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

Base Information

• Chemical Name: (R)-3-Chloro-1,2-propanediol
• CAS No.: 57090-45-6
• Molecular Formula: C3H7ClO2
• Molecular Weight: 110.54
• Hs Code.: 29053200
• European Community (EC) Number: 435-560-9,611-463-9
• UNII: 64YMO02KAE
• DSSTox Substance ID: DTXSID00205710
• Nikkaji Number: J72.478E
• Wikidata: Q27109076
• ChEMBL ID: CHEMBL1794186

Synonyms:57090-45-6;(R)-3-Chloro-1,2-propanediol;(R)-(-)-3-Chloro-1,2-propanediol;(2R)-3-chloropropane-1,2-diol;(R)-3-Chloropropane-1,2-diol;alpha-Chlorohydrin, (-)-;1,2-Propanediol, 3-chloro-, (R)-;CCRIS 7387;1,2-Propanediol, 3-chloro-, (2R)-;(-)-alpha-chlorohydrin;312745-09-8;UNII-64YMO02KAE;64YMO02KAE;CHEBI:18663;(R)-(-)-alpha-Monochlorohydrin;(2r)-3-chloro-1,2-propanediol;MFCD00135169;(2R)-(-)-3-Chloropropane-1,2-diol;(R)-MONOCHLOROHYDRIN;SCHEMBL58389;MLS001074871;(R)-(-)-alpha-Chlorohydrin;H-ARG-PRO-OHSULFATESALT;(R)-alpha-Glycerol chlorohydrin;CHEMBL1794186;DTXSID00205710;(R)-.ALPHA.-CHLOROHYDRIN;(R)-3-chloro-propane-1,2-diol;HMS2232L24;(2R)-3-chloranylpropane-1,2-diol;(R)-()-3-Chloro-1,2-propanediol;.ALPHA.-CHLOROHYDRIN, (-)-;AKOS015848751;AC-7038;AM81449;CS-W018500;GS-3238;(-)-3-CHLORO-1,2-PROPANEDIOL;Glycerol (R)-(-)-alpha-Monochlorohydrin;SMR000469516;(R)-(-)-3-Glycerol alpha-monochlorohydrin;LS-188656;M0967;EC 435-560-9;A831310;Q27109076;(R)-(-)-3-Chloro-1,2-propanediol, 97%, optical purity ee: 98% (GLC)

Chemical Property of (R)-3-Chloro-1,2-propanediol

Chemical Property:

• Appearance/Colour: clear light yellow liquid
• Vapor Pressure: 0.04 mm Hg ( 25 °C)
• Melting Point: - 40 °C
• Refractive Index: n20/D 1.48(lit.)
• Boiling Point: 213 °C at 760 mmHg
• PKA: 13.28±0.20(Predicted)
• Flash Point: 113.3 °C
• PSA: 40.46000
• Density: 1.303 g/cm³
• LogP: -0.42160
• Storage Temp.: 2-8°C
• Water Solubility.: soluble
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 110.0134572
• Heavy Atom Count: 6
• Complexity: 32

Purity/Quality:

≥99% ^*data from raw suppliers

(R)-(-)-3-Chloro-1,2-propanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-41-68-62-36/37/38-23/25-21
• Safety Statements: 26-28-39-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(CCl)O)O
• Isomeric SMILES: C([C@H](CCl)O)O

Technology Process of (R)-3-Chloro-1,2-propanediol

There total 30 articles about (R)-3-Chloro-1,2-propanediol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.4%

(R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Guidance literature:

With (R,R)-Salen-Co(II) catalyst; water; at 10 ℃; for 10h; Temperature; Time; Cooling with ice;

Reference yield: 49.5%

2,3-Dichloro-1-propanol (616-23-9) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4) + (S)-1,3-dichloro-1-propanol + epichlorohydrin (106-89-8,24969-06-0,13403-37-7)

Guidance literature:

With epoxide hydrolase from Agrobacterium radiobacter AD₁; halohydrin dehalogenase from Agrobacterium radiobacter AD₁; Tris-SO₄ buffer; In water; at 30 ℃; for 20h; pH=7.5; Further byproducts given;

DOI:10.1016/S0957-4166(99)00308-0

Reference yield: 46.0%

epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Guidance literature:

With water; dimeric chiral (salen)Co complex linked with Al; at 20 ℃; for 5h; Further Variations:; Catalysts; Product distribution;

DOI:10.1016/j.tetlet.2005.02.012

upstream raw materials:

3-methoxy-benzaldehyde

meta-hydroxybenzaldehyde

dimethyl sulfate

sulfuric acid

Downstream raw materials:

(4R)-4-(chloromethyl)-2,2-diphenyl-1,3-dioxolane

(R)-2-Chloromethyl-1,4-dioxa-spiro[4.5]decane

(R)-3-p-Tolylsulfanyl-propane-1,2-diol

(R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate

Refernces

A concise and convergent synthesis of PA-824

10.1021/jo1015807

The research focuses on the development of a concise and convergent four-step synthesis method for PA-824, a promising antituberculosis drug candidate. The purpose of this study was to improve upon the existing synthetic route used for large-scale production of PA-824, addressing concerns related to cost, safety, and efficiency. The new approach offers significant improvements by utilizing a safe alternative to the explosive 2,4-dinitroimidazole and a functionalized pseudosymmetrical glycidol derivative. Key chemicals used in the synthesis include (R)-3-chloro-1,2-propanediol, p-methoxybenzoyl chloride, 4-(trifluoromethoxy)benzyl alcohol, 2-chloro-4-nitroimidazole, and potassium hydroxide. The synthesis process culminates in the production of PA-824 with high yield and enantiomeric excess, demonstrating the potential for kilogram-scale production. The conclusions of the research highlight the efficiency, simplicity, and safety of the new synthetic method, which is crucial for the future production and distribution of affordable TB treatments, especially in developing regions where the disease is most prevalent.

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