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105-34-0

Basic Information
CAS No.: 105-34-0
Name: Methyl cyanoacetate
Article Data: 59
Cas Database
Molecular Structure:
Molecular Structure of 105-34-0 (Methyl cyanoacetate)
Formula: C4H5NO2
Molecular Weight: 99.0892
Synonyms: Acetic acid, cyano-, methyl ester;Cyanoacetic acid methyl ester;Methylcyenoecetatc;Methyl Cyanoacetate (MCA);Cyanoacetic acid, methyl ester;Methyl cyanoethanoate;Methyl 2-cyanoacetate;Usaf kf-22;Methylester kyseliny kyanoctove [Czech];
EINECS: 203-288-8
Density: 1.123 g/cm3
Melting Point: -13 °C
Boiling Point: 140.3 °C at 760 mmHg
Flash Point: 42.7 °C
Solubility: 54 g/L (20 ºC)
Appearance: clear colorless to very slighlty yellow liquid
Hazard Symbols: Xi
Risk Codes: N/A
Safety: 24/25
Transport Information: UN 3276
PSA: 50.09000
LogP: 0.07308
Synthetic route
67-56-1

methanol

372-09-8

cyanoacetic acid

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane for 1h; Ambient temperature;97%
With N-Bromosuccinimide at 70℃; for 20h;97%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 70℃; for 20h;97%
110-67-8

3-Methoxypropionitrile

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; cobalt(II) acetate In acetic acid at 130 - 190℃; under 6750.68 Torr; for 3 - 7h;
3154-54-9

methyl N-formylglycinate

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In dichloromethane at 0℃; for 1h;
67-56-1

methanol

105-56-6

ethyl 2-cyanoacetate

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
scandium tris(trifluoromethanesulfonate) at 64℃; for 8h;89%
With titanium(IV) isopropylate for 2h; Inert atmosphere; Reflux;80%
With potassium fluoride
acrylonitrile; triphenylphosphine at 25℃; for 1h;100 % Chromat.
With HZnPS-1, porous sulfonated zinc phosphonate material at 24.84℃; for 24h;520 mg
96-34-4

methyl chloroacetate

75-86-5

2-hydroxy-2-methylpropanenitrile

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
at 70℃; for 2.5h; Temperature;96.2%
74-87-3

methylene chloride

372-09-8

cyanoacetic acid

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In tert-butyl methyl ether; water
67-56-1

methanol

107-91-5

cyanoacetic acid amide

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With Amberlyst 15 at 60℃; for 18h;85%
35234-87-8

dimethyl 2,3-dicyanofumarate

109-77-3

malononitrile

A

101342-43-2

methyl tricyanoethylenecarboxylate

B

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
In acetic acid at 100℃; for 0.5h;A 30%
B n/a
143-33-9

sodium cyanide

96-34-4

methyl chloroacetate

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With PEG400 at 120℃; for 5h;84%
With water; acetic acid at 80 - 85℃;
51513-29-2

methyl malonamate

105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With lead acetate In dichloromethane for 12h; Reflux;86%
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  • Methyl Cyanoacetate CAS NO.105-34-0  CAS NO.105-34-0

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Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Specification

The CAS registry number of Methyl cyanoacetate is 105-34-0. Its EINECS registry number is 203-288-8. The IUPAC name is methyl 2-cyanoacetate. In addition, the molecular formula is C4H5NO2. What's more, it is a kind of clear colorless to very slighlty yellow liquid, which can be used as intermediates for medicine, pigment and pesticide. Besides, it is also used in the preparation of adhesive, methyl cyanopropenoate and vitamin 6.

Physical properties about this chemical are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 3; (6)#Freely Rotating Bonds: 2; (7)Polar Surface Area: 50.09 Å2; (8)Index of Refraction: 1.402; (9)Molar Refractivity: 22.26 cm3; (10)Molar Volume: 91.4 cm3; (11)Polarizability: 8.82 ×10-24cm3; (12)Surface Tension: 36.2 dyne/cm; (13)Density: 1.083 g/cm3; (14)Flash Point: 86.5 °C; (15)Enthalpy of Vaporization: 44.42 kJ/mol; (16)Boiling Point: 208 °C at 760 mmHg; (17)Vapour Pressure: 0.219 mmHg at 25°C.

Preparation of Methyl cyanoacetate: it can be prepared by cyanoethylolmethoxycarbonyl and sodium cyanide. Add sodium cyanide, methanol and solvent PTC into the reactor at first. Then heat it to 55 °C with stirring. Next, add cyanoethylolmethoxycarbonyl into yhe mixture in 15 minutes with stirring. The reaction should react for 3 hours. At last, through a series of filtration, distillation and vacuum distillation you can get the desired product.

Methyl cyanoacetate can be prepared by cyanoethylolmethoxycarbonyl and sodium cyanide

Uses of Methyl cyanoacetate: it can react with benzaldehyde to get 2-cyano-3t-phenyl-acrylic acid methyl ester. This reaction will need catalyst natural phosphate and solvent methanol. The reaction time is 15 minutes at reaction temperature of 20 °C. The yield is about 85%.

Methyl cyanoacetate can react with benzaldehyde to get 2-cyano-3t-phenyl-acrylic acid methyl ester

When you are using this chemical, please be cautious about it as the following:
During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCC(=O)OC
(2)InChI: InChI=1/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3
(3)InChIKey: ANGDWNBGPBMQHW-UHFFFAOYAG

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo skin 400mg/kg (400mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 920, 1986.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,