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3970-21-6 - 2-Methoxyethoxymethyl chloride, 94% - 1-(Chloromethoxy)-2-methoxyethane - MEM chloride - L01050 - Alfa Aesar

L01050 2-Methoxyethoxymethyl chloride, 94%

CAS Number
3970-21-6
Synonyms
1-(Chloromethoxy)-2-methoxyethane
MEM chloride

Size Price ($) Quantity Availability
5g 43.67
25g 131.84
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2-Methoxyethoxymethyl chloride, 94%

MDL
MFCD00000888
EINECS
223-589-8

Chemical Properties

Formula
C4H9ClO2
Formula Weight
124.57
Boiling Point
50-52°/13mm
Flash Point
54°(129°F)
Density
1.094
Refractive Index
1.4270
Sensitivity
Moisture Sensitive
Solubility
It hydrolyzes with water.

Applications

2-Methoxyethoxymethyl chloride, is used as selectively cleaved under aprotic conditions in the presence of a wide range of OH-protected reagents. It is used as an OH-protecting reagent. An examples of the target molecule MEM Chloride is the side chain of roxithromycin. It is also used in the protection of the OH groups in serine and threonine during peptide synthesis. Some of the other applications include 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 stereo controlled addition of ?-methoxyvinyllithium to a carbonyl in the synthesis of taxusin.

Notes

Moisture, Heat, water Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Keep away from oxidizing agents. Stable under recommended storage conditions.

Literature References

JH Rigby.; JAZ Wilson. Removal of methoxyethoxymethyl ethers with trimethylsilyl chloride-sodium iodide. Tetrahedron letters. 198425(14) , 1429-1432.

RS Gross.; DS Watt. A Lewis acid-catalyzed procedure for the conversion of 2-methoxyethoxymethyl ethers to carboxylic esters. Synthetic Communications. 198717(15) , 1749-1760.

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).

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.

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 ɑß-unsaturated sulfone: J. Am. Chem. Soc., 113, 3085 (1991); see 2,2,2-Trifluoroethanol, A10788, for another example.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H350-H226-H315-H319-H335

May cause cancer. Flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P210-P201-P261-P280-P281-P303+P361+P353-P305+P351+P338-P304+P340-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1900576
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2909.19
TSCA
Yes

Recommended

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  • A10885

    Methanesulfonamide, 98+%
  • A11801

    N-Ethyldiisopropylamine, 99%
  • A12174

    tert-Butyldimethylsilyl trifluoromethanesulfonate, 98%

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