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Name	METHYL 2-CYANOACRYLATE	EINECS	N/A
CAS No.	137-05-3	Density	1.08g/cm³
PSA	50.09000	LogP	0.23918
Solubility	N/A	Melting Point	-40 °C
Formula	C5H5 N O2	Boiling Point	174.5°Cat760mmHg
Molecular Weight	111.1	Flash Point	67.6°C
Transport Information	N/A	Appearance	N/A
Safety	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 NO_x and CN⁻.
Analytical Methods:		For occupational chemical analysis use OSHA: #ID-55.	Risk Codes	36/37/38
Molecular Structure		Hazard Symbols	Toxic by inhalation. TLV: TWA 2 ppm; STEL 4 ppm.
Synonyms	Acrylicacid, 2-cyano-, methyl ester (6CI,8CI); 2-Cyanoacrylic acid methyl ester;ADhere; CA 7; CA 7 (adhesive); Cemedine 3000; Cemedine 3000 Type-II; Cemedine3000DX; Cyanobond 5000; Cyanobond SS; Eastman 910; Eastman 910 Super Glue;Fimofix P 1048; Mecrilat; Mecrilate; Mecrylate; Methyl 2-cyanoacrylate; Methylcyanoacrylate; Methyl a-cyanoacrylate; Sicomet 7000; Three Bond 1701; a-Cyanoacrylic acid methyl ester

METHYL 2-CYANOACRYLATE Synthetic route

: 106647-47-6
2-acetoxy-2-cyano-propionic acid methyl ester

: 137-05-3
mecrilate

Conditions

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

: 50-00-0
formaldehyd

: 105-34-0
methyl 2-cyanoacetate

: 137-05-3
mecrilate

Conditions

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;

: 625-56-9
Chloromethyl acetate

: 105-34-0
methyl 2-cyanoacetate

: 137-05-3
mecrilate

Conditions

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

: 137-05-3
mecrilate

: 92406-83-2
(3R,5R,7R)-1-(buta-1,3-dien-2-yl)adamantane

: 4-Adamantan-1-yl-1-cyano-cyclohex-3-enecarboxylic acid methyl ester

Conditions

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

: 109-53-5
isobutyl vinyl ether

: 137-05-3
mecrilate

: 81245-85-4
2-isobutoxy-5-cyano-6-methoxy-3,4-dihydro-2H-pyran

Conditions

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%

: 62889-07-0
trimethyl((1-(thiophen-2-yl)vinyl)oxy)silane

: 137-05-3
mecrilate

: 4-Cyano-7-oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-4-carboxylic acid methyl ester

Conditions

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

: 137-05-3
mecrilate

: 1489-57-2
2-methylcyclohexa-1,3-diene

: 84959-09-1, 89104-75-6
2-cyano-2-methoxycarbonyl-5-methylbicyclo<2.2.2>oct-5-ene

Conditions

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

: 137-05-3
mecrilate

: 762269-61-4
5′-(4-(diphenylamino)phenyl)(2,2′-bithiophene)-5-carboxaldehyde

: methyl (E)-2-cyano-3-[5'-{4-(diphenylamino)phenyl}-(2,2'-bithiophen)-5-yl]acrylate

Conditions

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

: 137-05-3
mecrilate

: 2,4-Dicyano-2-ethyl-pentanedioic acid dimethyl ester

Conditions

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

: 119-65-3
isoquinoline

: 137-05-3
mecrilate

: 22110-53-8
1-adamantyl isocyanide

: 1-(adamantan-1-ylimino)-2-cyano-1,2,3,10b-tetrahydro-pyrrolo[2,1-a]isoquinoline-2-carboxylic acid methyl ester

Conditions

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

METHYL 2-CYANOACRYLATE Chemical Properties

Methyl 2-cyanoacrylate(137-05-3)'s molecular formula is C₉H₁₃NO₂ and its formula weight is 111.1.
The relative density of methyl 2-cyanoacrylate(137-05-3) is 1.1044(27/4°C) and it has a boiling point of 47-48°C(0.267kPa). The refractive index is about 1.443 (25 °C).
Methyl 2-cyanoacrylate(137-05-3) has the property of being dissolved in ether, chloroform, a chlorinated carbon, benzene, dioxane. It is not soluble in methanol and ethanol, and it gradually aggregated when exposed to air.
The molecular structure of methyl 2-cyanoacrylate(137-05-3):

METHYL 2-CYANOACRYLATE Uses

The characteristics of methyl 2-cyanoacrylate(137-05-3) is polymerizing quickly.
Methyl 2-cyanoacrylate(137-05-3) has a strong adhesion, usually used as monomers of adhesives and polymers , also used for adhesion of the skin incision and fresh wound.

METHYL 2-CYANOACRYLATE Toxicity Data With Reference

1.	eye-hmn TD50:4 ppm	AIHAAP American Industrial Hygiene Association Journal. 29 (1968),558.
2.	mmo-sat 100 µg/plate	ENMUDM Environmental Mutagenesis. 9 (Suppl 9)(1987),1.
3.	mmo-sat 300 µg/plate	MUREAV Mutation Research. 188 (1987),97.
4.	orl-rat LD50:1600 mg/kg	85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices. 6 (1991),965.
5.	ihl-rat LC50:101 ppm/6H	85INA8 Documentation of the Threshold Limit Values and Biological Exposure Indices. 6 (1991),965.

METHYL 2-CYANOACRYLATE Consensus Reports

Reported in EPA TSCA Inventory.

METHYL 2-CYANOACRYLATE 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 NO_x and CN⁻.

Analytical Methods:

For occupational chemical analysis use OSHA: #ID-55.

METHYL 2-CYANOACRYLATE Standards and Recommendations

OSHA PEL: TWA 2 ppm; STEL 4 ppm
ACGIH TLV: TWA 0.2 ppm
DFG MAK: 2 ppm (9.2 mg/m³)

METHYL 2-CYANOACRYLATE Analytical Methods

For occupational chemical analysis use OSHA: #ID-55.

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