3-氟-2-羧酸甲酯噻吩 | 100421-52-1

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-氟-2-羧酸甲酯噻吩
• 中文别名: 3-氟噻吩-2-羧酸甲酯；3-氟噻吩-2-甲酸甲酯；3-氟-2-噻吩羧酸甲酯
• 英文名称: methyl 3-fluorothiophene-2-carboxylate
• 英文别名: methyl 3-fluoro-2-thiophenecarboxylate
• CAS: 100421-52-1
• 化学式: C₆H₅FO₂S
• 分子量: 160.169
• InChiKey: UKIUEFZYSXIGPY-UHFFFAOYSA-N

物化性质

• 熔点：
  51-53℃
• 沸点：
  217℃
• 密度：
  1.323
• 闪点：
  85℃
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Methyl 3-Fluoro-2-thiophenecarboxylate Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Methyl 3-Fluoro-2-thiophenecarboxylate

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Methyl 3-Fluoro-2-thiophenecarboxylate
Percent: >97.0%(GC)
CAS Number: 100421-52-1
Chemical Formula: C6H5FO2S

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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.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. 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.
Methyl 3-Fluoro-2-thiophenecarboxylate

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Section 5. FIRE-FIGHTING MEASURES
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
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
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
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
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 refrigerator.
Store under inert gas.
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive, Air-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
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.
Eye protection: Safety glasses. A face-shield, if the situation requires.
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
Form: Crystal- Powder
White - Almost white
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:55°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]
Methyl 3-Fluoro-2-thiophenecarboxylate

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Soluble: 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, Hydrogen fluoride, Sulfur oxides
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
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
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

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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.
Methyl 3-Fluoro-2-thiophenecarboxylate

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

3-氟-2-羧酸甲酯噻吩是一种重要的噻吩衍生物。噻吩及其衍生物，如联噻吩、并二噻吩、并三噻吩和苯并二噻吩等，具有优异的供电性和载流子传输特性，常用于共轭聚合物及电子给体-受体体系的构建，并应用于有机光伏电池材料与器件、有机发光二极管、有机场效应晶体管以及电致变色显示器等领域。

制备

3-氟-2-羧酸甲酯噻吩由2,3-二氯丙腈为起始物料，首先制备关键中间体3-氨基-2-噻吩甲酸甲酯。随后通过重氮化及氟代反应得到目标产物。其合成路线如下：

2,3-二氯丙腈的制备

在装有搅拌器、温度计、通气插管和冷凝器的250 mL四口瓶中，投入丙烯腈与N,N-二甲基甲酰胺，搅拌降温至约5℃。开始缓慢通入氯气，控制通氯温度为5～10℃，当通氯量达120.0 mL时停止通氯，在10～15℃下保温反应5小时后，用氮气赶去多余氯气。反应结束后称重，得到2,3-二氯丙腈。

2-巯基乙酸甲酯的制备

在装有搅拌器、温度计、滴加漏斗和冷凝器的500 mL四口瓶中加入2-巯基乙酸与甲醇。在40℃下滴加浓硫酸，反应完成后于35～40℃保温8小时。静置分水后获得粗酯，并通过减压蒸馏收集1333 Pa下的42~43℃馏分得到2-巯基乙酸甲酯。

3-氨基-2-噻吩甲酸甲酯的制备

在装有搅拌器、温度计、滴加漏斗和冷凝器的500 mL四口瓶中加入28%甲醇钠200 g。10～15℃间滴加2-巯基乙酸甲酯53.8 g，再滴加溶有2,3-二氯丙腈65.0 g的100 mL甲醇溶液，保温反应6小时后减压蒸出甲醇。加入冷水200 mL搅拌洗涤、抽滤，并用冷水洗涤一次。烘干后得到3-氨基-2-噻吩甲酸甲酯，纯度为97.8%，收率为84.7%，熔点为60~63℃。

3-氟-2-噻吩羧酸甲酯的制备

首先将3-氨基-2-噻吩甲酸甲酯与NaNO₂和HBr反应生成溴化重氮苯，再在溴化亚铜催化下通过自由基机理分解得到溴苯及氮气。最后以无水KF为卤素置换剂进行卤素置换反应，从而制得3-氟-2-噻吩羧酸甲酯。

反应信息

• 作为反应物：
  描述：

  3-氟-2-羧酸甲酯噻吩 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到3-氟-2-噻吩甲醇
  参考文献：
  名称：

  通过氟原子取代提高聚合物场效应晶体管的性能并比较各种受体单元和通道迁移率的效果

  摘要：

  三种共轭共聚物，PDPP-2FTVT、PIID-2FTVT 和 PNDI-2FTVT，基于具有不同受体单元、二酮吡咯并吡咯 (DPP) 的 2,2′-(1E)-1,2-乙烯基双[3-氟噻吩] (2FTVT) 核)、异靛蓝 (IID) 和萘二亚胺 (NDI) 是为有机场效应晶体管 (OFET) 开发的。 2FTVT单元中吸电子氟原子和乙烯基键的结合不仅降低了前沿分子轨道能量，而且延长了吸收剖面并使聚合物主链平坦化，对增强分子相互作用和载流子性能表现出协同效应。所得共聚物 PDPP-2FTVT 表现出高度可靠的薄膜晶体管特性，与 PIID-2FTV 和 PNDI-2FTVT 相比，最高空穴迁移率为 1.93 cm V s。 PIID-2FTV 共聚物表现出双极性特性，空穴和电子迁移率分别为 0.71 cm V s 和 0.03 cm V s，而 PNDI-2FTVT 在三种共聚物中表现出最高的电子迁移率，为

  DOI：

  10.1016/j.orgel.2024.107069
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 盐酸 、 silica gel 作用下， 以 水 为溶剂， 反应 1.08h， 生成 3-氟-2-羧酸甲酯噻吩
  参考文献：
  名称：

  [EN] 3-OXO-TETRAHYDRO-FURO[3,2-B]PYRROL-4(5H)-YL) DERIVATIVES I
  [FR] DÉRIVÉS 3-OXO-TÉTRAHYDRO-FURO [3,2-B] PYRROL -4 (5H)-YL)

  摘要：

  这项发明涉及作为双重CatS/K抑制剂的酰胺氧代四氢-2H-呋喃[3.2-b]吡咯-4(5H)-基)衍生物，以及含有这些化合物的药物组合物，还涉及这些化合物用于治疗和/或预防疼痛以及其他疾病和/或紊乱。

  公开号：

  WO2015161928A1

文献信息

• [EN] N-SUBSTITUTED INDOLE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] UTILISATION DE DÉRIVÉS D'INDOLE N-SUBSTITUÉS COMME MODULATEURS DES RÉCEPTEURS DES PGE2
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2017085198A1

  公开（公告）日：2017-05-26

  The present invention relates to derivativesof formula (I) wherein (R1)n, R2, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及公式(I)的衍生物，其中(R1)n，R2，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，其制备方法，其药学上可接受的盐，以及作为药物的用途，含有一个或多个公式(I)化合物的药物组合物，特别是作为前列腺素2受体EP2和/或EP4的调节剂的用途。
• [EN] FACTOR XIa INHIBITORS<br/>[FR] INHIBITEURS DE FACTEUR XIA
  申请人：MERCK SHARP & DOHME

  公开号：WO2016168098A1

  公开（公告）日：2016-10-20

  The present invention provides a compound of Formula (I); and pharmaceutical compositions comprising one or more said compounds, and methods for using said compounds for treating or preventing thromboses, embolisms, hypercoagulability or fibrotic changes. The compounds are selective Factor XIa inhibitors or dual inhibitors of Factor XIa and plasma kallikrein.

  本发明提供了一种公式(I)的化合物；以及包含一个或多个所述化合物的药物组合物，以及使用所述化合物治疗或预防血栓、栓塞、高凝状态或纤维化变化的方法。这些化合物是选择性的因子XIa抑制剂或对因子XIa和血浆激肽酶的双重抑制剂。
• Synthesis of [¹⁸F]Fluoroarenes by Nucleophilic Radiofluorination of<i>N</i>-Arylsydnones
  作者：Maruthi Kumar Narayanam、Gaoyuan Ma、Pier Alexandre Champagne、Kendall N. Houk、Jennifer M. Murphy

  DOI：10.1002/anie.201707274

  日期：2017.10.9

  Easy to handle: A practical radiofluorination of anilines with [18F]fluoride is achieved via N-arylsydnone intermediates. This method displays broad functional group tolerance, is compatible to automation on a commercial radiosynthesis module and can facilitate rapid 18F-labeling of peptides.

  易于处理：苯胺与[ 18 F]氟化物的实际放射性氟化是通过N-芳基亚砜酮中间体实现的。该方法显示出宽泛的官能团耐受性，与商用放射合成模块上的自动化兼容，并且可以促进肽的18 F快速标记。
• [EN] NEW AMINO-PYRIMIDONYL-PIPERIDINYL DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS D'AMINO-PYRIMIDONYL-PIPÉRIDINYL, LEUR PROCÉDÉ DE PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2020079205A1

  公开（公告）日：2020-04-23

  Compounds of formula (I) wherein R1, R2, R3, R4, R5, n and Q are as defined in the description. Medicaments.

  式(I)中R1、R2、R3、R4、R5、n和Q的化合物如描述中所定义。药物。
• 五元杂环氧代羧酸类化合物及其医药用途
  申请人：中国科学院上海药物研究所

  公开号：CN112724127B

  公开（公告）日：2023-02-17

  本发明涉及五元杂环氧代羧酸类化合物及其医药用途。具体地，本发明涉及如式(I)所示的化合物、药用盐、前药、水合物、溶剂合物或晶型，也涉及所述化合物的制备方法、包含所述化合物的药物组合物以及其作为I型干扰素的分泌调节剂，尤其是作为STING激动剂，以及在制备预防和/或治疗与I型干扰素相关疾病的药物中的医药用途。