137-05-3

Basic information

• Product Name: CYANOACRYLIC ACID METHYL ESTER
• Synonyms: CA-7【adhesive】;Cemedine-3000 Type-11;2-CYANOMETHYLACRYLATE;methyl 2-cyanoprop-2-enoate;2-cyano-2-propenoicacidmethylester;2-cyano-2-propenoicacimethylester;alpha-Cyanoacrylic acid, methyl ester;alpha-cyanoacrylicacidmethylester
• CAS NO: 137-05-3
• Molecular Formula: C₅H₅NO₂
• Molecular Weight: 111.1
• EINECS: 205-275-2
• Product Categories: Organics
• Mol File: 137-05-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: -40 °C
• Boiling Point: bp 48-49°
• Flash Point: 67.6°C
• Appearance: /
• Density: nD25 1.443. d20 1.1044
• Vapor Pressure: 1.2mmHg at 25°C
• Refractive Index: n20D 1.4459
• CAS DataBase Reference: CYANOACRYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: CYANOACRYLIC ACID METHYL ESTER(137-05-3)
• EPA Substance Registry System: CYANOACRYLIC ACID METHYL ESTER(137-05-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-26
• Hazardous Substances Data: 137-05-3(Hazardous Substances Data)

Usage

Description

Methyl cyanoacrylate (MCA) 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.It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate. It is soluble in acetone, methyl ethyl ketone, nitro methane, and dichloromethane. MCA polymerizes rapidly in presence of moisture.

Chemical Properties

Different sources of media describe the Chemical Properties of 137-05-3 differently. You can refer to the following data:
1. Methyl cyanoacrylate is a thick, clear liquid adhesive. The odor threshold is 2.2 ppm.
2. Colorless liquid.

Uses

Different sources of media describe the Uses of 137-05-3 differently. You can refer to the following data:
1. Surgical aid (tissue adhesive).
2. In high-bond strength, fast-acting glues (e.g., Krazy Glue); surgical use as tissue adhesive

General Description

Clear slightly yellow liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

CYANOACRYLIC ACID METHYL ESTER is an unsaturated aliphatic nitrile and ester. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Hazard

Toxic by inhalation. Eye and upper respi-ratory tract irritant.

Health Hazard

Methyl 2-cyanoacrylate is an irritant of the eyes and nose and can induce occupational asthma.

Fire Hazard

Flash point data for CYANOACRYLIC ACID METHYL ESTER are not available but CYANOACRYLIC ACID METHYL ESTER is probably non-flammable.

Safety Profile

Moderately toxic by ingestion and inhalation routes. Experimental reproductive effects. A human eye irritant. Can bond the eyelids or skin surfaces instantly. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx and CN-.

Safety

Heating the polymer causes depolymerization of the cured MCA, producing gaseous products strongly irritant to lungs and eyes.

Potential Exposure

Methyl 2-cyanoacrylate is used in production of coatings and textiles; in the manufacture of quick-setting, high-strength, adhesive cements. Often found around the home; bonds eyes and skin in seconds. Keep out of the reach of children.

Shipping

UN3334 Aviation regulated liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material. Technical Name Required.

Incompatibilities

Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides (releasing heat, toxic, and possibly flammable gases), thiosulfates and dithionites (releasing hydrogen sulfate and oxides of sulfur). Reacts violently with water, bases, and peroxides. Contact with alcohols, water, amines, and alkalis can cause rapid polymerization

InChI:InChI=1/C5H5NO2/c1-4(3-6)5(7)8-2/h1H2,2H3

Synthetic route

2-acetoxy-2-cyano-propionic acid methyl ester (106647-47-6) → mecrilate (137-05-3)

Conditions	Yield
With copper at 535 - 550℃; under 200 Torr; Entsteht in polymerer Form;

formaldehyd (50-00-0) + methyl 2-cyanoacetate (105-34-0) → mecrilate (137-05-3)

Conditions	Yield
With piperidine at 80℃; Destillieren des Reaktionsprodukts bei 150grad und 1mm Druck;
With piperidine; methanol Erhitzen des Reaktionsprodukts mit Phosphor(V)-oxid, Schwefeldioxid und Hydrochinon unter vermindertem Druck;

Chloromethyl acetate (625-56-9) + methyl 2-cyanoacetate (105-34-0) → mecrilate (137-05-3)

Conditions	Yield
With sodium methylate at 35℃; Destillieren des Reaktionsprodukts bei 150grad und 1mm Druck;

mecrilate (137-05-3) + (3R,5R,7R)-1-(buta-1,3-dien-2-yl)adamantane (92406-83-2) → 4-Adamantan-1-yl-1-cyano-cyclohex-3-enecarboxylic acid methyl ester

Conditions	Yield
In benzene for 2h; Ambient temperature;	90%

isobutyl vinyl ether (109-53-5) + mecrilate (137-05-3) → 2-isobutoxy-5-cyano-6-methoxy-3,4-dihydro-2H-pyran (81245-85-4)

Conditions	Yield
In benzene at 28℃; for 72h;	87%
at 28℃; for 72h; Product distribution; Mechanism; var. temp., time, other solvent; var. electron-rich olefins;	86%
In benzene at 25℃;	62%

trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane (62889-07-0) + mecrilate (137-05-3) → 4-Cyano-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-4-carboxylic acid methyl ester

Conditions	Yield
In benzene at 25℃; for 3h;	81%

mecrilate (137-05-3) + 2-methylcyclohexa-1,3-diene (1489-57-2) → 2-cyano-2-methoxycarbonyl-5-methylbicyclo<2.2.2>oct-5-ene (84959-09-1, 89104-75-6)

Conditions	Yield
In benzene Heating;	75%
In benzene Heating;

mecrilate (137-05-3) + 5′-(4-(diphenylamino)phenyl)(2,2′-bithiophene)-5-carboxaldehyde (762269-61-4) → methyl (E)-2-cyano-3-[5'-{4-(diphenylamino)phenyl}-(2,2'-bithiophen)-5-yl]acrylate

Conditions	Yield
With piperidine In dichloromethane; acetonitrile at 20℃; for 1h; Inert atmosphere;	71%

mecrilate (137-05-3) → 2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h;	64%

isoquinoline (119-65-3) + mecrilate (137-05-3) + 1-adamantyl isocyanide (22110-53-8) → 1-(adamantan-1-ylimino)-2-cyano-1,2,3,10b-tetrahydro-pyrrolo[2,1-a]isoquinoline-2-carboxylic acid methyl ester

Conditions	Yield
In diethyl ether at 20℃; for 48h;	63%

mecrilate (137-05-3) + bromostyrene (103-64-0) → methyl 1-cyano-1,2-dihydronaphthalene-1-carboxylate (81245-90-1)

Conditions	Yield
at 110℃; for 17h;	60%

4-Methoxystyrene (637-69-4) + mecrilate (137-05-3) → Methyl 2-(p-Methoxyphenyl)-6-methoxy-5-cyano-3,4-dihydro-2H-pyran-4-carboxylate (77321-38-1)

Conditions	Yield
In acetonitrile at 25℃;	51%

mecrilate (137-05-3) + 3-oxo-3-phenyl-dithiopropionic acid (15185-51-0) → methyl 2-(benzoylmethylene)-4-imino-1,3-dithian-5-carboxylate (74598-48-4)

Conditions	Yield
In diethyl ether Ambient temperature;	51%

4-Methoxystyrene (637-69-4) + mecrilate (137-05-3) → dimethyl 5,10-dicyano-3-methoxy-1,4,4a,5,6,7-hexahydro-1,4-ethanonaphthalene-5,10-dicarboxylate (81245-89-8)

Conditions	Yield
In benzene at 28℃; for 24h;	50%

mecrilate (137-05-3) + tris(1-methylethyl)phosphine (6476-36-4) → C14H26NO2P (183994-96-9)

Conditions	Yield
In diethyl ether; hexane at 0℃;	48%

mecrilate (137-05-3) + 1-iodoadamantane (768-93-4) → Methyl 3-(1-adamantyl)-2-cyanopropanoate (113249-57-3)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In toluene for 2h; Heating;	36%

1-(2-furyl)-1-(trimethylsilyloxy)ethylene (62889-08-1) + mecrilate (137-05-3) → 4-Cyano-7-oxo-4,5,6,7-tetrahydro-benzofuran-4-carboxylic acid methyl ester

Conditions	Yield
In benzene at 25℃; for 3h;	36%

mecrilate (137-05-3) + ethyl 2-cyano-3,3-dimercaptoacrylate dipotassium salt → 6-Amino-2-[1-cyano-1-ethoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester (74598-55-3)

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	28%

mecrilate (137-05-3) + methylenecyclohexane (1192-37-6) → 2-Cyano-4-cyclohex-1-enyl-butyric acid methyl ester + 2-Methoxy-1-oxa-spiro[5.5]undec-2-ene-3-carbonitrile + 1-Cyano-spiro[3.5]nonane-1-carboxylic acid methyl ester + 1,3-Dicyano-spiro[5.5]undecane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0 - 25℃; for 1.5h; Further byproducts given;	A 26% B 4% C 2% D 8%

mecrilate (137-05-3) + methylenecyclohexane (1192-37-6) → 2-Cyano-4-cyclohex-1-enyl-butyric acid methyl ester + 2-Methoxy-1-oxa-spiro[5.5]undec-2-ene-3-carbonitrile + 1,3-Dicyano-spiro[5.5]undecane-1,3-dicarboxylic acid dimethyl ester + 2,4-Dicyano-2-(2-cyclohex-1-enyl-ethyl)-pentanedioic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0 - 25℃; for 1.5h; Further byproducts given;	A 26% B 4% C 8% D 4%

2-methyl-but-2-ene (513-35-9) + mecrilate (137-05-3) → 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile + 2-Cyano-4,5-dimethyl-hex-5-enoic acid methyl ester + 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester + 1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α) (77257-26-2)

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 4% C 25% D 6%

2-methyl-but-2-ene (513-35-9) + mecrilate (137-05-3) → 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile + 2,4-Dicyano-2-(2,3-dimethyl-but-3-enyl)-pentanedioic acid dimethyl ester + 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester + 1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α) (77257-26-2)

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 5% C 25% D 6%

2-methyl-but-2-ene (513-35-9) + mecrilate (137-05-3) → 2-Methoxy-5,6,6-trimethyl-5,6-dihydro-4H-pyran-3-carbonitrile + 1,3-Dicyano-4,4,5-trimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester + (1R,3S)-1-Cyano-2,2,3-trimethyl-cyclobutanecarboxylic acid methyl ester (77257-24-0) + 1-cyano-2,2,3-trimethyl-cyclobutan-carbonsaeure-methylester,(13α) (77257-26-2)

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at -78 - 25℃; for 1h; Further byproducts given;	A 5% B 25% C 3% D 6%

mecrilate (137-05-3) + potassium 2-cyano-3-methoxy-3-oxoprop-1-ene-1,1-bis(thiolate) (119491-91-7) → 6-Amino-2-[1-cyano-1-methoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester (74598-54-2)

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	25%

1,10-Decanediol (112-47-0) + mecrilate (137-05-3) → 1,10-decanediol bis-2-cyanoacrylate (60755-41-1)

Conditions	Yield
With toluene-4-sulfonic acid In xylene for 1h; transesterification; Heating;	25%

mecrilate (137-05-3) + 2-Cyano-3,3-dimercapto-acrylic acid isopropyl ester (74598-58-6) → 6-Amino-2-[1-cyano-1-isopropoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester (74598-56-4)

Conditions	Yield
With hydrogenchloride In dichloromethane; water for 16h;	23%

1-hexene (592-41-6) + mecrilate (137-05-3) → (E)-2-Cyano-non-5-enoic acid methyl ester + 6-Butyl-2-methoxy-5,6-dihydro-4H-pyran-3-carbonitrile + 2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester + 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 2% C 12% D 6%

1-hexene (592-41-6) + mecrilate (137-05-3) → (E)-2-Cyano-non-5-enoic acid methyl ester + 2-Butyl-1-cyano-cyclobutanecarboxylic acid methyl ester + 2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester + 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 1% C 12% D 6%

1-hexene (592-41-6) + mecrilate (137-05-3) → (E)-2-Cyano-non-5-enoic acid methyl ester + 2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester + 2,4-Dicyano-2-((E)-hept-3-enyl)-pentanedioic acid dimethyl ester + 4-Butyl-1,3-dicyano-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h; Further byproducts given;	A 17% B 12% C 3% D 6%

3-Methyl-cis-2-penten (922-62-3) + mecrilate (137-05-3) → 2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester (343858-00-4) + (E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester (345618-98-6) + 6-Ethyl-2-methoxy-5,6-dimethyl-5,6-dihydro-4H-pyran-3-carbonitrile + 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 1% D 10%

3-Methyl-cis-2-penten (922-62-3) + mecrilate (137-05-3) → 2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester (343858-00-4) + (E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester (345618-98-6) + 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester + 1-cyano-2-ethyl-2,3-dimethyl-cyclobutan-carbonsaeure-methylester,(12β) (77257-25-1)

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 10% D 2.9%

3-Methyl-cis-2-penten (922-62-3) + mecrilate (137-05-3) → 2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester (343858-00-4) + (E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester (345618-98-6) + 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester + (1R,2R,3R)-1-Cyano-2-ethyl-2,3-dimethyl-cyclobutanecarboxylic acid methyl ester (77287-01-5)

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given;	A 3.6% B 3.8% C 10% D 3.4%

3-Methyl-cis-2-penten (922-62-3) + mecrilate (137-05-3) → (E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester (345618-98-6) + 2,4-Dicyano-2-((E)-2,3-dimethyl-pent-3-enyl)-pentanedioic acid dimethyl ester (77257-21-7) + 2,4-Dicyano-2-(2-methyl-3-methylene-pentyl)-pentanedioic acid dimethyl ester (77257-23-9) + 1,3-Dicyano-4-ethyl-4,5-dimethyl-cyclohexane-1,3-dicarboxylic acid dimethyl ester

Conditions	Yield
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given. Title compound not separated from byproducts;	A 3.8% B 2% C n/a D 10%
With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 3h; Further byproducts given. Title compound not separated from byproducts;	A 3.8% B 2% C 1% D 10%

Upstream product

• 106647-47-6 2-acetoxy-2-cyano-propionic acid methyl ester 
• 50-00-0 formaldehyd 
• 105-34-0 methyl 2-cyanoacetate 
• 625-56-9 Chloromethyl acetate 

Downstream Products

• 71160-95-7 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid dimethyl ester 
• 71160-99-1 2-[1-Benzylamino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 1-benzyl ester 5-methyl ester 
• 29866-36-2 2-cyano-3,3-bis[(phenylmethyl)thio]-2-propenoic acid, methyl ester 
• 3578-07-2 n-decyl 2-cyanoacrylate 
• 74598-50-8 6-[2-(4-Chloro-phenyl)-acetylamino]-2-[1-cyano-1-ethoxycarbonyl-meth-(E)-ylidene]-4H-[1,3]dithiine-5-carboxylic acid methyl ester 
• 74598-48-4 methyl 2-(benzoylmethylene)-4-imino-1,3-dithian-5-carboxylate 
• 345618-98-6 (E)-2-Cyano-4,5-dimethyl-hept-5-enoic acid methyl ester 
• 77257-21-7 2,4-Dicyano-2-((E)-2,3-dimethyl-pent-3-enyl)-pentanedioic acid dimethyl ester 
• 77287-00-4 (1R,2R,3S)-1-Cyano-2-ethyl-2,3-dimethyl-cyclobutanecarboxylic acid methyl ester 
• 77287-02-6 (1R,2S,3R)-1-Cyano-2-ethyl-2,3-dimethyl-cyclobutanecarboxylic acid methyl ester 
• 343858-00-4 2-Cyano-4-methyl-5-methylene-heptanoic acid methyl ester