N,N-二乙基-4-溴苯磺酰胺 | 90944-62-0

• 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,N-二乙基-4-溴苯磺酰胺
• 中文别名: 4-溴-N,N-二乙基苯磺酰胺
• 英文名称: 4-bromo-N,N-diethylbenzenesulfonamide
• 英文别名: N,N-diethyl-4-bromobenzenesulfonamide
• CAS: 90944-62-0
• 化学式: C₁₀H₁₄BrNO₂S
• mdl: MFCD00587586
• 分子量: 292.197
• InChiKey: NRGTZJXYAAGKQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  356.4±44.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  适宜在室温和干燥的环境中存放。

SDS

Material Safety Data Sheet

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

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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: N,N-Diethyl 4-bromobenzenesulfonamide
CAS number: 90944-62-0

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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: C10H14BrNO2S
Molecular weight: 292.2

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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,N-二乙基-4-溴苯磺酰胺 在 chromium acetate hydroxide 、 高碘酸 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以76%的产率得到4-溴苯磺酰胺
  参考文献：
  名称：

  醋酸铬 (III) 催化过碘酸对 N-烷基磺酰胺和 N,N-二烷基磺酰胺的新型 N-脱烷基化反应

  摘要：

  已发现氢氧化铬 (III) 是 N-烷基磺酰胺和 N,N-二烷基磺酰胺的 N-脱烷基化的有效催化剂，可在室温下与乙腈中的高碘酸一起以良好至极好的收率提供磺酰胺。

  DOI：

  10.1055/s-2004-830851
• 作为产物：
  描述：

  三乙胺 、 4-溴苯磺酰氯 在 copper(I) oxide 、 氧气 作用下， 以 1,2-二氯乙烷 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以87%的产率得到N,N-二乙基-4-溴苯磺酰胺
  参考文献：
  名称：

  通过铜催化的叔胺的C-N键的氧化裂解 合成磺酰胺†

  摘要：

  开发了铜催化的磺酰氯与叔胺通过叔胺的氧化C–N键裂解的偶联反应。使用该策略以中等至良好的产率合成了磺酰胺。该反应适用于各种叔胺以及磺酰氯。

  DOI：

  10.1039/c6ob01208f

文献信息

• I₂/TBHP Mediated C–N and C–H Bond Cleavage of Tertiary Amines toward Selective Synthesis of Sulfonamides and β-Arylsulfonyl Enamines: The Solvent Effect on Reaction
  作者：Junyi Lai、Liming Chang、Gaoqing Yuan

  DOI：10.1021/acs.orglett.6b01412

  日期：2016.7.1

  A novel method toward synthesis of sulfonamides and β-arylsulfonyl enamines has been developed via I2/TBHP mediated C–N and C–H bond cleavage of tertiary amines, which features highly selective formation of two different target products depending on the reaction solvent. The experimental results reveal that H2O as the solvent could effectively achieve the C–N bond cleavage to produce sulfonamides due

  通过I 2 / TBHP介导的叔胺的C–N和C–H键裂解，已经开发了一种合成磺酰胺和β-芳基磺酰基烯胺的新方法，该方法具有高选择性地形成两种不同目标产物的特点，具体取决于反应溶剂。实验结果表明，由于H 2 O参与了H 2 O双重作用的反应过程，因此H 2 O作为溶剂可以有效地实现C–N键的裂解，生成磺酰胺。与H 2 O不同，有机溶剂（例如二甲基亚砜）可以促进叔胺的C–H键裂解，从而生成β-芳基磺酰基烯胺。
• [EN] NAPHTHYLACETIC ACIDS<br/>[FR] ACIDES NAPHTYLACÉTIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010055005A1

  公开（公告）日：2010-05-20

  The invention is concerned with the compounds of formula (I) and pharmaceutically acceptable salts and esters thereof, wherein X, Q, and R1-R6 are defined in the detailed description and claims. In addition, the present invention relates to methods of manufacturing and using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds of formula (I) are antagonists or partial agonists at the CRTH2 receptor and may be useful in treating diseases and disorders associated with that receptor such as asthma.

  本发明涉及式(I)的化合物以及药用可接受的盐和酯，其中X、Q和R1-R6在详细描述和权利要求中定义。此外，本发明还涉及制造和使用式(I)化合物的方法，以及包含此类化合物的药物组合物。式(I)的化合物是CRTH2受体的拮抗剂或部分激动剂，可用于治疗与该受体相关的疾病和失调，如哮喘。
• Eosin Y-Sensitized Photocatalytic Reaction of Tertiary Aliphatic Amines with Arenesulfonyl Chlorides under Visible-Light Irradiation
  作者：Ronghua Zhang、Yuguo Cai、Deli Sun、Song Xu、Qiguang Zhou

  DOI：10.1055/s-0036-1588828

  日期：2017.8

  A mild, practical, and environmentally friendly route to vinyl sulfones and sulfonamides has been developed based on the reaction of aliphatic amines with arenesulfonyl chlorides in the presence of eosin Y as a photocatalyst under visible light. The method permits the selective formation of vinyl sulfones or sulfonamides, depending on the oxidation environment and solvent. A wide range of products

  基于脂肪胺与芳烃磺酰氯在曙红Y作为光催化剂在可见光下的反应，开发了一种温和、实用且环保的乙烯基砜和磺酰胺途径。该方法允许选择性地形成乙烯基砜或磺酰胺，这取决于氧化环境和溶剂。在优化条件下以中等至良好的收率获得了广泛的产品。
• Charge-Transfer Complex Promoted Regiospecific C−N Bond Cleavage of Vicinal Tertiary Diamines
  作者：Ying Fu、Qin-Shan Xu、Chun-Zhao Shi、Zhengyin Du、Caiqin Xiao

  DOI：10.1002/adsc.201800591

  日期：2018.9.17

  A catalyst‐free, charge‐transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C−N

  提出了一种无催化剂，电荷转移的复合物，可促进磺酰氯与邻位叔二胺的偶联，从而生成磺酰胺。机理研究表明，这些反应是通过将邻位叔二胺电荷转移至磺酰氯而进行的，形成了不稳定的磺酰基季铵盐状复合物，从而诱导了邻位叔二胺的区域特异性分子内C-N键裂解。
• Rapid and Efficient Copper‐Catalyzed Finkelstein Reaction of (Hetero)Aromatics under Continuous‐Flow Conditions
  作者：Mao Chen、Saki Ichikawa、Stephen L. Buchwald

  DOI：10.1002/anie.201409595

  日期：2015.1.2

  efficient method for the copper‐catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N‐H and O‐H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous‐flow processes (amidation and Mg–I

  已经开发出一种使用连续流生成各种芳基碘化物的铜催化（杂）芳烃的Finkelstein反应的通用，快速，有效的方法。所描述的方法可以耐受各种官能团，包括N-H和O-H基团。另外，代替分离，在两个不同的多步连续流工艺（酰胺化和Mg-I交换/亲核加成）中使用了芳基碘溶液，以证明该方法的灵活性。