7324-02-9

Basic information

• Product Name: ALLYL-2-CYANOACRYLATE
• Synonyms: ALLYLCYANOACRYLATE;Prop-2-enyl-2-cyanpro-2-enoate;2-Cyanoacrylic acid allyl ester;2-Propenyl 2-cyanopropenoate;α-Cyanoacrylic acid allyl ester;2-Propenoic acid, 2-cyano-, 2-propen-1-yl ester;2-Propenoic acid, 2-cyano-, 2-propenyl ester;Einecs 230-796-7
• CAS NO: 7324-02-9
• Molecular Formula: C₇H₇NO₂
• Molecular Weight: 137.14
• EINECS: 230-796-7
• Mol File: 7324-02-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 219.3°C at 760 mmHg
• Flash Point: 92.9°C
• Appearance: /
• Density: 1.047g/cm³
• Vapor Pressure: 0.12mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: ALLYL-2-CYANOACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYL-2-CYANOACRYLATE(7324-02-9)
• EPA Substance Registry System: ALLYL-2-CYANOACRYLATE(7324-02-9)

Safety Data

• Hazardous Substances Data: 7324-02-9(Hazardous Substances Data)

Usage

General Description

ALLYL-2-CYANOACRYLATE, also known as cyanoacrylate, is a fast-acting adhesive that is commonly used in medical applications, particularly in wound closure and surgery. It is a clear, strong adhesive that forms bonds quickly when it comes into contact with moisture, making it ideal for sealing cuts and wounds. In addition to its medical uses, cyanoacrylate is also used in a variety of industrial and household applications, such as bonding plastics, rubber, and metals. However, it is important to handle cyanoacrylate with care as it can cause irritation and allergic reactions if it comes into contact with skin. Overall, allyl-2-cyanoacrylate is a versatile and widely used adhesive with a range of practical applications.

InChI:InChI=1/C7H7NO2/c1-3-4-10-7(9)6(2)5-8/h3H,1-2,4H2

Synthetic route

allyl cyanoacetate (13361-32-5) → allyl 2-cyanoacrylate (7324-02-9)

Conditions	Yield
With hydroquinone at 20℃; for 0.0833333h; Neat (no solvent);	80%

formaldehyd (50-00-0) + allyl cyanoacetate (13361-32-5) → allyl 2-cyanoacrylate (7324-02-9)

Conditions	Yield
With piperidine; phosphorus pentoxide; toluene-4-sulfonic acid; hydroquinone 1.) i-PrOH, 60 deg C, 2.) 170-190 deg C; Yield given. Multistep reaction;

allyl 2-cyanoacrylate (7324-02-9) + ethane-1,2-dithiol (540-63-6) → 3-[2-(2-Allyloxycarbonyl-2-cyano-ethylsulfanyl)-ethylsulfanyl]-2-cyano-propionic acid allyl ester (139022-57-4)

Conditions	Yield
In benzene for 3h;	65%

allyl 2-cyanoacrylate (7324-02-9) + tris(1-methylethyl)phosphine (6476-36-4) → C16H28NO2P

Conditions	Yield
With methanesulfonic acid In diethyl ether; Petroleum ether cooling;	47.3%

allyl 2-cyanoacrylate (7324-02-9) + ethyl aminocrotonate (626-34-6, 7318-00-5, 41867-20-3) → 2-[1-Amino-eth-(E)-ylidene]-4-cyano-pentanedioic acid 5-allyl ester 1-ethyl ester

Conditions	Yield
In benzene

allyl 2-cyanoacrylate (7324-02-9) + C10H19NO6 → (2S)-2-(7-(2-cyanoacryloyloxy)-2-hydroxyheptylamino)-2-deoxy-β-D-glucopyranose

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide In water at 70℃;

allyl 2-cyanoacrylate (7324-02-9) + C18H27NO10 → (2S)-2-(7-(2-cyanoacryloyloxy)-2-hydroxyheptylamino)-2-deoxy-β-D-glucopyranose 1,3,4,6-tetraacetate

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide In water at 70℃;

allyl 2-cyanoacrylate (7324-02-9) + Reaxys ID: 31988353 → Reaxys ID: 32048263

allyl 2-cyanoacrylate (7324-02-9) + N-(pent-4-en-1-yl)gallamide → N-(6-(2-cyanoacryloyloxy)octyl)gallamide

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide In water at 70℃;

allyl 2-cyanoacrylate (7324-02-9) + N-(non-8-en-1-yl)gallamide → N-(6-(2-cyanoacryloyloxy)dodecyl)gallamide

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide In water at 70℃;

allyl 2-cyanoacrylate (7324-02-9) + Reaxys ID: 32622503 → Reaxys ID: 32622502

allyl 2-cyanoacrylate (7324-02-9) + N-(prop-2-en-1-yl)gallamide → N-(6-(2-cyanoacryloyloxy)hexyl)gallamide

Conditions	Yield
With hydrogenchloride; dibenzoyl peroxide In water at 70℃;

Upstream product

• 13361-32-5 allyl cyanoacetate 
• 50-00-0 formaldehyd 

Relevant articles and documents

IMINIUM SALTS AND METHODS OF PREPARING ELECTRON DEFICIENT OLEFINS USING SUCH NOVEL IMINIUM SALTS

This invention relates to novel iminium salts, which may be in the form of ionic liquids, and a process for producing electron deficient olefins, such as 2-cyanoacrylates, using such an iminium salt, for instance in the form of an ionic liquid.