1-(2-溴苯基)-1H-吡唑 | 87488-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(2-溴苯基)-1H-吡唑
• 中文别名: 1-(2-溴苯基)吡唑
• 英文名称: 1-(2-bromophenyl)-1H-pyrazole
• 英文别名: 1-(2-bromophenyl)pyrazole
• CAS: 87488-84-4
• 化学式: C₉H₇BrN₂
• 分子量: 223.072
• InChiKey: QNDJHGODPWAKAO-UHFFFAOYSA-N

物化性质

• 沸点：
  296.6±23.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  请将药品存放在避光、干燥、室内常温的地方。

SDS

Name:	1-(2-Bromophenyl)-1H-pyrazole Material Safety Data Sheet
Synonym:
CAS:	87488-84-4

Section 1 - Chemical Product MSDS Name:1-(2-Bromophenyl)-1H-pyrazole Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
87488-84-4	1-(2-Bromophenyl)-1H-pyrazole	97+%	unlisted

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
Notes to Physician:

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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 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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 87488-84-4: 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: Liquid
Color: Yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C9H7BrN2
Molecular Weight: 223.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 87488-84-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(2-Bromophenyl)-1H-pyrazole - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
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.
WGK (Water Danger/Protection)
CAS# 87488-84-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 87488-84-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 87488-84-4 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：

  1-(2-溴苯基)-1H-吡唑 在 bis(triphenylphosphine)nickel(II) chloride 、 dichloro(1,5-cyclooctadiene)ruthenium(II) 、 环戊醇 、 四丁基碘化铵 、 锌 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 1-苯基吡唑
  参考文献：
  名称：

  钌催化未受约束的芳基-芳基键的还原裂解：反应发展和机理研究

  摘要：

  在一些重要的工业过程中发现了碳-碳键的断裂，例如石油裂解，并激发了许多合成方法的发展。然而，非极性无应变 C(芳基)-C(芳基)键仍然是最难被激活的键之一。作为对基本反应模式的详细研究，这里描述了我们开发的无应变 C(芳基)-C(芳基)键的 Ru 催化还原裂解的完整故事。在 2,2' 位置含有导向基团 (DG) 的多种联芳基化合物可作为有效底物。各种杂环，例如吡啶、喹啉、嘧啶和吡唑，可以用作DG。除氢气外，其他试剂，如汉茨酯、硅烷和醇类，也可用作末端还原剂。该反应的 pH 值为中性，不含氧化剂，因此可以容忍许多官能团。值得注意的是，已经实现了一锅 CC 激活/CC 耦合。计算和实验机理研究表明，该反应涉及一氢化钌（II）介导的 C（芳基）-C（芳基）活化，催化剂的静止状态是 η4 配位的二氯化钌（II）配合物，这可以激发基于该反应模式开发其他转化。

  DOI：

  10.1021/jacs.9b11605
• 作为产物：
  描述：

  1-苯基吡唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以75%的产率得到1-(2-溴苯基)-1H-吡唑
  参考文献：
  名称：

  用于非均相 C-H 官能化的 Tris-NHC 传播的自支撑聚合物基 Pd 催化剂

  摘要：

  成功地利用三维传播的含咪唑鎓介孔配位聚合物和基于有机聚合物的平台来开发用于氧化芳烃/杂芳烃 C-H 功能化反应的单点多相 Pd-NHC 催化剂。该催化剂在定向芳烃卤化、非定向芳烃和杂芳烃芳基化反应中是有效的。这些系统提供了高催化活性、优异的异质性和可回收性，使它们成为多相 C-H 功能化领域的有希望的候选者，而高效催化剂仍然稀缺。

  DOI：

  10.1039/d1cc04429j

文献信息

• Cu-Catalyzed Couplings of Heteroaryl Primary Amines and (Hetero)aryl Bromides with 6-Hydroxypicolinamide Ligands
  作者：David J. Bernhardson、Daniel W. Widlicka、Robert A. Singer

  DOI：10.1021/acs.oprd.9b00195

  日期：2019.8.16

  chemoselectivity and rate. The use of K2CO3 as the base enabled selective C–N coupling of aryl bromides over aryl chlorides with 2–5 mol % Cu at 80–120 °C. With K3PO4 as the base, aryl chlorides are capable of undergoing C–N coupling, though 5–10 mol % Cu is required at 120–130 °C. Members of the ligand family are straightforward to prepare in one step from 6-hydroxypicolinic acid and the corresponding

  已经确定了6-羟基吡啶甲酸酰胺配体家族是Cu催化的杂芳基溴化物和氯化物与杂芳基伯胺的偶联的有效支撑配体。C–N偶联是在80–120°C的DMSO或环丁砜中，以2-10 mol％CuI和支持配体的K 2 CO 3或K 3 PO 4为碱进行的。发现碱的强度对化学选择性和速率有影响。使用K 2 CO 3作为碱，可以在80–120°C的条件下，以2–5 mol％的Cu在芳基氯上进行芳基溴的选择性C–N偶联。含K 3 PO 4作为基础，芳基氯化物能够进行C–N偶联，尽管在120–130°C下需要5–10 mol％的Cu。配体家族的成员可以直接一步一步由6-羟基吡啶甲酸和相应的苯胺制备。
• 4-(Benzoimidazol-2-yl)-thiazole Compounds and Related Aza Derivatives
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：US20140371204A1

  公开（公告）日：2014-12-18

  The invention relates to compounds of Formula (I) wherein ring A, X, (R 1 ) n , R 2 , R 3 , R 4 , R 4′ , R 5 , n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

  本发明涉及式(I)化合物，其中环A、X、(R1)n、R2、R3、R4、R4′、R5、n和p如描述中所述；涉及药用可接受的盐，以及将此类化合物用作药物，尤其是用作CXCR3受体的调节剂。
• [EN] 4-(BENZOIMIDAZOL-2-YL)-THIAZOLE COMPOUNDS AND RELATED AZA DERIVATIVES<br/>[FR] COMPOSÉS DE 4-(BENZOIMIDAZOL-2-YLE)-THIAZOLE ET DÉRIVÉS AZA ASSOCIÉS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2013114332A1

  公开（公告）日：2013-08-08

  The invention relates to compounds of Formula (I) wherein ring A, X, (R1)n, R2, R3, R4, R4', R5, n, and p are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as modulators of the CXCR3 receptor.

  本发明涉及式(I)化合物，其中环A、X、(R1)n、R2、R3、R4、R4'、R5、n和p如描述中所述；涉及药用可接受的盐，以及将此类化合物用作药物，尤其是用作CXCR3受体的调节剂。
• Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
  作者：He Huang、Zack M. Strater、Michael Rauch、James Shee、Thomas J. Sisto、Colin Nuckolls、Tristan H. Lambert

  DOI：10.1002/anie.201906381

  日期：2019.9.16

  electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron

  可见光光催化和电催化是促进化学反应的两种强大策略。在这里，这两种模式结合在电光催化氧化平台中。该化学过程采用三氨基环丙烯 (TAC) 离子催化剂，通过电化学氧化形成环丙烯自由基阳离子中间体。自由基阳离子在可见光下进行光激发，产生具有氧化能力（3.33 V vs. SCE）的激发态物质，足以通过单电子转移（SET）氧化苯和卤代苯，从而导致 CH/NH 与唑类偶联。提供了光激发物质的强氧化行为的基本原理，同时通过顺式2,6-二甲基哌啶部分的特定构象合理化了催化剂的稳定性。
• Hypercrosslinked Polymer Platform-Anchored Single-Site Heterogeneous Pd–NHC Catalysts for Diverse C–H Functionalization
  作者：Tanmoy Mandal、Moumita Mondal、Joyanta Choudhury

  DOI：10.1021/acs.organomet.1c00182

  日期：2021.8.9

  new class of hypercrosslinked polymer (HCP) platform-anchored single-site heterogenized Pd–NHC catalysts for multipurpose C–H functionalization reactions. This new class is represented by a set of three catalysts, viz., HCP-B-MeNHC-Pd, HCP-B-BnNHC-Pd, and HCP-TPM-MeNHC-Pd, having a variation on the structural feature of the anchoring polymeric platform. All three catalysts were fully characterized via

  我们展示了一类新的超交联聚合物（HCP）平台锚定的单点异质化 Pd-NHC 催化剂，用于多用途 C-H 功能化反应。这一新类别由一组三种催化剂代表，即HCP-B- Me NHC-Pd、HCP-B- Bn NHC-Pd和HCP-TPM- Me NHC-Pd，在结构特征上有变化锚定聚合物平台。所有三种催化剂都通过各种固态表征和分析技术（如 X 射线光电子能谱、13C 交叉极化魔角自旋核磁共振、场发射扫描电子显微镜、能量色散 X 射线分析、热重分析和电感耦合等离子体-光发射光谱法。三种经常使用且非常有用的 C-H 官能化反应，即 C-H 卤化、乙酰氧基化和芳基化，用新催化剂进行了测试，发现它们具有高度的相容性和成功性。使用HCP-TPM- Me NHC-Pd在催化剂的作用下，卤化、乙酰氧基化和芳基化反应的官能化产物的产率分别高达 85%、75% 和 70%。这种新系统提供了诸如增强的活性、异质性和可回收性等苛刻的特性，使其成为非均相