N-环己基-4-溴苯磺酰胺 | 7454-76-4

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-环己基-4-溴苯磺酰胺
• 中文别名: 4-溴-N-环己基并苯磺酰胺；4-溴-N-环己基苯磺酰胺
• 英文名称: 4-bromo-N-cyclohexylbenzenesulfonamide
• 英文别名: N-cyclohexyl-4-bromobenzenesulfonamide
• CAS: 7454-76-4
• 化学式: C₁₂H₁₆BrNO₂S
• mdl: MFCD00450584
• 分子量: 318.235
• InChiKey: XATZMSCJHBJRTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104
• 沸点：
  413.7±47.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
N-Cyclohexyl 4-bromobenzenesulfonamide
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P302+P352: IF ON SKIN: Wash with soap and water
P321: Specific treatment (see on this label)
P405: Store locked up

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Section 3. Composition/information on ingredients.
N-Cyclohexyl 4-bromobenzenesulfonamide
Ingredient name:
CAS number: 7454-76-4

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C12H16BrNO2S
Molecular weight: 318.2

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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, nitrogen oxides, 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：

  N-环己基-4-溴苯磺酰胺 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-cyclohexyl-4-(6-fluoro-1H-indazol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Rational Design, Optimization, and Biological Evaluation of Novel MEK4 Inhibitors against Pancreatic Adenocarcinoma

  摘要：

  DOI：

  10.1021/acsmedchemlett.1c00376
• 作为产物：
  描述：

  4-溴苯硫酚 在 N-氯代丁二酰亚胺 、 四丁基氯化铵 、 水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 N-环己基-4-溴苯磺酰胺
  参考文献：
  名称：

  使用 N-氯代琥珀酰亚胺从硫醇中方便地一锅法合成磺酰胺和磺酰叠氮化物

  摘要：

  描述了从硫醇中方便地合成磺酰胺和磺酰叠氮化物。从硫醇原位制备磺酰氯是通过用 N-氯琥珀酰亚胺 (NCS)、四丁基氯化铵和水氧化来完成的。然后使磺酰氯在同一反应容器中进一步与过量的胺或叠氮化钠反应。

  DOI：

  10.1055/s-0030-1261232

文献信息

• One-Pot Synthesis of Sulfonamides and Sulfonyl Azides from Thiols using Chloramine-T
  作者：Behrooz Maleki、Saba Hemmati、Reza Tayebee、Sirous Salemi、Yasaman Farokhzad、Mehdi Baghayeri、Farrokhzad Mohammadi Zonoz、Elahe Akbarzadeh、Rohollah Moradi、Azam Entezari、Mohammad Reza Abdi、Samaneh Sedigh Ashrafi、Fereshteh Taimazi、Majid Hashemi

  DOI：10.1002/hlca.201200648

  日期：2013.11

  A convenient synthesis of sulfonamides and sulfonyl azides from thiols is described. In situ preparation of sulfonyl chlorides from thiols was accomplished by oxidation with chloramine‐T (=N‐chlorotosylamide=N‐chloro‐4‐methylbenzenesulfonamide), tetrabutylammonium chloride (Bu4NCl), and H2O. The sulfonyl chlorides were then further allowed to react with excess amine or NaN3 in the same pot.

  描述了由硫醇方便地合成磺酰胺和磺酰叠氮化物。通过用氯胺-T（= N-氯代甲苯磺酰胺= N-氯--4-甲基苯磺酰胺），四丁基氯化铵（Bu 4 NCl）和H 2 O氧化，可以完成从硫醇中磺酰氯的原位制备。在同一锅中与过量的胺或NaN 3反应。
• Synthesis of sulfonamides and sulfonic esters via reaction of amines and phenols with thiols using H2O2–POCl3 system
  作者：Kiumars Bahrami、Mohammad M. Khodaei、Jamshid Abbasi

  DOI：10.1016/j.tet.2012.04.040

  日期：2012.6

  oxychloride efficiently promoted the synthesis of sulfonamides and sulfonic esters from thiols with hydrogen peroxide in the presence of Amberlite IRA-400 (OH−). This method has been applied to a variety of substrates including nucleophilic and sterically hindered amines, and also phenols with excellent yields of sulfonamides and sulfonic esters. In most cases these reactions are highly selective, simple,

  三氯氧磷有效地与过氧化氢在的Amberlite IRA-400（OH存在促进磺酰胺和磺酸酯的合成从硫醇- ）。该方法已应用于多种底物，包括亲核胺和位阻胺，以及苯酚类，其磺酰胺和磺酸酯的收率都很高。在大多数情况下，这些反应具有高度的选择性，简单性和清洁性，可提供产率高且纯度高的产品。
• Convenient One-Pot Synthesis of Sulfonamides from Thiols and Disulfides Using 1,3-Dichloro-5,5-dimethylhydantoin (DCH)
  作者：Hojat Veisi

  DOI：10.5012/bkcs.2012.33.2.383

  日期：2012.2.20

  A convenient synthesis of sulfonamides from thiols and disulfides is described. In situ preparation of sulfonyl chlorides from thiols is accomplished by oxidation with 1,3-dichloro-5,5-dimethylhydantoin (DCH) under Nbenzyl-trimethylammonium chloride and water. The sulfonyl chlorides are then further allowed to react with excess amine in the same reaction vessel.

  描述了从硫醇和二硫化物方便合成磺胺类药物。从硫醇原位制备磺酰氯是通过在 N苄基-三甲基氯化铵和水下用 1,3-二氯-5,5-二甲基乙内酰脲 (DCH) 氧化来完成的。然后进一步使磺酰氯在同一反应容器中与过量胺反应。
• [EN] CYCLOALKYL NITRILE PYRAZOLO PYRIDONES AS JANUS KINASE INHIBITORS<br/>[FR] CYCLOALKYLNITRILE PYRAZOLOPYRIDONES UTILISÉES COMME INHIBITEURS DE LA JANUS KINASE
  申请人：MERCK SHARP & DOHME

  公开号：WO2014146490A1

  公开（公告）日：2014-09-25

  Compounds of formula I are provided, which are JAK inhibitors and are useful for the treatment of JAK-mediated diseases such as rheumatoid arthritis, asthma, COPD and cancer.

  公式I的化合物被提供，这些化合物是JAK抑制剂，对于治疗JAK介导的疾病，如类风湿性关节炎、哮喘、慢性阻塞性肺病（COPD）和癌症等疾病是有用的。
• Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
  作者：Yufan Liang、Xiaheng Zhang、David W. C. MacMillan

  DOI：10.1038/s41586-018-0234-8

  日期：2018.7

  to construct sp2 carbon–nitrogen (C–N) bonds using palladium, copper or nickel catalysis1,2. However, the incorporation of alkyl substrates to form sp3 C–N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge

  在过去的三十年中，利用钯、铜或镍催化构建 sp2 碳氮 (C-N) 键的方法的开发取得了相当大的进展1,2。然而，结合烷基底物形成sp3 C-N键仍然是交叉偶联化学领域的主要挑战之一。在这里，我们证明铜催化和光氧化还原催化的协同组合可以提供一个通用平台来应对这一挑战。该交叉偶联系统使用天然丰富的烷基羧酸和市售的氮亲核试剂作为偶联伙伴。它适用于各种伯、仲和叔烷基羧酸（通过碘鎓活化），以及大量氮亲核试剂：氮杂环、酰胺、磺酰胺和苯胺可以进行 C-N 偶联，提供 N-在室温下和短时间内（五分钟到一小时），烷基产品的效率从良好到优异。我们证明，这种 C-N 偶联方案使用含有多个胺基的底物进行高区域选择性，并且还可以应用于复杂的药物分子，从而能够快速构建分子复杂性和生物活性药物的后期功能化。铜催化和光氧化还原催化的结合在快速、室温偶联方案中形成 sp3 C-N 键，具有高效率和区域选择性以及广泛的底物范围。