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Cas Database

109-77-3

109-77-3

Identification

  • Product Name:Malononitrile

  • CAS Number: 109-77-3

  • EINECS:203-703-2

  • Molecular Weight:66.0623

  • Molecular Formula: C3H2N2

  • HS Code:29269090

  • Mol File:109-77-3.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT,DangerousN

  • Hazard Codes:T,N

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH311 Toxic in contact with skin H331 Toxic if inhaled H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. Half-upright position. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give one or two glasses of water to drink. Refer for medical attention . 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. (EPA, 1998) Rapid support of respiration and circulation is essential to successful treatment of cyanide intoxication. Massive cyanide overdoses have survived with only good supportive care. Immediate attention should be directed toward assisted ventilation, administration of 100% oxygen, insertion of intravenous lines, and institution of cardiac monitoring. Obtain an arterial blood gas immediately and correct any severe metabolic acidosis (pH below 7.15). Oxygen (100%) should be used routinely in moderate or severely symptomatic patients even in the presence of a normal pO2, since 100% O2 increases O2 delivery, may reactivate cyanide-inhibited mitochondrial enzymes, and potentiates the effect of thiosulfate. Avoid mouth to mouth resuscitation during CPR in order to prevent self poisoning. /Cyanides/

  • Fire-fighting measures: Suitable extinguishing media To fight fire, use water, fog, spray, foam. 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. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum spilled material with specialist equipment. If appropriate, moisten first to prevent dusting. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Cool. Separated from strong bases and food and feedstuffs. Well closed. Keep in a well-ventilated room.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted avg: 3 ppm (8 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Malononitrile
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  • Price:$ 55
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Malononitrile >98.0%(GC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Malononitrile >98.0%(GC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Malononitrile >98.0%(GC)(T)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Malononitrile Lonza quality, ≥99.0% (calculated, GC, KF)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Malononitrile for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Malononitrile Lonza quality, ≥99.0% (calculated, GC, KF)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Malononitrile for synthesis. CAS 109-77-3, EC Number 203-703-2, chemical formula NCCH CN., for synthesis
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Malononitrile Lonza quality, ≥99.0% (calculated, GC, KF)
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 45 Articles be found

-

Ardis et al.

, p. 1305 (1950)

-

Infrared Spectrum of Matrix-Isolated Hexamethylenetetramine in Ar and H2O at Cryogenic Temperatures

Bernstein, Max P.,Sanford, Scott A.,Allamandola, Louis J.,Chang, Sherwood

, p. 12206 - 12210 (1994)

The infrared spectra of hexamethylenetetramine (HMT) isolated in an argon matrix at 12 K, frozen in H2O at temperatures from 12 to 200 K, and as a pure solid, are reported.The results of ultraviolet photolysis of matrix-isolated HMT and HMT frozen in H2O ice are also presented, and implications for infrared astronomy and astrochemistry are discussed.Furthermore, a simple technique for incorporating large nonvolatile organic molecules into a matrix is described.

Cyanocarbon Acids: Direct Evidence That Their Ionization Is Not an Encounter-Controlled Process and Rationalization of the Unusual Solvent Isotope Effects

Hojatti, M.,Kresge, A. J.,Wang, W.-H.

, p. 4023 - 4028 (1987)

The rate of exchange of the acidic hydrogen of tert-butylmalononitrile was examined by using as a tracer, and the process was found not to be inhibited by hydronium ions in dilute aqueous hydrochloric acid solutions.This rules out the Swain-Grunwald mechanism for this reaction under these conditions.The bromination of malonitrile was investigated under conditions where reprotonation of the dicyanomethyl carbanion and its reaction with bromine occur at comparable rates, and the bromination reaction was found to have a specific rate twice that for reprotonation.Reprotonation therefore cannot be a diffusion-controlled process, and malonitrile is not a "normal" acid.The unusually large solvent kinetic isotope effects found for these cyanocarbon acid ionization reactions are explained by postulating that the transferring hydrogen and its positive charge are becoming associated with a solvent cluster rather than with a single water molecule.The thermodynamic acidity constant of malonitrile was determined to be 11.41 in aqueous solution at 25 deg C.

Hydrolysis study of fluoroorganic and cyano-based ionic liquid anions - Consequences for operational safety and environmental stability

Steudte, Stephanie,Neumann, Jennifer,Bottin-Weber, Ulrike,Diedenhofen, Michael,Arning, Juergen,Stepnowski, Piotr,Stolte, Stefan

, p. 2474 - 2483 (2012)

The hydrolytic stability of ionic liquid anions is a key property with regard to their technical applicability and environmental stability. From a technical point of view hydrolytic processes may lead to reduced durability, diminished technical performance and reduced operational safety in that corrosive and/or toxic hydrolysis products are formed. On the other hand, susceptibility to hydrolytic processes is advantageous where environmental stability and persistency are concerned, since hydrolysis is the most important abiotic degradation pathway in the environment. We investigated the hydrolytic stability of the most common ionic liquid anions, dicyanimide [N(CN) 2]-, tricyanmethanide [C(CN)3]-, tetracyanidoboranate [B(CN)4]-, bis(trifluoromethylsulphonyl)imide [(CF3SO2) 2N]-, trifluorotris(pentafluoroethyl)phosphate [(C 2F5)3PF3]- and 1,1,2,2-tetrafluoroethanesulphonic acid [H(C2F4)SO 3]-, as a function of pH (1, 7, 9 and 13) and temperature. The results show that there was no difference in hydrolytic stability as recorded for 1-ethyl-3-methylimidazolium (IM12) or for the alkali cations. All the anions were stable under neutral and slightly basic conditions (half-lives at 25 °C ?1 year). In strongly acidic and basic solutions, however, B(CN)4-, (CF3SO2)2N -, (C2F5)3PF3- and H(C2F4)SO3- were hydrolytically stable, whereas N(CN)2- and C(CN)3- were not. The kinetics of hydrolysis were recorded and Arrhenius plots were generated for the latter two anions. In addition, their hydrolysis pathways and the resulting products were identified via mass spectrometry. The cytotoxicity of hydrolysed IL solutions towards the mammalian cell line IPC-81 and the identified hydrolysis products (pure compounds) was investigated for a first estimate of their toxicological properties.

Preparation method of malononitrile and malononitrile prepared by preparation method

-

Paragraph 0056-0103, (2021/05/01)

The invention relates to the technical field of chemical synthesis methods, particularly to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation method comprises the following steps: mixing cyanoacetamide, a catalyst and a solvent, heating, refluxing, and introducing phosgene to synthesize malononitrile, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5-10.5), the solvent is any one of dichloromethane, dichloroethane or methylbenzene, and the catalyst is any one or more of diethylamine, N,N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene, wherein the required raw materials are cheap and easy to obtain, the synthetic reaction steps are few, harsh conditions are avoided, the operation is simple, stable and good in controllability, and the yield of the prepared malononitrile can reach 93% or above and is far higher than that of malononitrile obtained through other process schemes; and the preparation method is low in three-waste treatment cost, and has objective economic benefit.

Malononitrile preparation method and malononitrile prepared thereof

-

Paragraph 0056-0095; 0103, (2020/08/02)

The invention relates to the technical field of chemical synthesis methods, in particular to a malononitrile preparation method and malononitrile prepared thereof. The malononitrile preparation methodcomprises the following steps that cyanoacetamide, a catalyst and a solvent are mixed, heated, refluxed and introduced with phosgene, and malononitrile is synthesized, wherein the mass ratio of the cyanoacetamide to the catalyst to the solvent is (2.5-3.5):(0.005-0.02):(7.5 to 10.5); the solvent is any one of dichloromethane, dichloroethane or methylbenzene; and the catalyst is any one or more ofdiethylamine, N, N-dimethylformamide or pyridine. According to the invention, cyanoacetamide is adopted to synthesize malononitrile in one step under the action of phosgene; the method has the advantages of cheap and easily available required raw materials, few synthesis reaction steps, no harsh conditions, simple operation, stability and good controllability, the yield of the prepared malononitrile can reach 93% or above and is far higher than that of other process schemes, and the preparation method has the advantages of low three-waste treatment cost and objective economic benefits.

Preparation method of malononitrile

-

Paragraph 0044-0051, (2020/07/24)

The invention discloses a preparation method of an important organic synthesis raw material malononitrile, which comprises the following steps: performing a reaction on chloroacetonitrile and hydrogencyanide as raw materials in a tubular reactor, and separating the reaction product by condensation and negative pressure distillation to obtain the malononitrile. The method has the advantages of mild reaction conditions, simple separation and purification process, high product yield and purity, energy saving, environmental protection and low cost.

Synthetic method of malononitrile

-

Paragraph 0011-0030, (2020/01/08)

The invention belongs to the technical field of organic synthesis, and provides a malononitrile synthesis method. The synthetic method comprises the following steps: adding dichloromethane and sodiumcyanide into a reaction kettle at a molar ratio of (1: 1)-(3: 1), slowly adding a catalyst into the reaction kettle under stirring and heating conditions, controlling the temperature in the reaction kettle to be 90 DEG C, and carrying out thermal preservation reaction for 5-9 hours after feeding is finished; after the reaction is finished, adding deionized water into an obtained reaction product to wash an organic phase for a plurality of times, separating out the organic phase, drying the organic phase, and rectifying to obtain malononitrile; wherein the catalyst is a composition of aluminumtrichloride and tetrabutylammonium bromide. According to the method, the malononitrile product is directly synthesized by taking cheap dichloromethane as a raw material through a one-step method, theprocess route is simple, and the cost is low.

Synthesis method of malononitrile

-

Paragraph 0038-0041, (2019/02/06)

The invention discloses a synthesis method of malononitrile. Metal hydride and dihalomethane are used as an initial reactant system; under the existence of metal iodate catalysts, a dipolar aprotic solvent is used as a reaction auxiliary agent to prepare a target product of malononitrile. The method has the advantages that through the addition of the reaction auxiliary agent for reaction promotion, the malononitrile hydrolysis or alcoholysis due to polar solvents of water, alcohol and the like can be avoided; high yield and high quality of malononitrile are ensured; the malononitrile with theyield higher than 91.0 percent and the purity higher than 99.3 percent can be obtained.

Process route upstream and downstream products

Process route

5-Aminoquinoline
611-34-7,146614-41-7

5-Aminoquinoline

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
p-(N-dimethylamino benzylidene) malononitrile
2826-28-0

p-(N-dimethylamino benzylidene) malononitrile

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
In dimethylsulfoxide-d6; water-d2; at 60 ℃; Equilibrium constant;
Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

benzaldehyde
100-52-7

benzaldehyde

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
With piperidine; In water; dimethyl sulfoxide; at 20 ℃; Rate constant; Mechanism; μ = 0.5 M (KCl); relaxation time as a function of free amine concentration at various pH;
With water; acetate; In water; dimethyl sulfoxide; Equilibrium constant; with different buffers, solvent ratios, and catalysts;
With water; at 25 ℃; Rate constant; Equilibrium constant; Mechanism; pH=7.0; different pHs and buffer concentrations;
In dimethylsulfoxide-d6; water-d2; at 60 ℃; Equilibrium constant;
9-Cyano-10-methyl-10-thiaanthracene
59181-71-4

9-Cyano-10-methyl-10-thiaanthracene

ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

9-Cyano-9-methylthioxanthene
59181-21-4

9-Cyano-9-methylthioxanthene

9-Cyano-9-(dicyanomethyl)thioxanthene
59215-71-3

9-Cyano-9-(dicyanomethyl)thioxanthene

thio-xanthene-9-one
492-22-8

thio-xanthene-9-one

2,2,3,3-Tetracyanobutane
66223-43-6

2,2,3,3-Tetracyanobutane

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
In tetrahydrofuran; Mechanism;
8.5%
13%
11%
24%
120 mg
cycloheptylidene-malononitrile
10394-94-2

cycloheptylidene-malononitrile

malononitrile
109-77-3

malononitrile

cycloheptanone
502-42-1

cycloheptanone

Conditions
Conditions Yield
With borax; dipotassium hydrogenphosphate; In water; at 30 ℃; pH=7; Kinetics;
hexamethylenetetramine
100-97-0

hexamethylenetetramine

CYANAMID
420-04-2

CYANAMID

carbodiimide
151-51-9,25215-75-2

carbodiimide

malononitrile
109-77-3

malononitrile

trimethylamine
75-50-3

trimethylamine

Conditions
Conditions Yield
With water; at -173.1 ℃; for 14h; Product distribution; Irradiation; various temperatures, matrixes and products; measured by IR;
2-Methyl-1-hexen-1,1-dicarbonitril
42009-27-8

2-Methyl-1-hexen-1,1-dicarbonitril

n-hexan-2-one
591-78-6

n-hexan-2-one

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
With borax; dipotassium hydrogenphosphate; In water; at 30 ℃; pH=7; Kinetics;
4-Nitrobenzylidenemalononitrile
2700-23-4

4-Nitrobenzylidenemalononitrile

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
In dimethylsulfoxide-d6; water-d2; at 60 ℃; Equilibrium constant;
(1,2-Dimethylpropylidene)propanedinitrile
13017-52-2

(1,2-Dimethylpropylidene)propanedinitrile

3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
With borax; dipotassium hydrogenphosphate; In water; at 30 ℃; pH=7; Kinetics;
2-fluoren-9-ylidene-malononitrile
1989-32-8

2-fluoren-9-ylidene-malononitrile

9-fluorenone
486-25-9,952573-42-1

9-fluorenone

malononitrile
109-77-3

malononitrile

Conditions
Conditions Yield
With sodium hydroxide; In 1,4-dioxane; water; at 25 ℃; further nucleophil partner; molecular stacking effect on the kinetic order of the reaction;

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