(R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole (R)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷

CAS 112022-83-0 MFCD00078440

化学结构图

112022-83-0
SMILES: CB1OC(c2ccccc2)(c2ccccc2)C2CCCN12

化学属性

Mol. FormulaC18H20BNO
Mol. Weight277.17
Melting Point85-95
TSCANo
Density0.95
Flash Point4°(39°F)
Refractive indexn20/D 1.4602
Boiling Point111 °C
Appearance liq.
Stabilitymoisture sensitive

别名和识别编码

Chemical Name(R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole
Synonym (R)-(+)-2-甲基-CBS-噁唑硼烷 溶液 (R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE ?-2-甲基-CBS-恶唑硼烷 (R)-2-METHYL-CBS-OXAZABOROLIDINE (R)-methyloxazaborolidine,(R)-mecbs,intoluene (R)-2-甲基-CBS-氧杂硼啶单水合物 ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER (R)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷 (R)-(+)-甲基-CBS-恶唑硼烷 (R)-四氢-1-甲基-3,3-二苯基-1H,3H-吡咯并[1,2-c][1,3,2]噁唑硼烷 (R)-1-甲基,3,3-二苯基-四氢-吡咯并(1,2-c)(1,3,2)噁唑硼烷 (R)-3-甲基-CBS-氧杂硼啶 (R)-2-甲基-CBS-恶唑硼烷 (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborlidine (R)-(+)-2-甲基-CBS-噁唑硼烷 (R)-1-甲基,3,3-二苯基-四氢-吡咯并(1,2-c)(1,3,2)噁唑硼烷 (R)-Methyl oxazaborolidine, in toluene, 1M solution (R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2] OXAZABOROLE (R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZABOROLE (R)-3-甲基-CBS-氧杂硼啶, 1M SOLN. IN TOLUENE (R)-2-甲基-CBS-噁唑硼烷 (R)-2-METHYL-CBS-OXAZABOROLIDINE, 1M IN& (R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZOBOROLE (R)-3,3-DIPHENYL-1-METHYLTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]OXAZABOROLE (R)-3-甲基-CBS-氧杂硼啶 (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole (R)-3-甲基-CBS-氧杂硼啶 (R)-methyloxazaborolidine,(R)-mecbs,in ( R )-2-Methyl-CBS-Oxazaborolidine.H20 (R)-5,5-DIPHENYL-2-METHYL-3,4-PROPANO-1,3,2-OXAZABOROLIDINE (R)-ME (R)-Methyloxazaborolidine,1-1.5Mintoluene[(R)-MeCBS]
MDL NumberMFCD00078440
PubChem Substance ID9838490
Beilstein Registry Number9059874
CAS Number112022-83-0
EC Number250-023-7
Chemical Name Translation(R)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷
Reaxys-RN9059874
LabNetwork Molecule IDLN00009249
InChIInChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1
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分类

  • {SNA} Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Reduction

产品应用

  • CBS (Corey-Bakshi-Shibata) 噁唑硼烷催化剂已被用于前手性酮的非对称性还原。其他应用包括 α-羟基酸、α-氨基酸、C2 对称二茂铁二醇以及炔丙醇的对映选择性合成。

相关文献及参考

  • Chiral auxiliary for the highly enantioselective reduction of prochiral ketones, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.
  • Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (R)-2-Methyl-CBS-oxazaborolidine, L14582.
  • Anhydrous catalyst for CBS reduction reaction. For further information, see (S)-2-Methyl-CBS-oxazaborolidine monohydrate, L09219.

安全信息

WGK Germany3
Personal Protective Equipment Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Safety Statements
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
Packing GroupII
UN Number UN 1294 3/PG 2
Risk Statements
  • R11 Highly flammable 非常易燃
  • R19 May form explosive peroxides 可能生成易爆的过氧化物质
  • R36/37 Irritating to eyes and respiratory system 对眼睛和呼吸系统有刺激性
  • R40 Limited evidence of a carcinogenic effect 有限证据表明其致癌作用
Storage condition 0-10 Air & Moisture Sensitive 0-10°C 2-8°C 贮存温度:2-8°C
GHS Symbol
Hazard statements
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H351 Suspected of causing cancer 怀疑致癌
  • H225 Highly flammable liquid and vapour 高度易燃液体和蒸气
  • H302 Harmful if swallowed 吞食有害
  • H315 Causes skin irritation 会刺激皮肤
  • H304 May be fatal if swallowed and enters airways 吞食和进入呼吸道可能致命
  • H336 May cause drowsiness or dizziness 肯能导致嗜睡或头晕
  • H373 May causes damage to organs through prolonged or repeated exposure 长期或频繁接触可能会损伤器官
  • H361d Suspected of damaging the unborn child 怀疑对未出生婴儿造成伤害
Precautionary statements
  • 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。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛，皮肤或衣服。
  • 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。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P301+P310
  • P301+P312+P330
  • P305+P351+P338
  • P331 Do NOT induce vomiting.. 不要催吐。
  • P370+P378
  • P403+P235
Signal word
Hazard Codes
Hazard Class3

其他信息

  • MOL 文件:112022-83-0.mol
  • TCI Shanghai:(R)-2-甲基-CBS-恶唑硼烷 (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine,>;97.0%(T)(112022-83-0)
  • 用途一:Yield very high enantiseletivity in reduction of ketones. The CBS (Corey-Bakshi-Shibata) oxazaborolidine catalyst has been used in the asymmetric reduction of prochiral ketones.Other applications include the enantioselective synthesis of α-hydroxy acids, α-amino acids,3 C2 symmetrical ferrocenyl diols, and propargyl alcohols.
  • 下游产品:4-羟基-6-溴-2,3-二氢硫色烯-1,1-二氧化物
  • 外观:无色或浅黄色液体（甲苯溶液）
  • (R)-2-甲基-CBS-恶唑硼烷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D2130 (R)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 5G 3860元 2014/06/02 D2130 (R)-5,5-联苯-2-甲基-3,4-丙醇-1,3,2-恶唑硼烷 (R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine 1G 1070元 2010/05/25 L09230 (R)-2-甲基-CBS-氧杂硼啶单水合物, 94% (R)-2-Methyl-CBS-oxazaborolidine monohydrate, 94% 250mg 1988元
  • F:10
  • 稳定性:(R)-2-甲基-CBS-恶唑硼烷（112022-83-0）极易和空气中的水发生水解使其催化活性降低
  • 敏感性:Air & Moisture Sensitive
  • 存储注意事项:湿度敏感;空气敏感;热敏感;惰性气体保护
  • Alfa Aesar:(R)-3-甲基-CBS-氧杂硼啶,1Msoln.intoluene (R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene(112022-83-0)

系列性分类

  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  1. Chemical Synthesis 化学合成
  2. Catalysis and Inorganic Chemistry 催化剂和无机化学
  3. Boron 硼
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Reduction - Chiral Catalysts, Ligands, and Reagents
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Catalysts, Ligands, and Reagents - Asymmetric Synthesis
  4. Reduction - Chiral Catalysts, Ligands, and Reagents
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Isoxazoles 异恶唑
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Oxazoles 恶唑
  1. Chemical Synthesis 化学合成
  2. Organometallic Reagents 金属有机试剂
  3. Boronic Acids and Derivatives 硼酸和硼酸衍生物
  4. Boranes
  1. Functional Group 官能团索引
  2. boronic acid ester
  1. Corey Catalyst 科里催化剂
  2. Boron 硼
  1. Organocatalyst
  2. Boron
  1. Catalysts
  2. Boron

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