(S)-(-)-Methyl 2-chloropropionate Chemical Properties

Boiling point:

80-82 °C110 mm Hg(lit.)

Density 

1.143 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.417(lit.)

Flash point:

101 °F

storage temp. 

-20°C

form 

clear liquid

color 

Colorless to Almost colorless

optical activity

[α]20/D 26°, neat

BRN 

1720589

InChI

InChI=1S/C4H7ClO2/c1-3(5)4(6)7-2/h3H,1-2H3/t3-/m0/s1

InChIKey

JLEJCNOTNLZCHQ-VKHMYHEASA-N

SMILES

C(OC)(=O)[C@@H](Cl)C

CAS DataBase Reference

73246-45-4(CAS DataBase Reference)

NIST Chemistry Reference

Propanoic acid, 2-chloro-, methyl ester, (s)-(73246-45-4)

EPA Substance Registry System

Propanoic acid, 2-chloro-, methyl ester, (2S)- (73246-45-4)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-36-48/22

Safety Statements 

23-26-36

RIDADR 

UN 2933 3/PG 3

WGK Germany 

1

F 

19

HazardClass 

3

PackingGroup 

III

HS Code 

29159000

MSDS

• Language:English Provider:SigmaAldrich

(S)-(-)-Methyl 2-chloropropionate Usage And Synthesis

Uses

(-)-Methyl α-Chloropropionate is used in the preparation of TIPTP which is a therapeutic agent for rheumatoid arthritis.

Uses

Chiral starting material.

Synthesis

Step I, preparation of Vilmerier reagent: 71.4 g (0.6 mol) of thionyl chloride was added to a 250 mL four-necked flask, cooled to 5~10°C in an ice-water bath, and 50.4 g (0.69 mol) of dry N,N-dimethylformamide was slowly added, the reaction was exothermic obviously, and mechanically stirred for 2 h to obtain a colorless Vilmerier reagent solution. Step II, Synthesis of methyl (S)-2-chloropropionate: a small amount of dioxane was added to the Vilmerier reagent solution obtained in Step I via a constant pressure dropping funnel at 20~30°C to form a mixed solution. Subsequently, 62.4 g (0.6 mol) of (R)-lactic acid methyl ester was slowly added dropwise to the mixed solution, and the reaction was markedly exothermic and gas was generated. After the dropwise addition, the reaction was continued with stirring and heated to 55°C for 6 h to obtain a solution of methyl (S)-2-chloropropionate. After the reaction was completed, the reaction mixture was cooled. Step III, post-treatment: the (S)-2-chloropropionic acid methyl ester solution obtained in Step II was washed, desolventized and distilled to obtain the product (S)-2-chloropropionic acid methyl ester 54.4 g, with 86% yield and 87% optical purity.

References

[1] Patent: CN103232344, 2016, B. Location in patent: Paragraph 0036-0039

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