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Malononitrile

Product Name
Malononitrile
CAS No.
109-77-3
Chemical Name
Malononitrile
Synonyms
PROPANEDINITRILE;MALONITRILE;malonic;MALONODINITRILE;CH2(CN)2;MDN;DICYANOMETHANE;propanedinitrite;Malonic dinitrile;MALONIC ACID DINITRIL
CBNumber
CB2259712
Molecular Formula
C3H2N2
Formula Weight
66.06
MOL File
109-77-3.mol
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Malononitrile Property

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).
Dielectric constant
46.0
InChIKey
CUONGYYJJVDODC-UHFFFAOYSA-N
CAS DataBase Reference
109-77-3(CAS DataBase Reference)
NIST Chemistry Reference
Malononitrile(109-77-3)
EPA Substance Registry System
Malononitrile (109-77-3)
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Safety

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
Hazardous Substances Data
109-77-3(Hazardous Substances Data)
Toxicity
LD50 i.p. in mice: 12.9 mg/kg (Jones, Israel)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M1407
Product name
Malononitrile
Purity
≥99%
Packaging
5G
Price
$36.4
Updated
2024/03/01
Sigma-Aldrich
Product number
M1407
Product name
Malononitrile
Purity
≥99%
Packaging
100g
Price
$50.2
Updated
2024/03/01
Sigma-Aldrich
Product number
M1407
Product name
Malononitrile
Purity
≥99%
Packaging
500g
Price
$108
Updated
2024/03/01
Sigma-Aldrich
Product number
8.06189
Product name
Malononitrile
Purity
for synthesis
Packaging
100g
Price
$34.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.06189
Product name
Malononitrile
Purity
for synthesis
Packaging
250g
Price
$71
Updated
2024/03/01
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Malononitrile Chemical Properties,Usage,Production

Description

Malonitrile, also known as Malononitrile, is an aliphatic nitrile that can release cyanide through chemical or biological transformation. It was also used decades ago for treating certain forms of mental illness.

Chemical Properties

Malononitrile is a white powder or colorless, odorless crystalline substance. It may polymerize violently on prolonged heating at 130°C or at lower temperatures on contact with strong bases.

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

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.

Production Methods

Malononitrile can be synthesized by a continuous method where preheated acetonitrile and cyanogen chloride are introduced into a tube reactor until the reaction mixture reaches a temperature of about 780°C. Another way to prepare malononitrile is by reacting phosphorus pentachloride with cyanoacetamide, or by using phosphorus pentoxide to react with malonamide or cyanoacetamide.
DOI: 10.15227/orgsyn.010.0066

Definition

ChEBI: Malononitrile is a dinitrile that is methane substituted by two cyano groups. It is a dinitrile and an aliphatic nitrile.

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

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

Primary Irritant. Malononitrile is used in organic synthesis, as a lubricating oil additive, for thiamine synthesis, for pteridine-type anti-cancer 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 min, 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 induce vomiting. Do not make an unconscious person vomit.

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.

storage

Color Code—Blue: Health Hazard/Poison: Store in a secure poison location. Prior to working with this chemical you should be trained on its proper handling and storage. Store in a refrigerator under an inert atmosphere for prolonged storage. Keep away from strong bases. May polymerize violently on prolonged heating at 129℃ or in contact with strong bases at lower temperatures. May spontaneously explode on storing above 7080℃.

Shipping

This compound requires a shipping label of “POISONOUS/TOXIC MATERIALS.” It falls in Hazard Class 6.1 and Packing Group II.

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.

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.

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
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Malononitrile Suppliers

Shanghai Rolead Chemical Technology Co., Ltd.
Tel
021-69992220 13701886816
Fax
021-69992237
Email
roleadchem@163.com
Country
China
ProdList
4760
Advantage
50
Shanghai Kaisai Chemical Co., Ltd
Tel
021-33516722 13701817765
Fax
021-33516776
Email
kaisaichem@163.com
Country
China
ProdList
4752
Advantage
58
Baynoe Chem (Suzhou) Co., Ltd.
Tel
18934593683
Email
sales06@baynoe.com
Country
China
ProdList
708
Advantage
58
Shandong Dexin Fine Chemical Co. LTD
Tel
13475558980 13475558980
Email
644535754@qq.com
Country
China
ProdList
299
Advantage
58
Zibo Chuanggu Chemical Technology Co., Ltd.
Tel
00-15864498288 15864498288
Email
15864498288@163.cn
Country
China
ProdList
41
Advantage
58
shanghai hehua chemical co.,ltd
Tel
15121167815
Email
bangge121@sina.com
Country
China
ProdList
163
Advantage
58
Shandong Hima Supply chain Management Co., LTD
Tel
13011607593
Email
904987017@qq.com
Country
China
ProdList
130
Advantage
58
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30132
Advantage
84
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View Lastest Price from Malononitrile manufacturers

Henan Bao Enluo International TradeCo.,LTD
Product
Malononitrile 109-77-3
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-08-04
Hebei Guanlang Biotechnology Co,.LTD
Product
Malononitrile 109-77-3
Price
US $9.00/KG
Min. Order
1KG
Purity
99.9
Supply Ability
1 ton
Release date
2023-05-10
Hebei Guanlang Biotechnology Co,.LTD
Product
Malononitrile 109-77-3
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2023-05-10

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