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 Structure
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
Fp 146 °F
storage temp. Flammables area
solubility Chloroform, Ethyl Acetate
form liquid
color red-brown
PH<7 (H2O)
explosive limit8.8-20.2%(V)
Water Solubility reacts
Sensitive Moisture Sensitive
BRN 635814
Stability:Moisture Sensitive
InChIKeyINUNLMUAPJVRME-UHFFFAOYSA-N
CAS DataBase Reference625-36-5(CAS DataBase Reference)
NIST Chemistry ReferencePropanoyl chloride, 3-chloro-(625-36-5)
EPA Substance Registry SystemPropanoyl 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
21
TSCA Yes
HazardClass 6.1
PackingGroup I
HS Code 29159080
MSDS Information
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3-Chloropropionyl chloride Usage And Synthesis
Description3-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 PropertiesClear colorless to dark brown liquid. Soluble in ethanol, ether and chloroform. Slightly soluble in water.
Uses3-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.
Preparation3-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.
Synthesis of 3-Chloropropionyl chloride
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.
Reactions of 625-36-5_1
(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.
Reactions of 625-36-5_2
(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 ExplosibilityNonflammable
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.
Synthesis3-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.
2,2-DICHLOROCYCLOPROPANECARBONYL CHLORIDE DIMETHYLMALONYL CHLORIDE 3-CHLOROTETRAFLUOROPROPIONYL CHLORIDE 3-Chloropivaloyl chloride 2,3-DICHLOROPROPIONYL CHLORIDE Malonyl chloride 2-CHLOROPROPIONYL CHLORIDE [1-14C] [R,(-)]-2-Chloropropionyl chloride 3,4-DICHLOROPENTAFLUOROBUTYRYL CHLORIDE [S,(+)]-2-Chloropropionyl chloride Cyclopropanecarbonyl chloride, 2,2-dichloro-1-methyl- (9CI) DIETHYLMALONIC ACID DICHLORIDE 2-CHLOROPROPIONYL CHLORIDE,ALPHA-CHLOROPROPIONYL CHLORIDE (R)-3-CHLORO-2-METHYLPROPIONYL CHLORIDE A-CHLOROPROPIONYL CHLORIDE 3,5,6-TRICHLOROOCTAFLUOROHEXANOYL CHLORIDE 3-Chloropropionyl chloride alpha-chloroproionyl chloride

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