540080
(S)-(+)-Epichlorohydrin
98%
Synonym(s):
(S)-(+)-2-(Chloromethyl)oxirane
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About This Item
Empirical Formula (Hill Notation):
C3H5ClO
CAS Number:
Molecular Weight:
92.52
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1420784
Assay:
98%
vapor density
3.2 (vs air)
vapor pressure
12.5 mmHg ( 20 °C)
assay
98%
optical activity
[α]20/D +35°, c = 1 in methanol
optical purity
ee: 97% (GLC)
autoignition temp.
1421 °F
expl. lim.
21 %
refractive index
n20/D 1.438 (lit.)
bp
92-93 °C/360 mmHg (lit.)
density
1.183 g/mL at 25 °C (lit.)
functional group
chloro, ether
SMILES string
ClC[C@@H]1CO1
InChI
1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
InChI key
BRLQWZUYTZBJKN-GSVOUGTGSA-N
Application
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.
Chiral building block in the enantioselective syntheses of hydroxyisoxazolidines and (+)-cis-sylvaticin, a potential antitumor agent.
Legal Information
Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.
signalword
Danger
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
Storage Class
3 - Flammable liquids
flash_point_f
89.6 °F - closed cup
flash_point_c
32 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Ryosuke Munakata et al.
Journal of the American Chemical Society, 126(36), 11254-11267 (2004-09-10)
A total synthesis of the macquarimicins A-C (1-3), novel natural products with intriguing tetra- or pentacyclic frameworks, has been achieved. The synthesis features an extensive investigation of the biosynthesis-based intramolecular Diels-Alder (IMDA) reactions of (E,Z,E)-1,6,8-nonatrienes. Considering possible biosynthetic sequences, four
Timothy J Donohoe et al.
Journal of the American Chemical Society, 128(42), 13704-13705 (2006-10-19)
The double oxidative cyclization of dienes is a viable procedure for making complex natural products containing cis-THF units. A double deprotection/double oxidative cyclization strategy using catalytic osmium tetroxide was used to construct the bisheterocyclic core of cis-sylvaticin and ultimately confirm
Elfatih Elzein et al.
Bioorganic & medicinal chemistry letters, 14(4), 973-977 (2004-03-12)
We describe the synthesis of novel inhibitors of fatty acid oxidation as potential metabolic modulators for the treatment of stable angina. Replacement of the 2H-benzo[d]1,3-dioxolene ring system in our initial lead 3 with different benzthiazoles, benzoxazoles and introducing small alkyl