3-溴苯磺胺 | 89599-01-9

• 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: 3-溴苯磺胺
• 中文别名: 间溴苯磺酰胺；3-溴苯磺酰胺；3-溴苯-1-磺酰胺
• 英文名称: 3-bromobenzenesulfonamide
• 英文别名: m-bromobenzenesulfonamide；3-bromobenzenesulphonamide
• CAS: 89599-01-9
• 化学式: C₆H₆BrNO₂S
• mdl: MFCD00084903
• 分子量: 236.089
• InChiKey: MUBJNMWVQGHHLG-UHFFFAOYSA-N

物化性质

• 熔点：
  151-156 °C(lit.)
• 沸点：
  375.8±44.0 °C(Predicted)
• 密度：
  1.754±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  按规定使用和贮存的物质不会分解，并应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2935009090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉、干燥的地方。

SDS

Name:	3-Bromobenzenesulfonamide Material Safety Data Sheet
Synonym:	None Known
CAS:	89599-01-9

Section 1 - Chemical Product MSDS Name:3-Bromobenzenesulfonamide Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
89599-01-9	3-Bromobenzenesulfonamide	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 89599-01-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 151 - 156 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H6BrNO2S
Molecular Weight: 236.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 89599-01-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Bromobenzenesulfonamide - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 89599-01-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 89599-01-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 89599-01-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3-溴苯磺胺是一类重要的医药合成中间体。由于其官能团含有卤素和磺酰氯，因此具有较强的化学活性。

3-溴苯磺酰胺可用作医药合成的中间体，可通过两种方法制备：一是由3-溴苯磺酰氯与氨水反应得到；二是通过间溴苯四氟化硼重氮盐一步法制得。

作为一种胺类衍生物，3-溴苯磺胺主要用作医药中间体。其制备过程如下：

在氮气保护下，将间溴苯四氟化硼重氮盐（338.5 mg，1.25 mmol）、NaN₃（32.5 mg，0.5 mmol）、PPh₃（157.4 mg，0.6 mmol）、Na₂S₂O₅（190.1 mg，1.0 mmol）、TBAB（241.7 mg，0.75 mmol）和MeCN/H₂O（2/1，1 mL）加入Schlenk反应管中。反应在80℃下搅拌12小时后降至室温，再向体系中加入10 mL水稀释，并用乙酸乙酯萃取三次（每次10 mL），然后使用无水硫酸钠干燥、过滤并浓缩，最后通过柱层析分离得到白色固体3-溴苯磺酰胺。

反应信息

• 作为反应物：
  描述：

  3-溴苯磺胺 在 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 、 硫酸 、 溶剂黄146 、 silver carbonate 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 25.0h， 生成 2-氨基-5-溴苯磺酰胺
  参考文献：
  名称：

  苯甲磺酰胺与磺酰叠氮化物的铱催化邻位C-H酰胺化

  摘要：

  我们在此开发了铱催化的苯磺酰胺与磺酰叠氮化物的铱催化直接CH活化/ CN键形成反应。酰胺化反应为合成2-氨基苯磺酰胺类化合物提供了良好的合成方案。该策略具有广泛的底物范围，在无外部氧化剂的条件下可耐受各种官能团，并且仅释放分子氮作为唯一的副产物。此外，还研究了初步机理并提供了建议的反应途径。

  DOI：

  10.1002/adsc.201900573
• 作为产物：
  描述：

  3-溴苯磺酰氯 在 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 3-溴苯磺胺
  参考文献：
  名称：

  新型口服Ⅰ型CDK8抑制剂抗急性髓系白血病的发现

  摘要：

  CDK8 在急性髓性白血病、结直肠癌和其他癌症中起着关键作用。在这里，总共设计和合成了 54 种化合物。其中，最强效的化合物43 ( 3-(1H-pyrrolo[2,3-b]pyridin- 5-yl )benzamide ) 是一种新型 CDK8 Ⅰ抑制剂，对 CDK8 表现出很强的抑制活性 (IC 50  = 51.9 nM) ), 良好的激酶选择性，良好的抗AML细胞增殖活性（molm-13 GC 50  = 1.57 ± 0.59 μM），体内毒性低（急性毒性：2000 mg/kg）。进一步的机理研究表明，该化合物可以靶向 CDK8，然后磷酸化 STAT-1 和 STAT-5，从而抑制 AML 细胞增殖。此外，化合物43显示出相对良好的生物利用度（F = 28.00%），并且可以在体内以剂量依赖的方式抑制AML肿瘤的生长。该研究有助于进一步开发更有效的 CDK8 抑制剂来治疗 AML。

  DOI：

  10.1016/j.ejmech.2023.115214

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES
  申请人：Van Goor Fredrick F.

  公开号：US20110098311A1

  公开（公告）日：2011-04-28

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及包含上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• In Situ Generation of Oxazole Ylide and Interception with Sulfonamide: Construction of Amidines Using Two Diazo Molecules
  作者：Jijun Chen、Wenhao Long、Yanwei Zhao、Haiyan Li、Yonggao Zheng、Pengcheng Lian、Xiaobing Wan

  DOI：10.1002/cjoc.201800208

  日期：2018.9

  A novel generation of oxazole ylide and interception with sulfonamide have been well developed to construct fully substituted amidines. This copper‐catalyzed four‐component reaction incorporates two diazo molecules to target amidines and shows broad substrate scope, excellent functional groups tolerance and good to excellent yields.

  已经开发出新一代的恶唑叶立德并用磺酰胺截获，以构建完全取代的am。该铜催化的四组分反应结合了两个重氮分子以靶向am，并显示出广泛的底物范围，出色的官能团耐受性和良好的优异收率。
• Derivatives of purine, their preparation process and pharmaceutical compositions containing them
  申请人：Haesslein Jean-Luc

  公开号：US20050187228A1

  公开（公告）日：2005-08-25

  A compound of the formula wherein R is defined as in the specification, which compounds have an inhibitory effect vis-à-vis cycline-dependent kinase proteins (cdk) and are endowed with antimitotic properties.

  其中R在规范中定义，该化合物具有对细胞周期依赖性激酶蛋白（cdk）具有抑制作用并具有抗有丝分裂特性。
• [EN] 5-MEMBERED HETEROARYLAMINOSULFONAMIDES FOR TREATING CONDITIONS MEDIATED BY DEFICIENT CFTR ACTIVITY<br/>[FR] HÉTÉROARYLAMINOSULFONAMIDES À 5 CHAÎNONS POUR LE TRAITEMENT D'ÉTATS À MÉDIATION PAR UNE ACTIVITÉ CFTR DÉFICIENTE
  申请人：GENZYME CORP

  公开号：WO2021097057A1

  公开（公告）日：2021-05-20

  The invention relates to heteroaryl compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

  这项发明涉及杂环芳基化合物，其药用盐以及药物制剂。本文还描述了这些化合物的组成以及在治疗由CFTR活性不足介导的疾病和病况的方法中的使用，特别是囊性纤维化。