4-溴吡啶-2-羧酸 | 30766-03-1

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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: 4-溴吡啶-2-羧酸
• 中文别名: 4-溴皮考啉酸；4-溴-2-吡啶甲酸；4-溴-2-吡啶羧酸；4-溴吡啶-2-甲酸；4-溴吡啶羧酸；2-甲酸-4-溴吡啶
• 英文名称: 4-bromo-2-picolinic acid
• 英文别名: 4-bromopicolinic acid；4-bromopyridine-2-carboxylic acid；4-bromo-2-pyridinecarboxylic acid；4-bromopyridinecarboxylic acid；4‐bromopicolinic acid
• CAS: 30766-03-1
• 化学式: C₆H₄BrNO₂
• 分子量: 202.007
• InChiKey: RPHHYRNGCJYQSP-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174
• 沸点：
  347.8±27.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)
• 溶解度：
  微溶于DMSO、甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S24/25,S36/37
• 危险类别码：
  R20/21/22
• 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：
  -20°C 冰箱

SDS

4-Bromo-2-pyridinecarboxylic Acid Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 4-Bromo-2-pyridinecarboxylic Acid

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 4-Bromo-2-pyridinecarboxylic Acid
Percent: >98.0%(GC)(T)
CAS Number: 30766-03-1
Synonyms: 4-Bromopicolinic Acid
C6H4BrNO2
Chemical Formula:

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
4-Bromo-2-pyridinecarboxylic Acid

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Very pale yellow
No data available
Odour:
4-Bromo-2-pyridinecarboxylic Acid

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:179°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Slightly soluble: Hot methanol

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen bromide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
4-Bromo-2-pyridinecarboxylic Acid

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

4-溴吡啶-2-羧酸为细针状晶体，密度为1.813 g/cm³，沸点为347.8°C（760 mmHg）。

合成方法

在10 L玻璃反应釜中通入氮气30分钟，加入5 L纯化水和2.0 kg（13.23 mol）的4-溴-2-甲基吡啶，搅拌30分钟后，逐步加入5.3 kg（33.54 mol）高锰酸钾。随后升温至70~80℃并保温反应3小时。反应液冷却至室温后，缓慢倒入5 L冰水混合物中，并搅拌30分钟。过滤后向滤液中加入等体积的二氯甲烷（4.5 L），搅拌析晶2小时，最后经过过滤和干燥处理得到1.9 kg白色固体4-溴吡啶-2-羧酸。

反应信息

• 作为反应物：
  描述：

  4-溴吡啶-2-羧酸 在 水 、 氢溴酸 作用下， 反应 16.0h， 生成 2-氨基-4-溴吡啶
  参考文献：
  名称：

  WO2008/57468

  摘要：

  公开号：
• 作为产物：
  描述：

  2-甲基吡啶氧化物 在 potassium permanganate 、 乙酰溴 、 硫酸 、 硝酸 、 三氯化磷 作用下， 以 氯仿 、 水 为溶剂， 反应 11.0h， 生成 4-溴吡啶-2-羧酸
  参考文献：
  名称：

  新型1,4-二氢吡啶类钙拮抗剂。I.4-（取代的吡啶基）-1，4-二氢吡啶衍生物的合成和降血压活性。

  摘要：

  合成了一系列4-（取代的吡啶基）-1,4-二氢吡啶衍生物，并研究了它们的降压作用。几种化合物，2-（N-苄基-N-甲基氨基）乙基甲基1,4-二氢-2,6-二甲基-4-（3-硝基-2-吡啶基）-3,5-吡啶二甲酸（2b）， 4-（4-硝基-2-吡啶基）类似物（2g），4-（3-三氟甲基-2-吡啶基）类似物（2c），4-（2-三氟甲基-3-吡啶基）类似物（3e），4-发现（4-氰基-2-吡啶基）类似物（2e），4-（2-氰基-3-吡啶基）类似物（3d）和4-（6-溴-2-吡啶基）类似物（2i）具有与尼卡地平类似的降压活动；特别是2c和3e的持续时间约为尼卡地平的两倍，而2e具有在所有合成衍生物中最有效的降压活性。

  DOI：

  10.1248/cpb.38.2446

文献信息

• NOVEL GLUCOKINASE ACTIVATORS AND METHODS OF USING SAME
  申请人：Ryono Denis E.

  公开号：US20080009465A1

  公开（公告）日：2008-01-10

  Compounds are provided which are phosphonate and phosphinate activators and thus are useful in treating diabetes and related diseases and have the structure wherein is a heteroaryl ring; R 4 is —(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 ), —(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g , —(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g , —(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10 ), or —(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10 ); R 5 and R 6 are independently selected from H, alkyl and halogen; Y is R 7 (CH 2 ) s or is absent; and X, n, Z, m, R 4 , R 5 , R 6 , R 7 , and s are as defined herein; or a pharmaceutically acceptable salt thereof. A method for treating diabetes and related diseases employing the above compounds is also provided.

  提供了磷酸酯和磷酸酯激活剂，因此在治疗糖尿病和相关疾病方面非常有用，并具有以下结构： 其中 是杂环芳基环； R 4 为—(CH 2 ) n -Z-(CH 2 ) m —PO(OR 7 )(OR 8 )、—(CH 2 ) n Z-(CH 2 ) m —PO(OR 7 )R g 、—(CH 2 ) n -Z-(CH 2 ) m —OPO(OR 7 )R g 、—(CH 2 ) n Z—(CH 2 ) m —OPO(R 9 )(R 10) 或—(CH 2 ) n Z—(CH 2 ) m —PO(R 9 )(R 10) ； R 5 和R 6 分别选择自H、烷基和卤素； Y为R 7 (CH 2 ) s 或不存在；以及 X、n、Z、m、R 4 、R 5 、R 6 、R 7 和s如本文所定义；或其药用盐。 还提供了一种利用上述化合物治疗糖尿病和相关疾病的方法。
• [EN] HISTONE DEMETHYLASE INHIBITORS<br/>[FR] INHIBITEURS D'HISTONES DÉMÉTHYLASES
  申请人：CHRYSALIS INC

  公开号：WO2017143011A1

  公开（公告）日：2017-08-24

  This disclosure relates to compounds that inhibit histone demethylase activity. In particular, the disclosure relates to compounds that inhibit histone lysine demethylase KDM5B, pharmaceutical compositions and methods of use, such as methods of treating cancer using the compounds and pharmaceutical compositions disclosed herein.

  这份披露涉及抑制组蛋白去甲基化酶活性的化合物。具体而言，该披露涉及抑制组蛋白赖氨酸去甲基化酶KDM5B的化合物，以及使用这些化合物和药物组合物的方法，例如使用本文披露的化合物和药物组合物治疗癌症的方法。
• Reductive Amination of Ketonic Compounds Catalyzed by Cp*Ir(III) Complexes Bearing a Picolinamidato Ligand
  作者：Kouichi Tanaka、Takashi Miki、Kunihiko Murata、Ayumi Yamaguchi、Yoshihito Kayaki、Shigeki Kuwata、Takao Ikariya、Masahito Watanabe

  DOI：10.1021/acs.joc.9b01565

  日期：2019.9.6

  Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low

  带有2-吡啶甲酸酰胺部分的Cp * Ir配合物可作为有效的催化剂，用于在酮的转移氢化条件下，使用甲酸铵作为氮源和氢源，对酮类化合物进行直接还原胺化，从而生成伯胺。清洁且操作简单的转化过程是在相对较低的温度下以高达20,000的底物与催化剂的摩尔比（S / C）进行的，并且对伯胺表现出出色的化学选择性。
• Divergent Synthesis of Enantioenriched β-Functional Amines via Desymmetrization of <i>meso</i>-Aziridines with Isocyanides
  作者：Xiangqiang Li、Qian Xiong、Mingming Guan、Shunxi Dong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acs.orglett.9b02242

  日期：2019.8.2

  enantioselective ring-opening desymmetrization of meso-aziridines with isocyanides was achieved in the presence of a chiral N,N′-dioxide/Mg(OTf)2 complex. The in situ generated chiral 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous H2O and TMSN3, enabling a collective synthesis of various chiral vicinal amino-oxazoles, spiroindolines,

  在手性N，N'-二氧化物/ Mg（OTf）2络合物的存在下，内消旋氮杂环丁烷与异氰酸酯的高度对映选择性开环脱对称。原位产生的手性1,4-两性离子中间体被分子内基于氧和碳的亲核试剂或外源H 2 O和TMSN 3成功捕获，从而可以合成各种手性邻位氨基恶唑，螺二氢吲哚和β-氨基酰胺和四唑衍生物，具有中等至高收率，具有出色的对映选择性。
• Rhodium(III)-Catalyzed Oxidative Olefination of Picolinamides: Convenient Synthesis of 3-Alkenylpicolinamides
  作者：Jun Zhou、Bo Li、Zhen-Chao Qian、Bing-Feng Shi

  DOI：10.1002/adsc.201300895

  日期：2014.3.24

  A rhodium(III)‐catalyzed selective olefination of picolinamide derivatives has been developed. The reaction shows high regioselectivity, low catalyst loading (0.5 mol%), high yield and good functional group tolerance, providing a convenient strategy for the synthesis of 3‐alkenylpicolinamides.

  已开发了铑（III）催化的吡啶甲酰胺衍生物的选择性烯烃化反应。该反应显示出高区域选择性，低催化剂负载量（0.5 mol％），高收率和良好的官能团耐受性，为合成3-链烯基吡啶甲酸酰胺提供了便利的策略。