15802-18-3

Basic information

• Product Name: CYANOACRYLICACID
• Synonyms: 2-CYANOPROP-2-ENOIC ACID;CYANOACRYLICACID;2-Cyanoacrylic acid;Aron α-A;2-Propenoic acid, 2-cyano-
• CAS NO: 15802-18-3
• Molecular Formula: C₄H₃NO₂
• Molecular Weight: 97.07
• Mol File: 15802-18-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 93-94 °C
• Boiling Point: 266.3°Cat760mmHg
• Flash Point: 114.9°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 0.00251mmHg at 25°C
• Refractive Index: 1.47
• PKA: 1.30±0.11(Predicted)
• CAS DataBase Reference: CYANOACRYLICACID(CAS DataBase Reference)
• NIST Chemistry Reference: CYANOACRYLICACID(15802-18-3)
• EPA Substance Registry System: CYANOACRYLICACID(15802-18-3)

Safety Data

• Hazardous Substances Data: 15802-18-3(Hazardous Substances Data)

Usage

General Description

Cyanoacrylic acid, also known as methyl cyanoacrylate, is a type of fast-acting adhesive commonly used in household and industrial applications. It is a clear, colorless liquid that solidifies rapidly when it comes into contact with moisture, making it ideal for bonding a wide range of materials including metal, plastic, and rubber. Cyanoacrylic acid has a strong bonding capability and is resistant to heat, water, and chemicals. It is often used in medical and veterinary settings for wound closure and tissue bonding, as well as in manufacturing and construction for quick and durable bonding of materials. However, it is important to handle cyanoacrylic acid carefully as it can cause skin and eye irritation, and exposure to its vapors can be harmful if inhaled.

InChI:InChI=1/C4H3NO2/c1-3(2-5)4(6)7/h1H2,(H,6,7)

Upstream product

• 50-00-0 formaldehyd 
• 52688-04-7 2-pentyl cyanoacetate 
• 5459-58-5 cyanoacetic acid butyl ester 
• 99842-68-9 2-phenylethyl cyanoacetate 
• 71091-89-9 n-octyl triflate 

Downstream Products

• 37891-36-4 tert-butyl 2-cyanoacrylate 
• 1245746-73-9 2-cyano-3-(7-(4-(diphenylamino)phenyl)-4,4'-dihexylclopentadithiophene-2-yl)acrylic acid 
• 1422536-23-9 2-cyano-3-(10-(4-methoxyphenyl)-10H-phenothiazin-3-yl)acrylic acid 
• 900182-08-3 3-(5-4-(diphenylamino)styryl)thiophen-2-yl-2-cyanoacrylic acid 
• 1398574-24-7 5-(4-bis(9,9-dimethyl-9H-fluoren-2-yl)amino)-10,15-diphenyl-20-(4-cyanoacrylphenyl)porphyrin zinc(II) 

Relevant articles and documents

PROCESS FOR PREPARING ELECTRON DEFICIENT OLEFINS

This invention relates to a process for preparing electron deficient olefins, such as 2-cyanoacrylates, using an acid catalyzed two-step process including an esterification reaction followed by a Knoevenagel condensation reaction.

Modified cyanoacrylate monomers and methods of preparation

Difunctional monomers of the formula, STR1 where R is an organic linking group derived from a diol or a dihalide of the formula X--R--X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.

Modified cyanoacrylate monomers and methods of preparation

Difunctional monomers of the formula, STR1 where R is an organic linking group derived from a diol or a dihalide of the formula X-R-X, where X is either chlorine, bromine, iodine, or hydroxy, are prepared by reacting a conjugated diene, exemplified by anthracene, with an ester of 2-cyanoacrylic acid to form the Diels-Alder adduct of the ester. The ester adduct is hydrolyzed to ultimately obtain either the Diels-Alder adduct of either 2-cyanoacrylic acid--alkali metal salt or 2-cyanoacryloyl halide. These latter intermediates are respectively reacted with either the dihalide or the diol to afford the bis-Diels-Alder adduct of the R substituted bis (2-cyanoacrylate) monomer. The protective diene group may then be removed, for example, by reaction with excess maleic anhydride and the resulting difunctional monomer isolated. The difunctional monomers thus prepared can be utilized as crosslinking agents in blends comprising one or more of these difunctional monomers and at least one monofunctional monomer, exemplified by an ester of 2-cyanoacrylic acid. Alternately, one or more difunctional monomers can be homopolymerized or copolymerized to a highly crosslinked polymer. The copolymerized compositions of the monomer blends are particularly useful as adhesives, especially in dental applications for coating or sealing enamel surfaces of teeth to allay decay, or for the bonding of brackets to teeth in orthodontics the bond being substantially more resistant to moisture than where the monofunctional monomer is used alone.