(S)-Epichlorohydrin

Base Information

• Chemical Name: (S)-Epichlorohydrin
• CAS No.: 67843-74-7
• Molecular Formula: C3H5ClO
• Molecular Weight: 92.5251
• Hs Code.: 29038900
• European Community (EC) Number: 482-080-0
• UNII: SCR89B4R6O
• DSSTox Substance ID: DTXSID3045801
• Nikkaji Number: J146.651H
• Wikidata: Q27117047
• Metabolomics Workbench ID: 55539
• Mol file: 67843-74-7.mol

Synonyms:(S)-(+)-Epichlorohydrin;67843-74-7;(S)-Epichlorohydrin;(2S)-2-(chloromethyl)oxirane;(S)-2-(Chloromethyl)oxirane;(S)-(Chloromethyl)oxirane;s-epichlorohydrin;Epichlorohydrin, (+)-;Oxirane, (chloromethyl)-, (2S)-;(+)-epichlorohydrin;CCRIS 6388;Oxirane, (chloromethyl)-, (S)-;UNII-SCR89B4R6O;BRN 1420784;SCR89B4R6O;(S)-1-Chloro-2,3-epoxypropane;5-17-01-00021 (Beilstein Handbook Reference);(S)-3-Chloropropylene Oxide;(S)-(+)-Epichlorohydrin, 98%;2-(Chloromethyl)oxirane #;Epichlorhydrins;(s)-epichlorohydrine;(5)-epichlorohydrin;(s)-(+)-1-chloro-2,3-epoxypropane;(S)-epi-chlorohydrin;(S)-Chloromethyloxirane;(S)-(+)epichlorhydrin;(s)-(+)epichlorohydrin;(S)-(+)-Epichlorhydrin;(S)-2-chloromethyloxirane;(S)-2-chloromethyl-oxirane;BIDD:ER0280;DTXSID3045801;CHEBI:37145;(S)-(+)-2-chloromethyl-oxirane;STR07310;(S)-(+)-2-(Chloromethyl)oxirane;MFCD00077760;AKOS015995109;AC-7035;Oxirane, 2-(chloromethyl)-, (2S)-;(2S)-(+)-3-Chloro-1,2-propenoxide;LS-101031;AM20090809;CS-0015935;E0533;EN300-54612;EC 482-080-0;A835901;Q-200031;Q27117047

Chemical Property of (S)-Epichlorohydrin

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 13.8 mm Hg ( 21.1 °C)
• Melting Point: 57 °C(lit.)
• Refractive Index: n20/D 1.438(lit.)
• Boiling Point: 116.1 °C at 760 mmHg
• Flash Point: 33.9 °C
• PSA: 12.53000
• Density: 1.205 g/cm³
• LogP: 0.62400
• Storage Temp.: 2-8°C
• Water Solubility.: insoluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 92.0028925
• Heavy Atom Count: 5
• Complexity: 37.9

Purity/Quality:

99% ^*data from raw suppliers

(S)-Epichlorohydrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-10-23/24/25-34-43
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CCl
• Isomeric SMILES: C1[C@H](O1)CCl
• Uses: S-enantiomer of Epichlorohydrin, (S)-Epichlorohydrin), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links. It is used as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. Also, it is used as stabilizer. (S)-(+)-Epichlorohydrin is utilized for the synthesis of macquarimicins and hydroxyisoxazolidines and (+)-cis-sylvaticin, which is a potential antitumor agent. It is used to synthesize inhibitors of fatty acid oxidation as potential metabolic modulators. It acts as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels, lacquers and cement for celluloid. It is also used as a stabilizer and also useful as a bifunctional alkylating agent with the potential to form DNA cross-links. Used to synthesize inhibitors of fatty acid oxidation as potential metabolic modulators.

Technology Process of (S)-Epichlorohydrin

There total 23 articles about (S)-Epichlorohydrin 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: 93.7%

1,3-Dichloro-2-propanol (96-23-1) → (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7)

Guidance literature:

With halohydrin dehalogenase from Agrobacterium radiobacter AD₁ (HheC mutant P₁₇₅S/W₂₄₉P); In aq. phosphate buffer; pH=8; Concentration; Reagent/catalyst; Temperature; pH-value; Solvent; enantioselective reaction; Enzymatic reaction;

DOI:10.1016/j.catcom.2015.09.025

Reference yield: 93.0%

1,2-Epoxy-3-bromopropane (3132-64-7,82584-73-4) → (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + (2R)-3-bromo-1,2-propanediol (14437-88-8)

Guidance literature:

With (R,R)-Jacobsen catalyst; water; In tetrahydrofuran; at 4 ℃; for 24h;

DOI:10.1021/jo981332d

Reference yield: 87.0%

O-benzyl carbamate (621-84-1) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → (S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + [(R)-3-chloro-2-hydroxypropyl]carbamic acid benzyl ester (641617-19-8)

Guidance literature:

With air; 4-nitro-benzoic acid; (R,R)-((t-Bu)4-salen)Co(II); In various solvent(s); at 0 ℃; for 24h;

DOI:10.1021/ol048322l

upstream raw materials:

1,3-Dichloro-2-propanol

(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)

(R)-2,3-Dichloro-1-propanol

epichlorohydrin

Downstream raw materials:

(S)-1-chloroheptane-2-ol

(αS, 2R) 1-(2-exo-bicyclo<2,2,1>hept-2-ylphenoxy)-3-<(1-methylethyl)amino>-2-propanol

(αS, 2S) 1-(2-exo-bicyclo<2,2,1>hept-2-ylphenoxy)-3-<(1-methylethyl)amino>-2-propanol

(1R,5S)-methyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate

Refernces

• 1、 Xue, Feng,Ya, Xiangju,Xiu, Yuansong,Tong, Qi,Wang, Yuqi,Zhu, Xinhai,Huang, He. "Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium". . p. 629 - 637. Retrieved 2019/01/25.
• 2、 Blechschmidt, Daniel R.,Woodhouse, Matthew D.,Inagaki, Sebastien,Whitfield, Melita,Ogunsanya, Ayokunnumi,Yoder, Aaron,Lilly, Daniel,Heim, Eric W.,Soucie, Luke N.,Liang, Jian,Liu, Yu. "Aromatic donor-acceptor interaction promoted catalyst assemblies for hydrolytic kinetic resolution of epichlorohydrin". supporting information. p. 172 - 180. Retrieved 2019/01/04.