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Merck

107271

(±)-3-Chloro-1,2-propanediol

98%

Synonym(s):

α-Chlorohydrin, α-Glycerol chlorohydrin, α-Monochlorohydrin, 3-MCPD

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About This Item

Linear Formula:
ClCH2CH(OH)CH2OH
CAS Number:
96-24-2
Molecular Weight:
110.54
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24846761
EC Number:
202-492-4
Beilstein/REAXYS Number:
635684
MDL number:
MFCD00004712
Assay:
98%

Key Documents

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InChI key

SSZWWUDQMAHNAQ-UHFFFAOYSA-N

InChI

1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2

SMILES string

OCC(O)CCl

vapor pressure

0.04 mmHg ( 25 °C)

assay

98%

Quality Level

100

bp

213 °C (lit.)

solubility

H2O: soluble, alcohol: soluble, diethyl ether: soluble

density

1.322 g/mL at 25 °C (lit.)

functional group

chloro, hydroxyl

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General description

3-Chloro-1,2-propanediol undergoes enantioselective transformation to (R)-3-chloro-1,2-propanediol by the cell extract of Corynebacterium sp. strain N-1074 . It is a contaminant found in food in free (diol) form as well as in an esterified (with fatty acids) form.

Application

(±)-3-Chloro-1,2-propanediol may be used in manufacture of dye intermediates.

Biochem/physiol Actions

3-Chloro-1,2-propanediol is a potent rodent chemosterilant.

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Oral - Carc. 2 - Eye Dam. 1 - Met. Corr. 1 - Repr. 1B - Skin Irrit. 2 - STOT RE 1 - STOT SE 1

target_organs

Kidney, Testes

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP3271
BCCN6506
BCCM0791
BCCM3803
BCCL4568

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Antifertility activity of 3-chloro-1, 2-propanediol (U-5897) on male rats.
E Samojlik et al.
Biology of reproduction, 2(2), 299-304 (1970-04-01)
T Nakamura et al.
Journal of bacteriology, 174(23), 7613-7619 (1992-12-01)
During the course of the transformation of 1,3-dichloro-2-propanol (DCP) into (R)-3-chloro-1,2-propanediol [(R)-MCP] with the cell extract of Corynebacterium sp. strain N-1074, epichlorohydrin (ECH) was transiently formed. The cell extract was fractionated into two DCP-dechlorinating activities (fractions Ia and Ib) and
W Seefelder et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 25(4), 391-400 (2008-03-19)
3-Mono-chloropropane-1,2-diol (3-MCPD) is a contaminant that occurs in food in its free (diol) form as well as in an esterified (with fatty acids) form. Using a simple intestinal model, it was demonstrated that 3-MCPD monoesters and 3-MCPD diesters are accepted
Ching-Yu Lin et al.
Reproductive toxicology (Elmsford, N.Y.), 28(1), 75-80 (2009-06-06)
Sperm ATP is derived primarily from either glycolysis or mitochondrial oxidative phosphorylation. In the present studies, (1)H NMR spectroscopy was used to characterize the metabolite profile in primate sperm treated either with alpha-chlorohydrin (ACH), a known inhibitor of sperm glycolysis
K Yamazaki et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 30(1), 52-68 (2012-08-23)
A new, direct analytical method for the determination of 3-chloro-1,2-propanediol fatty acid esters (3-MCPD esters) was developed. The targeted 3-MCPD esters included five types of monoester and 25 [corrected] types of diester. Samples (oils and fats) were dissolved in a
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