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2-Methoxyethoxymethyl chloride

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2-Methoxyethoxymethyl chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.446 Edit this at Wikidata
EC Number
  • 223-589-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3Key: BIAAQBNMRITRDV-UHFFFAOYSA-N
SMILES
  • COCCOCCl
Properties
Chemical formula C4H9ClO2
Molar mass 124.56 g·mol
Appearance colorless liquid
Density 1.094 g cm
Boiling point 50–52 °C (122–126 °F; 323–325 K) 13 mm Hg
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H226, H302, H315, H319, H335
Precautionary statements P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Methoxyethoxymethyl chloride is an organic compound with formula CH3OCH2CH2OCH2Cl. A colorless liquid, it is classified as a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxyethoxy ether (MEM) protecting group. MEM protecting groups are generally preferred to methoxymethyl (MOM) protecting groups, both in terms of formation and removal.

Typically, the alcohol to be protected is deprotonated with a non-nucleophilic base such as N,N-diisopropylethylamine (DIPEA, Hunig's base) in dichloromethane followed by addition of 2-methoxyethoxymethyl chloride.

The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.

Safety

The closely related chloromethyl methyl ether is a known human carcinogen.

References

  1. "2-Methoxyethoxymethyl chloride". pubchem.ncbi.nlm.nih.gov.
  2. Wuts, Peter G. M. (2001). "2-Methoxyethoxymethyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm100. ISBN 0471936235.
  3. Corey, E. J.; Gras, Jean-Louis; Ulrich, Peter (1976-03-01). "A new general method for protection of the hydroxyl function". Tetrahedron Letters. 17 (11): 809–812. doi:10.1016/S0040-4039(00)92890-9.
  4. Lee, Hong Myung; Nieto-Oberhuber, Cristina; Shair, Matthew D. (2008-12-17). "Enantioselective Synthesis of (+)-Cortistatin A, a Potent and Selective Inhibitor of Endothelial Cell Proliferation". Journal of the American Chemical Society. 130 (50): 16864–16866. doi:10.1021/ja8071918. ISSN 0002-7863. PMID 19053422. S2CID 207132632.
  5. Amano, Seiji; Takemura, Noriaki; Ohtsuka, Masami; Ogawa, Seiichiro; Chida, Noritaka (1999-03-26). "Total synthesis of paniculide A from d-glucose". Tetrahedron. 55 (13): 3855–3870. doi:10.1016/S0040-4020(99)00096-4.
  6. bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
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