(2R)-2-(chloromethyl)oxirane

• ChemBase ID: 85872
• Molecular Formular: C3H5ClO
• Molecular Mass: 92.5242
• Monoisotopic Mass: 92.00289246
• SMILES: O1[C@H](C1)CCl
• Canonical SMILES: ClC[C@H]1CO1
• InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m0/s1
• InChIKey: BRLQWZUYTZBJKN-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 67843-74-7; 51594-55-9
• EC Number: 424-280-2
• MDL Number: MFCD00077759; MFCD00077760
• Beilstein Number: 1420785
• PubChem SID: 162072988; 24878437; 24868777
• PubChem CID: 2734062

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(lit.); 114°C; 116-117°C
• Flash Point: 32 °C; 32°C(90°F); 33°C; 89.6 °F
• Auto Ignition Point: 772 °F
• Density: 1.18; 1.180; 1.180 g/mL at 20 °C(lit.)
• Refractive Index: 1.4380; n20/D 1.438; n20/D 1.438(lit.)
• Vapor Pressure: 10 mmHg ( 16.6 °C)
• Vapor Density: 3.29 (vs air)
• Optical Rotation: [α]20/D -34°, 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/Corrosive/Carcinogenic
• RTECS: RR0427000
• 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: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• Explode Limits: 21 %
• GHS Hazard statements: H226-H301-H311-H314-H317-H331-H350; H301-H311-H331-H317-H350-H314-H226
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P310; P210-P301+P310-P303+P361+P353-P305+P351+P338-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+%; 99%
• Grade: puriss.
• Optical Purity: ee: 97% (GLC); ee: 98% (GLC)
• Empirical Formula (Hill Notation): C3H5ClO

DETAILS

Sigma Aldrich - 540072

Application
Building block for the synthesis of a key intermediate in the synthesis of stable PGI2 analogue UT-15.1
Used in the synthesis of chiral morpholines and dioxanes via a Mitsunobu diol-cyclization. Chiral building block in the enantioselective synthesis of trans-2,4-disubstituted piperidines.
Packaging
5, 25 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Sigma Aldrich - 45325

Other Notes
Chiral building block which reacts with various nucleophiles at the epoxide function yielding chlorohydrins 1,2,3

Toronto Research Chemicals - E582305

R-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)