2-Methoxyethoxymethyl chloride

2-Methoxyethoxymethyl chloride Basic information

Product Name:	2-Methoxyethoxymethyl chloride
Synonyms:	ALKOXYETHOXYMETHYLCHLORIDE;BETA-METHOXYETHOXYMETHYL CHLORIDE;ETHYLENE GLYCOL CHLOROMETHYL METHYL ETHER;1-(Chloromethoxy)-2-methoxyethane~MEM chloride;Alcoxyethoxymethylchloride;Methoxxxy ethoxy Chloromethane;2-Methoxyethoxymethyl chloride, technical grade;2-METHOXYETHOXYMETHYL CHLORIDE
CAS:	3970-21-6
MF:	C4H9ClO2
MW:	124.57
EINECS:	223-589-8
Product Categories:	Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry
Mol File:	3970-21-6.mol

2-Methoxyethoxymethyl chloride Chemical Properties

Melting point	200-202 °C
Boiling point	50-52 °C/13 mmHg (lit.)
density	1.091 g/mL at 25 °C (lit.)
refractive index	n20/D 1.427(lit.)
Fp	>230 °F
storage temp.	2-8°C
solubility	Chloroform, Methanol
form	Liquid
Specific Gravity	1.091
color	Clear colorless to yellow
Water Solubility	It hydrolyzes with water.
Sensitive	Moisture Sensitive
BRN	1900576
Exposure limits	ACGIH: TWA 0.001 ppm
InChIKey	BIAAQBNMRITRDV-UHFFFAOYSA-N
CAS DataBase Reference	3970-21-6(CAS DataBase Reference)
NIST Chemistry Reference	«BETA»-methoxyethoxymethyl chloride(3970-21-6)
EPA Substance Registry System	Ethane, 1-(chloromethoxy)-2-methoxy- (3970-21-6)

Safety Information

Hazard Codes	T
Risk Statements	45-10-36/37/38-20/21/22-46-40-23/24/25-20/22
Safety Statements	53-26-36/37/39-45-16-23
RIDADR	UN 2810 6.1/PG 2
WGK Germany	3
F	10-21
Hazard Note	Toxic
TSCA	Yes
HazardClass	3
PackingGroup	III
HS Code	29091990

MSDS Information

Provider	Language
beta-Methoxyethoxymethyl chloride	English
SigmaAldrich	English
ACROS	English
ALFA	English

2-Methoxyethoxymethyl chloride Usage And Synthesis

Chemical Properties	CLEAR COLOURLESS LIQUID
Uses	OH-protecting reagent. MEM ethers are stable to a variety of reaction conditions and are selectively cleaved under aprotic conditions in the presence of a wide rangeof OH-protected moieties.
Uses	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.
Uses	2-Methoxyethoxymethyl Chloride is an OH-protecting reagent. 2-Methoxyethoxymethyl Chloride is used in the modification of antibiotics.
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.

2-Methoxyethoxymethyl chloride Preparation Products And Raw materials

Preparation Products

Roxithromycin-->3,4-DIBROMO-5-HYDROXY-5H-FURAN-2-ONE-->DME-->BIS(2-METHOXYETHOXY)METHANE-->(2-METHOXYETHOXYMETHYL)TRIETHYLAMMONIUM CHLORIDE-->Benzaldehyde, 4-[(2-methoxyethoxy)methoxy]-

2-Methoxyethoxymethyl chloride

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