1187-27-5

Basic information

• Product Name: METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE
• Synonyms: METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE;(E)-2-cyano-3-dimethylamino-acrylic acid methyl ester;(E)-2-cyano-3-dimethylaminoprop-2-enoic acid methyl ester;2-cyano-3-dimethylamino-acrylic acid methyl ester;2-cyano-3-dimethylaminoprop-2-enoic acid methyl ester;methyl (2E)-2-cyano-3-(dimethylamino)acrylate;methyl (E)-2-cyano-3-dimethylamino-prop-2-enoate;methyl (E)-2-cyano-3-dimethylaminoprop-2-enoate
• CAS NO: 1187-27-5
• Molecular Formula: C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• Mol File: 1187-27-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 105-107°C
• Boiling Point: 330.3°Cat760mmHg
• Flash Point: 153.6°C
• Appearance: /
• Density: 1.088g/cm³
• Vapor Pressure: 0.000168mmHg at 25°C
• Refractive Index: 1.473
• CAS DataBase Reference: METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE(1187-27-5)
• EPA Substance Registry System: METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE(1187-27-5)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• HazardClass: IRRITANT
• Hazardous Substances Data: 1187-27-5(Hazardous Substances Data)

Usage

General Description

METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE is a chemical compound with the molecular formula C8H11NO2. It is a clear, colorless to slightly yellow liquid that is soluble in organic solvents. This chemical is commonly used in the synthesis of pharmaceuticals, agrochemicals, and organic compounds. It is also used as a building block in the production of specialty polymers and materials. Additionally, METHYL 2-CYANO-3-(DIMETHYLAMINO)ACRYLATE is known for its strong adhesive and bonding properties, making it a popular ingredient in adhesive formulations. However, it is important to handle this chemical with care due to its potential health hazards, including skin and eye irritation, and respiratory issues if inhaled.

InChI:InChI=1/C7H10N2O2/c1-9(2)5-6(4-8)7(10)11-3/h5H,1-3H3

Upstream product

• 1186-70-5 bis(dimethylamino)methoxymethane 
• 105-34-0 methyl 2-cyanoacetate 
• 5780-17-6 (bis-ethylsulfanyl-methyl)-dimethyl-amine 
• 94815-01-7 N-Dimethoxymethyl-N',N'-dimethylformamidin 
• 55883-89-1 methoxymethylenecyanoacetic acid methyl ester 
• 124-40-3 dimethyl amine 
• 129016-33-7 (E)-3-Amino-2-cyano-acrylic acid methyl ester 
• 5043-87-8 β-(dimethylamino)acrolein aminal 
• 51513-20-3 3-dimethyl-amino-1,1,3-trimethoxypropane 
• 68-12-2 N,N-dimethyl-formamide 
• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 

Downstream Products

• 58046-50-7 N-hydroxyethyl-5-amino-1H-pyrazole-4-carboxylic acid 

Relevant articles and documents

Isomerizational and conformational study of methyl-2-cyano-3- methoxyacrylate and methyl-2-cyano-3-aminoacrylate and its N-methyl derivatives

The isomers and conformers of four push-pull compounds: methyl-2-cyano-3-methoxyacrylate (MCMA) H3COCHC(CN)(COOCH 3), methyl-2-cyano-3-aminoacrylate (MCAA) H2NCHC(CN) (COOCH3), methyl-2-cyano-3-methylaminoacrylate (MCMAA) H 3CNHCHC(CN)(COOCH3) and methyl-2-cyano-3- dimethylaminoacrylate (MCDMAA) (H3C)2NCHC(CN)(COOCH 3) have been studied experimentally by vibrational and NMR spectroscopy and theoretically by the ab initio calculations at MP2 level in 6-311++G basis set. The IR and Raman spectra of all compounds as a solid and solute in various solvents have been recorded in the region 4000-50 cm -1. The NMR spectra were obtained in chloroform, acetonitrile and DMSO at room temperature. Because both electron-withdrawing groups are different, all studied compounds can exist as E and Z isomers and then conformational possibilities are given by the rotation of the methylester and methoxy or methylamino groups. NMR spectra revealed that both MCMA and MCDMAA compounds without the possibility of intramolecular hydrogen bonding were prepared as a pure E isomer whereas in the case of the compounds with the possibility of intramolecular bonding MCAA and MCMAA a mixture of both E and Z isomers was obtained. X-ray analysis shows the presence of two EZ and EE conformers in solid MCMA. For this compound the possible second conformer was detected by NMR in more polar solvent DMSO. Vibrational spectra revealed the existence of two EZa and EEa conformers with Z and E orientation of methylester group and with anti orientation of dimethylamino group for MCDMAA. For MCAA and MCMAA the Z isomer with Z orientation of methylester group and with intramolecular hydrogen bond is the most stable one. In more polar surrounding (DMSO) the isomerization of ZZ or ZZa conformers of MCAA and MCMAA, respectively to E isomers occurred. These experimental findings have been supported by ab initio solvent effect calculations.

Heterocyclic compound

A compound represented by the formula (I): wherein each symbol is as described in the SPECIFICATION, or a salt thereof has a PDE2A inhibitory action, and is useful as a prophylactic or therapeutic drug for schizophrenia, Alzheimer’s disease and the like.