(R)-(-)-3-Chloro-1,2-propanediol Chemical Properties

Melting point:

-40°C

Boiling point:

213 °C(lit.)

alpha 

-0.9 º (neat)

Density 

1.321 g/mL at 20 °C(lit.)

vapor pressure 

0.04 mm Hg ( 25 °C)

refractive index 

n20/D 1.48(lit.)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

soluble in Chloroform, Methanol

form 

clear liquid

pka

13.28±0.20(Predicted)

Specific Gravity

1.322

color 

Colorless to Brown

optical activity

[α]20/D 1°, neat

Water Solubility 

soluble

BRN 

2202928

InChI

1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2/t3-/m0/s1

InChIKey

SSZWWUDQMAHNAQ-VKHMYHEASA-N

SMILES

OC[C@@H](O)CCl

LogP

0.5 at 25℃

CAS DataBase Reference

57090-45-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-41-68-62-36/37/38-23/25-21

Safety Statements 

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

RIDADR 

UN 2689 6.1/PG 3

WGK Germany 

3

RTECS 

TY4025000

F 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29053200

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials

Hazard Classifications

Acute Tox. 2 Inhalation
Acute Tox. 3 Oral
Carc. 2
Eye Dam. 1
Met. Corr. 1
Repr. 1B
Skin Irrit. 2
STOT RE 1 Oral
STOT SE 1 Oral

MSDS

• Language:English Provider:(R)-(-)-3-Glycerol alpha-monochlorohydrin
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(R)-(-)-3-Chloro-1,2-propanediol Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

(R)-(-)-3-Chloro-1,2-propanediol is used as a reagent in the synthesis of PA-824, which is a promising antituberculosis drug candidate that has been synthesized. It is also used in the manufacture of L-carnitine, which is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria.

Definition

ChEBI: The (R)-stereoisomer of 3-chloro-1,2-propanediol.

Health Hazard

The toxicological evaluation revealed that (R)-(-)-3-Chloro-1,2-propanediol was genotoxic in humans and had anti-fertility effects in male rats. The discharge of this compound into wastewater might cause serious environmental hazards[1].

Synthesis

Method 1 (CN202111237118.2):

After mixing and reacting (R)epichlorohydrin, (RR)Salen cobalt(III) catalyst completely, diluting with water, filtering, separating out the precipitate of (RR)Salen cobalt(III) catalyst, and then distilling the water under reduced pressure, and then distilling under reduced pressure to obtain (R)-3-chloro-1,2-propanediol. The (R)-3-chloro-1,2-propanediol prepared by this method has a chemical purity of >99.5% and a chiral purity (EE) of >99.8%, and has the advantages of simple synthesis, low cost, and easy to be applied industrially.

Method 2 (CN201510206172.9):

1) In the presence of an acidic catalyst, (S)-3-chloro-1,2-epoxypropane and water were subjected to a ring-opening reaction to obtain a ring-opening mixture; 

2) The base was subjected to a neutralization reaction with the ring-opening mixture to obtain the neutralized mixture; 

3) The alkali was neutralized with the ring-opening mixture to obtain the ring-opening mixture; 

4) The base was subjected to the ring-opening reaction with the ring-opening mixture;

5) The alkali was subjected to the ring-opening mixture. p>

3) Removing water from the neutralization mixture and filtering to obtain the filtrate; 

4) Fractionating the filtrate at 30-35 pa and 125-128??C to produce (R)-3-chloro-1,2-propanediol.

This method has excellent yields, and the (R)-3-chloro-1,2-propanediol has excellent total purity and low water content, especially the chiral purity can be as high as 99.5%.

References

[1] Yun‐Xu Yang. “Practical and Efficient Utilisation of (R)-3-chloro-1,2-Propanediol in Synthesis of L-Carnitine.” Journal of Chemical Research-s 93 1 (2011): 371–372.

(R)-(-)-3-Chloro-1,2-propanediol(57090-45-6)Related Product Information

• 1-Methoxy-2-propanol
• Propylene glycol
• 1,3-Propanediol
• 2-METHYL-1,3-PROPANEDIOL
• Glycerol
• 1-Methoxy-2-propyl acetate
• 1-Phenoxy-2-propanol
• (R)-(-)-1,2-Propanediol
• DI(PROPYLENE GLYCOL) BUTYL ETHER
• Nitroglycerin
• (R)-3-CHLORO-1,2-PROPANEDIOL ACETONIDE,(R)-3-CHLORO-1,2-PROPANEDIOL ACETONIDE
• 3-CHLORO-1,2-PROPANE-D5-DIOL
• 3-Chloro-1,2-propanediol
• Difluorochloromethane
• 3-Chloro-1,2-propanediol dinitrate,3-Chloro-1,2-propanediol dinitrate
• 3-Chloro-1,2-propanediol 1-acetate,3-Chloro-1,2-propanediol 1-acetate
• (S)-4-Chloromethyl-2,2-dimethyl-1,3-dioxolane
• (S)-(+)-3-Chloro-1,2-propanediol