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35660

Sigma-Aldrich

Bis(2-chloroethyl) ether

puriss., ≥99.0% (GC)

Synonym(s):

2,2′-Dichlorodiethyl ether

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About This Item

Linear Formula:
(ClCH2CH2)2O
CAS Number:
111-44-4
Molecular Weight:
143.01
Beilstein/REAXYS Number:
605317
EC Number:
203-870-1
MDL number:
MFCD00000975
UNSPSC Code:
12352100
PubChem Substance ID:
329755200
NACRES:
NA.22

vapor pressure

0.4 mmHg ( 20 °C)

Quality Level

200

grade

puriss.

assay

≥99.0% (GC)

form

liquid

refractive index

n20/D 1.456 (lit.)
n20/D 1.457

bp

65-67 °C/15 mmHg (lit.)

mp

−47 °C (lit.)

density

1.22 g/mL at 25 °C (lit.)

functional group

chloro

SMILES string

ClCCOCCCl

InChI

1S/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2

InChI key

ZNSMNVMLTJELDZ-UHFFFAOYSA-N

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General description

Bis(2-chloroethyl) ether is a chemical intermediate. 2-Chloroethyl β-D-glucosiduronic acid is the major metabolite of bis(2-chloroethyl)ether.

Application

Bis(2-chloroethyl) ether may be used as a solvent and soil fumigant. It may be used in the preparation of macrocyclic polyethers, dibenzo-18-crown-6 polyether and dicyclohexyl-18-crown-6 polyether.

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Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Carc. 2 - Flam. Liq. 3

supp_hazards

EUH018

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

131.0 °F - closed cup

flash_point_c

55.0 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5612
BCCC7908
BCCC0875
BCBV7497
BCBT5043

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Thiodiglycolic acid: a major metabolite of bis(2-chloroethyl)ether.
R D Lingg et al.
Toxicology and applied pharmacology, 47(1), 23-34 (1979-01-01)
Macrocyclic Polyethers: Dibenzo-18-crown-6 Polyether and Dicyclohexyl-18-crown-6 Polyether.
Pedersen CJ.
Organic Syntheses, 66-66 (1972)
Kevin McClay et al.
Applied and environmental microbiology, 73(21), 6870-6875 (2007-09-18)
Degradation of bis(2-chloroethyl) ether (BCEE) was observed to occur in two bacterial strains. Strain ENV481, a Xanthobacter sp. strain, was isolated by enrichment culturing of samples from a Superfund site located in the northeastern United States. The strain was able
K Norpoth et al.
Journal of cancer research and clinical oncology, 112(2), 125-130 (1986-01-01)
Either 40 mumole or 160 mumole 2,2'-DDE was injected into male Wistar rats and the metabolites, TdGA and HEMA, were determined in the 24-h urine specimens. Comparative investigations were carried out giving equimolar amounts of chloroethanol and 2-chloroacetaldehyde diethyl acetal.
Alex Christensen et al.
Water research, 43(16), 3910-3921 (2009-05-12)
The objective of this study was to evaluate the extent of improvement in the biodegradability of persistent organic compounds by pre-oxidation by using Sequential Batch Reactors (SBRs). Dichlorodiethyl ether (DCDE), a non-biodegradable compound, was used as a test chemical. Ozonation
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