Chemistry:2-Methoxyethoxymethyl chloride
| |
| Identifiers | |
|---|---|
3D model (JSmol)
|
|
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C4H9ClO2 | |
| Molar mass | 124.56 g·mol−1 |
| Appearance | colorless liquid |
| Density | 1.094 g cm−3 |
| Boiling point | 50–52 °C (122–126 °F; 323–325 K) 13 mm Hg |
| Hazards | |
| GHS pictograms |   
|
| GHS Signal word | Danger |
| H226, H302, H315, H319, H335 | |
| P203Script error: No such module "Preview warning".Category:GHS errors, P210, P233, P240, P241, P242, P243, P261, P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P270, P271, P280, P301+317Script error: No such module "Preview warning".Category:GHS errors, P302+352, P303+361+353, P304+340, P305+351+338, P318Script error: No such module "Preview warning".Category:GHS errors, P319Script error: No such module "Preview warning".Category:GHS errors, P321, P330, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-Methoxyethoxymethyl chloride is an organic compound with formula CH
3OCH
2CH
2OCH
2Cl. 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.[2] 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) in dichloromethane followed by addition of 2-methoxyethoxymethyl chloride.[3] [4]
The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.[5]
Safety
The closely related chloromethyl methyl ether is a known human carcinogen.[6]
References
- ↑ "2-Methoxyethoxymethyl chloride" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/77590#section=Safety-and-Hazards.
- ↑ Wuts, Peter G. M. (2001). "2-Methoxyethoxymethyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm100. ISBN 0471936235.
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition
 |  |
