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

---

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

---

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.

---

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.

---

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.

---

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.

---

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.

---

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.

---

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

---

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.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

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.

---

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.

---

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