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109-77-3

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Identification

Name
Malononitrile
CAS
109-77-3
Synonyms
AKOS BBS-00004370
CYANOACETONITRILE
DICYANOMETHANE
MALONIC ACID DINITRILE
MALONITRILE
MALONODINITRILE
MALONONITRILE
MDN
METHYLENE CYANIDE
METHYLENE DICYANIDE
PROPANEDINITRILE
CH2(CN)2
Cyanoaceticnitrile
dicyanmethane
dicyano-methan
Dwumetylosulfotlenku
icycanomethane
malonic
Malonic dinitrile
malonicdinitrile
EINECS(EC#)
203-703-2
Molecular Formula
C3H2N2
MDL Number
MFCD00001883
Molecular Weight
66.06
MOL File
109-77-3.mol

Chemical Properties

Appearance
Malononitrile is a white powder or colorless, odorless crystalline substance.
Appearance
Solidified melt
Melting point 
30-32 °C (lit.)
mp 
30-32 °C(lit.)

Boiling point 
220 °C (lit.)
bp 
220 °C(lit.)

density 
1.049 g/mL at 25 °C(lit.)

vapor pressure 
1 hPa (50 °C)
refractive index 
1.4150
Fp 
234 °F

storage temp. 
2-8°C

solubility 
133g/l
pka
11(at 25℃)
form 
Crystalline Low Melting Mass
color 
White to yellow-brown
Specific Gravity
1.049
PH
pH : 4.5
Water Solubility 
13.3 g/100 mL (20 ºC)
Usage
The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups.
Usage
Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet
Usage
Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamine, pesticides, special dyestuffs for color photography and synthetic fibres. Product Data Sheet
Detection Methods
GC
Merck 
14,5711
BRN 
773697
Exposure limits
TLV-TWA 8 mg/m3 (3 ppm) (NIOSH).
InChIKey
CUONGYYJJVDODC-UHFFFAOYSA-N
CAS DataBase Reference
109-77-3(CAS DataBase Reference)
NIST Chemistry Reference
Malononitrile(109-77-3)
EPA Substance Registry System
109-77-3(EPA Substance)

Safety Data

Hazard Codes 
T,N
Risk Statements 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
Safety Statements 
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S27:Take off immediately all contaminated clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
RIDADR 
UN 2647 6.1/PG 2

WGK Germany 
3

RTECS 
OO3150000


8
Autoignition Temperature
365 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29269090
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-. See also NITRILES.
Hazardous Substances Data
109-77-3(Hazardous Substances Data)
Toxicity
LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)

Raw materials And Preparation Products

Raw materials
Phosphorus oxychloride-->Sodium chloride-->Ethyl cyanoacetate-->Dichloroethane-->2-Cyanoacetamide-->Dehydrolyzing agent-->Allene
Preparation Products
5-AMINO-4-ISOXAZOLECARBONITRILE-->5-(AMINOMETHYL)PYRIMIDIN-4-AMINE-->1,4,5,8-Naphthalenetetracarboxylic acid-->2-AMINO-3-CYANO-4-CHLORO-5-FORMYLTHIOPHENE-->3-CYANO-7-ETHOXYCOUMARIN-->4-AMINOPYRIMIDINE-5-CARBOXAMIDE-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE-->5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE-->2,4,6-Triaminopyrimidine-->3-CYANO-7-METHOXYCOUMARIN-->Azimsulfuron-->4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE-->5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER-->2-Amino-3-cyanopyridine-->2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE-->2-AMINO-3,5-DICYANOPYRIDINE-->2,4-DIAMINOPYRIMIDINE-5-CARBOXYLIC ACID-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE-->2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE-->4-Amino-6-methylpyrimidine-5-carbonitrile ,97%-->2-AMINO-3-CYANO-4-METHYL-5-CARBMETHOXY THIOPHENE-->2,4-DIAMINOPYRIMIDINE-5-CARBONITRILE-->2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE-->2-Aminonicotinic acid-->Levosimendan-->4-AMINO-1,2,5-OXADIAZOLE-3-CARBONITRILE-->2-AMINO-6-METHYL-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBONITRILE-->5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE-->2-AMINO-4-METHYL-QUINOLINE-3-CARBONITRILE-->[2-[4-(dihexylamino)-2-methylbenzylidene]benzo[b]thien-3(2H)-ylidene]malononitrile S,S-dioxide -->4,6-Dimethyl-2-hydroxypyridine-->2,4,6-TRIAMINO-5-NITROPYRIMIDINE-->4,6-DIAMINO-2-MERCAPTOPYRIMIDINE-->3,5-Difluorophenylacetic acid-->4-AMINOPYRIMIDINE-5-CARBONITRILE-->4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE-->2-AMINO-6-CHLORO-3,5-DICYANOPYRIDINE-->Solvent Red 197

Hazard Information

General Description
A white-colored crystalline solid. Denser than water and soluble in water. Toxic by ingestion and may severely irritate skin and eyes. May polymerize violently if exposed to temperatures above 266°F. Used to make other chemicals.
Reactivity Profile
MALONONITRILE(109-77-3) is a white, low-melting powder (m. p. 30.5° C), toxic, combustible. Violent polymerization on contact with strong bases (sodium hydroxide, potassium hydroxide) or when heated above 130° C. When stored at 70-80° C for 2 months, spontaneous explosion (decomposition) occurred [Bretherick, 5th ed., 1995, p. 394].
Air & Water Reactions
Soluble in water.
Hazard
Toxic by ingestion and inhalation.
Health Hazard
Metabolized by body to cyanide and thiocyanate; effects of inhalation of toxic fumes will be related to cyanide. Causes brain and heart damage related to lack of cellular oxygen. It is classified as extremely toxic. Probable oral lethal dose for humans is 5-50 mg/kg, or between 7 drops and 1 teaspoonful, for a 70 kg (150 lb.) person.
Potential Exposure
Malononitrile is used in organic synthesis; as a lubricating oil additive; for thiamine synthesis; for pteridine-type anticancer agent synthesis; and in the synthesis of photosensitizers, acrylic fibers, and dyestuffs. It has also been used in the treatment of various forms of mental illness. It has been used as a leaching agent for gold
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and i
Fire Hazard
When heated to decomposition, malononitrile emits highly toxic fumes (cyanide). May polymerize violently on prolonged heating. Avoid heat. Hazardous polymerization may occur, at prolonged heating at 266F or contact with strong bases at lower temperatures.
Shipping
UN2647 Malononitrile, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
Incompatibilities
Incompatible with strong bases. May polymerize violently on prolonged heating @ 129C, or in contact with strong bases at lower temperatures. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Description
Malonitrile is an aliphatic nitrile. It can release cyanide through either chemical or biological transformation. Malonitrile was used decades ago for treating certain forms of mental illness.
Chemical Properties
Malononitrile is a white powder or colorless, odorless crystalline substance.
Waste Disposal
Generators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal
Chemical Properties
Solidified melt
Chemical Properties
Malononitrile may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.
Uses
The chemical properties of malononitrile are determined by the nucleophilicity of the malononitrile anion, formed by deprotonation with relatively weak bases and by the two electrophilic cyano groups.
Uses
Malononitrile is used in organic synthesis.
Uses
Malononitrile is an important building block for the syntheses of pharmaceuticals (e.g. triamterene, adenine and methotrexate), thiamin (vitamin B1), pesticides dyestuffs for color photography and synthetic fibers (e.g. vinylidene cyanide). Product Data Sheet
Uses
In organic synthesis.
Definition
ChEBI: A dinitrile that is methane subtituted by two cyano groups.
Production Methods
Malononitrile is prepared by continuous introduction of preheated acetonitrile and cyanogen chloride into a tube reactor until the reaction mixture reaches a temperature of approximately 780°C.
Industrial uses
Malononitrile is used primarily as an intermediate in the synthesis of drugs and vitamins (thiamine). It has also been employed in the manufacture of photosensitizes, acrylic fibers and dyestuffs and as an oil-soluble polar additive in lubricating oil.
Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.
Environmental Fate
When heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.
Metabolism
The in vitro metabolsim of malononitrile has been described by Stern et al. In the presence of thiosulphate, brain, liver and kidney slices metabolized malononitrile to thiocyanate. The formation of thiocyanate from malononitrile and thiosulphate was greatest in the presence of liver slices, lowest in brain, and intermediate with kidney slices. The liver enzyme system was saturated at a concentration of 3.3 mM malononitrile and a pH optimum of 7.0. This enzyme system was inhibited by cysteine and glutathione and inactivated by boiling. Stern et al indicated that thiosulphate increased cyanide and thiocyanate formed from malononitrile in tissue slices.
Purification Methods
Crystallise the nitrile from water, EtOH, *benzene or chloroform. Distil it in a vacuum from, and store over, P2O5. [Bernasconi et al. J Am Chem Soc 107 7692 1985, Gratenhuis J Am Chem Soc 109 8044 1987, Beilstein 2 IV 1892.]
Toxicity evaluation
The acute toxicity of malonitrile and related alkyl nitriles is thought to be due to release of cyanide through metabolism of the parent compound. Signs of acute malonitrile intoxication including dyspnea, ataxia, and convulsions are similar to those noted with acute cyanide intoxication. The onset and duration indicate that these nitriles require metabolism to elicit toxicity. Cyanide and thiocyanate have both been found in urine and blood after malonitrile exposure.

Material Safety Data Sheet(MSDS)

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