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| | (R)-(-)-3-Chloro-1,2-propanediol Basic information |
| Product Name: | (R)-(-)-3-Chloro-1,2-propanediol | | Synonyms: | (R)-3-CHLORO-1,2-PROPANEDIOL ,98%MIN;(R)-(-)-3-Chloro-1,2-propanediol,98%;(R)-(-)-3-Chloro-1;R(-)3-Chloro-1,3-propanediol;1,2-Propanediol, 3-chloro-, (2R)-;(R)-(-)-3-Chloro-1,2-propanediol, ee: 99%;(R)-(-)-alpha-Chlorohydrin
Glycerol (R)-(-)-alpha-Monochlorohydrin
(R)-(-)-alpha-Monochlorohydrin;(R)-(-)-3-Chloro-1,2 | | CAS: | 57090-45-6 | | MF: | C3H7ClO2 | | MW: | 110.54 | | EINECS: | 611-463-9 | | Product Categories: | Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound;57090-45-6 | | Mol File: | 57090-45-6.mol |  |
| | (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.) | | Fp | >230 °F | | storage temp. | Inert atmosphere,2-8°C | | solubility | soluble in Chloroform, Methanol | | pka | 13.28±0.20(Predicted) | | form | clear liquid | | color | Colorless to Brown | | Specific Gravity | 1.322 | | Optical Rotation | [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) |
| 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 |
| | (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. | | Antimicrobial activity | (R)-(-)-3-Chloro-1,2-propanediol has been shown to be active against bacterial strains such as corynebacterium and coryneform bacteria. | | 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 125-128C 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.
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| | (R)-(-)-3-Chloro-1,2-propanediol Preparation Products And Raw materials |
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