3-Chloropropionyl chloride
3-Chloropropionyl chloride Basic information
- Product Name:
- 3-Chloropropionyl chloride
- Synonyms:
-
- 3-CHLOROPROPIONYL CHLORIDE FOR SYNTHESIS
- 3 - chlorine propionyl chloride
- -Chloropropanoylchloride
- Chloropropionyl chloride
- Propionyl chloride, 3-chloro-
- BETA-CHLOROPROPIONYL CHLORIDE
- 3-Chloropropionyl chlorode
- 3-CHLOROPROPIONYL CHLORIDE, TECH.
- CAS:
- 625-36-5
- MF:
- C3H4Cl2O
- MW:
- 126.97
- EINECS:
- 210-890-4
- Product Categories:
-
- Halogen compounds
- API Intermediate
- Acid Halides
- Carbonyl Compounds
- Organic Building Blocks
- Pyridines ,Halogenated Heterocycles
- Mol File:
- 625-36-5.mol
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
- 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 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.
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.
3-Chloropropionyl chloride Preparation Products And Raw materials
Preparation Products
Raw materials
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