(methylsulfanyl)methane borane

• ChemBase编号: 139969
• 分子式: C2H9BS
• 平均质量: 75.96886
• 单一同位素质量: 76.05180169
• SMILES: B.CSC
• Canonical SMILES: CSC.B
• InChI: InChI=1S/C2H6S.BH3/c1-3-2;/h1-2H3;1H3
• InChIKey: RMHDLBZYPISZOI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (methylsulfanyl)methane borane
• IUPAC传统名: dimethyl sulfide borane
• 别名: 硼烷二甲基硫醚络合物; 硼烷二甲基硫醚络合物 溶液; 硼烷二甲硫醚; 硼烷甲基硫醚络合物; 硼烷二甲基硫醚; 硼烷二甲基硫醚络合物,2M甲苯溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 2M 四氢呋喃溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲基硫醚络合物, 通常 5M乙醚溶液, 氩气下可重封的ChemSeal™瓶包装; 硼烷二甲硫醚络合物; (Dimethyl sulfide)trihydroboron; BMS; Borane-dimethyl sulfide; Borane dimethyl sulfide complex; Trihydro[thiobis[methane]]boron; Borane dimethyl sulfide complex solution; Borane methyl sulfide complex; Dimethyl sulfide borane; Borane-methyl sulfide; Borane-dimethyl sulfide complex; Borane-dimethyl sulfide complex, 2M in toluene; Borane-dimethyl sulfide complex, 2M in THF; Borane-dimethyl sulfide complex, nominally 5M in ether; Borane-Methyl sulfide coMplex

登记号

• CAS号: 13292-87-0
• EC号: 236-313-6
• MDL号: MFCD00013189
• Beilstein号: 3663489
• PubChem SID: 24851335; 24868320; 24849576; 24851530; 162234215; 24851577; 24851529; 24850657
• PubChem CID: 9833925

理论计算性质

• 质子受体: 0
• 质子供体: 0
• LogD (pH = 5.5): 1.2235795
• LogD (pH = 7.4): 1.2235795
• Log P: 1.2235795
• 摩尔折射率: 18.8917 cm^3
• 极化性: 7.4785047 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

• 外观: Liquid
• 熔点: -38°C
• 沸点: ~34 °C; ca 44°C dec.
• 闪点: 1.4 °F; -1°C(30°F); -1°C(31°F); -17 °C; -17°C(-1°F); 18 °C; -31 °F; -35 °C; -35°C(-31°F); -40 °C; -40 °F; 44.6 °F; 64.4 °F; 7 °C; 7°C(45°F)
• 密度: 0.74 g/mL at 25 °C; 0.789; 0.789 g/mL at 25 °C; 0.801; 0.801 g/mL at 20 °C(lit.); 0.801 g/mL at 25 °C(lit.); 0.855; 0.855 g/mL at 25 °C; 0.856; 0.856 g/mL at 25 °C; 1.287 g/mL at 25 °C
• 折射率: 1.4570

安全信息

• 保存注意事项: Air & Moisture Sensitive
• RTECS编号: PV5080000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 高度易燃性(Highly flammable) (F+); 有毒(Toxic) (T); X; 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3398; 3399; UN2924; UN3399
• 德国WGK号: 1; 3
• 联合国危险货物等级: 3; 4.3
• 联合国危险货物包装类别(PG): 1; 2; I; II
• 危险公开号: 11-14/15-19-22-37/38-41; 11-14/15-19-37-41; 11-14/15-22-38-41-48/20-63-67; 11-14/15-25-37/38-41; 11-14/15-36-40; 11-14/15-37/38-41; 12-14/15-19-20/22-37/38-41-67; 12-14/15-19-22-37/38-41-67; 12-14/15-19-22-38-41-67; 63-11-14/15-38-41-48/20-65-67
• 安全公开号: 16-23-26-33-36/37/39-43; 16-23-26-33-36/39; 16-23-26-36/37/39-43-45; 16-26-29-33-36/37/39-43; 16-26-36/37/39-43-62; 16-26-36/37-43; 16-26-39-43
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS06; GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H224-H260-H302-H315-H318-H335-H336; H224-H260-H315-H318-H335-H336; H224-H261-H314-H318-H302-H336; H225-H260-H301 + H311-H315-H318-H335; H225-H260-H301-H335-H314-H318; H225-H260-H302 + H312-H304-H315-H318-H336-H361d-H373; H225-H260-H315-H318-H335; H225-H260-H318-H315-H361-H373-H302-H336; H225-H261-H318-H315-H302-H335; H225-H261-H318-H351
• GHS警示性声明: P210-P223-P231 + P232-P261-P370 + P378-P422; P210-P231 + P232-P280-P305 + P351 + P338-P422; P210-P280-P243-P305+P351+P338-P370+P378I-P402+P404; P210-P280-P305+P351+P338-P309+P311-P370+P378I-P402+P404; P280-P305+P351+P338-P301-P315-P370+P378I-P402+P404
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3398 4.3/PG 2; UN 3399 4.3/PG 1
• 欧盟补充危害声明: May form explosive peroxides., Reacts violently with water.; Reacts violently with water.
• 保存温度: 2-8°C

产品相关信息

• 纯度: 94%
• 浓度: ~5 M in diethyl ether; >90% in dimethyl sulfide; 1.0 M in methylene chloride; 2.0 M in diethyl ether; 2.0 M in THF; 2.0 M in toluene; 2M in THF; 2M in toluene; 5.0 M in diethyl ether; nominally 5M in ether
• 级别: purum; technical
• 包装: packaged under Argon in resealable ChemSeal? bottles
• 线性分子式: (CH3)2S · BH3

详细说明

Sigma Aldrich - 447145

包装
100 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 179825

Application
与树枝状聚合物负载的 L-吡咯烷醇共同用于茚酮和四氢萘酮的不对称还原反应。二茂铁基-1,3-二酮转化为 1,3-二醇的 CBS 催化不对称还原反应。C3-对称三脚羟基酰胺催化的酮高度不对称还原反应。
用于硼氢化还原和其他应用的试剂。1,2
Other Notes
10.0-10.2M 以 BH3 存在。可含过量甲基硫醚。
包装
25, 4×25, 100, 800 mL in Sure/Seal™
8, 18 L in Kilo-Lab™
View returnable container options.

Sigma Aldrich - 194824

包装
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 15587

Other Notes
方便而稳定的硼烷来源，用于硼氢化反应，综述6,7,8；α-羟基酯的选择性还原反应9
包装
25, 100 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4
• Synthesis of cage compounds5

Sigma Aldrich - 193038

包装
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

Sigma Aldrich - 192120

Application
与树枝状聚合物负载的 L-吡咯烷醇共同用于茚酮和四氢萘酮的不对称还原反应。6二茂铁基-1,3-二酮转化为手性 1,3-二醇的 CBS 催化不对称还原反应。7C3-对称三脚羟基酰胺催化的酮高度不对称还原反应。8
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5
包装
100, 800 mL in Sure/Seal™

Sigma Aldrich - 192112

包装
100, 800 mL in Sure/Seal™
Application
Reactant used as a regioselective reducing agent1,2Reactant involved in:
• Hydroboration / oxidation3,4Synthesis of cage compounds5

参考文献

• Stable, convenient reagent for a wide range of reduction and hydroboration reactions. Reviews: Org. Prep. Proced. Int., 13, 225 (1981); Chem. Rev., 76, 773 (1976); A. Pelter et al, Borane Reagents, Academic Press, N.Y. (1988).
• Carboxylic acids are readily reduced to alcohols: J. Org. Chem., 38, 2786 (1973).
• Conditions for reduction of amino acids to amino alcohols without racemization are described for L-valine: Org. Synth. Coll., 7, 530 (1990).
• By use of refluxing THF as solvent, the reduction can be extended to include esters, primary, secondary and tertiary amides and nitriles: J. Org. Chem., 47, 1389 (1982); Synth. Commun., 21, 1579 (1991).
• The selectivity of BMS in reducing free acids more rapidly than esters is reversed in the case of monoesters of malonic acids. The borane binds initially to the acid function, but reduces the ester group intramolecularly: Tetrahedron Lett., 30, 6687 (1989):
  
• For a discussion of the effect of the alkene structure on hydroboration with borane dimethyl sulfide, see: J. Org. Chem., 48, 644 (1983). For cis-anti-Markovnikov hydration of alkenes by hydroboration with BMS, followed by H₂O₂ oxidation of the borane, see: J. Org. Chem., 39, 1437 (1974).