1-溴-4-丁基硫代苯 | 121392-35-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 1-溴-4-丁基硫代苯
• 英文名称: n-butyl 4-bromophenyl sulfide
• 英文别名: 1-Bromo-4-butylsulphanylbenzene；1-Bromo-4-butylthiobenzene；1-bromo-4-butylsulfanylbenzene
• CAS: 121392-35-6
• 化学式: C₁₀H₁₃BrS
• 分子量: 245.183
• InChiKey: CYFJLXXVMAJKNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Bromo-4-butylthiobenzene
Synonyms: (4-Bromophenyl)(butyl)sulfane; 4-bromophenyl butyl sulfide; S-butyl 4-bromothiophenol

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 1-Bromo-4-butylthiobenzene
CAS number: 121392-35-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C10H13BrS
Molecular weight: 245.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-溴-4-丁基硫代苯 在 氢氧化钾 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 生成 3-(4-butylsulfanylphenyl)propiolic acid
  参考文献：
  名称：

  Synthesis, transition temperatures, and optical properties of compounds with simple phenyl units linked by double bond, triple bond, ester or propiolate linkages

  摘要：

  已合成一系列化合物，含有通过-CHCH-、-COO-、-CC-或-CC-COO-连接基团连接的4-丁硫基苯基和4-氰基或4-异硫氰酸苯基单元。介绍了这些新型化合物的合成，并讨论了其转变温度和光学参数，与相关的联苯参考系统进行了比较。酯连接基团降低了光学各向异性性和极化率各向异性性，但其他连接基团则增加了光学各向异性性（高达Δn = 0.50）和极化率各向异性性[高达Δα = 45.2 ų（10−30 m³）]。

  DOI：

  10.1039/b001164i
• 作为产物：
  描述：

  丁基硫基苯 生成 1-溴-4-丁基硫代苯
  参考文献：
  名称：

  New series of thio-derivatives of basic benzhydryl ethers and thioethers

  摘要：

  这项发明包括具有镇静性能的硫代或磺代基本苯基二苯基醚和硫醚，其化学式表示为，其中R为氢、氯、溴或碘；R1和R2为烷基磺酰基、烷基硫醇基、苯基或取代苯基硫醇基、环烷基或取代环烷基硫醇基或氢，除非其中一个是氢；Z为氧或硫；X为二烷胺基烷基、吗啉基取代烷基、哌啶基取代烷基或N-烷基取代C-哌啶基；以及它们的酸或季铵盐。它们可以通过将化学式的二苯基卤化物与适当的氨基醇或氨基硫醇或它们的碱金属盐反应来制备；或者通过将氨基卤化物与适当取代的苯基醇或苯基硫醇醇或其碱金属盐反应来制备。溶剂可以存在。示例揭示了以下化合物的盐酸盐或柠檬酸盐的制备：苯基二甲基氨基乙基硫化物，其中苯基基被p-甲基、p-乙基、p-异丙基、o-、m-和p-丁基、m-和p-己基、p-环己基、p-辛基和p-苯基硫醇基取代，以及p,p1-双(n-己基、丙基和丁基硫醇基)基和p-丁基磺酰基取代；p-丁基和m-溴-p1-丁基硫醇基和p,p1-双(丁基硫醇基)-苯基二乙基氨基乙基硫化物；m-和p-丁基硫醇基苯基二甲基氨基乙基醚；p-丁基硫醇基苯基二(4-吗啉基)乙基醚和硫化物；p-丁基硫醇基苯基二甲基氨基丙基醚和硫化物；p-丁基硫醇基苯基四(1-甲基)-哌啶基硫化物；p-甲基硫醇基苯基二(1-哌啶基)-乙基醚；p-己基硫醇基苯基二(4-吗啉基)-乙基硫化物。作为起始原料使用的p-烷基硫醇基苯基氯化物是通过将p-烷基硫醇基苯酮（从p-烷基苯基硫醇基获得）与锌和氢氧化钠还原为醇，然后用无水HCl饱和得到的。p-苯基硫醇基衍生物类似制备。m-烷基硫醇基苯基氯化物类似地从m-烷基硫醇基苯酮制备，后者是通过m-烷基硫醇基苯酰氯、苯和无水AlCl3在CS2中反应获得的。烷基硫醇基苯基硫醇基硫醇通过将氯化物与硫脲沸腾制备，得到的烷基硫醇基苯基硫醇基硫脲盐随后与水合氢氧化钠水解。p-丁基磺酰基苯酮是通过在冰乙酸中用过氧化氢氧化p-丁基硫醇基苯酮得到的。m-溴-p1-丁基硫醇基苯基氯化物是通过将丁基苯硫化物与m-溴苯甲酰氯在Friedel-Crafts合成中反应得到m-溴-p1-丁基硫醇基苯酮，然后通过锌和KOH还原为醇，再用HCl处理得到。由溴化p-正丁基苯硫化物制备的p-溴苯基-n-正丁硫醚通过用CO2与格氏试剂衍生物碳化得到p-丁基硫醇基苯甲酸。酸氯化物通过与氯化硫酰反应得到，然后与p-正丁基苯硫化物反应，得到p,p1-双(正丁硫醇基)-苯酮。这经还原得到p,p1-双(正丁硫醇基)-苯醇，再经HCl处理得到氯化物。类似方法可制备p,p1-双(丙基和己基硫醇基)-衍生物。

  公开号：

  US02830088A1

文献信息

• A mild and efficient copper-catalyzed coupling of aryl iodides and thiols using an oxime–phosphine oxide ligand
  作者：Di Zhu、Lei Xu、Fan Wu、Boshun Wan

  DOI：10.1016/j.tetlet.2006.05.178

  日期：2006.8

  A mild and efficient copper-catalyzed system for the coupling of aryl iodides and thiols was developed using a readily prepared and highly stable oxime–phosphine oxide ligand. Good to excellent yields were obtained.

  使用易于制备且高度稳定的肟-氧化膦配体，开发了一种温和而有效的铜催化体系，用于芳基碘化物和硫醇的偶联。获得了良好的优良的收率。
• Recyclable Heterogeneous Supported Copper-Catalyzed Coupling of Thiols with Aryl Halides: Base-Controlled Differential Arylthiolation of Bromoiodobenzenes
  作者：Sukalyan Bhadra、Bojja Sreedhar、Brindaban C. Ranu

  DOI：10.1002/adsc.200900358

  日期：2009.10

  Alumina-supported copper sulfate efficiently catalyzes the S-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic

  氧化铝负载的硫酸铜可在无氧，无配体的条件下，有效地催化芳基，杂芳族和脂肪族硫醇与芳基以及杂芳基卤化物的S-芳基化反应。该协议通过在芳香族卤化物中通过硫醇与碘代和溴代取代基的碱基控制的差分偶联，轻松获得各种硫醚以及不对称的双硫醚。该催化剂便宜，对空气不敏感，环境友好且可回收。
• Application of a novel 1,3-diol with a benzyl backbone as chiral ligand for asymmetric oxidation of sulfides to sulfoxides
  作者：Paramartha Gogoi、Trimurthulu Kotipalli、Kiran Indukuri、Somasekhar Bondalapati、Pipas Saha、Anil K. Saikia

  DOI：10.1016/j.tetlet.2012.03.077

  日期：2012.5

  A chiral 1,3-diol with a benzyl backbone has been used for the asymmetric oxidation of sulfides to sulfoxides. Moderate to good yields and enantioselectivity (upto 87% ee) have been observed.

  具有苄基主链的手性1，3-二醇已用于硫化物不对称氧化为亚砜。已经观察到中等至良好的产率和对映选择性（高达87％ee）。
• [EN] DERIVATIVES OF 4- (IMIDAZOL-5-YL)-2-(4-SULFOANILINO) PYRIMIDINE WITH CDK INHIBITORY ACTIVITY<br/>[FR] DERIVES DE 4- (IMIDAZOL-5-YL)-2-(4-SULFOANILINO) PYRIMIDINE A ACTIVITE INHIBITRICE CDK
  申请人：ASTRAZENECA AB

  公开号：WO2003076436A1

  公开（公告）日：2003-09-18

  Compounds of the formula (I): wherein R1, R2, R3, R4, R5 and p are as defined within and a pharmaceutically acceptable salts and in vivo hydrolysable esters are described. Also described are processes for their preparation and their use as medicaments, particularly medicaments for producing a cell cycle inhibitory (anti-cell-proliferation) effect in a warm-blooded animal, such as man.

  公式（I）的化合物：其中R1、R2、R3、R4、R5和p的定义如下，并且描述了药学上可接受的盐和体内可水解酯。还描述了它们的制备过程以及它们作为药物的用途，特别是作为用于在温血动物（如人）中产生细胞周期抑制（抗细胞增殖）效果的药物。
• New series of thio-derivatives of basic benzhydryl ethers and thioethers
  申请人：HERMAN HUBNER OLUF

  公开号：US02830088A1

  公开（公告）日：1958-04-08

  The invention comprises thio- or sulphonyl-substituted basic benzhydryl ethers and thioethers having sedative properties and represented by the formula wherein R is hydrogen, chlorine, bromine or iodine; R1 and R2 are alkylsulphonyl, alkylmercapto, phenyl- or substituted phenylmercapto, cycloalkyl- or substituted cycloalkylmercapto or hydrogen, and may be the same except when one of them is hydrogen; Z is oxygen or sulphur; and X is dialkylaminoalkyl, morpholinyl-substituted alkyl, piperidyl-substituted alkyl or N-alkyl-substituted C-piperidyl; and their acid or quaternary ammonium salts. They may be prepared by reacting a benzhydryl halide of the formula with the appropriate amino-alcohol or amino-thio-alcohol or their alkali metal salts; or by reacting the amino-halide with an appropriately substituted benzhydrol or benzhydryl-thio-alcohol or an alkali metal salt thereof. Solvents may be present. Examples disclose the preparation of hydrochlorides or citrates of the following compounds: benzhydryl 2-dimethylaminoethyl sulphides in which the benzhydryl group is substituted by p-methyl, p-ethyl, p-isopropyl-, o-, m- and p-butyl-, m- and p-hexyl-, p-cyclohexyl-, p-octyl- and p-phenyl-mercapto groups and by p,p1-bis(n-hexyl-, propyl- and butyl-mercapto) groups and by p-butyl sulphonyl: the p-butyl- and m-bromo-p1-butylmercapto and p,p1-bis(butylmercapto)-benzyhydryl 2-diethyl aminoethyl sulphides: m- and p-butyl-mercapto-benzhydryl 2-dimethylaminoethyl ethers: p-butylmercaptobenzhydryl-4-dimethyl-aminobutyl ether: p-butylmercaptobenzhydryl 2-(4-morpholinyl) ethyl ether and sulphide; p-butyl mercaptobenzhydryl 2-dimethylaminopropyl ether and sulphide: p-butylmercaptobenzhydryl 4-(1-methyl)-piperidyl sulphide: p-methylmercaptobenzhydryl 2-(1 - piperidyl) - ethyl ether: p-hexylmercaptobenzhydryl 2-(4-morpholinyl)-ethyl sulphide. The p-alkylmercaptobenzhydryl chlorides, used as starting materials, are prepared by reducing the p-alkyl mercaptobenzophenones (obtained from the p-alkylphenyl sulphides) with zinc and sodium hydroxide to the alcohol and then saturating with anhydrous HCl. The p-phenylmercapto-derivative is similarly prepared. The m-alkyl mercaptobenzhydryl chlorides are similarly prepared from the m-alkylmercaptobenzophenones which are obtained from the m-alkylmercaptobenzoyl chloride, benzene and anhydrous AlCl3 in CS2. The alkylmercaptobenzhydryl mercaptans are prepared by boiling the chloride with thiourea yielding the alkylmercaptobenzhydrylisothiouronium chloride which is then hydrolysed with aqueous sodium hydroxide. p-Butyl sulphonylbenzophenone is obtained by oxidizing p-butyl mercaptobenzophenone with hydrogen peroxide in glacial acetic acid. m - Bromo - p1 - butylmercaptobenzhydryl chloride is prepared by reacting butyl phenyl sulphide with m-bromobenzoyl chloride by the Friedel-Crafts synthesis to yield m-bromo-p1-butylmercaptobenzophenone, which is reduced by zinc and KOH to the alcohol which is then treated with HCl. p - Bromophenyl - n - butyl sulphide, prepared by brominating p-n-butyl phenyl sulphide, is converted to p-butyl mercaptobenzoic acid by carbonation of a Grignard derivative with CO2. The acid chloride, obtained by treatment with thionyl chloride, is reacted with butyl phenyl sulphide as above, yielding p,p1-bis (butylmercapto)-benzophenone. This is reduced to give p,p1-bis(butylmercapto)-benzhydrol, which is treated with HCl to give the chloride. Similar methods produce the p,p1-bis(propyl-and hexyl-mercapto)-derivatives.

  这项发明包括具有镇静性能的硫代或磺代基本苯基二苯基醚和硫醚，其化学式表示为，其中R为氢、氯、溴或碘；R1和R2为烷基磺酰基、烷基硫醇基、苯基或取代苯基硫醇基、环烷基或取代环烷基硫醇基或氢，除非其中一个是氢；Z为氧或硫；X为二烷胺基烷基、吗啉基取代烷基、哌啶基取代烷基或N-烷基取代C-哌啶基；以及它们的酸或季铵盐。它们可以通过将化学式的二苯基卤化物与适当的氨基醇或氨基硫醇或它们的碱金属盐反应来制备；或者通过将氨基卤化物与适当取代的苯基醇或苯基硫醇醇或其碱金属盐反应来制备。溶剂可以存在。示例揭示了以下化合物的盐酸盐或柠檬酸盐的制备：苯基二甲基氨基乙基硫化物，其中苯基基被p-甲基、p-乙基、p-异丙基、o-、m-和p-丁基、m-和p-己基、p-环己基、p-辛基和p-苯基硫醇基取代，以及p,p1-双(n-己基、丙基和丁基硫醇基)基和p-丁基磺酰基取代；p-丁基和m-溴-p1-丁基硫醇基和p,p1-双(丁基硫醇基)-苯基二乙基氨基乙基硫化物；m-和p-丁基硫醇基苯基二甲基氨基乙基醚；p-丁基硫醇基苯基二(4-吗啉基)乙基醚和硫化物；p-丁基硫醇基苯基二甲基氨基丙基醚和硫化物；p-丁基硫醇基苯基四(1-甲基)-哌啶基硫化物；p-甲基硫醇基苯基二(1-哌啶基)-乙基醚；p-己基硫醇基苯基二(4-吗啉基)-乙基硫化物。作为起始原料使用的p-烷基硫醇基苯基氯化物是通过将p-烷基硫醇基苯酮（从p-烷基苯基硫醇基获得）与锌和氢氧化钠还原为醇，然后用无水HCl饱和得到的。p-苯基硫醇基衍生物类似制备。m-烷基硫醇基苯基氯化物类似地从m-烷基硫醇基苯酮制备，后者是通过m-烷基硫醇基苯酰氯、苯和无水AlCl3在CS2中反应获得的。烷基硫醇基苯基硫醇基硫醇通过将氯化物与硫脲沸腾制备，得到的烷基硫醇基苯基硫醇基硫脲盐随后与水合氢氧化钠水解。p-丁基磺酰基苯酮是通过在冰乙酸中用过氧化氢氧化p-丁基硫醇基苯酮得到的。m-溴-p1-丁基硫醇基苯基氯化物是通过将丁基苯硫化物与m-溴苯甲酰氯在Friedel-Crafts合成中反应得到m-溴-p1-丁基硫醇基苯酮，然后通过锌和KOH还原为醇，再用HCl处理得到。由溴化p-正丁基苯硫化物制备的p-溴苯基-n-正丁硫醚通过用CO2与格氏试剂衍生物碳化得到p-丁基硫醇基苯甲酸。酸氯化物通过与氯化硫酰反应得到，然后与p-正丁基苯硫化物反应，得到p,p1-双(正丁硫醇基)-苯酮。这经还原得到p,p1-双(正丁硫醇基)-苯醇，再经HCl处理得到氯化物。类似方法可制备p,p1-双(丙基和己基硫醇基)-衍生物。