16490-68-9

Usage

Uses

Used in Chemical Industry:
2-Chloroacrylamide is used as a key compound in the synthesis of polymers and coatings, contributing to the development of various industrial products. Its application in this industry is due to its reactive nature, which allows for the formation of polymers with specific properties.
Used in Safety and Health Regulations:
2-Chloroacrylamide is used as a reference point in the establishment of safety guidelines and regulations. Its toxic nature necessitates the development of strict safety procedures and the use of appropriate protective equipment to minimize health risks associated with exposure.
Used in Research and Development:
2-Chloroacrylamide serves as a subject of study in research aimed at understanding the effects of neurotoxic substances on human health. This research is crucial for the development of safer alternatives and the improvement of protective measures against toxic chemicals.

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

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

Relevant academic research and scientific papers

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.