Malononitrile Chemical Properties
- Melting point:30-32 °C (lit.)
- Boiling point:220 °C (lit.)
- Density 1.049 g/mL at 25 °C (lit.)
- vapor pressure 1 hPa (50 °C)
- refractive index 1.4150
- Flash point:234 °F
- storage temp. 2-8°C
- solubility 133g/l
- pka11(at 25℃)
- form Crystalline Low Melting Mass
- Specific Gravity1.049
- color White to yellow-brown
- PHpH : 4.5
- Water Solubility 13.3 g/100 mL (20 ºC)
- Merck 14,5711
- BRN 773697
- Exposure limitsTLV-TWA 8 mg/m3 (3 ppm) (NIOSH).
- CAS DataBase Reference109-77-3(CAS DataBase Reference)
- NIST Chemistry ReferenceMalononitrile(109-77-3)
- EPA Substance Registry SystemMalononitrile (109-77-3)
- 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
- Autoignition Temperature365 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29269090
- Hazardous Substances Data109-77-3(Hazardous Substances Data)
- ToxicityLD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)
Malononitrile Usage And Synthesis
- DescriptionMalonitrile 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 PropertiesMalononitrile may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.
- Chemical PropertiesSolidified melt
- Chemical PropertiesMalononitrile is a white powder or colorless, odorless crystalline substance.
- UsesIn organic synthesis.
- UsesMalononitrile 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
- UsesThe 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.
- UsesMalononitrile is used in organic synthesis.
- DefinitionChEBI: A dinitrile that is methane subtituted by two cyano groups.
- Production MethodsMalononitrile 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.
- General DescriptionA 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.
- Air & Water ReactionsSoluble in water.
- Reactivity ProfileMalononitrile 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].
- HazardToxic by ingestion and inhalation.
- Health HazardMetabolized 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.
- Health HazardIn the late 1940's, malononitrile was used experimentally in the treatment of schizophrenia and depression. Patients were given an iv infusion of 5% malononi-trile for 10-69 min. The total dose during such treatments was 1-6 mg/kg and treatments were given 2-3 times/wk. Ten to twenty min after beginning infusion, all patients experienced tachycardia. In addition, redness, nausea, vomiting, headache, shivering, muscle spasms, and numbness were reported with varying frequency.
- Health HazardMalononitrile is a highly toxic compound by all toxic routes. Its acute toxicity is somewhat greater than that of the aliphatic mononitriles, propionitrile, and butyronitrile. The increased toxicity may be attributed to the greater degree of reactivity in the molecule arising from two- CN functional groups. The acute toxic symptoms in test animals have not been well documented. An intraperitoneal dose of 10 mg/kg was lethal to rats.
LD50 value, intravenous (rabbits): 28 mg/kg
LD50 value, oral (mice): 19 mg/kg
Malononitrile is an eye irritant. The irritation from 5 mg in 24 hours was severe in rabbits’ eyes. There is no report of teratogenic and carcinogenic action in animals or humans.
- Fire HazardWhen 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.
- Industrial usesMalononitrile 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
Malononitrile was used formerly in treatment of various forms of mental illness such as alteration of psychic functions and schizophrenic disorders.
- Safety ProfilePoison 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.
- Potential ExposureMalononitrile 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
- Environmental FateWhen heated to decomposition, nitriles may release cyanide. Malonitrile appears to decompose rapidly in contact with soil and sediment.
- MetabolismThe 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.
- ShippingUN2647 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
- Purification MethodsCrystallise 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 evaluationThe 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.
- IncompatibilitiesIncompatible 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.
- Waste DisposalGenerators of waste containing this contaminant (≥100 kg/mo) must conform to EPA regulations governing storage, transportation, treatment, and waste disposal
Malononitrile Preparation Products And Raw materials
- Raw materialsPhosphorus oxychlorideSodium chlorideEthyl cyanoacetateDichloroethane2-CyanoacetamideDehydrolyzing agentAllene
- Preparation Products5-AMINO-4-ISOXAZOLECARBONITRILE5-(AMINOMETHYL)PYRIMIDIN-4-AMINE1,4,5,8-Naphthalenetetracarboxylic acid2-AMINO-3-CYANO-4-CHLORO-5-FORMYLTHIOPHENE3-CYANO-7-ETHOXYCOUMARIN4-AMINOPYRIMIDINE-5-CARBOXAMIDE2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE2,4,6-Triaminopyrimidine3-CYANO-7-METHOXYCOUMARINAzimsulfuron4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER2-Amino-3-cyanopyridine2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE2-AMINO-3,5-DICYANOPYRIDINE2,4-DIAMINOPYRIMIDINE-5-CARBOXYLIC ACID2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE4-Amino-6-methylpyrimidine-5-carbonitrile ,97%2-AMINO-3-CYANO-4-METHYL-5-CARBMETHOXY THIOPHENE2,4-DIAMINOPYRIMIDINE-5-CARBONITRILE2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE2-Aminonicotinic acidLevosimendan4-AMINO-1,2,5-OXADIAZOLE-3-CARBONITRILE2-AMINO-6-METHYL-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBONITRILE5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE2-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-hydroxypyridine2,4,6-TRIAMINO-5-NITROPYRIMIDINE4,6-DIAMINO-2-MERCAPTOPYRIMIDINE3,5-Difluorophenylacetic acid4-AMINOPYRIMIDINE-5-CARBONITRILE4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE2-AMINO-6-CHLORO-3,5-DICYANOPYRIDINESolvent Red 1972-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE
- 1H-Pyrrole-3-carboxaldehyde, 5-(2-fluorophenyl)-1-(3-pyridinylsulfonyl)- 1-(5-(2-fluorophenyl)-1H-pyrrol-3-yl)-N-methylmethanamine 5-(4-fluorophenyl)-1H-pyrrole-3-carbonitrile PYRIDINE-2-SULFONIC ACID (5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl) methanol 1-methylpyridin-1-ium-4-sulfonate 1-(2-chloro-5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl)-N-methylmethanamine 2-[2-(2-Fluorophenyl)-2-oxoethyl]propanedinitrile 3-N,N-dimethylsulfamoylpyridine 3-CHLOROPYRIDINE N-OXIDE 3,5-Pyridinedisulfonyl dichloride RARECHEM AL BY 0489 N-NITROSO-DI-ISO-PROPYLAMINE 1H-Pyrrole-3-carbonitrile,5-(2-fluorophenyl)-1-(3-pyridinylsulfonyl)- Vonoprazan Impurity 24 Vonoprazan Impuirty 32 2-chloro-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde 5-(2-fluorophenyl)-N-methyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carboxamide
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