2-溴甲基-1-苯磺酰基-1h-吲哚 | 337508-54-0

• 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: 2-溴甲基-1-苯磺酰基-1h-吲哚
• 英文名称: 2-(N-benzenesulfonyl)indolyl methyl bromide
• 英文别名: 2-bromomethyl-1-phenylsulfonylindole；2-(bromomethyl)-1-(phenylsulfonyl)-1H-indole；1-(benzenesulfonyl)-2-(bromomethyl)indole
• CAS: 337508-54-0
• 化学式: C₁₅H₁₂BrNO₂S
• 分子量: 350.236
• InChiKey: SYYPBRKVYRCLJS-UHFFFAOYSA-N

物化性质

• 沸点：
  516.1±42.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  C
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R34
• 海关编码：
  2933990090

SDS

Name:	2-(Bromomethyl)-1-(phenylsulfonyl)-1h-indole 97% Material Safety Data Sheet
Synonym:
CAS:	337508-54-0

Section 1 - Chemical Product MSDS Name:2-(Bromomethyl)-1-(phenylsulfonyl)-1h-indole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
337508-54-0	2-(Bromomethyl)-1-(phenylsulfonyl)-1H-	97%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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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 immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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.
Extinguishing Media:
Use foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 337508-54-0: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 118 - 120 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: C15H12BrNO2S
Molecular Weight: 350.24

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 337508-54-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-(Bromomethyl)-1-(phenylsulfonyl)-1H-indole - 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: CORROSIVE SOLID, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 337508-54-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 337508-54-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 337508-54-0 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

反应信息

• 作为反应物：
  描述：

  2-溴甲基-1-苯磺酰基-1h-吲哚 在 potassium tert-butylate 、 palladium diacetate 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 9-(phenylsulfonyl)-9H-naphtho[2,1-c]carbazole
  参考文献：
  名称：

  芳基甲基砜的合成效用：涉及Pd（0）催化的Heck偶联反应的芳族和杂芳族化合物的环π-延伸

  摘要：

  已经实现了一种简单且通用的合成环状噻吩，二苯并噻吩和咔唑类似物的方法，该方法涉及在DMF中使用t- BuOK作为碱，将2-溴-1-（苯基磺酰基甲基）芳烃/杂芳烃与芳基甲基溴/杂芳基甲基溴进行烷基化。然后在80–140°C下在DMF中存在K 2 CO 3的情况下进行Pd（0）介导的分子内Heck偶联。此协议的有吸引力的特征是，各种各样的π共轭杂环的可通过arylmethylsulfones和苄基溴化物的适当选择可以容易地访问。

  DOI：

  10.1021/acs.joc.7b01813
• 作为产物：
  描述：

  1-(苯磺酰)-1H-吲哚-2-甲醛 在 硫酸 、 氢溴酸 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-溴甲基-1-苯磺酰基-1h-吲哚
  参考文献：
  名称：

  4-取代的D-谷氨酸类似物：具有抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。

  摘要：

  描述了显示全细胞抗菌活性的第一种有效的谷氨酸消旋酶（MurI）抑制剂。具有（2R，4S）立体化学并且带有芳基，杂芳基，肉桂基或联芳基甲基取代基的光学纯的4-取代的D-谷氨酸类似物代表一类新型的谷氨酸消旋酶抑制剂。对D-Glu核心的探索导致了对铅化合物（-）-8和10的鉴定。发现2-萘基甲基衍生物10是有效的竞争性谷氨酸消旋酶活性抑制剂（K（i）= 16 nM，圆二色性）分析; IC（50）= 0.1 microg / mL高效液相色谱（HPLC）分析）。彻底的结构-活性关系（SAR）研究导致苯并噻吩衍生物（例如69和74）具有更高的效价（HPLC法分别测定IC（50）= 0.036和0.01 microg / mL）。这些化合物对肺炎链球菌PN-R6表现出强大的全细胞抗菌活性，并且与酶法测定具有良好的相关性。化合物69、74和联芳基衍生物52在体内鼠大腿感染模型中显示抗肺炎链球菌的功效。本

  DOI：

  10.1021/jm020901d

文献信息

• [EN] BENZIMIDAZOLE OR INDOLE AMIDES AS INHIBITORS OF PIN1<br/>[FR] AMIDES DE BENZIMIDAZOLE OU D'INDOLE EN TANT QU'INHIBITEURS DE PIN1
  申请人：PFIZER

  公开号：WO2006040646A1

  公开（公告）日：2006-04-20

  The invention relates to compounds of the formula (1) and to pharmaceutically acceptable salts and solvates thereof, wherein the variables are defined herein. The invention also relates to methods of treating abnormal cell growth in mammals by administering the compounds of formula (1) and to pharmaceutical compositions for treating such disorders that contain the compounds of formula (1). The invention also relates to methods of preparing the compounds of formula (1).

  这项发明涉及公式（1）的化合物，以及其药学上可接受的盐和溶剂化合物，其中变量在此处定义。该发明还涉及通过给予公式（1）的化合物来治疗哺乳动物中的异常细胞生长的方法，以及用于治疗包含公式（1）化合物的这类疾病的药物组合物。该发明还涉及制备公式（1）化合物的方法。
• Imidazo 4,5-C Pyridine Compounds and Methods of Antiviral Treatment
  申请人：Bondy S. Steven

  公开号：US20070244148A1

  公开（公告）日：2007-10-18

  The present invention relates to a pharmaceutical composition for the treatment or prevention of viral infections comprising as an active principle at least one imidazo[4,5-c]pyridine prodrug having the general formula (Z): The invention also relates to processes for the preparation of compounds according to the invention having above mentioned general formula and their use as a medicine or to treat or prevent viral infections.

  本发明涉及一种用于治疗或预防病毒感染的药物组合物，其包含至少一种具有以下通式（Z）的咪唑[4,5-c]吡啶前药作为活性成分：本发明还涉及制备符合上述通式的化合物的方法以及它们作为药物或用于治疗或预防病毒感染的用途。
• IMIDAZO[4,5-c]PYRIDINE COMPOUNDS AND METHODS OF ANTIVIRAL TREATMENT
  申请人：Bondy Steven S.

  公开号：US20100028301A1

  公开（公告）日：2010-02-04

  The present invention relates to pharmaceutical compositions for the treatment or prevention of viral infections comprising as an active principle at least one imidazo[4,5-c]pyridine prodrug having the general Formula (A) wherein the substituents are described in the specification. The invention also relates to processes for the preparation and screening of compounds according to the invention having above mentioned general Formula and their use in the treatment or prophylaxis of viral infections.

  本发明涉及一种制备用于治疗或预防病毒感染的药物组合物，其包含至少一种咪唑并[4,5-c]吡啶前药作为活性成分，其通式为（A），其中取代基在规范中描述。该发明还涉及根据上述通式制备和筛选化合物的方法以及它们在治疗或预防病毒感染中的应用。
• Imidazo[4,5-d]pyrimidines, their uses and methods of preparation
  申请人：Puerstinger Gerhard

  公开号：US20090208456A1

  公开（公告）日：2009-08-20

  The present invention relates to pharmaceutical compositions for the treatment of prevention of viral infections comprising as an active principle at least one imidazo[4,5-c]pyrimidine having the general formula (A), wherein the substituents are described in the specification. The invention also relates to processes for the preparation of compounds according to the invention having above mentioned general formula, their pharmaceutically acceptable formulations and their use as a medicine or to treat or prevent viral infections.

  本发明涉及制备用于治疗或预防病毒感染的药物组合物，其中至少包括一种具有通式（A）的咪唑并[4,5-c]嘧啶类活性成分，其中取代基如规范所述。本发明还涉及制备符合上述通式的化合物的过程，其药学上可接受的配方以及它们作为药物或用于治疗或预防病毒感染的用途。
• Synthesis of Cytotoxic Quino[4,3-<i>b</i>]carbazole Frameworks through an Intramolecular Diels–Alder Reaction
  作者：Vinayagam Pavunkumar、Kesavan Harikrishnan、Arasambattu K. Mohanakrishnan

  DOI：10.1021/acs.joc.3c01909

  日期：2024.1.5

  successfully exploited for the synthesis of quino[4,3-b]carbazole and its analogues. This reaction proceeds through a [4 + 2] cycloaddition followed by elimination and deprotection of phenylsulfonyl units to afford the quinocarbazoles in moderate to good yields. The reaction features a broad substrate scope and remarkable functional group forbearance. A preliminary in vitro cytotoxicity evaluation of representative

  位置异构吲哚-2/3-苯基乙烯基-N-炔基化（ N-苯磺酰基）胺的分子内狄尔斯-阿尔德反应已成功用于合成喹诺[4,3- b ]咔唑及其类似物。该反应通过[4+2]环加成进行，然后消除苯磺酰基单元并脱保护，以中等至良好的产率提供喹啉咔唑。该反应具有广泛的底物范围和显着的官能团耐受性。针对 NCI-H460 人类癌细胞培养物，对代表性喹啉[4,3- b ]咔唑进行了初步的体外细胞毒性评估。在评估的喹啉[4,3- b ]咔唑中，五种含氟喹啉咔唑显示出纳米摩尔范围（0.8–2.0 nm）GI 50值。还对代表性喹咔唑进行了紫外可见光谱和荧光光谱研究。与玫瑰树碱一样，四种喹咔唑显示出双重发射，证实了极性质子溶剂中存在对醌类互变异构形式。