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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
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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

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Application

Building block for the synthesis of a key intermediate in the synthesis of stable PGI2 analogue UT-15.[1]
Used in the synthesis of chiral morpholines and dioxanes via a Mitsunobu diol-cyclization.[2] Chiral building block in the enantioselective synthesis of trans-2,4-disubstituted piperidines.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT3771V
MKBQ9103V
MKBG3602V
MKBH0150V
MKBG8952V

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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)
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
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

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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