(R)-(-)-3-Chloro-1,2-propanediol
[CAS# 57090-45-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: (R)-(-)-3-Chloro-1,2-propanediol
• Synonyms: (R)-(-)-3-Glycerol alpha-monochlorohydrin
• Molecular Formula: C₃H₇ClO₂
• Molecular Weight: 110.54
• CAS Registry Number: 57090-45-6
• EC Number: 435-560-9
• SMILES: C([C@H](CCl)O)O

Properties

• Density: 1.322
• Boiling point: 213 °C
• Refractive index: 1.479-1.481
• alpha: -0.9 ° (neat)
• Water solubility: soluble

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS08 Danger
• Risk Statements: H290-H300-H301-H311-H315-H318-H330-H331-H351-H360-H370-H372
• Safety Statements: P203-P234-P260-P261-P262-P264-P264+P265-P270-P271-P280-P284-P301+P316-P302+P352-P304+P340-P305+P354+P338-P308+P316-P316-P317-P318-P319-P320-P321-P330-P332+P317-P361+P364-P362+P364-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - single exposure	STOT SE	1	H370
Carcinogenicity	Carc.	2	H351
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	3	H311

• Transport Information: UN 2689

Discovery and Applications

(R)-(-)-3-Chloro-1,2-propanediol is a chiral compound that has gained importance due to its role as an intermediate in the synthesis of various chemicals, pharmaceuticals, and biologically active molecules. The discovery of this compound is rooted in the study of chiral halohydrins, which are key building blocks in asymmetric synthesis. The (R)-enantiomer of 3-chloro-1,2-propanediol is of particular interest due to its optical activity and its application in producing enantiomerically pure compounds.

This compound has the chemical structure of a chloro alcohol, with a hydroxyl group at both the first and second carbon positions and a chlorine atom at the third. The (R)-configuration indicates that the molecule has a specific three-dimensional arrangement, which is significant for its reactivity and application in stereospecific synthesis. The development of methods for synthesizing (R)-(-)-3-chloro-1,2-propanediol came from the need for enantiopure intermediates in the pharmaceutical and fine chemical industries.

One of the major applications of (R)-(-)-3-chloro-1,2-propanediol is in the synthesis of chiral epoxides. This is achieved through a ring-closure reaction, where the chloro group is displaced by a nucleophile, forming an epoxide. Chiral epoxides are essential intermediates in the production of a variety of pharmaceuticals and agrochemicals, including beta-blockers, which are used to treat cardiovascular conditions. The stereochemistry of the epoxide formed from (R)-(-)-3-chloro-1,2-propanediol is crucial in determining the biological activity of the final product, as many drugs require a specific three-dimensional configuration to be effective.

In addition to its use in producing epoxides, (R)-(-)-3-chloro-1,2-propanediol is also used as a precursor in the synthesis of glycerol derivatives. These derivatives are applied in the production of surfactants, emulsifiers, and other functional additives in the cosmetics and food industries. The chiral nature of the molecule allows for the production of optically active glycerol derivatives, which can be important in applications where stereochemistry influences the performance of the final product.

The compound has also been investigated in the context of organic synthesis, particularly in the field of asymmetric catalysis. Researchers have explored the use of (R)-(-)-3-chloro-1,2-propanediol in the development of new catalysts for enantioselective reactions, where its stereochemistry helps induce chirality in other molecules. This opens pathways for creating complex, enantiomerically pure compounds that are otherwise difficult to synthesize.

Environmental and safety concerns have also driven research into the handling and processing of (R)-(-)-3-chloro-1,2-propanediol. The compound is classified as toxic and must be used with caution, especially in large-scale industrial applications. Researchers have focused on developing more environmentally friendly methods for its production and utilization, aiming to reduce harmful byproducts and improve the safety profile of processes involving this substance.

References

2021. Biocatalytic approaches for the synthesis of optically pure vic-halohydrins. Applied Microbiology and Biotechnology, 105(8).
DOI: 10.1007/s00253-021-11266-2

2006. Synthesis of 1,2-Difunctionalized Fine Chemicals through Catalytic, Enantioselective Ring-Opening Reactions of Epoxides. Synthesis, 2006(22).
DOI: 10.1055/s-2006-950348

1992. Resolution and some properties of enzymes involved in enantioselective transformation of 1,3-dichloro-2-propanol to (R)-3-chloro-1,2-propanediol by Corynebacterium sp. strain N-1074. Journal of Bacteriology, 174(23).
DOI: 10.1128/jb.174.23.7613-7619.1992