(S)-(-)-2-Chloropropionic acid Chemical Properties

Melting point:

4 °C

Boiling point:

77 °C/10 mmHg (lit.)

alpha 

-14.5 º (c=neat)

Density 

1.249 g/mL at 25 °C (lit.)

vapor pressure 

5hPa at 20℃

refractive index 

n20/D 1.436

Flash point:

140 °F

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

pka

2.83(at 25℃)

form 

Liquid

color 

Clear light yellow

Water Solubility 

soluble

BRN 

1720257

LogP

0.82 at 20.5℃

CAS DataBase Reference

29617-66-1(CAS DataBase Reference)

NIST Chemistry Reference

(S)-(-)-2-chloropropionic acid(29617-66-1)

Safety Information

Hazard Codes 

C

Risk Statements 

21/22-35-48/22

Safety Statements 

23-26-28-36/37/39-45

RIDADR 

UN 2511 8/PG 3

WGK Germany 

1

RTECS 

UA2451950

HazardClass 

8

PackingGroup 

III

HS Code 

29159080

MSDS

• Language:English Provider:2-Chloropropanoic acid
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(S)-(-)-2-Chloropropionic acid Usage And Synthesis

Description

(S)-2-chloropropanoic acid is a monocarboxylic acid that is propanoic acid substituted at position 2 by a chloro group (the S-enantiomer). It has a role as a neurotoxin. It is a monocarboxylic acid and a chlorocarboxylic acid. It is functionally related to propionic acid. It is a conjugate acid of a (S)-2-chloropropanoate.

Chemical Properties

Colourless Oil

Uses

Through the stereo displacement of (S)-(-)-2-Chloropropionic acid PPAR Agonist can be synthesized via asymmetric hydrogenation of a cinnamic acid derivative.

Definition

ChEBI: A monocarboxylic acid that is propanoic acid substitued at position 2 by a chloro group (the S-enantiomer).

General Description

2-Chloropropionic acid is an essential raw material for synthesising pesticides, dyes and medicines. Its application involves many sectors of the national economy and people's daily lives. It is an essential fine chemical product. In particular, (S)-(-)-2-Chloropropionic acid is a crucial intermediate for synthesising highly efficient and low-toxic aromatic oxygen propionic acid herbicides. For example, it can be used to synthesize (R)-2-(4-hydroxyphenoxy) propionic acid (ester) intermediates, fenthionyl, fenthionyl, fenthionyl, etc. At present, the preparation methods of (S)-(-)-2-chloropropionic acid and (R)-(+)-2-chloropropionic acid include: (1) chemical resolution method; (2) bioenzymatic resolution method; (3) chromatographic resolution method; (4) asymmetric synthesis method, etc.

Flammability and Explosibility

Non flammable

Synthesis

JP 061172846 provides a method for resolving racemic 2-chloropropionic acid using an optically active 2-aryl-2-isopropylethylamine as a resolving agent to obtain (S)-(-)-2-Chloropropionic acid (yield 24.2% and enantiomeric excess 83.2%). DE 4328231 provides a method for catalyzing the hydrolysis of 2-chloropropionic acid esters by a hydrolase (Pseudomonas Lipase) to hydrolyze (S)-2-chloropropionic acid esters to generate (S)-(-)-2-Chloropropionic acid.

Purification Methods

Purify the acid by fractionating twice through a 115cm Podbielniak column (p 11, calculated 50 theoretical plates at atmospheric pressure) using a take-off ratio of 1:5. The acid chloride is prepared by dissolving the acid in SOCl2, adding a few drops of PCl3, refluxing and then distilling through a 30cm column, b 53o/100mm, [] -4.6o (neat), d 1.2689, n1.4368. [Fu et al. J Am Chem Soc 76 6954 1954, Beilstein 2 IV 745.]

(S)-(-)-2-Chloropropionic acid(29617-66-1)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
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• (S)-2-CHLOROSUCCINIC ACID
• DIISOPROPYL CHLOROMALONATE
• 2,2-DICHLOROPROPIONIC ACID SODIUM SALT
• (S)-2-CHLOROPROPIONIC ACID LSOBUTYL ESTER,(S)-2-Chloropropionic acid 2-methylpropyl ester