2-氨基-4-硝基苯甲醇 | 78468-34-5

• 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-硝基苯甲醇
• 中文别名: (2-氨基-4-硝基苯基)甲醇；(2 -氨基- 4 -硝基苯基)甲醇
• 英文名称: 2-amino-4-nitrobenzyl alcohol
• 英文别名: (2-amino-4-nitrophenyl)methanol；(2-Amino-4-nitrophenyl)methan-1-ol；2-Amino-4-nitrobenzenemethanol
• CAS: 78468-34-5
• 化学式: C₇H₈N₂O₃
• 分子量: 168.152
• InChiKey: NFOINKSCQYECSI-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  424.1±30.0 °C(Predicted)
• 密度：
  1.432±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2922199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,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-nitrobenzenemethanol
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-nitrobenzenemethanol
CAS number: 78468-34-5

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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: C7H8N2O3
Molecular weight: 168.2

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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.

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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-硝基苯甲醇 在 manganese dioxide silica gel 、 乙酸乙酯 、 hexanes 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以to afford 2-amino-4-nitrobenzaldehyde (550 mg, 86% yield) as an orange solid的产率得到2-氨基-4-硝基苯甲醛
  参考文献：
  名称：

  ARYL LACTAM KINASE INHIBITORS

  摘要：

  本披露通常涉及可以抑制AAK1（适配器相关激酶1）的化合物，包含这些化合物的组合物，以及抑制AAK1的方法。

  公开号：

  US20160152621A1
• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 吡啶 、 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 四氯化碳 、 氯仿 、 水 为溶剂， 反应 45.0h， 生成 2-氨基-4-硝基苯甲醇
  参考文献：
  名称：

  Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

  摘要：

  In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 degreesC and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 degreesC. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00459-0

文献信息

• Investigations into the Potential Role of Metabolites on the Anti-Leukemic Activity of Imatinib, Nilotinib and Midostaurin
  作者：Paul W. Manley

  DOI：10.2533/chimia.2019.561

  日期：——

  The efficacy and side-effects of drugs do not just reflect the biochemical and pharmacodynamic properties of the parent compound, but often comprise of cooperative effects between the properties of the parent and active metabolites. Metabolites of imatinib, nilotinib and midostaurin have been synthesised and evaluated in assays to compare their properties as protein kinase inhibitors with the parent drugs. The N-desmethyl-metabolite of imatinib is substantially less active than imatinib as a BCR-ABL1 kinase inhibitor, thus providing an explanation as to why patients producing high levels of this metabolite show a relatively low response rate in chronic myeloid leukaemia (CML) treatment. The hydroxymethylphenyl and N-oxide metabolites of imatinib and nilotinib are only weakly active as BCR-ABL1 inhibitors and are unlikely to play a role in the efficacy of either drug in CML. The 3-(R)-HO-metabolite of midostaurin shows appreciable accumulation following chronic drug administration and, in addition to mutant forms of FLT3, potently inhibits the PDPK1 and VEGFR2 kinases (IC50 values

  药物的功效和副作用不仅仅反映了母化合物的生化和药效特性，而且通常包括母化合物和活性代谢物之间的协同效应。已经合成和评估了伊马替尼、尼洛替尼和米多斯他林的代谢物，以比较它们作为蛋白激酶抑制剂的特性与母药的区别。伊马替尼的N-去甲基代谢物作为BCR-ABL1激酶抑制剂的活性明显低于伊马替尼，这解释了为什么产生高水平该代谢物的患者在慢性髓细胞白血病（CML）治疗中显示相对较低的反应率。伊马替尼和尼洛替尼的羟甲基苯和N-氧代谢物作为BCR-ABL1抑制剂的活性很弱，不太可能在CML中发挥作用。米多斯他林的3-(R)-HO-代谢物在长期用药后显示出明显的积累，并且除了FLT3的突变形式外，还强力抑制PDPK1和VEGFR2激酶（IC50值

• 一种选择性钠通道调节剂及其制备和应用
  申请人：明慧医药（上海）有限公司

  公开号：CN112300051A

  公开（公告）日：2021-02-02

  本发明提供了作为选择性钠通道调节剂的化合物及合成和使用方法，具体地，本发明提供了一种如式(I)所示的化合物，及其制备方法和作为选择性钠通道调节剂的用途。所述的化合物表现出作为钠通道调节剂的优异活性。
• Vanilloid receptor ligands and their use in treatments
  申请人：——

  公开号：US20030195201A1

  公开（公告）日：2003-10-16

  Compounds having the general structure 1 and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.

  具有一般结构1的化合物以及含有它们的组合物，用于治疗急性疼痛、炎症性和神经性疼痛、牙痛、普通头痛、偏头痛、丛集性头痛、混合性血管和非血管综合症、紧张性头痛、一般炎症、关节炎、风湿病、骨关节炎、炎症性肠病、炎症性眼病、炎症性或不稳定的膀胱病、银屑病、具有炎症成分的皮肤疾病、慢性炎症状况、炎症性疼痛及其相关的过度疼痛和异常疼痛、神经性疼痛及其相关的过度疼痛和异常疼痛、糖尿病性神经病疼痛、灼痛、交感神经维持的疼痛、去神经综合症、哮喘、上皮组织损伤或功能障碍、单纯疱疹、在呼吸、生殖泌尿、胃肠或血管区域的内脏运动障碍、伤口、烧伤、过敏性皮肤反应、瘙痒、白癜风、一般胃肠病、胃溃疡、十二指肠溃疡、腹泻、由坏死性剂引起的胃部病变、毛发生长、血管运动性或过敏性鼻炎、支气管障碍或膀胱障碍。
• [EN] ARYL AMIDE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE L'ARYLAMIDE KINASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2015006100A1

  公开（公告）日：2015-01-15

  The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

  本公开涉及一般可抑制AAK1（适配器相关激酶1）的化合物，包括这些化合物的组合物，以及抑制AAK1的方法。
• [EN] TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE<br/>[FR] TÉTRAHYDRONAPHTYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE ET COMPOSÉS BICYCLIQUES APPARENTÉS POUR L'INHIBITION DE L'ACTIVITÉ DE RORGAMMA ET LE TRAITEMENT DE MALADIE
  申请人：MERCK SHARP & DOHME

  公开号：WO2015095795A1

  公开（公告）日：2015-06-25

  The invention provides certain bicylic heterocyclic compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2, R3, R4, and Cy are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds of the Formula (I) or pharmaceutically acceptable salts thereof, and methods of using the compounds of the Formula (I) or pharmaceutically acceptable salts thereof or pharmaceutical compositions comprising the same for treating diseases or conditions mediated by RORgammaT.

  这项发明提供了公式（I）的某些双环杂环化合物或其药学上可接受的盐，其中X1、X2、R1、R2、R3、R4和Cy如本文所定义。该发明还提供了包括公式（I）的这种化合物或其药学上可接受的盐的药物组合物，以及使用公式（I）的这种化合物或其药学上可接受的盐或包含相同的药物组合物治疗由RORgammaT介导的疾病或症状的方法。