Methyl cyanoacetate Chemical Properties

Melting point:

-13 °C

Boiling point:

204-207 °C(lit.)

Density 

1.123 g/mL at 25 °C(lit.)

vapor density 

3.41 (vs air)

vapor pressure 

0.2 mm Hg ( 20 °C)

refractive index 

n20/D 1.417(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

54g/l

form 

Liquid

pka

2.75±0.10(Predicted)

color 

Clear colorless to very slightly yellow

Water Solubility 

54 g/L (20 ºC)

Sensitive 

Light Sensitive

BRN 

773945

Dielectric constant

29.4（21℃）

LogP

-0.47 at 25℃

CAS DataBase Reference

105-34-0(CAS DataBase Reference)

NIST Chemistry Reference

Acetic acid, cyano-, methyl ester(105-34-0)

EPA Substance Registry System

Acetic acid, cyano-, methyl ester (105-34-0)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

1

RTECS 

AG4375000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29269095

Toxicity

guinea pig,LDLo,skin,400mg/kg (400mg/kg),"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 920, 1986.

MSDS

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Methyl cyanoacetate Usage And Synthesis

Description

Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds. It is often used as a nucleophile in the electrochemical oxidation of catechols. Methyl Cyanoacetate is also a reagent in the synthesis of Methyl 2-Amino-4-trifluoromethylthiophene-3-carboxylate; a compound used in the synthesis of DPP-IV inhibitors for treating type-2 diabetes. In addition, it is an intermediate in the preparation of α-cyanoacrylate, malononitrile, and 1,1-cyclohexanediacetic acid dyes. It is used as UV absorber or stabilizer, intermediate for pharmaceuticals. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds.

Chemical Properties

clear colorless to very slighlty yellow liquid

Uses

pharmaceutical intermediate

Uses

Methyl cyanoacetate is an intermediate in the preparation of α-cyanoacrylate, malononitrile, 1,1-cyclohexanediacetic acid dye. It is used as UV absorber or stabiliser, intermediate for pharmaceuticals. It may be used in the synthesis of various 1,2,5-tricarbonyl compounds.

Definition

ChEBI: Methyl cyanoacetate is an alkyl cyanoacetate ester.

General Description

Methyl cyanoacetate is the intermediate product in pharmaceutical organic synthesis as well as in the synthesis of some biologically active compounds used in agriculture. It undergoes calcite or fluorite catalyzed Kn?venagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α-cyanocinnamic esters.

Synthesis

GENERAL METHOD: A mixture of cyanoacetic acid, methanol and N-bromosuccinimide was placed in a 25 mL reaction tube and the reaction was stirred at 70°C for 2-40 hours. Upon completion of the reaction, the reaction mixture is cooled to room temperature and subsequently evaporated under reduced pressure to remove methanol. Unless otherwise stated in Section 3.2.6, the subsequent isolation and purification steps were as follows: the residue was dissolved in ethyl acetate and washed sequentially with 10 mL of 10% aqueous Na2S2O3 solution, 5 mL of saturated aqueous NaHCO3 solution and 10 mL of distilled water. The aqueous phase was back-extracted with ethyl acetate (3 x 5 mL). All organic layers were combined, dried with anhydrous Na2SO4 and finally evaporated under reduced pressure to remove the solvent.

Purification Methods

Purify the ester by shaking with 10% Na2CO3 solution, wash well with water, dry with anhydrous Na2SO4, and distil it. [Beilstein 2 H 584, 2 I 253, 2 II 530, 2 III 1628, 2 IV 1889.]

References

[1] Synthesis, 1980, # 7, p. 547 - 551
[2] Molecules, 2018, vol. 23, # 9,
[3] Synthetic Communications, 1988, vol. 18, # 8, p. 847 - 854
[4] Patent: US2553065, 1949,
[5] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566

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