3-Chloropropionyl chloride Chemical Properties

Melting point:

-32 °C

Boiling point:

143-145 °C(lit.)

Density 

1.33 g/mL at 25 °C(lit.)

vapor pressure 

10.0 hPa

RTECS 

UC3934000

refractive index 

n20/D 1.457(lit.)

Flash point:

146 °F

storage temp. 

Flammables area

solubility 

Chloroform, Ethyl Acetate

form 

liquid

color 

red-brown

PH

<7 (H2O)

explosive limit

8.8-20.2%(V)

Water Solubility 

reacts

Sensitive 

Moisture Sensitive

BRN 

635814

Stability:

Moisture Sensitive

InChIKey

INUNLMUAPJVRME-UHFFFAOYSA-N

CAS DataBase Reference

625-36-5(CAS DataBase Reference)

NIST Chemistry Reference

Propanoyl chloride, 3-chloro-(625-36-5)

EPA Substance Registry System

Propanoyl chloride, 3-chloro- (625-36-5)

Safety Information

Hazard Codes 

T+

Risk Statements 

14-22-26-34-35-10

Safety Statements 

23-26-36/37/39-45-38-16-8

RIDADR 

UN 3390 6.1/PG 1

WGK Germany 

1

F 

21

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

I

HS Code 

29159080

MSDS

• Language:English Provider:3-Chloropropionyl chloride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Chloropropionyl chloride Usage And Synthesis

Description

3-Chloropropionyl chloride is an important bifunctional reagent. It is capable of acylation and possesses a 2-chloro-ethyl fragment (CH2CH2Cl), which can be subjected to nucleophilic substitution and serves as a masked vinyl group. It can be used as a starting material in many reactions to construct a variety of (hetero)cyclic compounds.

Chemical Properties

Clear colorless to dark brown liquid. Soluble in ethanol, ether and chloroform. Slightly soluble in water.

Uses

3-Chloropropionyl chloride is a reagent used in the synthesis of Beclamide (B119400), which is a chlorinated benzylpropanamide used as an anticonvulsant drug. It is used in the treatment of tonic-clonic seizyres and has sedative properties.

Preparation

3-Chloropropionyl chloride (1) is commercially available and can be prepared from β-propiolactone (2) and thionyl chloride.1 Other standard methods available for the preparation of acyl chlorides can also be applied: the reaction of acrylic acid (3) or 3-chloropropionic acid (4) with thionyl chloride, phosphoryl chloride, phosgene, or phosphorus trichloride.

Reactions

(1) The Friedel¨CCrafts acylation of tert-butylbenzene (5) with 3-chloropropionyl chloride (1) followed by cyclization provid- ed indanone 6, which was further transformed into urea derivative 7, a potent TRPV1 antagonist.

(2) A novel high-yielding one-pot microwave-assisted synthesis of condensed 5-substituted pyranoisoquinoline-1,6-diones 9 from 2-substituted isoquinoline-1,3-diones 8 and 3-chloropropionyl chloride (1) was reported.

(3) Acylation of 2-aminophenol (12) with 3-chloropropionyl chloride (1), followed by cyclization in the presence of polyphosphoric acid (PPA), gave benzoxazole 13, which was further reacted with 4-chlorophenyl-1-piperazine to yield the target benzo[d]oxazole analogue 14, a selective dopamine D4 receptor ligand.

Flammability and Explosibility

Non flammable

Synthesis

3-Chloropropionyl chloride is produced by reaction of acrylic acid with hydrogen chloride and phosgene in the presence of, for example,dimethylformamide as catalyst, or by reaction of propiolactone with thionyl chloride.

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