(2-氨基-4-溴苯基)甲醇 | 946122-05-0

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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-氨基-4-溴苯基)甲醇
• 中文别名: 2-氨基-4-溴苄醇
• 英文名称: (2-amino-4-bromophenyl)methanol
• 英文别名: 2-amino-4-bromobenzyl alcohol
• CAS: 946122-05-0
• 化学式: C₇H₈BrNO
• mdl: MFCD07779492
• 分子量: 202.051
• InChiKey: JHLFDAZFHWATIS-UHFFFAOYSA-N

物化性质

• 沸点：
  347.8±27.0 °C(Predicted)
• 密度：
  1.660±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: (2-Amino-4-bromophenyl)methanol
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: (2-Amino-4-bromophenyl)methanol
CAS number: 946122-05-0

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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: C7H8BrNO
Molecular weight: 202.1

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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

反应信息

• 作为反应物：
  描述：

  (2-氨基-4-溴苯基)甲醇 在 [N-(naphthalen-1-yl)picolinamide]Cp*Ir(III) chloride 、 potassium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 以83 %的产率得到2-氨基-4-溴苯甲醛
  参考文献：
  名称：

  Cp*Ir(III) 配合物通过 ADC 策略催化无溶剂合成喹啉、吡咯和吡啶

  摘要：

  创建了由吡啶甲酰胺基部分结合在一起的三重 Ir( III ) 配合物。在我们早期的研究中，我们证明了在催化量的 Cp*Ir( III ) 催化剂和t BuOK 存在下，在甲苯中由酮或仲醇与伯醇生产 α-烷基化酮的配合物的催化活性使用借氢技术在 110 °C 下进行。早期许多研究小组以2-氨基醇和酮或仲醇衍生物为起始原料合成了喹啉、吡咯和吡啶衍生物，但这些情况下的反应条件并不适合绿色合成，如催化剂负载量较多、碱含量较高等。负荷大、反应时间长、温度高。此外，大多数反应都含有磷化氢（一种危险的副产品）以及催化剂。考虑到这些缺点，我们在前期工作取得优异成果后尝试扩大催化剂的用途，并通过无受体脱氢偶联（ADC）程序在90℃下成功生产了喹啉、吡咯和吡啶衍生物。在纯净/无溶剂条件下 –110 °C，这些含氮杂环化合物的产率达到了良好甚至异常的收率。这种方法很有吸引力，因为它对环境无害，并且可以“绿色”合

  DOI：

  10.1039/d4ob00459k
• 作为产物：
  描述：

  2-氨基-4-溴苯甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到(2-氨基-4-溴苯基)甲醇
  参考文献：
  名称：

  Identification and Preliminary Structure-Activity Relationship Studies of 1,5-Dihydrobenzo[e][1,4]oxazepin-2(3H)-ones That Induce Differentiation of Acute Myeloid Leukemia Cells In Vitro

  摘要：

  急性髓系白血病（AML）是最具侵略性的血液癌症类型，目前仍然需要新的治疗方法，这些方法应具有良好的耐受性，并能提高患者的长期生存率。诱导分化已经成为一种有希望替代传统细胞毒性化疗的方法，但已知的药物在遗传上不同的患者群体中缺乏疗效。之前，我们建立了一种表型筛选方法，用以识别能够在一系列AML细胞系中刺激分化的 small molecules(小分子)。利用这种策略，我们识别出了一种1,5-二氢苯并[e][1,4]恶嗪-2(3H)-酮的击中化合物。本文中，我们报告了该击中化合物的体外验证、结构-活性关系（SAR）研究以及选定化合物的药代动力学特征。

  DOI：

  10.3390/molecules26216648

文献信息

• ANTI-CANCER AGENTS
  申请人：Peng Xiaohua

  公开号：US20130045949A1

  公开（公告）日：2013-02-21

  Described herein are compounds that may be selectively activated to produce active anti-cancer agents in tumor cells. Also disclosed are pharmaceutical compositions comprising the compounds, and methods of treating cancer using the compounds.

  本文描述了一些化合物，这些化合物可以被选择性地激活，以在肿瘤细胞中产生活性抗癌剂。还公开了包括这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。
• N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature
  作者：Jingxiu Xu、Qingmao Chen、Zhigao Luo、Xiaodong Tang、Jinwu Zhao

  DOI：10.1039/c9ra04926f

  日期：——

  A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedländer reaction from 2-aminobenzyl alcohol and aryl ketones using DMSO as an oxidant at room temperature is reported. A series of quinolines were synthesized in acceptable yields.

  报道了一种在室温下以 DMSO 为氧化剂，通过 N-杂环卡宾铜催化 2-氨基苯甲醇和芳基酮间接 Friedländer 反应合成喹啉的简便实用方法。以可接受的收率合成了一系列喹啉。
• Novel bicyclic sulfonamide derivatives which are L-CPT1 inhibitors
  申请人：Ackermann Jean

  公开号：US20070191603A1

  公开（公告）日：2007-08-16

  The invention is concerned with novel heterobicyclic derivatives of formula (I) wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , V, W, X and Y are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit L-CPT1 and can be used as medicaments.

  这项发明涉及公式（I）的新异双环衍生物，其中R1、R2、R3、R4、R5、R6、V、W、X和Y的定义如描述和索赔中所述，以及其生理上可接受的盐和酯。这些化合物抑制L-CPT1，可用作药物。
• Ruthenium-catalyzed acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones to quinolines in the presence of carbonate salt
  作者：Xiangchao Xu、Yao Ai、Rongzhou Wang、Liping Liu、Jiazhi Yang、Feng Li

  DOI：10.1016/j.jcat.2020.12.016

  日期：2021.3

  Cl][Cl] was designed, synthesized and found to be a general and highly efficient catalyst for the synthesis of quinolines via acceptorless dehydrogenative coupling of o-aminobenzyl alcohols with ketones in the presence of carbonate salt. It was confirmed that NH units in the ligand are crucial for catalytic activity. The application of this catalytic system for the scale-gram synthesis of biologically

  设计，合成了带有功能性2,2'-联苯并咪唑配体[（p- Cymene）Ru（BiBzImH 2）Cl] [Cl]的钌配合物，它是通过无受体合成喹啉的通用高效催化剂。碳酸盐存在下邻氨基苄醇与酮的脱氢偶联。证实了配体中的NH单元对于催化活性至关重要。还进行了该催化体系在生物活性分子的规模克合成中的应用。值得注意的是，这项研究展示了金属-配体双功能催化剂在无受体脱氢反应中的新潜力。
• Acceptorless Dehydrogenative Cyclization of <i>o</i>-Aminobenzyl Alcohols with Ketones to Quinolines in Water Catalyzed by Water-Soluble Metal–Ligand Bifunctional Catalyst [Cp*(6,6′-(OH)₂bpy)(H₂O)][OTf]₂
  作者：Rongzhou Wang、Hongjun Fan、Wei Zhao、Feng Li

  DOI：10.1021/acs.orglett.6b01518

  日期：2016.8.5

  cyclization of o-aminobenzyl alcohols with ketones to quinolines in water has been accomplished. In the presence of [Cp*Ir(6,6′-(OH)2bpy)(H2O)][OTf]2, a series of desirable products were obtained in high yields. Notably, this research exhibits the potential for the construction of heterocycles via acceptorless dehydrogenative reactions in water catalyzed by water-soluble metal–ligand bifunctional catalysts

  现已完成了将邻氨基苯甲醇与酮进行无受体脱氢环化反应以制得水中喹啉的策略。在[Cp * Ir（6,6'-（OH）2 bpy）（H 2 O）] [OTf] 2的存在下，以高收率获得了一系列所需产物。值得注意的是，这项研究显示了在水溶性金属-配体双功能催化剂催化的水中通过无受体脱氢反应构建杂环的潜力。