| Identification | More | [Name]
(S)-(+)-Epichlorohydrin | [CAS]
67843-74-7 | [Synonyms]
1-CHLORO-2,3-EPOXYPROPANE
2,3-EPOXYPROPYL CHLORIDE
(+/-)-2-(CHLOROMETHYL)OXIRANE
2-(CHLOROMETHYL)OXIRANE
3-Chloro-1，2-epoxypropane
3-CHLOROPROPYLENE OXIDE
AKOS BBS-00004288
ALPHA-EPICHLOROHYDRIN
CHLOROMETHYLOXIRANE
EPICHLORHYDRIN
(+/-)-EPICHLOROHYDRIN
EPICHLOROHYDRIN
EPICHLOROHYDRINE
G-CHLOROPROPYLENE OXIDE
OXIRANE, (CHLOROMETHYL)-, (2S)-
(S)-(+)-1-CHLORO-2,3-EPOXYPROPANE
(S)-1-CHLORO-2,3-EPOXYPROPANE
S(+)-2-(CHLOROMETHYL)OXIRANE
(S)-3-CHLOROPROPYLENE OXIDE
(S)-(+)-CHLOROMETHYLOXIRANE | [EINECS(EC#)]
203-439-8 | [Molecular Formula]
C3H5ClO | [MDL Number]
MFCD00005132 | [Molecular Weight]
92.52 | [MOL File]
67843-74-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless to light yellow liqui | [Melting point ]
−57 °C(lit.)
| [alpha ]
34 º (589nm, c=1, MeOH) | [Boiling point ]
92-93 °C360 mm Hg(lit.)
| [density ]
1.183 g/mL at 25 °C(lit.)
| [vapor density ]
3.2 (vs air)
| [vapor pressure ]
13.8 mm Hg ( 21.1 °C)
| [refractive index ]
n20/D 1.438(lit.)
| [Fp ]
93 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Liquid | [color ]
Clear colorless to very pale yellow | [explosive limit]
21% | [Optical Rotation]
[α]20/D +35°, c = 1 in methanol | [Water Solubility ]
insoluble | [BRN ]
1420784 | [Dielectric constant]
22.9（20℃） | [InChI]
1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1 | [InChIKey]
BRLQWZUYTZBJKN-GSVOUGTGSA-N | [SMILES]
ClC[C@@H]1CO1 | [CAS DataBase Reference]
67843-74-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R45:May cause cancer.
R10:Flammable.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R34:Causes burns.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2023 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
TX4900000
| [Autoignition Temperature]
1421 °F | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29103000 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 3 Dermal
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral
Carc. 1B
Eye Dam. 1
Flam. Liq. 3
Skin Corr. 1B
Skin Sens. 1 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to light yellow liqui | [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.
| [Definition]
ChEBI: (S)-epichlorohydrin is an epichlorohydrin. It is functionally related to a (R)-1,2-epoxypropane. It is an enantiomer of a (R)-epichlorohydrin. | [Synthesis]
The general procedure for the synthesis of (S)-(+)-epichlorohydrin from 1-chloro-2,3-epoxypropane is as follows: first, 463 kg of racemic epichlorohydrin was mixed with 19.2 kg of the catalyst [(1-RR)-(dibenzoyl-LLA)] made from Example 1 of the Preparation and the mixture was cooled to 5 °C. Subsequently, 49.5 kg of water was slowly added and the reaction continued at 20°C for 7 hours. Upon completion of the reaction, the reaction mixture was subjected to reduced-pressure thin-film evaporation at less than 30 °C to afford 190 kg of (S)-epichlorohydrin with an optical purity of 99.8% ee and a yield of 82%. The above reaction process was repeated by adding new racemic epichlorohydrin and water to the evaporated residue to again obtain (S)-epichlorohydrin with an optical purity of more than 99.0%ee. | [References]
[1] Patent: WO2008/153280, 2008, A1. Location in patent: Page/Page column 41
[2] Patent: WO2008/153280, 2008, A1. Location in patent: Page/Page column 28
[3] Tetrahedron Asymmetry, 2003, vol. 14, # 22, p. 3633 - 3638
[4] Journal of the American Chemical Society, 1995, vol. 117, # 21, p. 5897 - 5898
[5] Journal of the American Chemical Society, 1999, vol. 121, # 17, p. 4147 - 4154 |
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