1-(chloromethoxy)-2-methoxyethane

• ChemBase编号: 89340
• 分子式: C4H9ClO2
• 平均质量: 124.56606
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1-(chloromethoxy)-2-methoxyethane
• IUPAC传统名: 1-(chloromethoxy)-2-methoxyethane
• 别名: 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; MEM chloride; 1-(Chloromethoxy)-2-methoxyethane; 2-Methoxyethoxymethyl chloride; 2,5-Dioxahexyl chloride; β-METHOXYETHOXYMETHYL CHLORIDE; β-Methoxyethoxymethyl chloride; MEM-chloride; 2-Methoxyethoxymethyl chloride

登记号

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

理论计算性质

• LogD (pH = 7.4): 0.6913309
• Log P: 0.6913309
• 摩尔折射率: 28.6954 cm^3
• 极化性: 11.404148 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true
• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 0.6913309

分子性质

理化性质

• 沸点: 50-52 °C/13 mmHg(lit.); 50-52°C/13mm; 50-52°C/13mm
• 闪点: 113 °C; 129.2 °F; 235 °F; 54 °C; 54°C; 54°C(129°F)
• 密度: 1.09 g/ml; 1.091; 1.091 g/mL at 25 °C(lit.); 1.094
• 折射率: 1.4270; n20/D 1.427(lit.); n20/D 1.428

安全信息

• 保存条件: 2-8°C, Desiccate
• 保存注意事项: Flammable/Carcinogenic/Toxic/Harmful/Irritant/Lachrymatory/Moisture Sensitive/Store under Argon/Keep Cold; Moisture Sensitive
• 欧盟危险性物质标志: 有毒(Toxic) (T); 刺激性(Irritant) (Xi)
• 联合国危险货物编号: 2810; UN1992
• 德国WGK号: 3
• 联合国危险货物等级: 3; 6.1
• 联合国危险货物包装类别(PG): 2; III
• 危险公开号: 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
• 安全公开号: 53-26-45; 53-45; S:26
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H226-H302-H315-H319-H335-H350; H302-H315-H319-H335-H350; H350-H226-H315-H319-H335
• GHS警示性声明: P201-P261-P305 + P351 + P338-P308 + P313; P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A
• 个人保护装置: 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
• 保存温度: -20°C; 2-8°C

产品相关信息

• 纯度: ≥95% (GC); 94%
• 级别: purum; technical grade
• 线性分子式: CH3OCH2CH2OCH2Cl

详细说明

MP Biomedicals - 02155411

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

Sigma Aldrich - 357480

Application
羟基保护试剂。MEM 醚在各种反应条件下均可保持稳定，并且当多种羟基保护基团存在时，在非质子条件下可发生选择性裂解。1,2
包装
5, 25 g in glass bottle

Sigma Aldrich - 64735

Other Notes
有用的保护基试剂1

参考文献

• 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).