3970-21-6 Usage
Description
2-Methoxyethoxymethyl chloride, also known as MEM chloride, is a versatile chemical compound that serves as an OH-protecting reagent. It is a clear, colorless liquid with unique properties that make it suitable for various applications in different industries.
Uses
Used in Pharmaceutical Industry:
2-Methoxyethoxymethyl chloride is used as an OH-protecting reagent for the modification of antibiotics. It plays a crucial role in the synthesis of roxithromycin, where it is used to protect the OH groups in serine and threonine during peptide synthesis.
Used in Organic Chemistry:
2-Methoxyethoxymethyl chloride is used as an OH-protecting reagent that is selectively cleaved under aprotic conditions in the presence of a wide range of OH-protected reagents. This selective cleavage property makes it valuable in organic chemistry for protecting hydroxyl groups during various reactions.
Used in Organometallic Reactions:
The chelating ability of the MEM ether makes it useful as a stereodirecting group in organometallic reactions. It was first noted in the stereo-controlled addition of γ-methoxyvinyllithium to a carbonyl in the synthesis of taxusin.
Used in Coordination Chemistry:
2-Methoxyethoxymethyl chloride has the ability to coordinate with metals, which is thought to accelerate the cleavage by Lewis acids. This property makes it a valuable compound in coordination chemistry for enhancing reaction rates and selectivity.
Purification Methods
Possible impurities are methoxyethanol (b 124o/atm), HCHO and HCl which can be removed below the boiling point of MEMCl. Purify MEMCl by fractional distillation in a vacuum. If too impure, prepare it from methoxyethanol (152g) and s-trioxane (66g) by bubbling a stream of dry HCl (with stirring) until a clear mixture is obtained. Dilute with pentane (900mL), dry (3hours over 100g MgSO4, at 5o), evaporate and the residue is distilled in a vacuum. It is MOISTURE SENSITIVE and TOXIC. The MEM.NEt3+Cl-salt, prepared by reaction with 1.3 equivalents of Et3N (16hours/25o) and dried in a vacuum, has m 58-61o, and is moisture sensitive. [Corey et al. Tetrahedron Lett 809 1976, Yoshimatsu et al. J Org Chem 59 1011 1994, Greene & Wuts Protective Groups in Organic Synthesis edn, J Wiley & Sons NY 1991.] Carcinogen.
Check Digit Verification of cas no
The CAS Registry Mumber 3970-21-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,9,7 and 0 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3970-21:
(6*3)+(5*9)+(4*7)+(3*0)+(2*2)+(1*1)=96
96 % 10 = 6
So 3970-21-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H8N4O2S/c16-18(17,11-7-3-4-8-12-11)15-10-6-2-1-5-9(10)13-14-15/h1-8H
3970-21-6Relevant articles and documents
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Corey,E.J. et al.
, p. 809 - 812 (1976)
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BREAST CANCER RESISTANCE PROTEIN (BCRP) INHIBITOR
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Page/Page column 13, (2010/02/14)
The invention provides a drug which inhibits BCRP. A breast cancer resistance protein inhibitor containing, as an active ingredient, a diphenylacrylonitrile derivative represented by the following formula (1): [wherein, each of 8 R's, which are the same or different from one another, represents a hydrogen atom, a hydroxyl group, a nitro group, an amino group, an acetylamino group (-NHCOCH3 group), a cyano group (-CN group), a formyl group (-CHO group), -COOR1 (R1 is hydrogen or C1-C4 alkyl) , -O(CH2)nCOOR2 (n=1-7: R2 is hydrogen or C1-C4 alkyl) , -OOCCH2CH2COOR3 (R3 is hydrogen, C1-C4 alkyl, (Z)-2-(3,4-dimethoxy-phenyl)-3-(4-hydroxy-phenyl)-acrylonitrile, or glycopyranosyl), a C1-C8 alkoxy group, a C1-C4 alkyl group, a halogen atom, a C1-C4 alkoxy C1-C4 alkoxy C1-C4 alkoxy group, a C2-C8 acyloxy group, a C2-C8 halogenoacyloxy group, a methylenedioxy group, a trifluoromethyl group, a phosphate group (i.e., -OP(O) (OH)2) or a salt thereof, a sulfate group (i.e., -OSO3H) or a salt thereof, a glycopyranosyl group or a salt thereof, a phosphate ester of a glycopyranosyl group or a salt of the ester, a sulfate ester of a glycopyranosyl group or a salt of the ester, or a piperidinopiperidinocarbonyloxy group], an ester thereof, or a salt thereof.
Enantioselective synthesis of cyclopentanoids, II. - Asymmetric synthesis of a novel homochiral prostaglandin building unit via Bridgehead enolates with bicyclo[3.3.0]octane skeleton
Gais,Lindner,Lied,et al.
, p. 1179 - 1212 (2007/10/02)
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Preparation of Alkoxymethyl and Alkoxyethoxymethyl Derivatives of Acylanilines using Polyethylene Glycols as Phase Transfer Catalysts
Zupancic, Boris G.,Sopcic, Mirko
, p. 942 - 944 (2007/10/02)
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