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2-Methoxyethoxymethyl chloride

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2-Methoxyethoxymethyl chloride Basic information

Product Name:
2-Methoxyethoxymethyl chloride
Synonyms:
  • ALKOXYETHOXYMETHYLCHLORIDE
  • BETA-METHOXYETHOXYMETHYL CHLORIDE
  • ETHYLENE GLYCOL CHLOROMETHYL METHYL ETHER
  • MEM CHLORIDE
  • 1-CHLOROMETHOXY-2-METHOXYETHANE
  • 1-(Chloromethoxy)-2-methoxyethane~MEM chloride
  • Alcoxyethoxymethylchloride
  • Methoxxxy ethoxy Chloromethane
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
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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.)
Flash point:
>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)
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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
10-21
Hazard Note 
Toxic
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29091990

MSDS

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2-Methoxyethoxymethyl chloride Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS LIQUID

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

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 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

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