5-溴吡啶-2-羧酸甲酯 | 29682-15-3

• 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: 5-溴吡啶-2-羧酸甲酯
• 中文别名: 甲基5-溴甲基吡啶酸酯；5-溴皮考林酸甲酯；5-溴-2-吡啶甲酸甲酯；2-甲酸甲酯-5-溴吡啶；5-溴吡啶-2-甲酸甲酯；5-溴吡啶甲酸甲酯
• 英文名称: methyl 5-bromopicolinate
• 英文别名: methyl 5-bromopyridine-2-carboxylate；5-bromopyridine-2-carboxylic acid methyl ester；methyl 5-bromo-2-picolinate；methyl 5-bromo-2-pyridinecarboxylate
• CAS: 29682-15-3
• 化学式: C₇H₆BrNO₂
• mdl: MFCD04112493
• 分子量: 216.034
• InChiKey: JEURNBCYNWNADN-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103°C
• 沸点：
  290.9±20.0 °C(Predicted)
• 密度：
  1.579±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  如果遵照规格使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将贮藏器密封保存，并存放在阴凉、干燥处。同时，确保工作环境具有良好的通风或排气设施。

SDS

Name:	Methyl 5-bromo-2-pyridinecarboxylate Material Safety Data Sheet
Synonym:	Methyl 5-bromopicolinat
CAS:	29682-15-3

Section 1 - Chemical Product MSDS Name:Methyl 5-bromo-2-pyridinecarboxylate Material Safety Data Sheet
Synonym:Methyl 5-bromopicolinat

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
29682-15-3	Methyl 5-bromo-2-pyridinecarboxylate	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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled. Can produce delayed pulmonary edema.
Chronic:
No information found.

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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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. 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 cool, dry place. Store in a tightly closed container.

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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# 29682-15-3: 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: 100-102 deg C
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: C7H6BrNO2
Molecular Weight: 216.03

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not currently available.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 29682-15-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 5-bromo-2-pyridinecarboxylate - 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# 29682-15-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 29682-15-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 29682-15-3 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

吡啶及其衍生物是合成杂环化合物类农药和医药的重要中间体。由于吡啶替代苯环后可得到的新化合物通常具有更高的生物活性或更低的毒性，因此5-溴吡啶-2-羧酸甲酯这类化合物被广泛用作医药合成中的重要中间体。

制备方法

在装有机械搅拌器、恒压滴液漏斗和温度计的100 mL四口瓶中，加入60 mL质量分数为65%的硫酸和40 mmol的吡啶-2-羧酸甲酯。搅拌下缓慢加入NaBrO3（6.0 g，40 mmol），并控制反应温度在25～35 ℃，反应4小时后冷却至室温。将反应混合物置于冰浴中，用稀碱溶液中和至呈碱性。然后用二氯甲烷萃取三次（每次15 mL），无水MgSO4干燥，过滤除去固体物质，并蒸除溶剂。最后通过减压蒸馏收集馏分，即可得到5-溴吡啶-2-羧酸甲酯。

反应信息

• 作为反应物：
  描述：

  5-溴吡啶-2-羧酸甲酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 、 N,N-二甲基甲酰胺 、 calcium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 2-(氯甲基)-5-苯基吡啶
  参考文献：
  名称：

  [EN] URIDINE NUCLEOSIDE DERIVATIVES, COMPOSITIONS AND METHODS OF USE
  [FR] DÉRIVÉS D'URIDINE NUCLÉOSIDE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION

  摘要：

  这项披露涉及尿苷核苷衍生物，包含治疗有效量的这些核苷衍生物的组合物，以及使用这些核苷衍生物或组合物治疗对P2Y6受体的化合物（如激动剂）具有反应的疾病的方法，例如神经疾病，包括神经退行性疾病（如阿尔茨海默病、帕金森病）和创伤性中枢神经系统损伤、疼痛、唐氏综合症（DS）、青光眼和炎症性疾病。

  公开号：

  WO2018058148A1
• 作为产物：
  描述：

  2,5-二溴吡啶 在 正丁基锂 、 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 5-溴吡啶-2-羧酸甲酯
  参考文献：
  名称：

  Ligand creation via linking—a rapid and convenient method for construction of novel supported PyOX-ligands

  摘要：

  A novel supported amino alcohol linker was synthesized and utilized for attachment of picolinic acid derivatives onto different supports. When the resin bound molecule was further activated, the PyOX-moiety could be constructed reliably in enantiopure form. Furthermore, an efficient Pd-catalyzed modification of a picolinic acid derivative is presented. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.073
• 作为试剂：
  描述：

  5-溴-2-吡啶羧酸 、 硫酸 、 甲醇 在 乙酸乙酯 、 碳酸氢钠 、 Brine 、 Sodium sulfate-III 、 5-溴吡啶-2-羧酸甲酯 作用下， 反应 4.0h， 以to afford the title compound methyl 5-bromopicolinate (5.1 g, crude) as an off-white solid which的产率得到5-溴吡啶-2-羧酸甲酯
  参考文献：
  名称：

  N-ARYLMETHYL SULFONAMIDE NEGATIVE MODULATORS OF NR2A

  摘要：

  本发明公开了选择性负调节含有NR2A亚基的NMDA受体的化合物、包含该化合物的制药组合物以及使用该化合物治疗疾病的方法。

  公开号：

  US20150141433A1

文献信息

• [EN] IMIDAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS IMIDAZOLE UTILES COMME INHIBITEURS DE LA FAAH
  申请人：MERCK & CO INC

  公开号：WO2009152025A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病性神经病、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• [EN] OXAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS D'OXAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2010017079A1

  公开（公告）日：2010-02-11

  The present invention is directed to certain oxazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzeimer Disease, and Parkinson's Disease.

  本发明涉及某些噁唑衍生物，其可用作脂肪酸酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• 三唑并哒嗪类衍生物、其制备方法、药物组合物和用途
  申请人：上海赛默罗生物科技有限公司

  公开号：CN112979655A

  公开（公告）日：2021-06-18

  本发明涉及三唑并哒嗪类衍生物、其制备方法、药物组合物和用途。本发明提供一种通式(I)所示的化合物、其顺反异构体、其对映异构体、其非对映异构体、其外消旋体、其溶剂合物、其水合物或其药学上可以接受的盐或其前体药物，其制备方法，含有该化合物的药物组合物以及所述化合物作为α5‑GABAA受体调节剂的用途，其中R1，R2和Z如说明书中所定义。
• [EN] COMPOUNDS USEFUL AS CSF1 MODULATORS<br/>[FR] COMPOSÉS UTILES EN TANT QUE MODULATEURS DU FACTEUR 1 DE STIMULATION DE COLONIES
  申请人：REDX PHARMA PLC

  公开号：WO2016051193A1

  公开（公告）日：2016-04-07

  This invention relates to novel compounds and to pharmaceutical compositions comprising the novel compounds. More specifically, the invention relates to compounds useful as Colony Stimulating Factor 1 Receptor (cFMS) modulators (e.g. cFMS inhibitors). This invention also relates to processes for preparing the compounds, uses of the compounds in treatment and methods of treatment employing the compounds. Specifically, the invention relates to the use of the compounds for the treatment of cancer and autoimmune diseases.

  这项发明涉及新颖化合物以及包含这些新颖化合物的药物组合物。更具体地，该发明涉及用作集落刺激因子1受体（cFMS）调节剂（例如cFMS抑制剂）的化合物。这项发明还涉及制备这些化合物的方法，这些化合物在治疗中的用途以及利用这些化合物进行治疗的方法。具体而言，该发明涉及利用这些化合物治疗癌症和自身免疫性疾病。
• <i>Ex situ</i> generation of stoichiometric HCN and its application in the Pd-catalysed cyanation of aryl bromides: evidence for a transmetallation step between two oxidative addition Pd-complexes
  作者：Steffan K. Kristensen、Espen Z. Eikeland、Esben Taarning、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1039/c7sc03912c

  日期：——

  methodology was also suitable for the synthesis of 13C-labelled benzonitriles with ex situ generated 13C-hydrogen cyanide. Stoichiometric studies with the metal complexes were undertaken to delineate the mechanism for this catalytic transformation. Treatment of Pd(P(tBu)3)2 with H13CN in THF provided two Pd-hydride complexes, (P(tBu)3)2Pd(H)(13CN), and [(P(tBu)3)Pd(H)]2Pd(13CN)4, both of which were isolated

  首次报道了使用接近化学计量和气态氰化氢的钯催化芳基溴化物氰化的方案。采用两室反应器在密闭环境中安全释放异位生成的HCN，事实证明该方法在Ni催化的氢氰化反应中非常有效。随后，利用该装置将一定范围的芳基和杂芳基溴化物（28个实例）直接高产率地转化为相应的苄腈，而无需使用氰化物盐。在二恶烷-水溶剂混合物中，使用Pd（0）预催化剂P（t Bu）3 -Pd-G3和弱碱乙酸钾实现氰化。该方法也适用于13的合成C-标记的苄腈与异位生成13 C-氰化氢。进行了金属配合物的化学计量研究，以描述这种催化转化的机理。在THF中用H 13 CN处理Pd（P（t Bu）3）2提供了两种Pd-氢化物配合物（P（t Bu）3）2 Pd（H）（13 CN）和[（P（t Bu） ）3）Pd（H）] 2 Pd（13 CN）4，两者均已分离，并通过NMR光谱和X射线晶体结构分析进行了表征。当在KOAc存在下在THF∶水混合物中进行相同的反应时，仅形成（P（t

表征谱图