2H-1,3,2-benzodioxaborole

• ChemBase编号: 88485
• 分子式: C6H5BO2
• 平均质量: 119.9137
• 单一同位素质量: 120.0382598
• SMILES: O1c2ccccc2OB1
• Canonical SMILES: B1Oc2c(O1)cccc2
• InChI: InChI=1S/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H
• InChIKey: CENMEJUYOOMFFZ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2H-1,3,2-benzodioxaborole
• IUPAC传统名: catecholborane
• 别名: 儿茶酚硼烷 溶液; 儿茶酚硼烷; 儿茶酚硼烷; Catecholborane solution; Catecholborane; 1,3,2-Benzodioxaborole; Catecholborane; Benzo[d][1,3,2]dioxaborole; 1,3,2-Benzodioxaborole; 1,3,2-benzodioxaborole; 7,9-dioxa-8λ2-borabicyclo[4.3.0]nona-1,3,5-triene; Catecholborane

登记号

• CAS号: 274-07-7
• EC号: 205-991-5
• MDL号: MFCD00005846
• Beilstein号: 972072
• PubChem SID: 162075431; 24851357; 24853519
• PubChem CID: 6327445
• Chemspider ID: 10617125
• 维基百科标题: Catecholborane

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.2384
• LogD (pH = 7.4): 2.2384
• Log P: 1.4184
• 摩尔折射率: 51.7702 cm^3
• 极化性: 13.616939 Å^3
• 极化表面积: 26.28 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 外观: Colorless liquid
• 熔点: 12 °C; 12 °C(lit.); 12°C; 12°C
• 沸点: 50 °C/50 mmHg; 50 °C/50 mmHg(lit.); 50°C; 50°C/50mm
• 闪点: 1.4 °F; -17 °C; 2 °C; 2°C; 2°C(35°F); 35.6 °F
• 密度: 0.958 g/mL at 25 °C; 1.125; 1.125 g/cm3, liquid; 1.125 g/mL at 25 °C(lit.)
• 折射率: 1.5025; n20/D 1.507(lit.)

安全信息

• 保存注意事项: Highly Flammable/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); 易燃性(Flammable) (F); X
• 联合国危险货物编号: 2924; UN2924
• 德国WGK号: 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 11-14-19-34-37; 11-14-34; 11-14-34-48/20-63-67; R11, R14, R34
• 安全公开号: 16-26-36/37/39-45; 26-36/37/39-43-45; 8-26-36/37/39-45; S16, S26, S36/37/39, S43, S45
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS07; GHS08
• GHS警示词: Danger
• NFPA704:
  

  4

  1

  2

  W
• GHS危险声明: H224-H314-H318-H361-H373-H336; H225-H314; H225-H314-H318; H225-H314-H335
• GHS警示性声明: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P261-P280-P305 + P351 + P338-P310; P210-P280-P305 + P351 + P338-P310
• 个人保护装置: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2
• 欧盟补充危害声明: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥90% (GC); 50% w/w in toluene (98% dry wt.); 97%; 98%
• 浓度: 1.0 M in THF
• 级别: technical
• Empirical Formula (Hill Notation): C6H5BO2

详细说明

Apollo Scientific Ltd - OR40616

Packaged in Safebreak bottles

Sigma Aldrich - 188913

Application
单官能硼氢化试剂，可将 β-羟基酮还原为 1,3-二醇。1可影响 α,β-烯酮共轭还原反应。2
用于制备 B-烷基儿茶酚硼烷，B-烷基儿茶酚硼烷又可产生烷基自由基，与醌作用形成芳基醚。可用于与亚甲基双(噁唑啉)作用制备 C2-对称硼络合物，亚甲基双(噁唑啉)还可用于酮的不对称还原反应。
包装
25, 100 g in Sure/Seal™

Sigma Aldrich - 225762

包装
100, 800 mL in Sure/Seal™
Application
用于烯烃的过渡金属催化硼氢化反应。1,2,3

Sigma Aldrich - 12345

Caution
储存时可能变浑浊

参考文献

• Mild, selective hydroborating agent: J. Am. Chem. Soc., 97, 5249 (1975); Tetrahedron, 32, 981 (1976). Use of Rh(I) and Ir(I) catalysis increases stereo- and regioselectivity: J. Am. Chem. Soc., 114, 6671, 6674 (1992). For Rh catalyzed enantioselective hydroboration of alkenylboronic acids, see: Tetrahedron: Asymmetry, 7, 5 (1996). Hydroboration of olefins can be accomplished at room temperature in the presence of N,N-dimethylacetamide: J. Org. Chem., 61, 3224 (1996).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 666 (2007).