4-bromovalero-nitrile
tetra-n-butylammonium cyanide
2-methylglutaronitrile
Conditions | Yield |
---|---|
With copper(l) iodide In acetonitrile at 20℃; for 24h; Inert atmosphere; UV-irradiation; | 82% |
Conditions | Yield |
---|---|
With dicobalt octacarbonyl; benzene at 130℃; |
1,3-dichlorobutane
sodium cyanide
A
4-chloro-valeronitrile
B
2-methylglutaronitrile
Conditions | Yield |
---|---|
With 2-methoxy-ethanol at 160℃; unter Druck; | |
With 2-methoxy-ethanol at 159 - 163℃; under 1765.2 - 2059.4 Torr; |
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With ethanol |
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide |
Conditions | Yield |
---|---|
With dicobalt octacarbonyl; benzene at 130℃; |
2-Methyl-glutaconsaeuredinitril
2-methylglutaronitrile
Conditions | Yield |
---|---|
palladium on activated charcoal (hydrogenation); |
methanol
carbon monoxide
acrylonitrile
A
2-methylglutaronitrile
B
4,4-dimethoxybutanenitrile
C
propiononitrile
Conditions | Yield |
---|---|
With dicobalt octacarbonyl; hydrogen In methanol at 100℃; under 129287 Torr; for 8h; Product distribution; Mechanism; var. catalysts, time and temp.; |
carbon monoxide
acrylonitrile
cyclohexanol
A
2-methylglutaronitrile
B
3-Cyano-propionic acid cyclohexyl ester
C
Cyano-methyl-acetic acid cyclohexyl ester
D
2,4-dicyano-2-methylbutanoic acid cyclohexyl ester
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Rate constant; Mechanism; electrochemical hydrodimerization; |
sulfuric acid
dihydrogen peroxide
propiononitrile
A
meso-2,3-dimethyl-succinonitrile
B
hexanedinitrile
C
2-methylglutaronitrile
Conditions | Yield |
---|---|
at 28℃; |
2-methylglutaronitrile
Conditions | Yield |
---|---|
With pyridine; copper at 110℃; |
1,3-dichlorobutane
sodium cyanide
A
4-chloro-valeronitrile
B
2-methylglutaronitrile
Conditions | Yield |
---|---|
at 159 - 163℃; unter Druck; |
hydrogen cyanide
4-Pentenenitrile
A
hexanedinitrile
B
2-methylglutaronitrile
C
alpha-ethylsuccinonitrile
Conditions | Yield |
---|---|
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
2-hydroxy-2-methylpropanenitrile
A
hexanedinitrile
B
2-methylglutaronitrile
C
alpha-ethylsuccinonitrile
Conditions | Yield |
---|---|
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
cis-2-pentenenitrile
A
hexanedinitrile
B
2-methylglutaronitrile
C
alpha-ethylsuccinonitrile
Conditions | Yield |
---|---|
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
2-methylglutaronitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 500 °C 2: Pd-C / (hydrogenation) View Scheme |
hydrogen cyanide
cis-2-pentenenitrile
2-pentenenitrile
3-Pentenenitrile
tiglonitrile
4-Pentenenitrile
(Z)-pent-2-enenitrile
A
pentanonitrile
B
hexanedinitrile
C
2-methylglutaronitrile
D
4-ethenylcyclohexene
Conditions | Yield |
---|---|
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
hydrogen cyanide
hexanedinitrile
buta-1,3-diene
A
cis-2-pentenenitrile
B
2-pentenenitrile
C
3-Pentenenitrile
D
(Z)-2-methyl-2-butenenitrile
E
tiglonitrile
F
4-Pentenenitrile
G
2-METHYL-3-BUTENENITRILE
H
2-methylglutaronitrile
I
4-ethenylcyclohexene
J
(Z)-pent-2-enenitrile
Conditions | Yield |
---|---|
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
hydrogen cyanide
buta-1,3-diene
A
1-butylene
B
cis-2-pentenenitrile
C
2-pentenenitrile
D
3-Pentenenitrile
E
(Z)-2-methyl-2-butenenitrile
F
tiglonitrile
G
4-Pentenenitrile
H
2-METHYL-3-BUTENENITRILE
I
2-methylglutaronitrile
J
4-ethenylcyclohexene
K
(Z)-pent-2-enenitrile
Conditions | Yield |
---|---|
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
hydrogen cyanide
buta-1,3-diene
A
1-butylene
B
cis-2-pentenenitrile
C
2-pentenenitrile
D
3-Pentenenitrile
E
(Z)-2-methyl-2-butenenitrile
F
tiglonitrile
G
4-Pentenenitrile
H
2-METHYL-3-BUTENENITRILE
I
2-methylglutaronitrile
J
(Z)-pent-2-enenitrile
Conditions | Yield |
---|---|
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
hydrogen cyanide
buta-1,3-diene
A
cis-2-pentenenitrile
B
2-pentenenitrile
C
3-Pentenenitrile
D
(Z)-2-methyl-2-butenenitrile
E
tiglonitrile
F
4-Pentenenitrile
G
2-METHYL-3-BUTENENITRILE
H
2-methylglutaronitrile
I
4-ethenylcyclohexene
J
(Z)-pent-2-enenitrile
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
2-hydroxy-2-methylpropanenitrile
A
hexanedinitrile
B
2-methylglutaronitrile
C
alpha-ethylsuccinonitrile
Conditions | Yield |
---|---|
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
2-methylglutaric acid
Conditions | Yield |
---|---|
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
4-cyanopentanoic acid
Conditions | Yield |
---|---|
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
3-methylpiperidinehydrochloride
Conditions | Yield |
---|---|
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
1,12-dodecanedioic acid
A
3-methyl-piperidine-2,6-dione
B
1,12-dodecanedinitrile
Conditions | Yield |
---|---|
With aluminum (III) chloride at 200℃; for 5h; | A 88% B 81% |
2-methylglutaronitrile
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; water-d2 at 70℃; for 24h; Inert atmosphere; | 86% |
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
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 . |
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
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): Xn
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 ,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.
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