625-36-5 Usage
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–Crafts 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
Nonflammable
Synthesis
Different sources of media describe the Synthesis of 625-36-5 differently. You can refer to the following data:
1. 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.
2. 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.
Check Digit Verification of cas no
The CAS Registry Mumber 625-36-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 5 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 625-36:
(5*6)+(4*2)+(3*5)+(2*3)+(1*6)=65
65 % 10 = 5
So 625-36-5 is a valid CAS Registry Number.
InChI:InChI=1/C3H4Cl2O/c4-2-1-3(5)6/h1-2H2
625-36-5Relevant articles and documents
SYNTHESIS OF 7,7-DIMETHYLBICYCLO-OCTANE BY ACETYLATING A DICOBALTOHEXACARBONYL 4-METHYLPENT-3-EN-1-YNE-1 COMPLEX
Veretenov, A. L.,Gybin, A. S.,Smit, V. A.,Chertkov, V. A.,Shashkov, A. S.
, p. 1725 - 1733 (1989)
Dicobaltohexacarbonyl 4-methyl-pent-3-en-1-yne complexes have been acylated with acryloyl and crotonoyl tetrafluoroborates followed by methanolysis to make acylmethoxy adducts containing hem-dimethyl moieties.Conditions have been defined under which such adducts containing enone systems are selectively reduced to allyl alcohols with retention of the cobaltocarbonyl moieties.The latter can be converted by Quand-Poson reaction to the inaccessible polyfunctional derivatives of 7,7-dimethylbicyclooctane.
Preparation method of 3-chloropropionyl chloride
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Paragraph 0019-0021, (2021/10/27)
The invention provides a preparation method of 3-chloropropionyl chloride, wherein the preparation method comprises the following steps: mixing acrylic acid with a certain amount of catalyst, dropwise adding a certain amount of trichlorotoluene at a certain temperature under the protection of nitrogen, reacting for a period of time, and performing vacuum rectification to respectively obtain 3-chloropropionyl chloride and benzoyl chloride. The preparation method has the following beneficial effects: 1) acrylic acid and trichlorotoluene are adopted as raw materials, 3-chloropropionyl chloride is prepared in the presence of a catalyst, and benzoyl chloride with wide application is produced as a byproduct; the reaction route is environment-friendly, the process is simple, no emission is generated, and the requirement of atom economy is met; and the technical problem that toxic raw materials are used in the prior art is solved, and the technical problem that by-products polluting the environment are possibly generated in the prior art is also solved; and 2) the method is low in production cost, and in addition, the reaction route is combined with the specific reaction conditions, so that the yield of the obtained product is quite high and reaches 95% or above.
Preparation method of 3-chloropropionyl chloride
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Paragraph 0017-0021, (2021/03/05)
The invention relates to a preparation method of 3-chloropropionyl chloride. Beta-propiolactone and bis(trichloromethyl) carbonate react under the action of a catalyst to generate 3-chloropropionyl chloride. The preparation method of 3-chloropropionyl chloride is economical, environmentally friendly, simple in reaction route, little in waste gas, safe and controllable.
