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67843-74-7 molecular structure
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(2S)-2-(chloromethyl)oxirane

ChemBase ID: 85871
Molecular Formular: C3H5ClO
Molecular Mass: 92.5242
Monoisotopic Mass: 92.00289246
SMILES and InChIs

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

Cite this record

CBID:85871 http://www.chembase.cn/molecule-85871.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
67843-74-7
51594-55-9
MDL Number
MFCD00077759
MFCD00077760
Beilstein Number
1420784
PubChem SID
24878439
162072987
24868781
PubChem CID
149428

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 0.6772814  LogD (pH = 7.4) 0.6772814 
Log P 0.6772814  Molar Refractivity 20.057 cm3
Polarizability 8.123073 Å3 Polar Surface Area 9.23 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Boiling Point
114°C expand Show data source
116-117°C expand Show data source
92-93 °C/360 mmHg(lit.) expand Show data source
Flash Point
32 °C expand Show data source
32°C expand Show data source
32°C(90°F) expand Show data source
89.6 °F expand Show data source
Auto Ignition Point
1421 °F expand Show data source
Density
1.180 expand Show data source
1.183 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
1.4380 expand Show data source
n20/D 1.438 expand Show data source
n20/D 1.438(lit.) expand Show data source
Vapor Pressure
12.5 mmHg ( 20 °C) expand Show data source
Vapor Density
3.2 (vs air) expand Show data source
Optical Rotation
[α]20/D +35°, c = 1 in methanol expand Show data source
[α]20/D +44.5±1°, neat expand Show data source
+35 (c=1 in methanol) expand Show data source
Hydrophobicity(logP)
0.46 expand Show data source
Storage Warning
Toxic/Flammable expand Show data source
RTECS
RR0427100 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2023 expand Show data source
UN2023 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
2 expand Show data source
II expand Show data source
Risk Statements
45-10-23/24/25-34-43 expand Show data source
Safety Statements
53-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS05 expand Show data source
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
Explode Limits
21 % expand Show data source
GHS Hazard statements
H226-H301-H311-H314-H317-H331-H350 expand Show data source
H300-H310-H330-H317-H350-H314-H318-H226 expand Show data source
GHS Precautionary statements
P201-P261-P280-P301 + P310-P305 + P351 + P338-P310 expand Show data source
P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A expand Show data source
Personal Protective Equipment
Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 2023 6.1/PG 2 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.5% (sum of enantiomers, GC) expand Show data source
95% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
puriss. expand Show data source
Optical Purity
ee: 97% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C3H5ClO expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - 540080 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Romano, K.P. et al.: Chem. Res. Toxicol., 20, 832 (2007)
  • • Smyth, H.F., et al.: J. Ind. Hyg. Toxicol., 30, 63 (2007)
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PATENTS

PATENTS

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INTERNET

INTERNET

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