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.
An easy access to homopropargylic ethers
Guedin-Vuong, Denis,Nakatani, Yoichi
, p. 245 - 252 (2007/10/02)
Chloromethyl ethers, obtained from alcohols, formaldehyde and HCl, react regioselectively, as shown previously in one case by L.Miginiac, with allenyl aluminium reagents derived from propargyl bromides and aluminium, to give homopropargyl ethers.No evidence for the presence of allenyl ethers was obtained in the cases described.This condensation is used to obtain a protected acetylenic synthon 1, required for the synthesis of an ecdysteroid analogue (1).
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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