Name | Methyl Cyanoacetate |
Synonyms | 2-cyanopropanoate Methyl Cyanoacetate methyl2-cyanoacetate methylcyanoethanoate Methyl 2-cyanoacetate Methyl cyanoethanoate Tofacitinib Impurity 198 Cyanoacetic acid methyl ester Aceticacid,cyano-,methylester Pemetrexed disodium Impurity 12 Methylester kyseliny kyanoctove |
CAS | 105-34-0 |
EINECS | 203-288-8 |
InChI | InChI:1S/C4H5NO2/c1-7-4(6)2-3-5/h2H2,1H3 |
Molecular Formula | C4H5NO2 |
Molar Mass | 99.09 |
Density | 1.123g/mLat 25°C(lit.) |
Melting Point | -13 °C |
Boling Point | 204-207°C(lit.) |
Flash Point | >230°F |
Water Solubility | 54 g/L (20 ºC) |
Solubility | 54g/l |
Vapor Presure | 0.2 mm Hg ( 20 °C) |
Vapor Density | 3.41 (vs air) |
Appearance | Liquid |
Color | Clear colorless to very slightly yellow |
BRN | 773945 |
pKa | 2.75±0.10(Predicted) |
Storage Condition | Sealed in dry,Room Temperature |
Sensitive | Light Sensitive |
Refractive Index | n20/D 1.417(lit.) |
Physical and Chemical Properties | Colorless to yellowish transparent liquid. melting point -22.5 ℃ boiling point 204~207 ℃ relative density 1.1225 refractive index 1.4174 solubility insoluble in water. Miscible with ethanol and ether. |
Use | Intermediates for organic synthesis, pharmaceuticals, dyes and preparation of α-cyanoacrylate quick-drying adhesives |
Hazard Symbols | Xi - Irritant![]() |
Safety Description | 24/25 - Avoid contact with skin and eyes. |
UN IDs | 3276 |
WGK Germany | 1 |
RTECS | AG4375000 |
TSCA | Yes |
HS Code | 29269095 |
Hazard Note | Irritant |
Hazard Class | 6.1(b) |
Packing Group | III |
Downstream Products | Cyanoacetamide 4-Chloro-2,6-diaminopyrimidine |
colorless to yellowish transparent liquid, flammable. Boiling Point 204~207 deg C. Melting Point -22.5 °c. The relative density was 1.1225. Refractive index 4174. Insoluble in water. Miscible with ethanol and ether.
This product is organic synthesis, medicine, dye intermediates, mainly used in the manufacture of adhesives, 2 methyl cyanoacrylate, vitamin B6, etc.
LogP | -0.47 at 25℃ |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Product description | methyl cyanoacetate is an intermediate product of some bioactive compounds used in pharmaceutical organic synthesis and synthetic agriculture. It undergoes a calcite-or fluorite-catalyzed condensation reaction of knövenagel with an aromatic aldehyde to give the corresponding arylarylene maleonitrile and (E )-α-cyanate ester. |
Application | methyl cyanoacetate is an important pharmaceutical and chemical raw material; Methyl cyanoacetate can be used as raw material to synthesize cyanoacetamide, malononitrile, gabapentin, pyrimidine amine and other important chemical products. |
preparation method | in one equipped with a stirrer, 99% g (1 mol) of industrial-grade 99% methyl cyanoacetate, G (3mol) of industrial-grade tert-butanol, and 3g of analytically pure sodium tert-butoxide are added to the ml three-mouth bottle of the thermometer and rectification device, and the mixture is stirred and heated to 80 ° C. And reacted for 10 hours. After the tert-butyl alcohol was recovered under reduced pressure, the feed liquid was adjusted to pH 8 with acetic acid and subjected to rectification. 125g of tert-butyl cyanoacetate was obtained in a yield of 88% and a product purity of 99% (GC). |
Application | methyl cyanoacetate, like ethyl cyanoacetate, is also an important intermediate of pesticides, preparing 2-amino -4, 6-dimethoxypyrimidine is useful in the preparation of sulfonylurea herbicides and is also an intermediate of the pharmaceutical methyl 2-cyanoacrylate. This product is an intermediate of organic synthesis, medicine and dye. It is mainly used in the manufacture of adhesives (e. G., medical adhesive methyl 2-cyanoacrylate), vitamin B6, malononitrile, and the like. Using a similar process can be prepared ethyl cyanoacetate, butyl cyanoacetate, mainly used as adhesives, cyanoacrylate quick-drying adhesive, can be used for medicine or automobile parts, household appliances assembly bonding. used in organic synthesis, medicine, dye intermediates and preparation of α-cyanoacrylate quick drying adhesive methyl cyanoacetate is a pharmaceutical, dye intermediates, mainly used in the manufacture of adhesives, vitamin B6, etc. |
production method | 1. Esterification of chloroacetic acid with methanol methyl chloroacetic acid is esterified with methanol to produce methyl chloroacetate. After rectification, the refined product of methyl chloroacetate was obtained, and the crude product was obtained by cyanation reaction with sodium cyanide. Then the crude product was filtered, distilled under normal pressure and distilled under reduced pressure to obtain methyl cyanoacetate. 2. Cyanoacetic acid and methanol esterification method cyanoacetic acid, methanol and sulfuric acid were added into the reactor, heated to reflux for 3H, cooled to 10 ℃, neutralized with sodium carbonate solution, distilled at 132-136 ℃ and 2.133kPa, methyl cyanoacetate product was obtained. The preparation method is similar to the preparation method of ethyl cyanoacetate, I .e., obtained by the action of cyanoacetic acid and methanol in the presence of sulfuric acid. NCCH2COOH CH3OH[H2SO4]→NCCH2COOCH3 H2O |