3-Chloropropionyl chloride Property

Melting point:

-32 °C

Boiling point:

143-145 °C(lit.)

Density 

1.33 g/mL at 25 °C(lit.)

vapor pressure 

10.0 hPa

refractive index 

n20/D 1.457(lit.)

RTECS 

UC3934000

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H330Fatal if inhaled

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Chloropropionyl chloride Chemical Properties,Usage,Production

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.