64-17-5

ethanol

sulfuric acid
7664-93-9

sulfuric acid

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

urea
57-13-6

urea

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

dimethylacetylenediurein

dimethylacetylenediurein

Acetaldehyde oxime
107-29-9

Acetaldehyde oxime

butane-2,3-dione mono-oxime
135636-66-7

butane-2,3-dione mono-oxime

A

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

B

oxy-trimethyloxadiazin;acetaldehyde

oxy-trimethyloxadiazin;acetaldehyde

3,3-Dichloro-2-butanone
2648-57-9

3,3-Dichloro-2-butanone

NH3O

NH3O

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

bis(dipiperidinyldithiocarbamato)nickel(II)
41476-75-9

bis(dipiperidinyldithiocarbamato)nickel(II)

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

nickel (dimethylglyoximate)(piperidine dithiocarbamate)

nickel (dimethylglyoximate)(piperidine dithiocarbamate)

Conditions
ConditionsYield
With ammonia In ethanol byproducts: C5H10NCS2NH4; addn. of aq. NH3 to a mixt. of nickel complex and ligand in EtOH, refluxing for 30 min; filtration, washing with ethanol, ether, drying in vac.; elem. anal.;100%
(phthaloyl)bis(triphenylphosphino)(chloro)cobalt
75895-97-5

(phthaloyl)bis(triphenylphosphino)(chloro)cobalt

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

(phthaloyl)(dimethylglyoxime)(triphenylphosphine)chloro-cobalt
101565-42-8

(phthaloyl)(dimethylglyoxime)(triphenylphosphine)chloro-cobalt

Conditions
ConditionsYield
In acetonitrile Co-complex, dimethylglyoxime, and MeCN were refluxed with stirring under an N2 atmosphere until all of the starting material had solubilized; soln. was cooled, MeCN removed, residue was triturated with Et2O; elem. anal.;100%
bis(N,N-diethyldithiocarbamato)nickel(II)
1079097-20-3, 14267-17-5, 52610-81-8

bis(N,N-diethyldithiocarbamato)nickel(II)

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

Ni((CH3CH2)2NCS2)(CH3CNOCNOHCH3)
110975-93-4

Ni((CH3CH2)2NCS2)(CH3CNOCNOHCH3)

Conditions
ConditionsYield
With ammonia In ethanol byproducts: (CH3CH2)2NCS2NH4; addn. of aq. NH3 to a mixt. of nickel complex and ligand in EtOH, refluxing for 30 min; filtration, washing with ethanol, ether, drying in vac.; elem. anal.;100%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III)

dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III)

Conditions
ConditionsYield
With oxygen In acetone at 20℃; for 1h; Schlenk technique; Inert atmosphere;100%
With air In acetone for 0.333333h; Sealed tube;99%
In acetone for 0.166667h;79%
cobalt(II) bromide hydrate

cobalt(II) bromide hydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

dibromo(dimethylglyoxime)(dimethylglyoximato)cobalt(III)

dibromo(dimethylglyoxime)(dimethylglyoximato)cobalt(III)

Conditions
ConditionsYield
With oxygen In acetone at 20℃; for 1h; Schlenk technique; Inert atmosphere;100%
rhenium(I) pentacarbonyl chloride
14099-01-5

rhenium(I) pentacarbonyl chloride

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

[ReCl(CO)3(dimethylglyoxime)]
1173885-94-3

[ReCl(CO)3(dimethylglyoxime)]

Conditions
ConditionsYield
In methanol Re complex was mixed with ligand (1 equiv.); MeOH was added; refluxed for 4 h; evapd.; elem. anal.;98%
cis-dichlorobis(dimethylsulfoxide)platinum(II)
75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9

cis-dichlorobis(dimethylsulfoxide)platinum(II)

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

cis-bis(α-glyoximate)platinum(II)

cis-bis(α-glyoximate)platinum(II)

Conditions
ConditionsYield
With triethylamine In methanol for 2h; Reflux;97%
rhodium(III) chloride trihydrate

rhodium(III) chloride trihydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

trans-dichloro(dimethylglyoximato)(dimethylglyoxime)rhodium(III)

trans-dichloro(dimethylglyoximato)(dimethylglyoxime)rhodium(III)

Conditions
ConditionsYield
In ethanol; water addn. of hot soln. of glyoxime in 95% aq. ethanol to boiling purple suspension of RhCl3; immediately discoloration of mixture to yellow; heating at reflux for 1 h; cooling to 0°C;; pptn.; drying;;96%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

iron(II) chloride

iron(II) chloride

C22H26B2FeN8O6

C22H26B2FeN8O6

Conditions
ConditionsYield
In methanol Reflux;96%
butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

3,4-dimethylfurazan
4975-21-7

3,4-dimethylfurazan

Conditions
ConditionsYield
With potassium hydroxide; caesium carbonate In ethylene glycol at 110 - 160℃;95%
With succinic acid anhydride at 160℃; Neat (no solvent);30%
With potassium hydroxide In ethylene glycol at 160 - 190℃;
butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

nickel(II) hydroxide

nickel(II) hydroxide

nickel(II) bis(dimethylglyoximate)

nickel(II) bis(dimethylglyoximate)

Conditions
ConditionsYield
In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min;95%
butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

nickel(II) bis(dimethylglyoximate)

nickel(II) bis(dimethylglyoximate)

Conditions
ConditionsYield
In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min;95%
In ethanol in concd. soln.; short heating on water bath; filtration, multiple washing with alcohol;
In ethanol in concd. soln.; short heating on water bath; filtration, multiple washing with alcohol;
nickel hydroxocarbonate

nickel hydroxocarbonate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

nickel(II) bis(dimethylglyoximate)

nickel(II) bis(dimethylglyoximate)

Conditions
ConditionsYield
In solid metal to ligand ratio 1:2, static load (10 MPa, shear angle 45-90°), contact time no more than 15 min;95%
sodium metavanadate * water

sodium metavanadate * water

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

6Na(1+)*5V(5+)*5V(4+)*23O(2-)*C4H6N2O2*5OH(1-)*11H2O=Na6V10O23(C4H6N2O2)(OH)5*11H2O

6Na(1+)*5V(5+)*5V(4+)*23O(2-)*C4H6N2O2*5OH(1-)*11H2O=Na6V10O23(C4H6N2O2)(OH)5*11H2O

Conditions
ConditionsYield
With H2SO4 In ethanol; water byproducts: H(1+); room temp.; addn. of aq. soln. of metal compd. (pH = 2.5, H2SO4) to soln. of ligand (in EtOH), stirring (pptn.); filtration, washing (H2O/EtOH = 1/1), drying (50°C); elem. anal.;95%
picoline
108-89-4

picoline

indium trichloride trihydrate

indium trichloride trihydrate

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

{Co(4-picoline)2(MeC(NOH)C(NO)Me)2}{InCl4(4-picoline)2}

{Co(4-picoline)2(MeC(NOH)C(NO)Me)2}{InCl4(4-picoline)2}

Conditions
ConditionsYield
In methanol addn. of CoCl2*6H2O in MeOH to dimethylglyoxime, heating (water bath), addn. of pyridine and MeOH soln. of InCl3*3H2O (ratio of Co/dioxime/In/amine 1:2:1:5, stirring), heating (stirring until substances dissolved); crystn. on cooling, filtration off, washing (MeOH, ether), drying (air); elem. anal.;94%
pyridine
110-86-1

pyridine

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

acetic acid
64-19-7

acetic acid

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

phenyl propargyl ketone
3623-15-2

phenyl propargyl ketone

(3-phenyl-1-propen-3-one-1-yl)(pyridine)bis(dimethylglyoximato)cobalt(III)
25153-21-3, 287200-31-1

(3-phenyl-1-propen-3-one-1-yl)(pyridine)bis(dimethylglyoximato)cobalt(III)

Conditions
ConditionsYield
With Zn In tetrahydrofuran under N2, Co(CH3COO)2*4H2O, dimethylglyoxime, pyridine and zinc dust were all combined in THF and refluxed 15 min, cooled to 25°C, C6H5COCCH was added, the mixt. was refluxed for 1 h, the mixt. was cooled to 25°C, CH3COOH was added; the soln. was poured into ice water containing pyridine, the product was extd. with CH3CH2OCOCH3, dried (MgSO4), concd. (vac.), the solid was triturated with pentane/(CH3CH2)2O; elem. anal.;94%
sodium metavanadate * water

sodium metavanadate * water

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

6Na(1+)*8V(5+)*2V(4+)*26O(2-)*2C4H6N2O2*2OH(1-)*16H2O=Na6V10O26(C4H6N2O2)2(OH)2*16H2O

6Na(1+)*8V(5+)*2V(4+)*26O(2-)*2C4H6N2O2*2OH(1-)*16H2O=Na6V10O26(C4H6N2O2)2(OH)2*16H2O

Conditions
ConditionsYield
With H2SO4 In ethanol; water byproducts: H(1+); room temp.; addn. of aq. soln. of metal compd. (pH = 4.0, H2SO4) to soln. of ligand (in EtOH), stirring (pptn.); filtration, washing (H2O/EtOH = 1/1), drying (50°C); elem. anal.;92%
(OCH3)((CH3)2CH)C4O2Co(P(C6H5)3)2Cl

(OCH3)((CH3)2CH)C4O2Co(P(C6H5)3)2Cl

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

(OCH3)((CH3)2CH)C4(O)2 cobalt(triphenylphosphine)(dimethylglyoxime)

(OCH3)((CH3)2CH)C4(O)2 cobalt(triphenylphosphine)(dimethylglyoxime)

Conditions
ConditionsYield
In acetonitrile 24 h/room temp.;;91%
In acetonitrile91%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

methacrylonitrile
126-98-7

methacrylonitrile

β-cyanopropylpyridinatocobaloxime

β-cyanopropylpyridinatocobaloxime

Conditions
ConditionsYield
With pyridine; sodium hydroxide; hydrogen In methanol; water addn. of alkene to soln. of CoCl2*6H2O, dimethylglyoxime and pyridine in MeOH (room temp.), degassing (N2, 20 min), addn. of aq. NaOH, degassing (15 min), exchange of N2 for H2 (<1 h); addn. of H2O, extn. (CH2Cl2), drying (MgSO4), evapn., chromy (silica gel) and/or recrystn (CH2Cl2-petroleum ether);91%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

6-Bromo-1-hexene
2695-47-8

6-Bromo-1-hexene

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

3-Bromo-4-methylpyridin
3430-22-6

3-Bromo-4-methylpyridin

(3-bromo-4-methylpyridine)bis(dimethylglyoximato)-5-hexenylcobalt(III)

(3-bromo-4-methylpyridine)bis(dimethylglyoximato)-5-hexenylcobalt(III)

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate In methanol stirring CoCl2, glyoxime in CH3OH at -20°C under N2; addn. of 50% aq. NaOH soln., 3-bromo-4-methylpyridine, NaBH4 in CH3OH; stirring at 20°C for 1 h; addn. of bromide at -20, stirring at 20°C in dark for 14 h;; addn. of water containing 1 drop 3-bromo-4-methylpyridine to oily residue; pptn.; drying; elem. anal.;91%
butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

3,5-dibromophenylboronic acid

3,5-dibromophenylboronic acid

iron(II) chloride

iron(II) chloride

C24H24B2Br4FeN6O6

C24H24B2Br4FeN6O6

Conditions
ConditionsYield
In methanol at 70℃; for 4h; Inert atmosphere; Schlenk technique;91%
-butyl vinyl ether
111-34-2

-butyl vinyl ether

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

dimethylglyoxal O,O'-di(1-butoxyethyl)dioxime
128224-27-1

dimethylglyoxal O,O'-di(1-butoxyethyl)dioxime

Conditions
ConditionsYield
With hydrogen bromide In diethyl ether at 25℃; for 48h;90%
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

{(pentamethylcyclopentadienyl)(dmg)rhodium(III)(Cl)}Cl

{(pentamethylcyclopentadienyl)(dmg)rhodium(III)(Cl)}Cl

Conditions
ConditionsYield
In methanol stirring for 5 min; concn. and layering with ether; elem. anal.;90%
uranium(VI) trioxide

uranium(VI) trioxide

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

uranyl diaquadimethylglyoximate trihydrate

uranyl diaquadimethylglyoximate trihydrate

Conditions
ConditionsYield
In water dimetylglyoxime added to suspn. of UO3 in H2O; mixt. stirred under heating for 6 h (molar ratio U:C4H8N2O2 = 1:1.23); ppt. filtered off; washed (H2O, EtOH, ether); dried on filter in air flow; elem. anal.;90%
(CH3)2C4O2Co(P(C6H5)3)2Cl

(CH3)2C4O2Co(P(C6H5)3)2Cl

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

(CH3)2C4(O)2 cobalt(triphenylphoshine)(dimethylglyoxime)(chloride)

(CH3)2C4(O)2 cobalt(triphenylphoshine)(dimethylglyoxime)(chloride)

Conditions
ConditionsYield
In acetonitrile 24 h/room temp.;;90%
In acetonitrile90%
hydrogenchloride
7647-01-0

hydrogenchloride

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

H{CoCl2(dmgH)2}

H{CoCl2(dmgH)2}

Conditions
ConditionsYield
With perhydrol In water heating mixture of CoCl2*6H2O and powdered dimethylglyoxime in H2O on a water-bath; addn. of perhydrol under stirring; addn. of excess HCl-soln. to the warm soln.;; washing with dild. HCl-soln., alcohol and ether;;90%
chloropentaamminerhodium(III) chloride

chloropentaamminerhodium(III) chloride

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

diamminebis(dimethylglyoxime)rhodium(III) chloride pentahydrate

diamminebis(dimethylglyoxime)rhodium(III) chloride pentahydrate

Conditions
ConditionsYield
With ammonium acetate In water heating all compounds in a sealed tube (10 hours/150 °C);; filtration; evapn. of the filtrate to dryness; washing (alc.); recrystn. from hot water;;90%
3-Methylpyridine
108-99-6

3-Methylpyridine

cobalt bromide hexahydrate

cobalt bromide hexahydrate

indium tribromide
13465-09-3

indium tribromide

butane-2,3-dione dioxime
95-45-4

butane-2,3-dione dioxime

{Co(3-picoline)2(MeC(NOH)C(NO)Me)2}{InBr4}

{Co(3-picoline)2(MeC(NOH)C(NO)Me)2}{InBr4}

Conditions
ConditionsYield
In methanol addn. of CoCl2*6H2O in MeOH to dimethylglyoxime, heating (water bath), addn. of pyridine and MeOH soln. of InCl3*3H2O (ratio of Co/dioxime/In/amine 1:2:1:5, stirring), heating (stirring until substances dissolved); crystn. on cooling, filtration off, washing (MeOH, ether), drying (air); elem. anal.;90%

Dimethylglyoxime Chemical Properties

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):

 

Dimethylglyoxime 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.

Dimethylglyoxime 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:
             

 

Dimethylglyoxime 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.

Dimethylglyoxime Consensus Reports

Reported in EPA TSCA Inventory.

Dimethylglyoxime 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

Dimethylglyoxime 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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