benzenethiol

• ChemBase编号: 75319
• 分子式: C6H6S
• 平均质量: 110.17684
• 单一同位素质量: 110.01902119
• SMILES: Sc1ccccc1
• Canonical SMILES: Sc1ccccc1
• InChI: InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
• InChIKey: RMVRSNDYEFQCLF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: benzenethiol
• IUPAC传统名: thiophenol
• 别名: 硫酚; 巯基苯; 硫酚; 苯硫酚; 苯硫酚; Phenyl mecaptan; Benzenethiol; Thiophenol 99%; Thiophenol; Thiophenol; Phenyl mercaptan; Thiophenol; Benzenethiol

登记号

• CAS号: 108-98-5
• EC号: 203-635-3
• MDL号: MFCD00004826
• Beilstein号: 506523
• 默克索引号: 149355
• PubChem SID: 24900127; 24854411; 162040237; 24846302; 24901811
• PubChem CID: 7969
• CHEBI ID: 48498
• CHEMBL: 119405
• Chemspider ID: 7681
• FEMA编号: 3616
• 美国药典/FDA物质标识码: 7K011JR4T0
• 维基百科标题: Thiophenol
• 欧洲委员会编号: 11585
• Flavis Number: 12.08

理论计算性质

• Acid pKa: 6.638429
• 质子受体: 0
• 质子供体: 1
• LogD (pH = 5.5): 2.037154
• LogD (pH = 7.4): 1.320617
• Log P: 2.066453
• 摩尔折射率: 34.0678 cm^3
• 极化性: 13.405632 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: colorless liquid, with unpleasant odour.
• 熔点: -15 °C; -15 °C(lit.); -15°C; -15°C
• 沸点: 168-169°C; 169 °C; 169 °C(lit.); 169°C
• 闪点: 122 °F; 50 °C; 55°C(131°F)
• 密度: 1.073; 1.073 g/mL at 25 °C(lit.); 1.075; 1.0766 g/mL
• 折射率: 1.588; 1.5900; n20/D 1.588(lit.)
• 蒸汽压: 1.4 mmHg ( 20 °C)
• 蒸汽密度: 3.8 (vs air)
• pKa: 8 (H₂O), 10 (DMSO)
• 感官: alliaceous (onion, garlic)

安全信息

• 保存注意事项: Air Sensitive; Very Toxic/Flammable
• RTECS编号: DC0525000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2337; UN2337
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1; I
• 危险公开号: 10-24/25-26-37/38-41-63; 10-24/25-26-41; R10 R24/25 R26 R41
• 安全公开号: 23-26-28-36/37/39-45; S23 S26 S28 S36/37/39 S45
• TSCA收录: 是
• GHS危险品标识: GHS02; GHS05; GHS06; GHS08
• GHS警示词: Danger
• 主要危害: Toxic
• GHS危险声明: H226-H300 +H310 + H330-H318; H300-H310-H330-H315-H335-H318-H226-H361
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P280-P305+P351+P338-P302+P352-P309-P310
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2337 6.1/PG 1

药理学性质

• 过敏源: no known allergens

产品相关信息

• 纯度: ≥98%; ≥98.0% (GC); ≥99%; 97%; 99+%
• 级别: analytical standard; purum
• 有效期: (limited shelf life, expiry date on the label)
• 线性分子式: C6H5SH

详细说明

Sigma Aldrich - T32808

包装
1 kg in Sure/Seal™
100, 500 g in Sure/Seal™

Sigma Aldrich - W361607

包装
1 kg in glass bottle
1 sample in glass bottle

Sigma Aldrich - 240249

包装
10 g in glass bottle
50 g in Sure/Seal™
Application
用于制备 β-内酯。1
Protocols & Applications
The Progress in Development of Dental Restorative Materials

参考文献

• For a detailed investigation of alkylation using, e.g. K₂CO₃ in acetone, see: Synth. Commun., 22, 1691 (1992). Unactivated aryl chlorides undergo nucleophilic substitution in the presence of K₂CO₃ in NMP to give aryl sulfides: J. Org. Chem., 56, 862 (1991).
• Michael additions occur readily with electron deficient alkenes. Subsequent chlorination with NCS and dehydrochlorination provides a stereoselective route to vinyl thioethers: J. Org. Chem., 46, 235 (1981):
  
• The Cu(I) derivative, phenylthiocopper forms complexes with alkyllithiums, which are useful alkyl transfer reagents, undergoing conjugate addition to enones, coupling with alkyl iodides to alkanes, and converting acid halides to ketones: J. Am. Chem. Soc., 95, 7788 (1973); Synthesis, 662 (1974); Org. Synth. Coll., 6, 248 (1988).
• Chlorination of PhSH with NCS: J. Org. Chem., 37, 1367 (1972), or SO₂Cl₂: Org. Synth. Coll., 8, 550 (1993), gives the useful reagent benzenesulfenyl chloride, PhSCl.
• Dilithiation of PhSH with n-BuLi and TMEDA gives exclusive ortho-metallation: J. Am. Chem. Soc., 111, 654, 665, 2327 (1989). Subsequent treatment of the dilithio species with DMF, followed by in situ reaction with chloroacetone provides a useful route to the benzo[b]thiophene system: J. Org. Chem., 58, 1293 (1993):
  
• Interception of the DMF adduct provides a source of the unstable 2-mercaptobenzaldehyde. Alternatively, ortho-metallated thiophenols can be formed by lithiation of the THP ether, in which coordination by oxygen favors ortho-lithiation: J. Am. Chem. Soc., 111, 658 (1989).