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Malononitrile

Malononitrile
Malononitrile structure
CAS No.
109-77-3
Chemical Name:
Malononitrile
Synonyms
MDN;malonic;CH2(CN)2;usafkf-19;usafa-4600;USAF KF-19;USAF a-4600;MALONITRILE;MALONONITRILE;dicyanmethane
CBNumber:
CB2259712
Molecular Formula:
C3H2N2
Formula Weight:
66.06
MOL File:
109-77-3.mol

Malononitrile 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
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)
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
Propanedinitrile(109-77-3)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS06,GHS09,GHS05,GHS07
Signal word  Danger
Hazard statements  H400-H301-H311-H331-H410-H300-H311+H331-H315-H317-H318
Precautionary statements  P264-P270-P271-P272-P301+P310+P330-P302+P352+P312+P361+P364-P304+P340+P311-P305+P351+P338+P310-P391-P403+P233-P405-P280h-P301+P310a-P304+P340-P501a-P261-P273-P280-P301+P310-P311-P501
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
8
Autoignition Temperature 365 °C
TSCA  Yes
HazardClass  6.1
PackingGroup  II
HS Code  29269090
Toxicity LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)

Malononitrile price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 690414 Malononitrile Lonza quality, ≥99.0% (calculated, GC, KF) 109-77-3 1kg $134 2018-11-13 Buy
Sigma-Aldrich 690414 Malononitrile Lonza quality, ≥99.0% (calculated, GC, KF) 109-77-3 10kg $1360 2018-11-13 Buy
TCI Chemical M0033 Malononitrile >98.0%(GC)(T) 109-77-3 25g $17 2018-11-22 Buy
TCI Chemical M0033 Malononitrile >98.0%(GC)(T) 109-77-3 100g $40 2018-11-22 Buy
Alfa Aesar A15046 Malononitrile, 99% 109-77-3 500g $82.1 2018-11-13 Buy

Malononitrile Chemical Properties,Uses,Production

Chemical Properties

Solidified melt

Chemical Properties

Malononitrile is a white powder or colorless, odorless crystalline substance.

Chemical Properties

Malononitrile may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.

Uses

Malononitrile is used in organic synthesis.

Uses

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

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

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.

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.

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.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Malononitrile 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].

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.

Health Hazard

In 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 Hazard

Malononitrile 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 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.

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.

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.

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

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.

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

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.]

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.

Waste Disposal

Generators 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 materials

Preparation Products

1,4,5,8-Naphthalenetetracarboxylic acid 2-Aminonicotinic acid 2-Amino-3-cyanopyridine 2-AMINO-6-CHLORO-3,5-DICYANOPYRIDINE 4-AMINO-1,2,5-OXADIAZOLE-3-CARBONITRILE 2-Chloro-4,6-dimethoxypyrimidine 5-AMINO-4-CYANO-3-METHYL-THIOPHENE-2-CARBOXYLIC ACID ETHYL ESTER 2-AMINO-3-CYANO-4-METHYL-5-CARBMETHOXY THIOPHENE 2,4-DIAMINOPYRIMIDINE-5-CARBOXYLIC ACID 2-AMINO-3,5-DICYANOPYRIDINE 3-CYANO-7-ETHOXYCOUMARIN 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBONITRILE 2-AMINO-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBONITRILE 2-AMINO-3-CYANO-4-CHLORO-5-FORMYLTHIOPHENE 2-AMINO-4-METHYL-QUINOLINE-3-CARBONITRILE 2,4,6-TRIAMINO-5-NITROPYRIMIDINE 2-AMINO-4,5-DIMETHYL-THIOPHENE-3-CARBONITRILE 2,4-DIAMINOPYRIMIDINE-5-CARBONITRILE 2,4,6-Triaminopyrimidine 3,5-Difluorophenylacetic acid 5-(AMINOMETHYL)PYRIMIDIN-4-AMINE [2-[4-(dihexylamino)-2-methylbenzylidene]benzo[b]thien-3(2H)-ylidene]malononitrile S,S-dioxide 4-AMINO-2-(METHYLTHIO)PYRIMIDINE-5-CARBONITRILE 2-OXO-6-PHENYL-4-(TRIFLUOROMETHYL)-1,2-DIHYDRO-3-PYRIDINECARBONITRILE Levosimendan 4,6-DIAMINO-2-MERCAPTOPYRIMIDINE 3-CYANO-7-METHOXYCOUMARIN 5-AMINO-4-ISOXAZOLECARBONITRILE 2-AMINO-6-METHYL-4,5,6,7-TETRAHYDROTHIENO[2,3-C]PYRIDINE-3-CARBONITRILE 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXAMIDE 4-AMINOPYRIMIDINE-5-CARBONITRILE 4,6-Dimethyl-2-hydroxypyridine 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE 4-Amino-6-methylpyrimidine-5-carbonitrile ,97% 4-AMINOPYRIMIDINE-5-CARBOXAMIDE Azimsulfuron 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE Solvent Red 197

Malononitrile Suppliers

Global( 279)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21671 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sale@mainchem.com CHINA 32447 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30001 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23980 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 sales@jushengtech.com CHINA 28236 58
Haihang Industry Co.,Ltd
86-531-88032799
+86 531 8582 1093 export@haihangchem.com CHINA 8918 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930501651
whatsapp: +8619930501651 breeduan@crovellbio.com CHINA 2292 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6372 58
Hubei xin bonus chemical co. LTD
86-13657291602
027-59338440 sales@guangaobio.com CHINA 23049 58

View Lastest Price from Malononitrile manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-23 Malononitrile
109-77-3
US $1.00 / kg 1kg 95%-99% as request career henan chemical co

Malononitrile Spectrum


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