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Boron tribromide 三溴化硼二氯甲烷溶液

规格: 1.0 M solution in methylene chloride, SpcSeal

CAS: 10294-33-4

产品编号: H11101

MDL: MFCD00011312

品牌: INFI

脱烷基试剂——三溴化硼

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 Name	Boron 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
CAS Number	10294-33-4
PubChem Substance ID	125307031
EC Number	233-657-9
MDL Number	MFCD00011312
Reaxys-RN	3903058
Merck Number	1347
Beilstein Registry Number	2384789
Chemical Name Translation	三溴化硼
LabNetwork Molecule ID	LN00163667

GHS Symbol

WGK Germany	3
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
RTECS	ED7400000
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 Group	I
Hazard Class	6.1/3, 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 H11101 Boron tribromide
三溴化硼二氯甲烷溶液

化学属性

Mol. Formula	BBr3
Mol. Weight	250.54
Boiling Point	91.3°C
Density	1.4496
Melting Point	-46°C
Refractive index	1.4340
TSCA	Yes
Flash Point	-4°C(lit.)
Vapor Density	8.6 (vs air)
Vapor Pressure	40 mmHg ( 14 °C)
Solubility	溶于四氯化碳。
Stability	对热、光线、湿度敏感
Appearance	pale yellow to orange liq.
pH	:A

*以上化合物性质及应用等信息仅供参考

手性催化剂及配体

合成砌块

医药中间体