| Identification | More | [Name]
Methyl cyanoacetate | [CAS]
105-34-0 | [Synonyms]
CYANOACETIC ACID METHYL ESTER
MALONIC ACID METHYL ESTER NITRILE
MCYA
METHYL CYANOACETATE
Aceticacid,cyano-,methylester
cyano-aceticacimethylester
Malonic methyl ester nitrile
Malonicacidmononitrilemethylester
Methyl 2-cyanoacetate
Methyl cyanoethanoate
methyl2-cyanoacetate
methylcyanoethanoate
Methylester kyseliny kyanoctove
methylesterkyselinykyanoctove
USAF kf-22
usafkf-22
MetthylCyanoacetate
Methylcyanacetat
(Methoxycarbonyl)acetonitrile | [EINECS(EC#)]
203-288-8 | [Molecular Formula]
C4H5NO2 | [MDL Number]
MFCD00001939 | [Molecular Weight]
99.09 | [MOL File]
105-34-0.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to very slighlty yellow liquid | [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.)
| [Fp ]
>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 | [Henry's Law Constant]
3.5×101 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [Dielectric constant]
29.4（21℃） | [InChI]
1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3 | [InChIKey]
ANGDWNBGPBMQHW-UHFFFAOYSA-N | [SMILES]
COC(=O)CC#N | [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]
105-34-0(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H319 | [Precautionary statements ]
P264-P280-P305+P351+P338-P337+P313 | [Hazard Codes ]
Xi | [Safety Statements ]
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
3276 | [WGK Germany ]
1
| [RTECS ]
AG4375000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29269095 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2 | [Toxicity]
guinea pig,LDLo,skin,400mg/kg (400mg/kg),"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 920, 1986. |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to very slighlty yellow liquid | [Uses]
pharmaceutical intermediate | [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 |
|
| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
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| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
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