Product Name

  • Name

    2-METHYLGLUTARONITRILE

  • EINECS 224-923-5
  • CAS No. 4553-62-2
  • Article Data35
  • CAS DataBase
  • Density 0.942 g/cm3
  • Solubility 1-5 g/100 ml
  • Melting Point -45 C
  • Formula C6H8 N2
  • Boiling Point 274 C
  • Molecular Weight 108.143
  • Flash Point 126 C
  • Transport Information HAZARD
  • Appearance Clear liquid
  • Safety Poison by intravenous route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN. See also NITRILES.
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 4553-62-2 (2-METHYLGLUTARONITRILE)
  • Hazard Symbols
  • Synonyms Glutaronitrile,2-methyl- (6CI,7CI,8CI); 1,3-Dicyanobutane; 2,4-Dicyanobutane;2-Methylglutaronitrile; 2-Methylpentanedinitrile; Diacrylonitrile; a-Methylglutarodinitrile; a-Methylglutaronitrile
  • PSA 47.58000
  • LogP 1.44986

Synthetic route

4-bromovalero-nitrile
14470-12-3

4-bromovalero-nitrile

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With copper(l) iodide In acetonitrile at 20℃; for 24h; Inert atmosphere; UV-irradiation;82%
hydrogen cyanide
74-90-8

hydrogen cyanide

3-pentenenitrile
4635-87-4

3-pentenenitrile

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With dicobalt octacarbonyl; benzene at 130℃;
1,3-dichlorobutane
1190-22-3

1,3-dichlorobutane

sodium cyanide
143-33-9

sodium cyanide

A

4-chloro-valeronitrile
13249-56-4

4-chloro-valeronitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With 2-methoxy-ethanol at 160℃; unter Druck;
With 2-methoxy-ethanol at 159 - 163℃; under 1765.2 - 2059.4 Torr;
1,3-dibromobutane
107-80-2

1,3-dibromobutane

sodium cyanide
143-33-9

sodium cyanide

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With methanol
1,3-dibromobutane
107-80-2

1,3-dibromobutane

potassium cyanide
151-50-8

potassium cyanide

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With ethanol
4-chloro-valeronitrile
13249-56-4

4-chloro-valeronitrile

sodium cyanide
143-33-9

sodium cyanide

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With N,N-dimethyl-formamide
hydrogen cyanide
74-90-8

hydrogen cyanide

buta-1,3-diene
106-99-0

buta-1,3-diene

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With dicobalt octacarbonyl; benzene at 130℃;
2-Methyl-glutaconsaeuredinitril
91808-25-2

2-Methyl-glutaconsaeuredinitril

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
palladium on activated charcoal (hydrogenation);
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

acrylonitrile
107-13-1

acrylonitrile

A

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

B

4,4-dimethoxybutanenitrile
14618-78-1

4,4-dimethoxybutanenitrile

C

propiononitrile
107-12-0

propiononitrile

Conditions
ConditionsYield
With dicobalt octacarbonyl; hydrogen In methanol at 100℃; under 129287 Torr; for 8h; Product distribution; Mechanism; var. catalysts, time and temp.;
carbon monoxide
201230-82-2

carbon monoxide

acrylonitrile
107-13-1

acrylonitrile

cyclohexanol
108-93-0

cyclohexanol

A

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

B

3-Cyano-propionic acid cyclohexyl ester
125847-90-7

3-Cyano-propionic acid cyclohexyl ester

C

Cyano-methyl-acetic acid cyclohexyl ester
125847-86-1

Cyano-methyl-acetic acid cyclohexyl ester

D

2,4-dicyano-2-methylbutanoic acid cyclohexyl ester
125847-81-6

2,4-dicyano-2-methylbutanoic acid cyclohexyl ester

Conditions
ConditionsYield
With pyridine; dicobalt octacarbonyl In toluene at 110℃; under 75005.9 - 90007.2 Torr; for 6h;A n/a
B 5.3 % Chromat.
C 28.9 % Chromat.
D 61.7 % Chromat.
acrylonitrile
107-13-1

acrylonitrile

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide Rate constant; Mechanism; electrochemical hydrodimerization;
sulfuric acid
7664-93-9

sulfuric acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

iron(II) sulfate

iron(II) sulfate

propiononitrile
107-12-0

propiononitrile

A

meso-2,3-dimethyl-succinonitrile
55903-51-0

meso-2,3-dimethyl-succinonitrile

B

hexanedinitrile
111-69-3

hexanedinitrile

C

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
at 28℃;
2,4-dicyano-2-methyl-butyric acid

2,4-dicyano-2-methyl-butyric acid

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
With pyridine; copper at 110℃;
1,3-dichlorobutane
1190-22-3

1,3-dichlorobutane

sodium cyanide
143-33-9

sodium cyanide

glycolmethyl ether

glycolmethyl ether

A

4-chloro-valeronitrile
13249-56-4

4-chloro-valeronitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
at 159 - 163℃; unter Druck;
hydrogen cyanide
74-90-8

hydrogen cyanide

4-Pentenenitrile
592-51-8

4-Pentenenitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

C

alpha-ethylsuccinonitrile
17611-82-4

alpha-ethylsuccinonitrile

Conditions
ConditionsYield
With {2-[(o-tolyl-O)2-P-O]-5-(1,1,3,3-Me4-butyl)benzene}2-SO2; Lewis acid; bis(1,5-cyclooctadiene)nickel (0) In N,N-dimethyl-formamide at 70℃; for 2h; sonication;
3-Pentenenitrile
16529-66-1

3-Pentenenitrile

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

C

alpha-ethylsuccinonitrile
17611-82-4

alpha-ethylsuccinonitrile

Conditions
ConditionsYield
With [BMMI][Tf2N]; tri-m-tolyl phosphite; zinc(II) chloride; bis(1,5-cyclooctadiene)nickel (0) at 70℃; for 3h; Product distribution; Further Variations:; Reagents; S;
hydrogen cyanide
74-90-8

hydrogen cyanide

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

C

alpha-ethylsuccinonitrile
17611-82-4

alpha-ethylsuccinonitrile

Conditions
ConditionsYield
With zinc(II) chloride In toluene at 50℃; for 16h; Conversion of starting material;
With iron(II) chloride; C54H64O6P2 In toluene at 50℃; for 6h; Conversion of starting material;
With iron(II) chloride In toluene at 25℃; for 72h; Conversion of starting material;
2-acetoxy-2-methyl-glutaronitrile
100377-27-3

2-acetoxy-2-methyl-glutaronitrile

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 500 °C
2: Pd-C / (hydrogenation)
View Scheme
hydrogen cyanide
74-90-8

hydrogen cyanide

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

2-pentenenitrile
26294-98-4

2-pentenenitrile

3-Pentenenitrile
16529-66-1

3-Pentenenitrile

tiglonitrile
30574-97-1

tiglonitrile

4-Pentenenitrile
592-51-8

4-Pentenenitrile

(Z)-pent-2-enenitrile
16545-78-1

(Z)-pent-2-enenitrile

A

pentanonitrile
110-59-8

pentanonitrile

B

hexanedinitrile
111-69-3

hexanedinitrile

C

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

D

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

Conditions
ConditionsYield
C48H52O4P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; zinc(II) chloride Product distribution / selectivity;
C44H44O6P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite; zinc(II) chloride Product distribution / selectivity;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

hydrogen cyanide
74-90-8

hydrogen cyanide

hexanedinitrile
111-69-3

hexanedinitrile

buta-1,3-diene
106-99-0

buta-1,3-diene

A

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

B

2-pentenenitrile
26294-98-4

2-pentenenitrile

C

3-Pentenenitrile
16529-66-1

3-Pentenenitrile

D

(Z)-2-methyl-2-butenenitrile
20068-02-4

(Z)-2-methyl-2-butenenitrile

E

tiglonitrile
30574-97-1

tiglonitrile

F

4-Pentenenitrile
592-51-8

4-Pentenenitrile

G

2-METHYL-3-BUTENENITRILE
16529-56-9

2-METHYL-3-BUTENENITRILE

H

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

I

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

J

(Z)-pent-2-enenitrile
16545-78-1

(Z)-pent-2-enenitrile

Conditions
ConditionsYield
Stage #1: (Z)-2-Butene; hydrogen cyanide; hexanedinitrile; buta-1,3-diene; C42H40O6P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 99.84℃;
Stage #2: nickel at 109.84℃; Product distribution / selectivity;
C48H52O4P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 89.84℃; Product distribution / selectivity;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

hydrogen cyanide
74-90-8

hydrogen cyanide

buta-1,3-diene
106-99-0

buta-1,3-diene

A

1-butylene
106-98-9

1-butylene

B

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

C

2-pentenenitrile
26294-98-4

2-pentenenitrile

D

3-Pentenenitrile
16529-66-1

3-Pentenenitrile

E

(Z)-2-methyl-2-butenenitrile
20068-02-4

(Z)-2-methyl-2-butenenitrile

F

tiglonitrile
30574-97-1

tiglonitrile

G

4-Pentenenitrile
592-51-8

4-Pentenenitrile

H

2-METHYL-3-BUTENENITRILE
16529-56-9

2-METHYL-3-BUTENENITRILE

I

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

J

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

K

(Z)-pent-2-enenitrile
16545-78-1

(Z)-pent-2-enenitrile

Conditions
ConditionsYield
Stage #1: (Z)-2-Butene; hydrogen cyanide; buta-1,3-diene; C48H52O4P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 83.84℃;
Stage #2: at 119.84℃; Product distribution / selectivity;
Stage #1: (Z)-2-Butene; hydrogen cyanide; buta-1,3-diene; C42H40O6P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 89.84℃;
Stage #2: zinc(II) chloride at 109.84℃; Product distribution / selectivity;
Stage #1: (Z)-2-Butene; hydrogen cyanide; buta-1,3-diene; C42H40O6P2; nickel(0)(cyclooctadienyl)2-complex at 89.84℃;
Stage #2: C42H40O6P2; nickel(0)(cyclooctadienyl)2-complex at 109.84℃; Product distribution / selectivity;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

hydrogen cyanide
74-90-8

hydrogen cyanide

buta-1,3-diene
106-99-0

buta-1,3-diene

A

1-butylene
106-98-9

1-butylene

B

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

C

2-pentenenitrile
26294-98-4

2-pentenenitrile

D

3-Pentenenitrile
16529-66-1

3-Pentenenitrile

E

(Z)-2-methyl-2-butenenitrile
20068-02-4

(Z)-2-methyl-2-butenenitrile

F

tiglonitrile
30574-97-1

tiglonitrile

G

4-Pentenenitrile
592-51-8

4-Pentenenitrile

H

2-METHYL-3-BUTENENITRILE
16529-56-9

2-METHYL-3-BUTENENITRILE

I

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

J

(Z)-pent-2-enenitrile
16545-78-1

(Z)-pent-2-enenitrile

Conditions
ConditionsYield
C48H52O4P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 83.84℃; Product distribution / selectivity;
C44H44O6P2; nickel(0)(cyclooctadienyl)2-complex at 89.84℃; Product distribution / selectivity;
C44H44O6P2; nickel(0)(cyclooctadienyl)2-complex at 89.84℃; Product distribution / selectivity;
C48H52O4P2 at 83.84℃; Product distribution / selectivity;
(Z)-2-Butene
590-18-1

(Z)-2-Butene

hydrogen cyanide
74-90-8

hydrogen cyanide

buta-1,3-diene
106-99-0

buta-1,3-diene

A

cis-2-pentenenitrile
25899-50-7

cis-2-pentenenitrile

B

2-pentenenitrile
26294-98-4

2-pentenenitrile

C

3-Pentenenitrile
16529-66-1

3-Pentenenitrile

D

(Z)-2-methyl-2-butenenitrile
20068-02-4

(Z)-2-methyl-2-butenenitrile

E

tiglonitrile
30574-97-1

tiglonitrile

F

4-Pentenenitrile
592-51-8

4-Pentenenitrile

G

2-METHYL-3-BUTENENITRILE
16529-56-9

2-METHYL-3-BUTENENITRILE

H

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

I

4-ethenylcyclohexene
100-40-3

4-ethenylcyclohexene

J

(Z)-pent-2-enenitrile
16545-78-1

(Z)-pent-2-enenitrile

Conditions
ConditionsYield
Stage #1: (Z)-2-Butene; hydrogen cyanide; buta-1,3-diene; C44H44O6P2; (m-tolyl-O-)(p-tolyl-O-)2P; (m-tolyl-O-)2(p-tolyl-O-)P; tri-m-tolyl phosphite; tri-p-tolylphosphite at 99.84℃;
Stage #2: Lewis acid at 109.84℃; Product distribution / selectivity;
hydrogen cyanide
74-90-8

hydrogen cyanide

A

hexanedinitrile
111-69-3

hexanedinitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

Conditions
ConditionsYield
Stage #1: 3-pentenenitrile With zinc(II) chloride at 25 - 70℃; for 1.08333h;
Stage #2: hydrogen cyanide at 70℃; for 2.5h; Product distribution / selectivity;
Stage #1: 3-pentenenitrile With zinc(II) chloride; C42H40O4P2; Ni(cod)2 at 25 - 40℃; for 1.08333h;
Stage #2: hydrogen cyanide at 40℃; for 1.46667h; Product distribution / selectivity;
Stage #1: 3-pentenenitrile With zinc(II) chloride; C44H44O4P2; Ni(cod)2 at 25 - 40℃; for 1.08333h;
Stage #2: hydrogen cyanide at 40℃; for 1.33333h; Product distribution / selectivity;
Stage #1: 3-pentenenitrile With zinc(II) chloride; C46H48O4P2; Ni(cod)2 at 25 - 40℃; for 1.08333h;
Stage #2: hydrogen cyanide at 40℃; for 1.36667h; Product distribution / selectivity;
Stage #1: 3-pentenenitrile With zinc(II) chloride; C36H26O4P2; Ni(cod)2 at 25 - 70℃; for 1.08333h;
Stage #2: hydrogen cyanide at 70℃; for 1h; Product distribution / selectivity;
3-pentenenitrile
4635-87-4

3-pentenenitrile

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

C

alpha-ethylsuccinonitrile
17611-82-4

alpha-ethylsuccinonitrile

Conditions
ConditionsYield
bis(1,5-cyclooctadiene)nickel (0); C68H92O6P2S; indium(III) trifluoroacetate at 70℃; for 3h; Conversion of starting material;
bis(1,5-cyclooctadiene)nickel (0); C56H68O12P2S; zinc(II) chloride at 70℃; for 3h; Conversion of starting material;
bis(1,5-cyclooctadiene)nickel (0); C68H68O8P2S; zinc(II) chloride at 70℃; for 3h; Conversion of starting material;
2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

2-methylglutaric acid
18069-17-5

2-methylglutaric acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 90℃; for 16h; Reagent/catalyst; Temperature; Inert atmosphere;96%
With hydrogenchloride
acid hydrolysis;
With sulfuric acid; water at 105 - 125℃; for 8.42h; Inert atmosphere;
2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

4-cyanopentanoic acid
23886-52-4

4-cyanopentanoic acid

Conditions
ConditionsYield
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 96h; pH=7.3;91%
With glycerol for 72h; culture of Fusarium merismoides TG-1; Yield given;
With hydrogenchloride 1) microbial hydrolysis by Acidovorax facilis 72W, ATCC 55746; pH 7.0 (potassium phosphate buffer), 25 deg C, 21.5 h; 2) pH 2.5; Yield given. Multistep reaction;
2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

3-methylpiperidinehydrochloride
58531-29-6

3-methylpiperidinehydrochloride

Conditions
ConditionsYield
Stage #1: 2-methylglutaronitrile With C46H178O41Si42; titanium(IV)isopropoxide In toluene at 100℃; for 24h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In toluene at 20℃; for 4h; Inert atmosphere; chemoselective reaction;
91%
2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

1,12-dodecanedioic acid
693-23-2

1,12-dodecanedioic acid

A

3-methyl-piperidine-2,6-dione
29553-51-3

3-methyl-piperidine-2,6-dione

B

1,12-dodecanedinitrile
4543-66-2

1,12-dodecanedinitrile

Conditions
ConditionsYield
With aluminum (III) chloride at 200℃; for 5h;A 88%
B 81%
2-methylglutaronitrile
4553-62-2

2-methylglutaronitrile

2-methylglutaronitrile-d3

2-methylglutaronitrile-d3

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; water-d2 at 70℃; for 24h; Inert atmosphere;86%

Methylglutaronitrile Chemical Properties

Empirical Formula: C6H8N2
Molecular Weight: 108.1411 g/mol
EINECS: 224-923-5 
Index of Refraction: 1.429
Density: 0.942 g/cm3
Flash Point: 137.7 °C
Enthalpy of Vaporization: 49.82 kJ/mol
Boiling Point: 260.5 °C at 760 mmHg
Vapour Pressure: 0.0122 mmHg at 25 °C
Melting point: -45 °C(lit.)
Solubility: Water soluble
Appearance: Amber liquid
Structure of Methylglutaronitrile (CAS NO.4553-62-2):
             
Product Categories: Cyanides/Nitriles;Nitrogen Compounds
 

Methylglutaronitrile Toxicity Data With Reference

1.    

mmo-sat 1 mg/plate

    EMMUEG    Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1.
2.    

ivn-mus LD50:56 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02814 .

Methylglutaronitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Methylglutaronitrile Safety Profile

Poison by intravenous route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN. See also NITRILES.
Hazard Codes of Methylglutaronitrile (CAS NO.4553-62-2): HarmfulXn
Risk Statements: 20/21/22
 R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37 
S36/37:Wear suitable protective clothing and gloves.

Methylglutaronitrile Specification

 Methylglutaronitrile ,its cas register number is 4553-62-2. It also can be called Pentanedinitrile, 2-methyl- ; Pentanedinitrile, methyl- ; Glutaronitrile, methyl- ; and 2-methylpentanedinitrile . Methylglutaronitrile (CAS NO.4553-62-2) may polymerize in the presence of metals and some metal compounds. It is readily absorbed through the skin and is combustible.