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540080

(S)-(+)-Epichlorohydrin

Name: (<I>S</I>)-(+)-Epichlorohydrin
Brand: ALDRICH

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

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24878439

MDL number:

MFCD00077760

Beilstein/REAXYS Number:

1420784

Assay:

98%

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Properties

vapor density

3.2 (vs air)

Quality Level

200

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

Description

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.

pictograms

GHS02,GHS06,GHS08,GHS05

signalword

Danger

hcodes

H226,H301 + H311 + H331,H314,H317,H350

pcodes

P210 - P280 - P301 + P310 + P330 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

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

Regulatory Information

危险化学品

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Total synthesis of macquarimicins using an intramolecular Diels-Alder approach inspired by a biosynthetic pathway.

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

Total synthesis of (+)-macquarimicin A.