2-(2-bromoethyl)-1,3-dioxolane

• ChemBase编号: 69721
• 分子式: C5H9BrO2
• 平均质量: 181.02776
• 单一同位素质量: 179.97859153
• SMILES: O1C(OCC1)CCBr
• Canonical SMILES: BrCCC1OCCO1
• InChI: InChI=1S/C5H9BrO2/c6-2-1-5-7-3-4-8-5/h5H,1-4H2
• InChIKey: GGZQLTVZPOGLCC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2-bromoethyl)-1,3-dioxolane
• IUPAC传统名: 2-(2-bromoethyl)-1,3-dioxolane
• 别名: 2-(2-溴乙基)-1,3-二噁茂烷; 2-(2-溴乙基)-1,3-二氧戊环; 2-(2-溴乙基)-1,3-二氧戊环烷; 3-Bromopropionaldehyde ethylene acetal; 2-(2-Bromoethyl)-1,3-dioxolane; 3-Bromopropanal 1,2-ethanediol acetal; 2-(2-Bromoethyl)-1,3-dioxolane

登记号

• CAS号: 18742-02-4
• EC号: 242-551-1
• MDL号: MFCD00003216
• Beilstein号: 103516
• PubChem SID: 162035446; 24853846; 24849942
• PubChem CID: 87776

理论计算性质

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.3522153
• LogD (pH = 7.4): 1.3522153
• Log P: 1.3522153
• 摩尔折射率: 33.6032 cm^3
• 极化性: 13.539787 Å^3
• 极化表面积: 18.46 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: brownish-yellow
• 沸点: 68-70 °C/8 mmHg(lit.); 68-70°C/8mm
• 闪点: 149 °F; 65 °C; 65°C(149°F)
• 密度: 1.512; 1.542 g/mL at 25 °C(lit.)
• 折射率: 1.4790; n20/D 1.479; n20/D 1.479(lit.)
• 疏水性(logP): 0.803

安全信息

• 保存注意事项: IRRITANT; Light Sensitive
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2810
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-36/37/38; 36/37/38
• 安全公开号: 26; 26-37
• TSCA收录: false; 否
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Danger
• GHS危险声明: H301-H315-H319-H335; H315-H319-H335-H227
• GHS警示性声明: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P301 + P310-P305 + P351 + P338
• 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 3
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥97.0% (GC); 95%; 95%, stab. with silver; 95+%; 96%; 98%
• 级别: purum
• 其他组分: silver wool as stabilizer
• Empirical Formula (Hill Notation): C5H9BrO2

详细说明

Sigma Aldrich - 230995

包装
10, 50 g in glass bottle
Application
与炔酰胺和叠氮化钠共同用于三唑的"一锅法"合成。
胺、1二噻烷、2和羧酰亚胺、3醛（通过格氏试剂）的烷基化试剂。4

Sigma Aldrich - 16156

Other Notes
掩蔽的 3-溴丙醛可用于格氏反应或取代反应1,2,3；用于环化反应的试剂4

参考文献

• For a review of 3-carbon homologating reagents, including many examples of Grignard and organocuprate reactions of these molecules, see: Chem. Rev., 84, 409 (1984).
• Masked ?-formylethyl synthon, compare preceding entry. The derived Grignard, which, unlike the dioxane analogue, is unstable above room temperature, shows similar attenuated reactivity in comparison with simple alkyl Grignard reagents, reacting with acid chlorides to give -ketoaldehydes without carbinol formation, and with enones to give, at low temperatures, predominantly the 1,4-addition product without the need for Cu catalysis:Tetrahedron Lett., 28, 3217 (1987).
• The Grignard undergoes coupling reactions (CuBr₂ + LiCl catalysis) with allylic halides: Tetrahedron Lett., 4549 (1979); J. Org. Chem., 46, 1504 (1981), allylic acetates: J. Am. Chem. Soc., 104, 2269 (1982), and primary alkyl bromides: J. Org. Chem., 48, 1767 (1983).