3-溴异烟酸 | 13959-02-9

• 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: 3-溴异烟酸
• 中文别名: 3-溴吡啶-4-羧酸；3-溴-4-羧基吡啶；3-溴吡啶-4-甲酸；3-溴-4-吡啶羧酸；3-溴-4-吡啶甲酸；3-溴-4-异烟酸
• 英文名称: 3-bromoisonicotinic acid
• 英文别名: 3-Bromopyridine-4-carboxylic acid；3-bromo-4-pyridinecarboxylic acid
• CAS: 13959-02-9
• 化学式: C₆H₄BrNO₂
• mdl: MFCD00040944
• 分子量: 202.007
• InChiKey: AVXWWBFBRTXBRM-UHFFFAOYSA-N

物化性质

• 熔点：
  237-238
• 沸点：
  403.1±30.0 °C(Predicted)
• 密度：
  1.813±0.06 g/cm3(Predicted)
• 闪点：
  197.

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2933399090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 3-Bromopyridine-4-carboxylic acid
CAS-No. : 13959-02-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S22 Do not breathe dust.
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C6H4BrNO2
Molecular Weight : 202,01 g/mol
Component Concentration
3-Bromopyridine-4-carboxylic acid
CAS-No. 13959-02-9 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 234 - 238 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point 235 °C - closed cup
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density 6,97 - (Air = 1.0)
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,128
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

性质

该物质为白色至米白色的粉末。

用途

3-溴异烟酸作为重要的异烟酸衍生物中间体，主要用于合成抗结核病药物。此外，它还用于制备酰胺、酰肼和酯类等衍生物。

制备过程

1. 装好反应装置，在三口烧瓶中依次加入3-溴-4-甲基吡啶（13g, 0.78mol）、Co0.27CuO3（0.5g）以及适量的水。
2. 开启搅拌，并在油浴中缓慢升温至90℃。开始通入氧气，保持反应温度直至不再吸收氧气为止。
3. 过滤出催化剂后，逐渐加入NaOH溶液调节pH值为4。继续搅拌10分钟，析出固体，得到粗产品3-溴异烟酸。
4. 使用丙酮进行重结晶，得到白色粉末状晶体，过滤并进行真空干燥处理。
5. 最终产得纯度较高的3-溴异烟酸14g，其收率为90%。经质谱分析（EI）测定，分子量为200.9425 ([M]+)。

反应信息

• 作为反应物：
  描述：

  3-溴异烟酸 在 dipotassium peroxodisulfate 、 copper(l) iodide 、 1,10-菲罗啉 、 氧气 、 sodium ethanolate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-nitro-7-phenyl-2,3,7,12-tetraazatricyclo[7.4.0.0^2,6]trideca-1(9),3,5,10,12-pentaen-8-one
  参考文献：
  名称：

  [EN] TRICYCLIC COMPOUNDS
  [FR] COMPOSÉS TRICYCLIQUES

  摘要：

  本文提供了Formula (I)的化合物，或其药用盐，包括包含本文描述的化合物（包括本文描述的化合物的药用盐）的药物组合物，以及合成这些化合物的方法。本文还提供了使用Formula (I)的化合物或其药用盐治疗疾病和/或病症的方法。

  公开号：

  WO2020243199A1
• 作为产物：
  描述：

  异烟酸 在 溴 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以96.3%的产率得到3-溴异烟酸
  参考文献：
  名称：

  一种3-氨基异烟酸甲酯的高收率合成方法

  摘要：

  本发明属于化学制药领域，具体公开一种3‑氨基异烟酸甲酯的高收率合成方法，以4‑吡啶羧酸为原料，经溴化、氨化、酯化得到所述3‑氨基异烟酸甲酯。本发明所述3‑氨基异烟酸甲酯的高收率合成方法，反应条件温和，总收率高，3‑溴‑4‑吡啶羧酸反应废弃滤液可以反复套用，提高原料的利用率，减少资源浪费，最大限度地降低整体工艺的成产成本，具有极高的应用。

  公开号：

  CN111018775A

文献信息

• INHIBITORS OF FIBROBLAST ACTIVATION PROTEIN
  申请人：Praxis Biotech LLC

  公开号：US20190185451A1

  公开（公告）日：2019-06-20

  Compounds and compositions for modulating fibroblast activation protein (FAP) are described. The compounds and compositions may find use as therapeutic agents for the treatment of diseases, including hyperproliferative diseases.

  描述了用于调节成纤维细胞活化蛋白（FAP）的化合物和组合物。这些化合物和组合物可能被用作治疗疾病的治疗剂，包括高增殖性疾病。
• 1-(2-PHENOXYMETHYLHETEROARYL)PIPERIDINE AND PIPERAZINE COMPOUNDS
  申请人：Stangeland Eric L.

  公开号：US20110230495A1

  公开（公告）日：2011-09-22

  The invention relates to compounds of formula I: where X, HAr, a, and R 1 through R 6 are as defined in the specification, or a pharmaceutically acceptable salt thereof. The compounds of formula I are serotonin and norepinephrine reuptake inhibitors. The invention also relates to pharmaceutical compositions comprising such compounds; methods of using such compounds; and process and intermediates for preparing such compounds.

  本发明涉及如下公式I的化合物： 其中X，HAr，a，以及R1至R6如说明书所述，或其药用可接受的盐。公式I的化合物是5-羟色胺和去甲肾上腺素再摄取抑制剂。本发明还涉及包含这些化合物的药物组合物；使用这些化合物的方法；以及制备这些化合物的方法和中间体。
• [EN] FUSED IMIDAZOLE DERIVATIVES AS IL-17 MODULATORS<br/>[FR] DÉRIVÉS D'IMIDAZOLE FUSIONNÉS UTILISÉS EN TANT QU'INHIBITEURS D'IL-17
  申请人：UCB BIOPHARMA SPRL

  公开号：WO2019138017A1

  公开（公告）日：2019-07-18

  A series of substituted fused bicyclic imidazole derivatives, including benzimidazole derivatives and analogues thereof, being potent modulators of human IL-17 activity, are accordingly of benefit in the treatment and/or prevention of various human ailments, including inflammatory and autoimmune disorders.

  一系列替代的融合双环咪唑衍生物，包括苯并咪唑衍生物及其类似物，作为强效的人IL-17活性调节剂，因此在治疗和/或预防各种人类疾病，包括炎症性和自身免疫性疾病方面具有益处。
• Discovery of 5-(3-Chlorophenylamino)benzo[<i>c</i>][2,6]naphthyridine Derivatives as Highly Selective CK2 Inhibitors with Potent Cancer Cell Stemness Inhibition
  作者：Yuanjiang Wang、Zhaodan Lv、Feihong Chen、Xing Wang、Shaohua Gou

  DOI：10.1021/acs.jmedchem.1c00131

  日期：2021.4.22

  concurrent CK2 along with cancer stem cell (CSC) inhibitory activities are rare in a single small molecule. Herein, a series of 5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine derivatives were synthesized using a known CK2 inhibitor, silmitasertib (CX-4945), as the lead compound. Among the resulting compounds, 1c exhibited stronger CK2 inhibitory activity with higher Clk2/CK2 selectivity than CX-4945

  多功能实体最近对于开发抗癌化疗药物具有吸引力。但是，在单个小分子中很少有具有并发CK2和癌症干细胞（CSC）抑制活性的实体。在此，使用已知的CK2抑制剂西米塔塞替尼（Cilmitasertib（CX-4945））作为前导化合物合成了一系列5-（3-氯苯基氨基）苯并[ c ] [2,6]萘啶衍生物。在所得化合物中，1c与CX-4945相比具有更强的CK2抑制活性和更高的Clk2 / CK2选择性。明显地，1c可以调节Akt1（ser129）-GSK-3β（ser9）-Wnt /β-catenin信号通路并抑制茎标记ALDH1A1，CSC表面抗原和茎基因的表达，显示出强大的CSC抑制活性。此外，与CX-4945钠盐相比，1c还显示出优异的药代动力学和抗肿瘤活性，且无明显毒性。1c的良好抗增殖和抗肿瘤活性，对CK2的高抑制选择性以及对癌细胞干性的有效抑制作用使该分子成为治疗癌症的候选药物。
• [EN] ANTI-RSV COMPOUNDS<br/>[FR] COMPOSÉS ANTI-VRS
  申请人：GILEAD SCIENCES INC

  公开号：WO2011005842A1

  公开（公告）日：2011-01-13

  The present invention relates to anti-RSV compounds of Formula (I) and methods for use of the compounds in the treatment and prevention of RSV infection.

  本发明涉及式(I)的抗RSV化合物，以及利用这些化合物在治疗和预防RSV感染中的方法。