Basic information
- Standard SMILES
COC(=O)CC#N- InChIKey
ANGDWNBGPBMQHW-UHFFFAOYSA-N- Molecular formula
- C4H5NO2
- Average molar mass
- 99.09 g/mol
- Monoisotopic mass
- 99.0320284
Overview
Methyl cyanoacetate is an alkyl cyanoacetate ester.
Names & identifiers
- Preferred name
- Methyl cyanoacetate
- IUPAC
- methyl 2-cyanoacetate
- English name
- Methyl cyanoacetate
- Molecular formula
- C4H5NO2
- Molecular weight
- 99.09
Names & synonyms
METHYL CYANOACETATEMethyl 2-cyanoacetate105-34-0Cyanoacetic acid methyl esterMethyl cyanoethanoateAcetic acid, cyano-, methyl esterUSAF KF-22Malonic methyl ester nitrileMethylester kyseliny kyanoctoveDTXSID80336493-Methoxy-3-oxopropanenitrileAcetic acid, 2-cyano-, methyl ester
Show more names
2-cyanopropanoateMCYAusafkf-2225KG,100KG,1TMethylcyanacetatMethyl Cyanoacetat
NSC 3113EINECS 203-288-8UNII-A28RI36V30Methylester kyseliny kyanoctove [Czech]BRN 07739452-cyanoacetic acid, methyl esterAI3-05599A28RI36V30
Database identifiers
- CAS
105-34-0- PubChem CID
- 7747
- DTXSID
DTXSID8033649- ChEMBL
CHEMBL1532013- ChEBI
CHEBI:51928- UNII
- A28RI36V30
- EC Number
- 203-288-8
- Nikkaji
- J4.029K
Properties
Computed structural properties
- XLogP
- -0.5
- Topological polar surface area
- 50.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 110
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitriles
SpringerMaterials PropertiesMoessbauer quadrupole effect
Vapor Pressure0.13 [mmHg]
Physical DescriptionColorless liquid with a mild odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- -13 °C · -13 °C
- Boiling point
- 204 · 204-207 °C(lit.)
- Density
- 1.123 g/mL · 1.123 g/mL at 25 °C(lit.)
- vapor density
- 3.41 · 3.41 (vs air)
- vapor pressure
- 0.2 mm · 0.2 mm Hg ( 20 °C)
- refractive index
- 20 · n20/D 1.417(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 54 g/l · 54g/l
- form
- Liquid
- pka
- 2.75 · 2.75±0.10(Predicted)
- color
- Clear colorless to very slightly yellow
- Water Solubility
- 54 g/L · 54 g/L (20 ºC)
- Sensitive
- Light Sensitive
- BRN
- 773945 · 773945
- Henry's Law Constant
- 3.5 · 3.5×101 mol/(m3Pa) at 25℃, Ebert et al. (2023)
- Dielectric constant
- 29.4 · 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 · -0.47 at 25℃
- CAS DataBase Reference
- 105 · 105-34-0(CAS DataBase Reference)
- FDA UNII
- 28 RI36V30 · A28RI36V30
- NIST Chemistry Reference
- Acetic acid, cyano-, methyl ester(105-34-0)
- EPA Substance Registry System
- Acetic acid, cyano-, methyl ester (105-34-0)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- Eyeshields, Gloves
- Hazard Codes
- Xi
- Safety Statements
- 24 · 24/25
- WGK Germany
- 1 · 1
- RTECS
- 4375000 · AG4375000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29269095 · 29269095
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 2 · Eye Irrit. 2
- Toxicity
- 400 mg/kg · guinea pig,LDLo,skin,400mg/kg (400mg/kg),"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 920, 1986.
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 19% (52 of 273) of reports.
Warning
H319 (81%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)
Aggregated GHS information provided per 273 reports by companies from 8 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Chemical: Acetic acid, cyano-, methyl ester
Status: Active Update: 05-11-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/5657
Acetic acid, cyano-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA strong eye irritant; [Alfa Aesar MSDS] See Ethyl cyanoacetate.
Hazard Classes and CategoriesEye Irrit. 2 (81%)
Toxicology
Adverse EffectsOther Poison - Chemical Asphyxiant
Safety data
- PPE
- Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- AG4375000
- 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.
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 24/25
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Uses & manufacturing
UsesUsed to make large scale and fine chemicals, pharmaceuticals, plastic products, and computer-electronic-optical equipment; [ExPub: ECHA REACH Registrations]
General Manufacturing InformationAcetic acid, 2-cyano-, methyl ester: ACTIVE
Applications
DescriptionMethyl 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.
Usespharmaceutical intermediate
UsesMethyl 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.
General DescriptionMethyl 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 Knvenagel condensation with aromatic aldehydes, giving the corresponding arylidenemalononitriles and (E)-α-cyanocinnamic esters.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Methyl cyanoacetate is an alkyl cyanoacetate ester.
Related reactions
309 records
Linked notes
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