tribromoborane

• ChemBase编号: 107043
• 分子式: BBr3
• 平均质量: 250.523
• 单一同位素质量: 247.7643164
• SMILES: BrB(Br)Br
• Canonical SMILES: BrB(Br)Br
• InChI: InChI=1S/BBr3/c2-1(3)4
• InChIKey: ILAHWRKJUDSMFH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: tribromoborane
• IUPAC传统名: boron tribromide
• 别名: 三溴化硼 溶液; 三溴化硼,1M在二氯甲烷溶剂中; 三溴化硼; Tribromoborane; BORON BROMIDE; BORON TRIBROMIDE; Boron tribromide solution; Boron tribromide, 1M soln. in dichloromethane; Tribromoboron; Boron tribromide

登记号

• CAS号: 10294-33-4
• EC号: 233-657-9
• MDL号: MFCD00011312
• 默克索引号: 141347
• PubChem SID: 24866111; 24852661; 24853799; 24852662; 162093474; 24852048; 24865221
• PubChem CID: 25134
• Chemspider ID: 16787736
• 维基百科标题: Boron_tribromide

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 2.3303
• LogD (pH = 7.4): 2.3303
• Log P: 2.3303
• 摩尔折射率: 26.2056 cm^3
• 极化性: 12.004274 Å^3
• 极化表面积: 0.0 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

• 溶解度: reacts violently in water
• 外观: colorless; colorless to amber; colorless to amber liquid; Liquid; Liquid, ampouled under argon
• 熔点: -46 °C(lit.); -46.3 °C; -46.3°C; -46°C
• 沸点: ~90 °C; ~90 °C(lit.); 90°C; 91.3 °C; 91.3°C
• 闪点: -1 °C; 1.4 °F; -17 °C; -18 °C; 195.8 °F; 30.2 °F; 91 °C
• 密度: 0.859 g/mL at 25 °C; 0.869 g/mL at 25 °C; 1.46 g/mL at 20 °C; 1.467; 1.467 g/mL at 25 °C; 2.60 g/mL at 20 °C(lit.); 2.643; 2.643 g/cm^3
• 折射率: 1.00207; 1.4340
• 蒸汽压: 40 mmHg ( 14 °C); 7.2 kPa (20 °C)
• 蒸汽密度: 8.6 (vs air)
• 粘度: 7.31 x 10^-4 Pa s (20 °C)
• 热容: 0.2706 J/K
• 标准摩尔生成焓 (ΔfH^o298): -0.8207 kJ/g

安全信息

• 保存注意事项: Moisture Sensitive
• RTECS编号: ED7400000
• 欧盟危险性物质标志: 腐蚀性(Corrosive) (C); Corrosive (C); 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); 剧毒(Highly toxic) (T+); Very toxic (T+)
• 联合国危险货物编号: 2692; 3384; 3390; UN2692; UN3390
• 德国WGK号: 3
• 联合国危险货物等级: 6.1; 8
• 联合国危险货物包装类别(PG): 1; I
• 危险公开号: 11-14-26/28-35-48/20-51/53-62-65; 11-14-26/28-35-50/53-65; 14-26/28-35; 14-26/28-35-40; R:12-26/28-35; R14, R26/28, R35
• 安全公开号: 26-28-36/37/39-45; 26-28-36/37/39-45-61-62; 9-26-28-36/37/39-45; S:9-26-28-45-36/37/39; S1/2, S9, S26, S28, S36/37/39, S45
• TSCA收录: 是
• 欧盟危险品索引: 005-003-00-0
• GHS危险品标识: GHS02; GHS05; : Skin Corr. 1B; GHS06; : Acute Tox. 2; GHS07; GHS08; GHS09
• GHS警示词: DANGER; Danger
• NFPA704:
  

  0

  3

  2

  W
• GHS危险声明: 330, 300, 314; H225-H300-H304-H314-H330-H336-H410; H225-H304-H314-H336-H361f-H373-H411; H300-H314-H330; H300-H314-H330-H351; H300-H330-H314; H300-H330-H314-H318; H300-H330-H314-H318-H351; H314-H351
• GHS警示性声明: P210-P260-P264-P273-P280-P284; P210-P261-P273-P280-P301 + P310-P305 + P351 + P338; P260-P264-P280-P284-P301 + P310-P305 + P351 + P338; P260-P264-P280-P284-P305 + P351 + P338-P310; P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; 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 2692 8/PG 1; UN 3384 6.1/PG 1; UN 3390 6.1/PG 1
• 欧盟补充危害声明: Reacts violently with water.

产品相关信息

• 纯度: ≥99%; ≥99.0% (AT); ≥99.99%; 99% min; 99.5%; 99.9%; 99.999% (metals basis)
• 浓度: ~1 M in methylene chloride; 1.0 M in heptane; 1.0 M in hexanes; 1.0 M in methylene chloride; 1M soln. in dichloromethane
• 级别: purum; ReagentPlus®
• Empirical Formula (Hill Notation): BBr3

详细说明

MP Biomedicals - 05202333

colorless to amber liquid

Sigma Aldrich - 211230

包装
100 mL in Sure/Seal™
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 230367

包装
5, 25, 100 g in ampule
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
与炔烃反应生成 2-烯基二溴硼烷，在 Diels-Alder 反应中与 BBN 相比表现出反向区域选择性。由 1-炔烃与提供三取代烯烃的卤代烷发生偶联反应生成的中间体。与手性磺酰胺反应生成手性缩水甘油酯、二醇乙酸酯、β-羟基酯和氨基酸酯的前体。可用于 13-15 族半导体材料前体的合成。

Sigma Aldrich - 202207

Application
在由香豆素支架11和梯形共轭聚合物12合成 benzopyrano benzopyran 类化合物的反应中用于裂解芳基甲基醚。
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
包装
100, 250 g in Sure/Seal™
2 kg in Sure/Seal™
25 g in ampule
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 211222

Application
在由香豆素支架合成 benzopyrano benzopyran 类化合物的反应中用于裂解芳基甲基醚。11
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
包装
10 mL in glass bottle
2 L in Sure/Seal™
2.5 L in glass bottle
4×25, 100, 800 mL in Sure/Seal™

Sigma Aldrich - 403857

包装
100 mL in Sure/Seal™
Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 419508

Application
在由香豆素支架合成 benzopyrano benzopyran 类化合物的反应中用于裂解芳基甲基醚。11
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10
包装
4×25, 100, 500 g in Sure/Seal™
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 15692

Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

Sigma Aldrich - 15690

Application
Reactant for preparation of:
• Drug intermediate 6-nitro-L-DOPA1
• Luminescent polystyrene derivatives with sterically protected carbazolylborane moieties2
• High-quality boron-doped graphene via Wurtz-type reductive coupling reaction3
• Mercapto-(+)-methamphetamine haptens for synthesis of (+)-methamphetamine conjugate vaccines with improved epitope densities4
• Micrometer-sized organic molecule-DNA hybrid structures5
• Borane complexes via electrophilic aromatic borylation reactions6
• A 5-HT2C receptor agonist7
• Biphenyl-derivatives possessing tertiary amino groups as β-secretase(BACE1) inhibitors for the treatment of Alzheimer′s disease8
• A highly near-IR region fluorescent p-extended boron aza-dipyrromethene moiety unit9
• Tetrahydroisoquinoline derivatives via intramolecular cyclization of methoxy-substituted N-phenethylimides10

参考文献

• Reagent for cleavage of ethers: Synthesis, 249 (1983). Converts alcohols to alkyl bromides under mild conditions: Tetrahedron Lett., 35, 1051 (1994). Cleavage of N-methoxymethyl: Tetrahedron Lett., 42, 8633 (2001), or N-benzyl: Tetrahedron Lett., 45, 4093 (2004) protecting groups can also be achieved under mild conditions. Alkynes undergo bromoboration; the products can be transformed, e.g. to trisubstituted alkenes: Tetrahedron Lett., 29, 1811 (1988), or enyne-allenes: Tetrahedron Lett., 35, 1829 (1994).
• Reagent for cleavage of ethers. For a brief feature of uses of the reagent in organic synthesis, see: Synlett, 1636 (2005). See also preceding entry.