| Identification | More | [Name]
2-Methoxyethoxymethyl chloride | [CAS]
3970-21-6 | [Synonyms]
1-CHLOROMETHOXY-2-METHOXYETHANE
2-METHOXYETHOXYMETHYL CHLORIDE
ALKOXYETHOXYMETHYLCHLORIDE
BETA-METHOXYETHOXYMETHYL CHLORIDE
ETHYLENE GLYCOL CHLOROMETHYL METHYL ETHER
MEM CHLORIDE
1-(chloromethoxy)-2-methoxy-ethan
1-Chloro-2,5-dioxahexane
2-Methoxy-1-(Chloromethoxy)
Ethane, 1-(chloromethoxy)-2-methoxy-
1-(Chloromethoxy)-2-methoxyethane~MEM chloride
Alcoxyethoxymethylchloride
Methoxxxy ethoxy Chloromethane
2-Methoxyethoxymethyl chloride, technical grade
METHOXYETHOXYCHLOROMETHANE
MEM Chlordie
MEM CHLORIDE (2-METHOXYETHOXYMETHYL CHLORIDE)
β-Methoxyethoxymethyl chloride, MEM-chloride
1-Methoxy-2-(chloromethoxy)ethane | [EINECS(EC#)]
223-589-8 | [Molecular Formula]
C4H9ClO2 | [MDL Number]
MFCD00000888 | [Molecular Weight]
124.57 | [MOL File]
3970-21-6.mol |
| Chemical Properties | Back Directory | [Appearance]
CLEAR COLOURLESS LIQUID | [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. ]
−20°C
| [solubility ]
Chloroform, Methanol | [form ]
Liquid | [color ]
Clear colorless to yellow | [Specific Gravity]
1.091 | [Water Solubility ]
It hydrolyzes with water. | [Sensitive ]
Moisture Sensitive | [BRN ]
1900576 | [Exposure limits]
ACGIH: TWA 0.001 ppm | [InChI]
1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3 | [InChIKey]
BIAAQBNMRITRDV-UHFFFAOYSA-N | [SMILES]
COCCOCCl | [CAS DataBase Reference]
3970-21-6(CAS DataBase Reference) | [NIST Chemistry Reference]
«BETA»-methoxyethoxymethyl chloride(3970-21-6) | [EPA Substance Registry System]
3970-21-6(EPA Substance) |
| Questions And Answer | Back Directory | [Preparation]
2-Methoxyethoxymethyl chloride can be synthesized by reacting 2-methoxyethanol with thionyl chloride. However, this method has some problems, requiring high temperatures and long reaction times to obtain high yields. Furthermore, thionyl chloride is a toxic substance and is environmentally unfriendly. |
| Safety Data | Back Directory | [Symbol(GHS) ]
  
GHS02,GHS06,GHS08 | [Signal word ]
Danger | [Hazard statements ]
H226-H302-H315-H319-H331-H335-H350 | [Precautionary statements ]
P210-P301+P312-P303+P361+P353-P304+P340+P311-P305+P351+P338-P308+P313 | [Hazard Codes ]
T | [Risk Statements ]
R45:May cause cancer.
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S16:Keep away from sources of ignition-No smoking .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 2810 6.1/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Toxic | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29091990 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 3 Inhalation
Acute Tox. 4 Oral
Carc. 1A
Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 an OH-protecting reagent. 2-Methoxyethoxymethyl Chloride is used in the modification of antibiotics. | [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. | [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. |
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