3-氨基-4-溴苯酚 | 100367-37-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 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-氨基-4-溴苯酚
• 英文名称: 3-amino-4-bromophenol
• CAS: 100367-37-1
• 化学式: C₆H₆BrNO
• 分子量: 188.024
• InChiKey: JJNOHJJIVAVDLP-UHFFFAOYSA-N

物化性质

• 沸点：
  300.1±22.0 °C(Predicted)
• 密度：
  1.768

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Amino-4-bromophenol
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: 3-Amino-4-bromophenol
CAS number: 100367-37-1

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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: C6H6BrNO
Molecular weight: 188.0

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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.

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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

制备方法与用途

简介

3-氨基-4-溴苯酚的合成方法是许多药物合成的重要起始原料，特别是作为众多溴苯酚化合物的关键中间体。然而，其合成过程中存在后处理产生的三废量大、污染严重以及成本高等问题。目前，国内尚无关于3-氨基-4-溴苯酚合成方法的相关报道或专利申请。

用途

3-氨基-4-溴苯酚是一种酚类衍生物，主要用作医药中间体。

反应信息

• 作为反应物：
  描述：

  3-氨基-4-溴苯酚 在 sodium sulfite 作用下， 以 水 为溶剂， 反应 18.0h， 以96%的产率得到3-氨基苯酚
  参考文献：
  名称：

  在水介质中用亚硫酸钠对苯酚和杂芳族化合物进行还原脱卤和脱卤磺化

  摘要：

  质子互变异构被用作在水介质中使用亚硫酸钠作为唯一试剂的（杂）芳基溴化物和碘化物的还原性脱卤化或（杂）芳基氯和氟化物的脱卤化磺化的工具。该方案不需要金属或相转移催化剂，避免使用有机溶剂作为反应介质。此方法特别适用于容易互变异构的底物（例如2-或4-卤代氨基酚和4-卤代间苯二酚），在温和的反应条件下（≤60°C）会进行脱卤或磺化。由于亚硫酸钠是一种廉价，安全且对环境无害的试剂，因此该方法至少具有三个潜在应用：（i）使用亚硫酸钠作为还原剂对卤素作为保护基进行脱保护；（ii）在温和的反应条件下磺化芳族卤化物，避免使用危险和腐蚀性的试剂/溶剂；（iii）将有毒的卤代芳族化合物转化为危害较小的化合物。

  DOI：

  10.1039/c9gc00467j
• 作为产物：
  描述：

  4-溴-3-硝基苯酚 在 iron(III) oxide 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以70.9%的产率得到3-氨基-4-溴苯酚
  参考文献：
  名称：

  3-氨基-4-溴苯酚的合成方法

  摘要：

  3‑氨基‑4‑溴苯酚的合成方法。其步骤为：(1)重氮化反应：将原料3‑硝基‑4‑氨基苯酚溶解在氢溴酸中，在0‑10℃下滴加亚硝酸钠水溶液反应1‑3h，得到的3‑硝基苯酚‑4‑重氮盐水溶液。(2)溴化反应：将步骤(1)所得溶液滴加至溴化亚铜的氢溴酸水溶液中，搅拌40‑50℃，进行反应经过析晶、过滤得到3‑硝基‑4‑溴苯酚固体；(3)还原反应：向步骤(2)所得固体溶于乙醇中的溶液中加入氧化铁催化剂，加热至50‑100℃，并向混合物中加入水合肼水溶液，进行2‑5h反应，得到3‑氨基‑4‑溴苯酚。本发明的3‑氨基‑4‑溴苯酚的合成方法设计合理、条件温和、易操作，产品收率较高，适合工业化生产。

  公开号：

  CN102060717B

文献信息

• FUSED HETEROCYCLIC DERIVATIVE AND USE THEREOF
  申请人：Sakai Nozomu

  公开号：US20090137595A1

  公开（公告）日：2009-05-28

  The present invention provides a fused heterocyclic derivative having a potent kinase inhibitory activity and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the specification, except a particular compound, or a salt thereof, and a pharmaceutical agent containing the compound or a prodrug thereof, which is a kinase (VEGFR, VEGFR2, PDGFR, Raf) inhibitor, an angiogenesis inhibitor, an agent for the prophylaxis or treatment of cancer, a cancer growth inhibitor or a cancer metastasis suppressor.

  本发明提供了一种具有强大激酶抑制活性的融合杂环衍生物及其用途。 一种由以下式（I）表示的化合物： 其中除了特定化合物或其盐外，每个符号如规范中定义，以及含有该化合物或其前药的药用剂，该化合物是激酶（VEGFR、VEGFR2、PDGFR、Raf）抑制剂，血管生成抑制剂，用于癌症的预防或治疗的药剂，癌症生长抑制剂或癌症转移抑制剂。
• [EN] HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS<br/>[FR] COMPOSÉS HÉTÉROAROMATIQUES ET LEUR UTILISATION COMME LIGANDS DE LA DOPAMINE D1
  申请人：PFIZER

  公开号：WO2014072881A1

  公开（公告）日：2014-05-15

  The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides thereof; processes and intermediates for preparation of; and compositions and uses thereof. The present invention further provides D1 agonists with reduced D1R desensitization, D1 agonists with a reduced β- arrestin recruitment activity relative to Dopamine, D1 agonists interacting significantly with the Ser188 but not significantly with the Ser202 of a D1R when binding to the D1R, D1 agonists interacting less strongly with the Asp103 and interacting less strongly with the Ser198 of a D1R when binding to the D1R, and their uses.

  本发明部分提供了化合物I的公式：及其药学上可接受的盐和N-氧化物；制备的过程和中间体；以及其组合物和用途。本发明进一步提供了具有减少D1R耐受性的D1激动剂，相对于多巴胺具有减少β-阿雷斯汀招募活性的D1激动剂，当结合到D1R时与D1R的Ser188显著相互作用但与Ser202的相互作用不显著的D1激动剂，当结合到D1R时与D1R的Asp103相互作用较弱并且与Ser198相互作用较弱的D1激动剂，以及它们的用途。
• Discovery of &lt;i&gt;meta&lt;/i&gt;-Amido Bromophenols as New Antitubercular Agents
  作者：Jie Liang、Yun-xiang Tang、Xiang-zheng Tang、Hua-ju Liang、Yamin Gao、Cuiting Fang、Tian-yu Zhang、Ming Yan

  DOI：10.1248/cpb.c18-00917

  日期：2019.4.1

  Gram-positive and Gram-negative bacteria. Moderate cytotoxicities and good metabolic stability were observed for the selected compounds. The results demonstrated meta-amido bromophenols as a new class of antitubercular agents with good potentials.

  设计并合成了一系列间位氨基溴酚衍生物。发现该化合物有效抑制结核分枝杆菌H37Ra的生长。它们还显示出对结核分枝杆菌H37Rv和耐多药菌株的中等抑制活性。该化合物对正常的革兰氏阳性和革兰氏阴性细菌没有抑制活性。对于所选化合物，观察到中等的细胞毒性和良好的代谢稳定性。结果表明，间酰胺基溴酚是一类具有良好潜力的新型抗结核药。
• Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor
  作者：Keith R. Fandrick、Wenjie Li、Yongda Zhang、Wenjun Tang、Joe Gao、Sonia Rodriguez、Nitinchandra D. Patel、Diana C. Reeves、Jiang-Ping Wu、Sanjit Sanyal、Nina Gonnella、Bo Qu、Nizar Haddad、Jon C. Lorenz、Kanwar Sidhu、June Wang、Shengli Ma、Nelu Grinberg、Heewon Lee、Youla Tsantrizos、Marc-André Poupart、Carl A. Busacca、Nathan K. Yee、Bruce Z. Lu、Chris H. Senanayake

  DOI：10.1002/anie.201501575

  日期：2015.6.8

  A practical and efficient synthesis of a complex chiral atropisomeric HIV integrase inhibitor has been accomplished. The combination of a copper‐catalyzed acylation along with the implementation of the BI‐DIME ligands for a ligand‐controlled Suzuki cross‐coupling and an unprecedented bis(trifluoromethane)sulfonamide‐catalyzed tert‐butylation renders the synthesis of this complex molecule robust, safe

  已经完成了一种实用有效的合成方法，用于合成复杂的手性阻转异构HIV整合酶抑制剂。铜催化的酰化与BI-DIME配体的结合使配体可控的Suzuki交叉偶联以及前所未有的双（三氟甲烷）磺酰胺催化的叔丁基化相结合，使该复杂分子的合成稳定，安全且经济。此外，相对于嵌入的阻转异构体，以不对称和非对映选择性的方式进行整体合成。
• [EN] PROCESS FOR THE PREPARATION OF AN HIV INTEGRASE INHIBITOR<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN INHIBITEUR DE L'INTÉGRASE DU VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2012138670A1

  公开（公告）日：2012-10-11

  The present invention is directed to an improved process for the preparation of Compounds of Formula (I) or salts thereof which are useful in the treatment of HIV infection. In particular, the present invention is directed to an improved process for the preparation of (2S)-2-tert-butoxy-2-(4-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)- 2-methylquinolin-3-yl)acetic acid or salt thereof which is useful in the treatment of HIV infection. R4 is selected from the group consisting of (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m), (n) and (o); and R6 and R7 are each independently selected from H, halo and (C1-6) alkyl.

  本发明涉及一种改进的工艺，用于制备化合物的化合物（I）或其盐，该化合物在治疗HIV感染中有用。具体而言，本发明涉及一种改进的工艺，用于制备对治疗HIV感染有用的(2S)-2-叔丁氧基-2-(4-(2,3-二氢吡喃并[4,3,2-de]喹啉-7-基)-2-甲基喹啉-3-基)乙酸或其盐。其中R4从(a)、(b)、(c)、(d)、(e)、(f)、(g)、(h)、(i)、(j)、(k)、(l)、(m)、(n)和(o)组成的群中选择；R6和R7分别独立选择自H、卤素和（C1-6）烷基。