4-三氟甲基烟酸 | 158063-66-2

• 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: 4-三氟甲基烟酸
• 中文别名: 4-三氟甲基吡啶-3-甲酸；4-三氟甲基-3-吡啶羧酸；4-(三氟甲基)吡啶-3-甲酸；4-(三氟甲基)烟酸；4-三氟甲基-3-吡啶甲酸
• 英文名称: 4-(trifluoromethyl)nicotinic acid
• 英文别名: 4-trifluoromethyl-3-pyridinecarboxylic acid；4-(trifluoromethyl)pyridine-3-carboxylic acid
• CAS: 158063-66-2
• 化学式: C₇H₄F₃NO₂
• 分子量: 191.109
• InChiKey: LMRJHNFECNKDKH-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C(lit.)
• 沸点：
  290.4±40.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）
• 稳定性/保质期：

  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36,S37/39
• 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,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  保存方法：将物品存放在密闭、阴凉、通风且干燥的地方。

SDS

Name:	4-(Trifluoromethyl)nicotinic acid 97% Material Safety Data Sheet
Synonym:	4-(Trifluoromethyl)pyridine-3-carboxylic aci
CAS:	158063-66-2

Section 1 - Chemical Product MSDS Name:4-(Trifluoromethyl)nicotinic acid 97% Material Safety Data Sheet
Synonym:4-(Trifluoromethyl)pyridine-3-carboxylic aci

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
158063-66-2	4-(Trifluoromethyl)nicotinic acid	97%	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.
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.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
Get medical aid. 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.
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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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# 158063-66-2: Personal Protective Equipment Eyes: Not available.
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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 145 - 148 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: C7H4F3NO2
Molecular Weight: 191

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, bases, amines.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 158063-66-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Trifluoromethyl)nicotinic 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 158063-66-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 158063-66-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 158063-66-2 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

4-三氟甲基烟酸是一种有价值的合成中间体。它可用于制备吡啶甲酰胺作为HCV NS5B聚合酶的棕榈位抑制剂，也可用于合成吡唑基甲酰苯胺作为Ca2+释放激活的Ca2+（CRAC）通道抑制剂。

简介

4-三氟甲基烟酸是含三氟甲基芳香化合物的一种，具有独特的生物活性。它可以作为制备其他农药或医药的前体物质。

应用

含吡啶杂环化合物因在生物体内具有较强的生理活性而受到广泛关注，已成功开发出许多商品，如吡虫啉、啶虫脒、烯啶虫胺等。氟啶虫酰胺是含三氟甲基的烟酰胺类化合物，是一种高效杀虫剂，4-三氟甲基烟酸为其关键中间体。氟啶虫酰胺合成工艺的主要难点在于4-三氟甲基烟酸的合成，而这一过程面临着极大挑战，从而限制了其推广使用。

制备

在100 mL三口烧瓶中依次加入5 g (0.0192 mol) 2,6-二氯-4-三氟甲基烟酸、0.3 g（含水量63.45%）10% Pd/C、5.25 g (0.0389 mol) CH₃COONa·3H₂O和20 mL乙醇，搅拌溶解后进行氮气置换三次以排除空气，再用氢气置换两次，在氢气气氛下室温搅拌反应8小时直至无氢气吸收结束。抽滤回收钯碳，并用乙醇洗涤滤饼三次，将滤液旋蒸除去溶剂。向得到的固体中加入20 mL水，充分振荡使其溶解后，加入盐酸调节pH至2～3，使用乙酸乙酯萃取三次，合并有机相并用饱和食盐水洗涤三次，无水硫酸钠干燥后旋蒸得到淡黄色固体3.3 g，产率为90.4%。

反应信息

• 作为反应物：
  描述：

  4-三氟甲基烟酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 N-hydroxy-N-methyl-4-(trifluoromethyl)pyridine-3-carboxamide
  参考文献：
  名称：

  [EN] TRIFLUOROMETHYLPYRIDINE CARBOXAMIDES AS PESTICIDES
  [FR] TRIFLUOROMÉTHYLPYRIDINE CARBOXAMIDES COMME PESTICIDES

  摘要：

  化合物的结构式 I（I），其中取代基如权利要求1所定义的那样，可用作杀虫剂。

  公开号：

  WO2014023531A1
• 作为产物：
  描述：

  4-三氟甲基吡啶 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.03h， 生成 4-三氟甲基烟酸
  参考文献：
  名称：

  三氟甲基取代的吡啶和喹啉的直接金属化和后续功能化

  摘要：

  根据试剂的选择，2-(三氟甲基)吡啶可以被选择性地金属化并随后在3-位或6-位被羧化或以其他方式官能化。“可选的位点选择性”也可以用 4-(三氟甲基)吡啶来实现，它可以在 2-位或 3-位去质子化。相反，3-（三氟甲基）吡啶发生亲核加成。和随之而来的解体。不管是什么基地。根据反应条件，2-（三氟甲基）喹啉在其 3-、4- 或 8- 位对锂试剂显示反应性，在 2-或 4-位对 3-（三氟甲基）喹啉和 4-（三氟甲基）喹啉)喹啉在 2 位或 3 位。因此可以进行准备。四种三氟甲基取代的吡啶羧酸和六种三氟甲基取代的喹啉羧酸，区域异构未受污染，并且以最直接的方式。[在 SciFinder (R) 上]

  DOI：

  10.1002/ejoc.200390216

文献信息

• SUBSTITUTED ARYL AND HETEROARYL CARBOXYLIC ACID HYDRAZIDES OR SALTS THEREOF AND USE THEREOF TO INCREASE STRESS TOLERANCE IN PLANTS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20180206495A1

  公开（公告）日：2018-07-26

  Substituted aryl- and heteroarylcarbonyl hydrazides The invention relates to substituted aryl- and heteroarylcarbonyl hydrazides of the general formula (I) or salts thereof where the radicals of the formula (I) are each as defined in the description for enhancing stress tolerance in plants to abiotic stress, and for enhancing plant growth and/or for increasing plant yield.

  该发明涉及通式（I）的取代芳基和杂芳基羰基肼或其盐，其中通式（I）的基团如描述中所定义，用于增强植物对非生物胁迫的耐受性，促进植物生长和/或增加植物产量。
• [EN] ROR-GAMMA INHIBITORS<br/>[FR] INHIBITEURS DE ROR-GAMMA
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2019063748A1

  公开（公告）日：2019-04-04

  The present invention relates to compounds of formula I and pharmaceutical compositions comprising compounds of formula I. Compounds of Formula I are useful in treatment of inflammatory, metabolic or autoimmune diseases which are mediated by RORy.

  本发明涉及公式I的化合物和包含公式I化合物的药物组合物。公式I的化合物在治疗由RORγ介导的炎症性、代谢性或自身免疫性疾病方面是有用的。
• [EN] INHIBITORS OF WDR5 PROTEIN-PROTEIN BINDING<br/>[FR] INHIBITEURS DE LA LIAISON PROTÉINE WDR5-PROTÉINE
  申请人：PROPELLON THERAPEUTICS INC

  公开号：WO2019046944A1

  公开（公告）日：2019-03-14

  The present application is directed to compounds of Formula I: (I) compositions comprising these compounds and their uses, for example as medicaments for the treatment of diseases, disorders or conditions mediated or treatable by inhibition of binding between WDR5 protein and its binding partners.

  本申请涉及到Formula I的化合物：(I) 包括这些化合物的组合物及其用途，例如作为治疗由于抑制WDR5蛋白与其结合伙伴之间结合而介导或可治疗的疾病、紊乱或状况的药物。
• COMPOUNDS AND USES THEREOF
  申请人：Yumanity Therapeutics, Inc.

  公开号：US20190330198A1

  公开（公告）日：2019-10-31

  The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.

  本发明涉及用于治疗神经系统疾病的化合物。本发明的化合物可以单独或与其他药用活性剂结合使用，用于治疗或预防神经系统疾病。
• NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF
  申请人：Florjancic S. Alan

  公开号：US20080058335A1

  公开（公告）日：2008-03-06

  The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1 , R 2 , R 3 , and L 1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R 1a , R 2a and (Rx)n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

  本发明涉及式(I)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1 ，R 2 ，R 3 和L 1 在规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。本发明还涉及式(II)的化合物，或药用盐、前药、前药的盐或其组合物， 其中R 1a ，R 2a 和(Rx)n如规范中定义，包含这种化合物的组合物，以及使用这种化合物和组合物治疗疾病和疾病的方法。

表征谱图