(R)-4-Chloro-3-hydroxybutyronitrile Chemical Properties

alpha 

11 º (neat)

Boiling point:

110 °C1 mm Hg(lit.)

Density 

1.250 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.474(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,Room Temperature

form 

clear liquid

pka

12.67±0.20(Predicted)

color 

Colorless to Light yellow

optical activity

[α]25/D +11.0°, neat

BRN 

1700586

InChI

InChI=1S/C4H6ClNO/c5-3-4(7)1-2-6/h4,7H,1,3H2/t4-/m1/s1

InChIKey

LHBPNZDUNCZWFL-SCSAIBSYSA-N

SMILES

C(#N)C[C@@H](O)CCl

CAS DataBase Reference

84367-31-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-21

HS Code 

29269090

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:(R)-4-Chloro-3-hydroxybutyronitrile
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(R)-4-Chloro-3-hydroxybutyronitrile Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid

Uses

(-)-Carnitine and (-)-γ-amino-β-hydroxybutyric acid have been prepared using this synthon.

Uses

(R)-(+)-4-Chloro-3-hydroxybutyronitrile is a chiral reagent used in asymmetric catalysis in organic synthesis.

Synthesis

(1) 19.19g (0.174mol) (R)-(-)-chloroglycerol, 50ml dichloromethane into a 250ml three-necked flask, under the condition of ice bath, 22.74g (0.191oml) dichlorosulfoxide was added slowly dropwise. React for 1h, add 40ml of water, the organic layer was washed twice with saturated saline, the aqueous layer was washed twice with ethyl acetate, the organic layers were combined and dried with anhydrous sodium sulfate. Filtration, filtrate concentrated under reduced pressure, obtained 27.23g colorless liquid. That is, cyclic sulfinic acid ester intermediate, without purification, directly used in the next step of the reaction, yield 100%.

(2) cast 10g (0.064mol) cyclic sulfinic acid ester, 30ml methanol to 100ml three-necked bottle, room temperature conditions, add 5.21g (0.08mol) KCN, stirring for 10min, and then raised to 50 ??, stirring vigorously for 12h. Concentrate under reduced pressure, add 15 ml of ethyl acetate and slowly add 20% H2SO4 solution dropwise. After stirring for 5h, add dilute NaCO3 solution washed twice, water washed twice, saturated brine washed once, the aqueous layer was washed with ethyl acetate, the organic layer was combined, and anhydrous sodium sulfate was added to dry. Decompression distillation was used to collect the 89-90??C/<1 mmHg fraction, yielding 6.51 g of colorless liquid, i.e., chlorobutyronitrile intermediate, with a yield of 85%.

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