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142670

Sigma-Aldrich

Chloromethyl ethyl ether

95%

Synonym(s):

(Chloromethoxy)ethane, Ethoxychloromethane, Ethoxymethyl chloride, Ethyl chloromethyl ether

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About This Item

Linear Formula:
C2H5OCH2Cl
CAS Number:
3188-13-4
Molecular Weight:
94.54
EC Number:
221-687-5
MDL number:
MFCD00000887
UNSPSC Code:
12352101
PubChem Substance ID:
24848532
NACRES:
NA.22

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.404 (lit.)

bp

82 °C (lit.)

density

1.019 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOCCl

InChI

1S/C3H7ClO/c1-2-5-3-4/h2-3H2,1H3

InChI key

FCYRSDMGOLYDHL-UHFFFAOYSA-N

Application

Chloromethyl ethyl ether can be used to prepare:
  • 6-Benzyl-1-(ethoxymethyl)-5-iodopyrimidine-2,4(1H,3H)-dione, a key intermediate in the preparation of MKC-442 analog.
  • Acylation catalyst for alcohols named 1,3-bis-[(R)-1-(2-naphthyl)ethyl]imidazoliumchloride by reacting with glyoxal-bis-[(R)-1-(2-naphthyl)ethyl]imine.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

66.2 °F - closed cup

Flash Point(C)

19 °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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Chiral N-heterocyclic carbenes as asymmetric acylation catalysts
Suzuki Y, et al.
Tetrahedron, 62(2-3), 302-310 (2006)
Three Routes for the Synthesis of 6-Benzyl-1-ethoxymethyl-2, 4-dioxo-1, 2, 3, 4-tetrahydropyrimidine-5-carbaldehyde
Petersen L, et al.
Synthesis, 2001(04), 0559-0564 (2001)
K Takahashi et al.
Mutation research, 156(3), 153-161 (1985-06-01)
The mutagenic characteristics of formaldehyde on bacteria were examined. All the tester strains of Escherichia coli deficient in DNA-repair enzymes tested in the present study were significantly more sensitive to the killing effect of formaldehyde than the corresponding wild-type strain.
bis(Chloromethyl) ether and technical-grade chloromethyl methyl ether.
Report on carcinogens : carcinogen profiles, 10, 56-57 (2004-08-24)
Tadeusz J Szalaty et al.
International journal of biological macromolecules, 119, 431-437 (2018-07-29)
In this research we use ionic liquids in combination with mild process conditions to provide a selective increase in the content of carbonyl groups in the kraft lignin structure. Such modification can improve the properties of the pristine biopolymer. In
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