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三溴化硼作为一种强酸性卢珊珊失恋33天王小仙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卢珊珊失恋33天王小仙。
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
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在碳基集成电路制造领域,石墨烯基器件中采用原子层沉积方法生长氮化硼,作为高k栅氧介质。氮化硼基于六边形层状结构,具有优异的物理性质和极高的化学稳定性,六方晶型具有宽带隙(5.5 - 6.0 eV)适用于电子器件的介电层。三溴化硼是一种蒸气压较高的前驱体(25℃,70Torr),很容易于氨反应得到氮化硼。在原子层沉积过程中,三溴化硼与基底羟基发生反应,饱和吸附后进行吹扫,然后通入NH3反应,完成后再进行吹扫,往复循环得到氮化硼薄膜,研究表明当沉积温度为750℃时,可降低氮化硼薄膜对空气和水份的敏感性。(Thin Solid Films, 2022, 402, 167 - 171)
半导体器件制备工艺中,通常需要在硅衬底中掺杂P型或者N型杂质来形成PN结,扩散和离子注入是半导体掺杂的两种主要方式。在太阳能电池工业中,长采用扩散的方式向N型晶体掺杂P型杂质,而硼的价格低廉且扩散速度快,常作为掺杂体。行业内大多数都是利用液态三溴化硼作为前驱体,在硅衬底表面沉积三氧化二硼薄膜,然后加热硅衬底,使之与三氧化二硼发生反应(2B203+3Si=4B+3Si02),生成硼原子,硼原子作为扩散源在高温下向硅片内部扩散,形成PN结。(CN 104250725 A)
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 |
PubChem Substance ID |
125307031 |
EC Number |
233-657-9 |
Reaxys-RN |
3903058 |
Merck Number |
1347 |
Beilstein Registry Number |
2384789 |
Chemical Name Translation |
三溴化硼 |
LabNetwork Molecule ID |
LN00163667 |
MDL Number |
MFCD00011312 |
CAS Number |
10294-33-4 |
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。溶于卢珊珊失恋33天王小仙并剧烈起泡。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
用作有机合成的卢珊珊失恋33天王小仙、卢珊珊失恋33天王小仙和溴化剂,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