(2S)-2-(chloromethyl)oxirane

• ChemBase ID: 85871
• Molecular Formular: C3H5ClO
• Molecular Mass: 92.5242
• Monoisotopic Mass: 92.00289246
• SMILES: O1C[C@H]1CCl
• Canonical SMILES: ClC[C@@H]1CO1
• InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
• InChIKey: BRLQWZUYTZBJKN-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(chloromethyl)oxirane
• IUPAC Traditional name: (S)-epichlorohydrin
• Synonyms: (2S)-(Chloromethyl)oxirane; (+)-2-(Chloromethyl)oxirane; (+)-Epichlorohydrin; (2S)-Epichlorohydrine; (S)-(+)-Epichlorohydrin; (S)-(Chloromethyl)oxirane; (S)-1-Chloro-2,3-epoxypropane; (S)-2-Chloromethyloxirane; (S)-Epichlorhydrin; 2(S)-Epichlorohydrin; (S)-Epichlorohydrin; (2S)-2-(chloromethyl)oxirane; (2R)-(-)-2-(Chloromethyl)oxirane; (R)-(-)-Epichlorohydrin; (2R)-(-)-3-Chloro-1,2-propenoxide; (S)-(+)-2-(Chloromethyl)oxirane; (S)-(+)-Epichlorohydrin; (S)-2-(chloromethyl)oxirane; (S)-(+)-1-Chloro-2,3-epoxypropane; (S)-(+)-2-(氯甲基)环氧乙烷; (S)-(+)-环氧氯丙烷

Database IDs

• CAS Number: 67843-74-7; 51594-55-9
• MDL Number: MFCD00077760; MFCD00077759
• Beilstein Number: 1420784
• PubChem SID: 162072987; 24868781; 24878439
• PubChem CID: 149428

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6772814
• LogD (pH = 7.4): 0.6772814
• Log P: 0.6772814
• Molar Refractivity: 20.057 cm^3
• Polarizability: 8.123073 Å^3
• Polar Surface Area: 9.23 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 114°C; 116-117°C; 92-93 °C/360 mmHg(lit.)
• Flash Point: 32 °C; 32°C; 32°C(90°F); 89.6 °F
• Auto Ignition Point: 1421 °F
• Density: 1.180; 1.183 g/mL at 25 °C(lit.)
• Refractive Index: 1.4380; n20/D 1.438; n20/D 1.438(lit.)
• Vapor Pressure: 12.5 mmHg ( 20 °C)
• Vapor Density: 3.2 (vs air)
• Optical Rotation: [α]20/D +35°, c = 1 in methanol; [α]20/D +44.5±1°, neat; +35 (c=1 in methanol)
• Hydrophobicity(logP): 0.46

Safety Information

• Storage Warning: Toxic/Flammable
• RTECS: RR0427100
• European Hazard Symbols: Toxic (T)
• UN Number: 2023; UN2023
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 45-10-23/24/25-34-43
• Safety Statements: 53-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Explode Limits: 21 %
• GHS Hazard statements: H226-H301-H311-H314-H317-H331-H350; H300-H310-H330-H317-H350-H314-H318-H226
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2023 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.5% (sum of enantiomers, GC); 95%; 98%; 98+%
• Grade: puriss.
• Optical Purity: ee: 97% (GLC)
• Empirical Formula (Hill Notation): C3H5ClO

DETAILS

Sigma Aldrich - 540080

Application
Chiral building block in the enantioselective syntheses of hydroxyisoxazolidines1 and (+)-cis-sylvaticin, a potential antitumor agent.2
Used in the total synthesis of Macquarimicins and in the total synthesis of the macrolide RK-397.
Used to synthesize inhibitors of fatty acid oxidation as potential metabolic modulators.
Packaging
5, 25 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Toronto Research Chemicals - E582310

S-enantiomer of 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, varnishe

REFERENCES

• Romano, K.P. et al.: Chem. Res. Toxicol., 20, 832 (2007)
• Smyth, H.F., et al.: J. Ind. Hyg. Toxicol., 30, 63 (2007)