1-(chloromethoxy)-2-methoxyethane

• ChemBase ID: 89340
• Molecular Formular: C4H9ClO2
• Molecular Mass: 124.56606
• Monoisotopic Mass: 124.02910721
• SMILES: O(CCOCCl)C
• Canonical SMILES: COCCOCCl
• InChI: InChI=1S/C4H9ClO2/c1-6-2-3-7-4-5/h2-4H2,1H3
• InChIKey: BIAAQBNMRITRDV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(chloromethoxy)-2-methoxyethane
• IUPAC Traditional name: 1-(chloromethoxy)-2-methoxyethane
• Synonyms: MEM chloride; 1-(Chloromethoxy)-2-methoxyethane; 2-Methoxyethoxymethyl chloride; 2,5-Dioxahexyl chloride; β-METHOXYETHOXYMETHYL CHLORIDE; β-Methoxyethoxymethyl chloride; MEM-chloride; 2-Methoxyethoxymethyl chloride; 2-甲烷氧基乙氧基甲基氯; β-甲氧基乙氧基甲基氯; 甲氧基乙氧基氯甲烷; 2-甲氧基乙氧基甲基氯

Database IDs

• CAS Number: 3970-21-6
• EC Number: 223-589-8
• MDL Number: MFCD00000888
• Beilstein Number: 1900576
• PubChem SID: 162076220; 24883528; 24861920
• PubChem CID: 77590

CALCULATED PROPERTIES

• LogD (pH = 7.4): 0.6913309
• Log P: 0.6913309
• Molar Refractivity: 28.6954 cm^3
• Polarizability: 11.404148 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.6913309

PROPERTIES

Physical Property

• Boiling Point: 50-52 °C/13 mmHg(lit.); 50-52°C/13mm; 50-52°C/13mm
• Flash Point: 113 °C; 129.2 °F; 235 °F; 54 °C; 54°C; 54°C(129°F)
• Density: 1.09 g/ml; 1.091; 1.091 g/mL at 25 °C(lit.); 1.094
• Refractive Index: 1.4270; n20/D 1.427(lit.); n20/D 1.428

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Flammable/Carcinogenic/Toxic/Harmful/Irritant/Lachrymatory/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 2810; UN1992
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 2; III
• Risk Statements: 45-10-20/22-36/37/38; 45-10-36/37/38; 45-20/22-36/37/38; 46-20/21/22-36/37/38; R:36
• Safety Statements: 53-26-45; 53-45; S:26
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H315-H319-H335-H350; H302-H315-H319-H335-H350; H350-H226-H315-H319-H335
• GHS Precautionary statements: P201-P261-P305 + P351 + P338-P308 + P313; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95% (GC); 94%
• Grade: purum; technical grade
• Linear Formula: CH3OCH2CH2OCH2Cl

DETAILS

MP Biomedicals - 02155411

(MEM chloride) 1 ml = approx. 1.09 g May contain up to 1% bis(chloromethyl) ether. CARCINOGEN!

Sigma Aldrich - 357480

Application
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.1,2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 64735

Other Notes
Useful protecting group reagent1

REFERENCES

• For use in the protection of the OH groups in serine and threonine during peptide synthesis, see: Int. J. Pept. Prot. Res., 25, 544 (1985). See also Appendix 6.
• Reagent for the protection of OH groups, in the presence of a base, e.g. NaH in THF or N-Ethyldiisopropylamine, A11801. The MEM-group is more readily and cleanly introduced than methoxymethyl (MOM) and is stable to a wide range of conditions. The MEM group is selectively cleaved by mild Lewis acids, e.g. ZnBr₂ or TiCl₄: Tetrahedron Lett., 809, 4701, 4705 (1976); 24, 3969 (1983), PPTS: Synth. Commun., 13, 1021 (1983), in situ generated TMS iodide: Tetrahedron Lett., 25, 1429 (1984), or CeCl₃: Org. Lett., 3, 1149 (2001).
• MEM ethers 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 stereocontrolled addition of ɑ-methoxyvinyllithium to a carbonyl in the synthesis of taxusin: J. Am. Chem. Soc., 110, 6558 (1988), and subsequently in the addition of MeLi to an ɑ?-unsaturated sulfone: J. Am. Chem. Soc., 113, 3085 (1991); see 2,2,2-Trifluoroethanol, A10788, for another example.
• For cleavage by PPTS, see: Synth. Commun., 1021 (1983). For cleavage by TMS chloride/ NaI or, less effectively, by preformed TMS iodide, see: Tetrahedron Lett., 25, 1429 (1984).