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540072

Sigma-Aldrich

(R)-(−)-Epichlorohydrin

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
Beilstein:
1420785
EC Number:
424-280-2
MDL number:
MFCD00077759
UNSPSC Code:
12352103
PubChem Substance ID:
24878437
NACRES:
NA.22

vapor density

3.29 (vs air)

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.)

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

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Application

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

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

604372

Epichlorohydrin-2-13C

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
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
Synlett, 2151-2151 (2006)
Alfonso Pérez-Garrido et al.
Bioorganic & medicinal chemistry, 16(10), 5720-5732 (2008-04-15)
The risk of the presence of haloacetic acids in drinking water as chlorination by-products and the shortage of experimental mutagenicity data for most of them requires a research work. This paper describes a QSAR model to predict direct mutagenicity for

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