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540080

(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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24878439
MDL number:
MFCD00077760
Beilstein/REAXYS Number:
1420784
Assay:
98%
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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.)

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

Application

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

Legal Information

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

signalword

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

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Deleterious substance

pdsc

Class I Designated Chemical Substances

prtr

Group 4: Flammable liquids + Type 2 petroleums + Hazardous rank III + Water insoluble liquid

fsl

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

540080-25G:4.548173168173E12 + 540080-5G:4.54817316818E12

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ2758
MKCX6222
MKCX4597
MKCW3294
13105DE

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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
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
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
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