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MALONONITRILE
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Name

MALONONITRILE

 EINECS 203-703-2
CAS No. 109-77-3 Density 1.049 g/cm3
PSA 47.58000 LogP 0.42366
Solubility 13.3 g/100 mL (20 °C) in water Melting Point 30-32 °C(lit.)
Formula C3H2N2 Boiling Point 218.499 °C at 760 mmHg
Molecular Weight 66.0623 Flash Point 112.222 °C
Transport Information UN 2647 6.1/PG 2 Appearance white crystalline powder
Safety 23-27-45-60-61 Risk Codes 23/24/25-50/53
Molecular Structure Molecular Structure of 109-77-3 (Malononitrile) Hazard Symbols ToxicT,DangerousN
Synonyms

Methylene cyanide;dicyanomethane;Propanedinitrile;Methane, dicyano-;Malononitrile (nominals);Malonodinitrile;Malonsaeuredinitril;Cyanoacetonitrile;Malonic acid dinitrile;Methylenedinitrile;Nitril kyseliny malonove;dicyanmethane;Malononitrile (Malonitrile);Malonic Dinitrile;DWUMETYLOSULFOTLENKU (POLISH);NITRIL KYSELINY MALONOVE (CZECH);RCRA WASTE NUMBER U149;Usaf a-4600;

Article Data 74

MALONONITRILE Synthetic route

123506-40-1

6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

2700-22-3

Benzylidenemalononitrile

A

35221-08-0

1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B

1867-37-4

Benzylmalononitrile

C

109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
123506-40-1

6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

709-79-5

2-cyano-3-phenylacrylamide

A

35221-08-0

1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B

1867-37-4

Benzylmalononitrile

C

109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
123506-40-1

6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

2025-40-3

ethyl benzylidenecyanoacetate

A

35221-08-0

1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B

1867-37-4

Benzylmalononitrile

C

109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
773837-37-9

sodium cyanide

74-95-3

1,2-dibromomethane

109-77-3

malononitrile

Conditions
ConditionsYield
With sodium iodide In dimethyl sulfoxide at 150℃; for 15h; Temperature; Sealed tube; Inert atmosphere;95.14%

potassium cyanide

74-95-3

1,2-dibromomethane

109-77-3

malononitrile

Conditions
ConditionsYield
With potassium iodide at 160℃; for 8h; Sealed tube; Inert atmosphere;95.01%
55042-38-1

3-(Chloromethyl)-2-benzoxazolinethione

151-50-8

potassium cyanide

A

71528-27-3

3-<(2-Benzoxazolyl)thiomethyl>-2(3H)-benzoxazolethione

B

109-77-3

malononitrile

Conditions
ConditionsYield
In acetone for 24h; Product distribution; Mechanism; Heating;A 95%
B n/a
107-91-5

cyanoacetic acid amide

109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine; phosgene In 1,2-dichloro-ethane at 75℃; for 15h; Solvent; Temperature; Reagent/catalyst;94%
With phosgene; trichlorophosphate at 70 - 73℃; for 5 - 7h; Temperature;93.59%
With pyridine; trichlorophosphate In water76%
75-44-5

phosgene

107-91-5

cyanoacetic acid amide

109-77-3

malononitrile

Conditions
ConditionsYield
With pyridine In 1,2-dichloro-ethane at 75℃; for 15h; Reagent/catalyst; Solvent; Temperature;94%
41526-42-5

3-chloromethyl-3H-benzothiazole-2-thione

151-50-8

potassium cyanide

A

77860-11-8

3-<(2-Benzothiazolyl)thiomethyl>-2(3H)-benzothiazolethione

B

109-77-3

malononitrile

Conditions
ConditionsYield
In acetone for 24h; Product distribution; Mechanism; Heating;A 92%
B n/a

potassium cyanide

75-09-2

dichloromethane

109-77-3

malononitrile

Conditions
ConditionsYield
With potassium iodide at 155℃; for 12h; Sealed tube; Inert atmosphere;91.04%

MALONONITRILE Chemical Properties

Malononitrile(109-77-3) is a nitrile and it is also called propanedinitrile with formula CH2(CN)2.  Malononitrile(109-77-3)'s Pka in water is 11, which is relatively acidic. malononitrile(109-77-3) is used as a suitable starting material for the Gewald reaction, in related chemistry. In Gewald reaction, a 2-aminothiophenethe is produced by nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base.

Product Name:Malononitrile
CAS No:109-77-3
Synonyms:AKOS BBS-00004370;METHYLENE DICYANIDE;METHYLENE CYANIDE;MALONODINITRILE;MALONITRILE;MALONONITRILE;MALONIC ACID DINITRILE;MDN
Molecular Formula:C3H2N2
Formula Weight:66.06
Density:1.049 g/mL at 25 °C(lit.)
Melting Point:30-32 °C(lit.)
Boiling Point:220 °C(lit.)
Refractive Index:1.4150
Flash Point:234 °F
Molecular Structure:

MALONONITRILE Uses

1. Malononitrile is used in the Knoevenagel condensation, such as CS gas' preparation.

2. malononitrile is used as a suitable starting material for the Gewald reaction in related chemistry. In Gewald reaction, the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene.

 

MALONONITRILE Toxicity Data With Reference

1.   

eye-rbt 5 mg/24H SEV

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,899.
2.   

orl-rat LD50:60,800 μg/kg

   28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,158.
3.   

skn-rat LD50:350 mg/kg

   MEPAAX    Medycyna Pracy. Industrial Medicine. 27 (1976),1.
4.   

LD50:20,550 μg/kg

   MEPAAX    Medycyna Pracy. Industrial Medicine. 27 (1976),1.
5.   

scu-rat LD50:31,500 μg/kg

   . 27 (1976),1.
   

orl-mus LD50:19 mg/kg

   KHZDAN    Khigiena i Zdraveopazvane. 9 (1966),50.
7.   

scu-rat LDLo:7 mg/kg

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 3 (1897),77.
8.   

ipr-mus LD50:13 mg/kg

   NATUAS    Nature. 228 (1970),1315.
   

LDLo:8 mg/kg

   AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 3 (1897),77.
10.   

ivn-mus

   

MALONONITRILE Consensus Reports

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

MALONONITRILE Safety Profile

Poison by ingestion, skin contact, subcutaneous, intravenous, and intraperitoneal routes. A severe eye irritant. Combustible when exposed to heat or flame. Polymerizes violently when heated to 130°C or on contact with strong base. May spontaneously explode when stored at 70–80°C. To fight fire, use water, fog, spray, foam. When heated to decomposition it emits toxic fumes of NOx and CN−.

Hazard Codes  T,N
Risk Statements  23/24/25-50/53
Safety Statements  23-27-45-60-61
RIDADR  UN 2647 6.1/PG 2
WGK Germany  3
RTECS  OO3150000
F  8
HazardClass  6.1
PackingGroup  II

MALONONITRILE Standards and Recommendations

NIOSH REL: (Nitriles) TWA 8 mg/m3
DOT Classification:  6.1; Label: Poison
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