2-Methoxyethoxymethyl chloride Property

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)

Safety

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H331Toxic if inhaled

H335May cause respiratory irritation

H350May cause cancer

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

2-Methoxyethoxymethyl chloride Chemical Properties,Usage,Production

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.