Chemistry:Methyl cyanoacrylate

Methyl cyanoacrylate
Names
	Preferred IUPAC name Methyl 2-cyanoprop-2-enoate
	Other names Methyl 2-cyanopropenoate; Methyl 2-cyanoacrylate; 2-Cyano-2-propenoic acid methyl ester; MCA; Methyl alpha-cyanoacrylate; Mecrylate; Ad/here; Adhere; CA 7; Cemedine 3000; Coapt; Cyanobond 5000; Eastman 910; Fimofix P 1048; Mecrilat; Mecrilate; Sicomet 7000; Three Bond 1701
Identifiers
CAS Number	137-05-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	8387 ;
PubChem CID	8711;
UNII	WN7979561R ;
	InChI InChI=1S/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 Key: MWCLLHOVUTZFKS-UHFFFAOYSA-N ; InChI=1/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 Key: MWCLLHOVUTZFKS-UHFFFAOYAW;
	SMILES C=C(C(OC)=O)C#N;
Properties
Chemical formula	C5H5NO2
Molar mass	111.1 g/mol
Density	1.1
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	48 to 49 °C (118 to 120 °F; 321 to 322 K) (2.5–2.7 mmHg)
Solubility in water	30% (20 °C)
Vapor pressure	0.2 mmHg (25 °C)
Hazards
Flash point	79 °C; 174 °F; 352 K
	NIOSH (US health exposure limits):
PEL (Permissible)	None
REL (Recommended)	TWA 2 ppm (8 mg/m3) ST 4 ppm (16 mg/m3)
IDLH (Immediate danger)	N.D.
Related compounds
Related ; Cyanoacrylates	Ethyl cyanoacrylate; Butyl cyanoacrylate; Octyl cyanoacrylate
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Methyl cyanoacrylate (MCA) (also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate)^[3] is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues.^[4]^[5] It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

Safety

Heating the polymer causes depolymerization of the cured MCA, producing gaseous products which are a strong irritant to the lungs and eyes. With regard to occupational exposure to MCA, the National Institute for Occupational Safety and Health recommends workers do not exceed exposures over 2 ppm (8 mg/m³) over an eight-hour workshift, or over 4ppm (16 mg/m³) over a short-term exposure.^[7]

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Names


Preferred IUPAC name Methyl 2-cyanoprop-2-enoate
Other names Methyl 2-cyanopropenoate Methyl 2-cyanoacrylate 2-Cyano-2-propenoic acid methyl ester MCA Methyl alpha-cyanoacrylate Mecrylate Ad/here Adhere CA 7 Cemedine 3000 Coapt Cyanobond 5000 Eastman 910 Fimofix P 1048 Mecrilat Mecrilate Sicomet 7000 Three Bond 1701^[1]
Identifiers
CAS Number	137-05-3^Y
3D model (JSmol)	Interactive image
ChemSpider	8387^Y
PubChem CID	8711
UNII	WN7979561R^Y
InChI InChI=1S/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3^Y Key: MWCLLHOVUTZFKS-UHFFFAOYSA-N^Y InChI=1/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3 Key: MWCLLHOVUTZFKS-UHFFFAOYAW
SMILES C=C(C(OC)=O)C#N
Properties
Chemical formula	C₅H₅NO₂
Molar mass	111.1 g/mol
Density	1.1
Melting point	−40 °C (−40 °F; 233 K)
Boiling point	48 to 49 °C (118 to 120 °F; 321 to 322 K) (2.5–2.7 mmHg)
Solubility in water	30% (20 °C)^[2]
Vapor pressure	0.2 mmHg (25 °C)^[2]
Hazards
Flash point	79 °C; 174 °F; 352 K^[2]
NIOSH (US health exposure limits):
PEL (Permissible)	None^[2]
REL (Recommended)	TWA 2 ppm (8 mg/m³) ST 4 ppm (16 mg/m³)^[2]
IDLH (Immediate danger)	N.D.^[2]
Related compounds
Related Cyanoacrylates	Ethyl cyanoacrylate Butyl cyanoacrylate Octyl cyanoacrylate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references