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Boron tribromide 三溴化硼甲苯溶液

规格: 2.0 M solution in toluene, SpcSeal
CAS: 10294-33-4
产品编号: H15629
MDL: MFCD00011312
品牌: INFI

脱烷基试剂——三溴化硼

三溴化硼作为一种强酸性路易斯酸可以用于脱烷基反应，反应机理如下图，首先甲基醚中氧原子的孤对电子进攻硼原子，溴离子离去，氧原子为正电性；然后溴离子进攻甲基碳正中心生成甲基溴；最后烷氧基二溴硼烷经过水解得到相应的羟基化合物。一般选择极性溶剂促进反应，例如乙二醇二甲醚和四氢呋喃。

图片来源网络

反应实例：

一般活性药物分子都具有手性中心，2021年报道的文献中尝试了HBr/AcOH, HCl/iPrOH, AlCl3脱甲基，会发生消旋或转化不完全；尝试利用蛋氨酸/甲基磺酸脱甲基需要长达3天的时间，并且长时间反应会导致产物消旋；最后利用三溴化硼可以完全脱甲基并顺便脱掉Boc，高效保护了化合物的手性。

图片来源：Org. Process Res. Dev. 2022, 26, 3, 710–729

Chemical NameBoron Tribromide
Synonym BORON TRIBROMIDE, REAGENTPLUS, >=99% BORON TRIBROMIDE, 99.995% 晶碱石 boron (III) bromide BORON TRIBROMIDE, REAGENTPLUS, 99.9% Bortribromid 三溴化硼(0402禁空运) boronbromide(bbr3) 三溴化硼,1M在二氯甲烷溶剂中 Boron tribromide tribromoborane 三溴化硼 BORON TRIBROMIDE, 1.0M SOLUTION IN HEPTA NE tribromo-boran Boron bromide (BBr3) BORON TRIBROMIDE SOLUTION, ~1 M IN DICHL OROMETHANE Borane,tribromo- Boron,tribromo- trona 天然碱 BORON TRIBROMIDE BBr3 三溴化硼 溶液 Borane, tribromo- BORON TRIBROMIDE, 1.0M SOLUTION IN HEXAN ES Tribromoboron tribromuredebore 溴化硼 boron tribromide 三溴硼烷(爆炸,禁止销售)BORON TRIBROMIDE, 99.9% 三溴硼烷 丝光晶碱石 BORON TRIBROMIDE, 1.0M SOLUTION IN DICHL OROMETHANE Boron tribromide Solution BORON BROMIDE Boron bromide 溴化硼;天然碱 三溴化硼, 99% MIN 碳酸钠石 tribromoboron Tribromoborane 天然碱;碳酸钠石 BBr3
PubChem Substance ID125307031
EC Number233-657-9
Reaxys-RN3903058
Merck Number1347
Beilstein Registry Number2384789
Chemical Name Translation三溴化硼
LabNetwork Molecule IDLN00163667
MDL NumberMFCD00011312
CAS Number10294-33-4
GHS Symbol
WGK Germany3
Hazard Codes T+ T+,C T+;C T+,C,F,N
Hazard statements
  • H290 May be corrosive to metals 可能腐蚀金属。
  • H314 Causes severe skin burns and eye damage 导致严重的皮肤灼伤和眼睛损伤
  • H330 Fatal if inhaled 吸入致命
  • H300 Fatal if swallowed 吞食致命
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H300+H330
  • H351 Suspected of causing cancer 怀疑致癌
    Personal Protective Equipment Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
    RTECSED7400000
    Precautionary statements
    • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
    • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
    • P305+P351+P338
    • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
    • P304+P340+P310
    • P501 Dispose of contents/container to..… 处理内容物/容器.....
    • P403+P233
    • P305+P351+P338+P310
    • P310 Immediately call a POISON CENTER or doctor/physician. 立即呼救解毒中心或医生/医师。
    • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
    • P301+P330+P331+P310
    • P303+P361+P353
    • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
    • P201 Obtain special instructions before use. 使用前获取专门指示。
    • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
    • P370+P378
    • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
    • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
    • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
    • P301+P310
    • P233 Keep container tightly closed. ?保持容器密闭。
    • P390 Absorb spillage to prevent material damage. 吸收溢出物，防止重大损害。
    • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
    • P273 Avoid release to the environment. 避免释放到环境中。
    • P308+P311
      Signal word
      Storage condition Moisture Sensitive 2-8℃易吸潮，密封充氩保存。 Poison room 充氩保存 易吸潮，密封充氩保存。 Moisture & Light Sensitive 0-10°C 避光，易吸潮，密封充氩保存。 0-10
      UN Number 3390 UN2692 3489 UN3390 UN3384
      Risk Statements
      • R35 Causes severe burns 会导致严重灼伤
      • R14 Reacts violently with water 遇水会猛烈反应
      • R26/28 Very toxic by inhalation and if swallowed 吸入及吞食都有剧毒
      • R11 Highly flammable 非常易燃
      • R50/53
      • R65 Harmful: may cause lung damage if swallowed 若吞咽可能伤害肺部器官
      • R67 Vapours may cause drowsiness and dizziness 蒸汽可能导致嗜睡和昏厥
      • R34 Causes burns 会导致灼伤
      • R62 Possible risk of impaired fertility 有削弱生殖能力的危险
      • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
        Safety Statements
        • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
        • S23 Do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) 不要吸入气体/烟雾/蒸汽/喷雾；
        • S57 Use appropriate containment to avoid environmental contamination 使用适当容器避免环境污染；
        • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
        • S28 After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) 皮肤接触后，立即用大量…（由生产厂家指定）冲洗；
        • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
        • S9 Keep container in a well-ventilated place 保持容器在通风良好的场所；
        • S16 Keep away from sources of ignition - No smoking 远离火源，禁止吸烟；
        • S33 Take precautionary measures against static discharges 对静电采取预防措施；
        • S62 If swallowed, do not induce vomiting: seek medical advice immediately and show this container or label where possible 吞食后不要催吐：立即求医并出示该容器或标签；
        • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
        • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中，参考特别指示/安全收据说明书；
          Packing GroupI
          Hazard Class6.1/3, 8
          Warnings 危化品目录(2015)
          Restrict 危险品
        • ⑴.易被水和醇等分解，受热会爆炸，对人体组织有强烈刺激作用，其蒸气剧毒，腐蚀性较强，具有强吸水性，见光、遇热易分解，接触空气冒白烟。为强路易式酸，能与碱反应形成络合物和加成物。
        • ⑵.在干燥空气中不变化。溶于无机酸并剧烈起泡。天然碱产于不同的盐湖沉积物中，主要产于碱湖及古代沉积矿床中，常与针碳钠钙石、水碱、泡碱、石盐、芒硝、钙芒硝、无水芒硝和石膏共生。遇空气中的湿气很容易水解。
        • ⑶.重要的工业原料，广泛用于玻璃、化工、轻工、纺织、漂染、冶金、石油加工、医药、食品等方面。
        • ⑷.用作半导体的掺杂材料，有机
        • 用作有机合成的催化剂、中间体和溴化剂，制造高纯硼及其它有机硼化合物的原料。
        • {ALF} 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).
        • {uni_hamburg} Short: II/25A
        • {ALD} Merck:14,1347
        • {ALF} 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.
        • {ALF} Reagent for cleavage of ethers: Synthesis, 249 (1983). Converts alcohols to alkyl bromides under mild conditions: Tetrahedron Lett., 35, 1051 (1994). Cl
          • 10294-33-4 H15629 Boron tribromide 三溴化硼甲苯溶液

          化学属性

          Refractive index1.4340
          TSCAYes
          Flash Point-4°C(lit.)
          Vapor Density8.6 (vs air)
          Vapor Pressure40 mmHg ( 14 °C)
          Solubility溶于四氯化碳。
          Appearance pale yellow to orange liq.
          Stabilitymoisture sensitive
          Boiling Point91.3°C
          Melting Point-46°C
          Mol. FormulaBBr3
          Mol. Weight250.52
          Density2.6
          pH:A

          *以上化合物性质及应用等信息仅供参考

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