CAS 3970-21-6|1-(Chloromethoxy)-2-methoxyethane|2,5-Dioxahexyl chloride|MEM chloride|1-(chloromethoxy)-2-methoxyethane|2-Methoxyethoxymethyl chloride|1-(chloromethoxy)-2-methoxyethane|β-METHOXY...

General Information

Structure

Molecular Formula

C₄H₉ClO₂

Molecular Mass

124.56606

Exact Mass

124.02910721

Charge

InChI

InChI=1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3

InChIKey

BIAAQBNMRITRDV-UHFFFAOYSA-N

Canonic Smiles

COCCOCCl

Isomeric Smiles

O(CCOCCl)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.6913309

LogD (pH = 7.4)

0.6913309

Log P

0.6913309

Molar Refractivity

28.6954

Polarizability

11.404148

Polar Surface Area

18.46

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1-(Chloromethoxy)-2-methoxyethane2,5-Dioxahexyl chlorideMEM chloride2-Methoxyethoxymethyl chlorideβ-METHOXYETHOXYMETHYL CHLORIDEβ-甲氧基乙氧基甲基氯2-Methoxyethoxymethyl chlorideβ-Methoxyethoxymethyl chloride2-甲氧基乙氧基甲基氯甲氧基乙氧基氯甲烷MEM-chloride2-甲烷氧基乙氧基甲基氯

IUPAC Traditional name

1-(chloromethoxy)-2-methoxyethane

IUPAC name

1-(chloromethoxy)-2-methoxyethane

Names and Identifiers

Registration numbers

EC Number

223-589-8

MDL Number

MFCD00000888

CAS Number

3970-21-6

PubChem SID

1620762202488352824861920

PubChem CID

77590

Beilstein Number

1900576

Registration numbers

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

MP Biomedicals

02155411

(MEM chloride) 1 ml = approx. 1.09 g May contain up to 1% bis(chloromethyl) ether. CARCINOGEN!

Sigma Aldrich

357480

Application
OH-protecting reagent. MEM ethers are stable to a variety of reaction conditions and are selectively cleaved under aprotic conditions in the presence of a wide rangeof OH-protected moieties.1,2
Packaging
5, 25 g in glass bottle

64735

Other Notes
Useful protecting group reagent1

Molecule Details

References

PubChem Literature

From Data Sources

• For cleavage by PPTS, see: Synth. Commun., 1021 (1983). For cleavage by TMS chloride/ NaI or, less effectively, by preformed TMS iodide, see: Tetrahedron Lett., 25, 1429 (1984).

• For use in the protection of the OH groups in serine and threonine during peptide synthesis, see: Int. J. Pept. Prot. Res., 25, 544 (1985). See also Appendix 6.

• Reagent for the protection of OH groups, in the presence of a base, e.g. NaH in THF or N-Ethyldiisopropylamine, A11801. The MEM-group is more readily and cleanly introduced than methoxymethyl (MOM) and is stable to a wide range of conditions. The MEM group is selectively cleaved by mild Lewis acids, e.g. ZnBr₂ or TiCl₄: Tetrahedron Lett., 809, 4701, 4705 (1976); 24, 3969 (1983), PPTS: Synth. Commun., 13, 1021 (1983), in situ generated TMS iodide: Tetrahedron Lett., 25, 1429 (1984), or CeCl₃: Org. Lett., 3, 1149 (2001).

• MEM ethers have the ability to coordinate to metals, which is thought to accelerate the cleavage by Lewis acids. The chelating ability of the MEM ether also makes it useful as a stereodirecting group in organometallic reactions, first noted in the stereocontrolled addition of ɑ-methoxyvinyllithium to a carbonyl in the synthesis of taxusin: J. Am. Chem. Soc., 110, 6558 (1988), and subsequently in the addition of MeLi to an ɑ?-unsaturated sulfone: J. Am. Chem. Soc., 113, 3085 (1991); see 2,2,2-Trifluoroethanol, A10788, for another example.

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

1-(chloromethoxy)-2-methoxyethane

IUPAC name

1-(chloromethoxy)-2-methoxyethane

Registration numbers

EC Number

223-589-8

MDL Number

MFCD00000888

CAS Number

3970-21-6

PubChem SID

1620762202488352824861920

PubChem CID

Beilstein Number

Molecule Details

(MEM chloride) 1 ml = approx. 1.09 g May contain up to 1% bis(chloromethyl) ether. CARCINOGEN!

Sigma Aldrich

357480

64735

Other Notes
Useful protecting group reagent1

References

PubChem Literature

From Data Sources

• For cleavage by PPTS, see: Synth. Commun., 1021 (1983). For cleavage by TMS chloride/ NaI or, less effectively, by preformed TMS iodide, see: Tetrahedron Lett., 25, 1429 (1984).

• For use in the protection of the OH groups in serine and threonine during peptide synthesis, see: Int. J. Pept. Prot. Res., 25, 544 (1985). See also Appendix 6.

Bioactivity

PubChem BioAssay

Properties

Molecule

ID:89340