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540080

Sigma-Aldrich

(S)-(+)-Epichlorohydrin

98%

Synonym(s):

(S)-(+)-2-(Chloromethyl)oxirane

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About This Item

Empirical Formula (Hill Notation):
C3H5ClO
CAS Number:
67843-74-7
Molecular Weight:
92.52
Beilstein:
1420784
MDL number:
MFCD00077760
UNSPSC Code:
12352005
PubChem Substance ID:
24878439
NACRES:
NA.22

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.)

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

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Application

Chiral building block in the enantioselective syntheses of hydroxyisoxazolidines and (+)-cis-sylvaticin, a potential antitumor agent.
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.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Ryosuke Munakata et al.
Journal of the American Chemical Society, 125(48), 14722-14723 (2003-12-04)
The first total synthesis of (+)-macquarimicin A (1), a novel inhibitor of neutral sphingomyelinase (N-SMase) with antiinflammatory activity, has been accomplished. The present work determined the absolute configuration of (+)-1 and revised the C(2)-C(3) geometry to be Z. The synthesis
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
Tetrahedron Letters, 47, 7635-7635 (2006)
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
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
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