2-氨基-5-溴烟酸 | 52833-94-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氨基-5-溴烟酸
• 中文别名: 5-溴-2-氨基烟酸；2-氨基-5-溴-3-吡啶甲酸；5-氨基-2-溴烟酸；2-氨基-5-溴烟碱酸；2-氨基-5-溴异烟酸；2-氨基-5-溴-烟酸
• 英文名称: 2-amino-5-bromonicotinicacid
• 英文别名: 2-amino-5-bromopyridine-3-carboxylic acid；5-bromo-2-aminonicotinic acid；2-amino-5-bromo-3-pyridine carboxylic acid；2-Amino-5-bromonicotinic acid
• CAS: 52833-94-0
• 化学式: C₆H₅BrN₂O₂
• mdl: MFCD01860227
• 分子量: 217.022
• InChiKey: IEPDTLRHISNBLB-UHFFFAOYSA-N

物化性质

• 熔点：
  253-255°C
• 沸点：
  350.4±42.0 °C(Predicted)
• 密度：
  1.909
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存于阴凉干燥处

SDS

Name:	2-Amino-5-Bromonicotinic Acid Material Safety Data Sheet
Synonym:	None Known
CAS:	52833-94-0

Section 1 - Chemical Product MSDS Name:2-Amino-5-Bromonicotinic Acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
52833-94-0	2-Amino-5-Bromonicotinic Acid	ca. 100	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 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. Do NOT use mouth-to-mouth resuscitation.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 52833-94-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Not available.
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: C6H5BrN2O2
Molecular Weight: 217

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 52833-94-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Amino-5-Bromonicotinic Acid - 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: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 52833-94-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 52833-94-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 52833-94-0 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

制备方法与用途

用途

2-氨基-5-溴烟酸是一种有机中间体，可通过2-氨基烟酸进行溴代制备。据文献报道，该化合物可用于合成6-吡唑取代喹唑啉类及其衍生物，这类化合物具有较高的酪氨酸激酶抑制活性，并对人乳腺癌细胞及肺腺癌细胞等表现出较强的抑制作用。

制备方法

2-氨基-5-溴烟酸是通过2-氨基烟酸进行溴代反应制得的中间体。

制备过程

在装有搅拌器和回流冷凝管的500mL三口瓶中，加入2-氨基烟酸（20.7g，0.15mol），并注入80mL乙酸。室温下进行搅拌，随后用恒压滴液漏斗滴加40mL乙酸和4.1mL溴素（0.08mol）的混合溶液。滴完后继续搅拌4-5小时。

完成反应后，过滤并使用乙酸洗涤产物。接着，在固体物质中加入100mL甲醇进行加热回流处理，10分钟后冷却至室温，再次过滤并干燥。最终得到白色固体2-氨基-5-溴烟酸31.2g，收率为96%。

通过1H NMR（400MHz，DMSO-d₆）分析其结构，结果显示δ值分别为：12.72 (s, 1H)，9.05 (d, J=2.4Hz, 1H)，8.63 (d, J=2.4Hz, 1H) 和8.36 (s, 1H)。MS分析显示其质量数为m/z (ESI+) 228.3 [M+H]+。

反应信息

• 作为反应物：
  描述：

  2-氨基-5-溴烟酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 反应 2.0h， 生成 5-溴-2-氯-3-吡啶羰酰氯
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS AS INHIBITORS OF FATTY ACID BIOSYSNTHESIS FOR BACTERIAL INFECTIONS

  摘要：

  这项发明涉及一种新型杂环化合物，可以特异性地抑制细菌FabI，并可用于治疗葡萄球菌感染。

  公开号：

  US20140249170A1
• 作为产物：
  描述：

  2-氨基烟酸 在 溴 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 8.0h， 以89%的产率得到2-氨基-5-溴烟酸
  参考文献：
  名称：

  2,4,6-三卤代吡啶并[2,3-d]嘧啶的区域选择性钯催化Suzuki-Miyaura偶联反应

  摘要：

  摘要 从相应的 2,4,6-三卤代吡啶并 [2,3-d] 嘧啶开发了一种有效的、区域选择性的、新颖的获取 2,4,6-三取代吡啶并[2,3-d]嘧啶的策略。涉及新型区域选择性卤素歧视的 Suzuki-Miyaura 偶联反应。

  DOI：

  10.1016/j.crci.2019.01.006
• 作为试剂：
  描述：

  2-氨基苯酚 以 PPA 、 2-氨基-5-溴烟酸 为溶剂， 生成 3-(benzoxazol-2-yl)-5-bromo-pyridin-2-amine
  参考文献：
  名称：

  PYRIDINE AND PYRAZINE DERIVATIVES - 083

  摘要：

  本发明涉及式I的吡啶和吡嗪衍生物 或其药用可接受的盐，其中W、G 1 、G 2 、G 3 、G 4 、J、环A、n和R 3 各自具有如前文描述中定义的任何含义；它们的制备过程，包含它们的药物组合物以及它们在制造用于治疗细胞增殖性障碍的药物中的应用。

  公开号：

  US20090118305A1

文献信息

• [EN] MERTK DEGRADERS AND USES THEREOF<br/>[FR] AGENTS DE DÉGRADATION DE MERTK ET LEURS UTILISATIONS
  申请人：KYMERA THERAPEUTICS INC

  公开号：WO2020010210A1

  公开（公告）日：2020-01-09

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用相同的方法。
• Pyrrolo-pyridine kinase modulators
  申请人：Arnold D. William

  公开号：US20060030583A1

  公开（公告）日：2006-02-09

  The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

  本发明提供了新型吡咯-吡啶激酶调节剂以及利用这些新型吡咯-吡啶激酶调节剂治疗由激酶活性介导的疾病的方法。
• [EN] HETEROARYL COMPOUNDS AND THEIR USE AS MER INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROARYLE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE MER
  申请人：DONG A SOCIO HOLDINGS CO LTD

  公开号：WO2018071343A1

  公开（公告）日：2018-04-19

  Compounds of formula (I) [Formula should be inserted here] and a pharmaceutically acceptable salt thereof, wherein A, R1, R2, R3, R4, R5, R6, R7, R24, X, L, n and p are as defined in the specification, are useful for treating or preventing Mer tyrosine kinase receptor modulated disease or conditions. Also described are pharmaceutical compositions of compounds of formula (I), and methods for using such compounds and compositions.

  式(I)的化合物及其药学上可接受的盐，其中A、R1、R2、R3、R4、R5、R6、R7、R24、X、L、n和p如规范中定义的那样，可用于治疗或预防Mer酪氨酸激酶受体调节的疾病或症状。还描述了式(I)的化合物的药物组合物，以及使用这些化合物和组合物的方法。
• [EN] AMINOTRIAZOLOPYRIDINES AS KINASE INHIBITORS<br/>[FR] AMINOTRIAZOLOPYRIDINES UTILISÉES EN TANT QU'INHIBITEURS DE KINASE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2018148626A1

  公开（公告）日：2018-08-16

  Compounds having formula (I) (IX), and enantiomers, and diastereomers, stereoisomers, pharmaceutically acceptable salts and prodrugs thereof, are useful as kinase modulators, including RIPK1 modulation. All the variables are as defined herein: (I), (II), (III), (IV), (V), (VI), (VII), (VIII), (IX).

  具有化学式（I）（IX）的化合物，以及其对映体、非对映体、立体异构体、药学上可接受的盐和前药，可用作激酶调节剂，包括RIPK1调节。所有变量的定义如下：（I）、（II）、（III）、（IV）、（V）、（VI）、（VII）、（VIII）、（IX）。
• Discovery of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines as Potent Inhibitors Targeting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction
  作者：Mingze Qin、Qi Cao、Shuaishuai Zheng、Ye Tian、Haotian Zhang、Jun Xie、Hongbo Xie、Yajing Liu、Yanfang Zhao、Ping Gong

  DOI：10.1021/acs.jmedchem.9b00312

  日期：2019.5.9

  Inhibition of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) interaction using small-molecule inhibitors is an emerging immunotherapeutic approach. A novel series of [1,2,4]triazolo[4,3- a]pyridines were designed and found to be potent inhibitors of the PD-1/PD-L1 interaction. Among them, compound A22 exhibited the most potent activity, as assessed by homogenous time-resolved

  使用小分子抑制剂抑制程序性细胞死亡1（PD-1）/程序性细胞死亡配体1（PD-L1）相互作用是一种新兴的免疫治疗方法。设计了一系列新的[1,2,4]三唑并[4,3-a]吡啶，并发现它们是PD-1 / PD-L1相互作用的有效抑制剂。其中，通过均相时间分辨荧光分析评估，化合物A22表现出最强的活性，IC50为92.3 nM。此外，在Hep3B / OS-8 / hPD-L1和CD3 T细胞的共培养模型中，A22剂量依赖性升高的干扰素-γ产生。我们得出的结论是，A22是开发PD-1 / PD-L1相互作用抑制剂的有前途的先导化合物。此外，我们探索了新合成的[1,2,4] triazolo [4，并证明了环融合策略可用于设计Bristol-Myers Squibb化学系列的类似物。这些研究为将来的药物设计铺平了道路。