16490-68-9

Basic information

• Product Name: 2-chloroacrylamide
• Synonyms: 2-chloroacrylamide;2-Chloro-2-propenamide;Einecs 240-547-4;2-PropenaMide, 2-chloro-
• CAS NO: 16490-68-9
• Molecular Formula: C₃H₄ClNO
• Molecular Weight: 105.52296
• EINECS: 240-547-4
• Mol File: 16490-68-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 94 °C(Solv: benzene (71-43-2))
• Boiling Point: 253.525 °C at 760 mmHg
• Flash Point: 107.128 °C
• Appearance: /
• Density: 1.239 g/cm³
• Vapor Pressure: 0.0182mmHg at 25°C
• Refractive Index: 1.474
• PKA: 10.76±0.50(Predicted)
• CAS DataBase Reference: 2-chloroacrylamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloroacrylamide(16490-68-9)
• EPA Substance Registry System: 2-chloroacrylamide(16490-68-9)

Safety Data

• Hazardous Substances Data: 16490-68-9(Hazardous Substances Data)

Usage

General Description

2-Chloroacrylamide is a chemical compound that is primarily used in the production of polymers and coatings. It is a colorless liquid, a powerful lachrymator, and also has properties as a neurotoxin. 2-chloroacrylamide can cause certain health related problems such as eye irritation, delayed sensory and motor nerve conduction, and skin sensitization. Due to its toxic nature, exposure or inappropriate handling of 2-chloroacrylamide should be avoided, therefore its use is carefully regulated by safety guidelines, often requiring the use of proper safety equipment and adherence to strict safety procedures.

InChI:InChI=1/C3H4ClNO/c1-2(4)3(5)6/h1H2,(H2,5,6)

Synthetic route

2-Chloroacrylonitrile (920-37-6) → 2-chloroacrylamide (16490-68-9)

Conditions	Yield
With 4-(benzyloxy)-1-hydroxy-2,2,6,6-tetramethylpiperidine In dichloromethane at 50℃; for 1h;	69%
With sulfuric acid

α,β-dichloropropionamide (19433-84-2) → 2-chloroacrylamide (16490-68-9)

Conditions	Yield
With sodium hydroxide; hydroquinone In water

2-chloroacrylamide (16490-68-9) → S-<2-Carbamoyl-2-chlorethyl>thioacetamid-hydrochlorid

Conditions	Yield
With hydrogenchloride In acetonitrile for 1h; Ambient temperature;	98%

2-chloroacrylamide (16490-68-9) + benzenecarbothioamide (2227-79-4) → S-<2-Carbamoyl-2-chlorethyl>thiobenzamid-Hydrochlorid (116077-25-9)

Conditions	Yield
With hydrogenchloride In dichloromethane for 2h; Ambient temperature;	96%

2-(azidomethyl)-1,3-difluorobenzene + 2-chloroacrylamide (16490-68-9) → rufinamide

Conditions	Yield
With triethylamine In ethanol for 24h; Temperature; Time; Reagent/catalyst; Solvent; Reflux;	76%

2-chloroacrylamide (16490-68-9) + sodium methansulfinate (20277-69-4) → 2-Chlor-3-methylsulfonyl-propionamid (10568-98-6)

Conditions	Yield
With sulfuric acid

2-chloroacrylamide (16490-68-9) + sodium ethanesulfinate (20035-08-9) → 2-Chloro-3-ethanesulfonyl-propionamide (10568-87-3)

Conditions	Yield
With hydrogenchloride

1-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyrrolidine (57440-57-0) + 2-chloroacrylamide (16490-68-9) → 1',5',7',8'-tetrahydrospiro<1,3-dioxolane-2,6'(2'H)-quinolin>-2'-one (120686-08-0)

Conditions	Yield
With water 1) dioxane, 12h, reflux 2) 10h, reflux; Multistep reaction;

Upstream product

• 920-37-6 2-Chloroacrylonitrile 
• 19433-84-2 α,β-dichloropropionamide 

Downstream Products

• 116077-25-9 S-<2-Carbamoyl-2-chlorethyl>thiobenzamid-Hydrochlorid 
• 106308-44-5 rufinamide 
• 120686-08-0 1',5',7',8'-tetrahydrospiro<1,3-dioxolane-2,6'(2'H)-quinolin>-2'-one 

Relevant articles and documents

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SYNTHESIS OF 3-(VINYLSULFONYL)ACRYLAMIDE

3-(Vinylsulfonyl)acrylamide was synthesized by the addition of 2-chloroethane-1-sulfinic acid to 2-chloroacrylamide and dehydrochlorination of the obtained 3-(2-chloroethylsulfonyl)-2-chloropropionamide.