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540072

(R)-(−)-Epichlorohydrin

Name: (<I>R</I>)-(−)-Epichlorohydrin
Brand: ALDRICH

99%

Synonym(s):

(R)-(−)-2-(Chloromethyl)oxirane

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About This Item

Empirical Formula (Hill Notation):

C₃H₅ClO

CAS Number:

51594-55-9

Molecular Weight:

92.52

UNSPSC Code:

12352103

NACRES:

NA.22

PubChem Substance ID:

24878437

EC Number:

424-280-2

Beilstein/REAXYS Number:

1420785

MDL number:

MFCD00077759

Assay:

99%

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Properties

vapor density

3.29 (vs air)

Quality Level

100

vapor pressure

10 mmHg ( 16.6 °C)

assay

99%

optical activity

[α]20/D −34°, c = 1 in methanol

optical purity

ee: 98% (GLC)

autoignition temp.

772 °F

expl. lim.

21 %

refractive index

n20/D 1.438 (lit.)

bp

114 °C (lit.)

density

1.180 g/mL at 20 °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-/m0/s1

InChI key

BRLQWZUYTZBJKN-VKHMYHEASA-N

Description

Application

Used in the synthesis of chiral morpholines and dioxanes via a Mitsunobu diol-cyclization. Chiral building block in the enantioselective synthesis of trans-2,4-disubstituted piperidines.

Building block for the synthesis of a key intermediate in the synthesis of stable PGI₂ analogue UT-15.

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

P202 - P210 - P280 - 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

wgk

WGK 3

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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Strategy for the enantioselective synthesis of trans-2,4-disubstituted piperidines: application to the CCR3 antagonist IS811.

Goss S Kauffman et al.

The Journal of organic chemistry, 71(23), 8975-8977 (2006-11-04)

A strategy for the enantioselective synthesis of trans-2,4-disubstituted piperidines is proposed and applied to the preparation of IS811, a potent CCR3 antagonist. The C2 stereocenter is derived from commercial (R)-epichlorohydrin, while the C4 stereocenter is installed via diastereoselective hydrogenation of

The intramolecular asymmetric Pauson-Khand cyclization as a novel and general stereoselective route to benzindene prostacyclins: synthesis of UT-15 (treprostinil).

Robert M Moriarty et al.

The Journal of organic chemistry, 69(6), 1890-1902 (2004-04-03)

A general and novel solution to the synthesis of biologically important stable analogues of prostacyclin PGI(2), namely benzindene prostacyclins, has been achieved via the stereoselective intramolecular Pauson-Khand cyclization (PKC). This work illustrates for the first time the synthetic utility and

Synlett, 2151-2151 (2006)

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Global Trade Item Number

SKU	GTIN
540072-5G	04061837641305
540072-25G	04061837641299