2-氟异丁酸甲酯 | 338-76-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-氟异丁酸甲酯
• 中文别名: 2-氟-2-甲基丙酸甲酯
• 英文名称: methyl α-fluoro-α-methylpropionate
• 英文别名: methyl 2-fluoro-2-methylpropanoate；methyl 2-fluoro-2-methylpropionate；methyl 2-fluoroisobutanoate；methyl 2-fluoroisobutyrate；ethyl 2-fluoroisobutyrate；methyl α-fluoroisobutyrate
• CAS: 338-76-1
• 化学式: C₅H₉FO₂
• 分子量: 120.124
• InChiKey: OEGBOFOVYSOERL-UHFFFAOYSA-N

物化性质

• 沸点：
  108-109
• 密度：
  1

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  3/8
• 危险品标志：
  F
• 安全说明：
  S16
• 危险类别码：
  R10
• 危险品运输编号：
  UN 3272
• 海关编码：
  2915900090
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-fluoro-2-methylpropionate
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2-fluoro-2-methylpropionate
CAS number: 338-76-1

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H9FO2
Molecular weight: 120.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen fluoride.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用

2-氟异丁酸甲酯作为农药中间体，可用于合成含氟三嗪基团类除草剂。这类化合物通过将苯氧基烷基胺中的羟基被三嗪基团取代制得。这类除草剂不仅具有显著的除草活性，而且对稻谷无毒害作用。

制备

1. 酯化反应：

   • 在反应器中加入2-羟基异丁酸甲酯（20.1g，0.17mol），搅拌并冷却至-10～-5℃。
   • 保持温度在-10～-5℃，滴加氯化亚砜（36.4g，0.31mol）。
   • 滴加完毕后，继续搅拌反应3小时。通过GC检测原料2-羟基异丁酸甲酯已完全反应，随后停止反应。

2. 氟化反应：

   • 将反应釜冷却至-15～-20℃，加入氟化氢（37.4g，1.87mol）和三乙胺（0.7g，6.80mmol），将步骤1所得液体转移至反应釜。
   • 停止冷却，缓慢升温，在40～45℃下搅拌反应3～5小时。通过GC检测原料已完全反应，结束反应。

3. 后处理及精馏：

   • 使用乙酸乙酯（300mL×3）萃取有机相，并用水（50mL）、饱和碳酸氢钠水溶液（50mL×2次）和水（50mL）洗涤。
   • 在干燥器中干燥去除水分，然后向有机相通入氯气。通过GC检测甲基丙烯酸甲酯含量低于0.2%时停止通氯气，随后转入精馏塔进行减压分馏。
   • 在150～160mmHg下收取温度为65～70℃的馏分，即得到2-氟异丁酸甲酯。通过GC检测其纯度达到99.5%，收率约为79.3%。

反应信息

• 作为反应物：
  描述：

  2-氟异丁酸甲酯 在 Ru-MACHO 、 氢气 、 sodium methylate 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、1.01 MPa 条件下， 反应 6.0h， 生成 2-氟-2-甲基丙烷-1-醇
  参考文献：
  名称：

  α-氟化酯与双功能钳型钌 (II) 催化剂的实际选择性加氢生成氟化醇或氟半缩醛

  摘要：

  用钳型双功能催化剂 RuHCl(CO)(dpa) 1a、反式-RuH2(CO)(dpa) 1b 和反式-RuCl2(CO)(dpa) 1c 在温和条件下选择性氢化氟化酯迅速进行，得到相应的氟化醇或半缩醛，收率良好至极好。在优化条件下，手性(R)-2-氟丙酸酯的加氢反应顺利进行，得到相应的手性醇，ee值没有出现严重下降。

  DOI：

  10.1021/ja403852e
• 作为产物：
  描述：

  2-溴代异丁酸甲酯 在 silver fluoride 作用下， 生成 2-氟异丁酸甲酯
  参考文献：
  名称：

  Fluorination of methyl isobutyrate with perchloryl fluoride

  摘要：

  DOI：

  10.1021/jo01275a064

文献信息

• [EN] ISOTOPICALLY ENRICHED OR FLUORINATED IMIDAZO[2,1-B][1,3]BENZOTHIAZOLES<br/>[FR] IMIDAZO[2,1-B][1,3]BENZOTHIAZOLES ENRICHIS EN ISOTOPES OU FLUORES
  申请人：AMBIT BIOSCIENCES CORP

  公开号：WO2011056764A1

  公开（公告）日：2011-05-12

  Provided herein are isotopically enriched or fluorinated imidazo[2,1- b][1,3]benzothiazoles, for example, of Formula (I). Also provided are pharmaceutical compositions comprising such compounds, and methods of their use for the treatment of a proliferative disease.

  本文提供了同位素富集或氟代的咪唑并[2,1-b][1,3]苯并噻唑化合物，例如，化合物的化学式（I）。还提供了包含这些化合物的药物组合物，以及它们用于治疗增生性疾病的方法。
• [EN] BIARYL COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS BIARYLES ET PROCÉDÉS D'UTILISATION DE CEUX-CI
  申请人：AMBIT BIOSCIENCES CORP

  公开号：WO2011022473A1

  公开（公告）日：2011-02-24

  Provided herein are compounds for treatment of KIT, CSF-1R and/or FLT3 kinase mediated diseases. Also provided are pharmaceutical compositions comprising the compounds and methods of using the compounds and compositions.

  本文提供了用于治疗KIT、CSF-1R和/或FLT3激酶介导疾病的化合物。还提供了包含这些化合物的药物组合物以及使用这些化合物和组合物的方法。
• Substituted 1,3,5- triazines
  申请人：Nihon Bayer Agrochem K. K.

  公开号：US06645915B1

  公开（公告）日：2003-11-11

  The invention relates to novel substituted 1,3,5-triazines of the general formula (I) in which A represents CHR3R4 or represents C1-halogenoalkyl-substituted C3-C6-cycloalkyl, C3-C6-alkinyl or C1-C4-cyanoalkyl, where R1, R2, R3 and R4 are each as defined in the description, and to processes for their preparation, to novel intermediates, including their preparation, and to the use of the compounds of the general formula (I) as herbicides.

  该发明涉及一种新型的通式（I）的取代1,3,5-三嗪 其中 A代表CHR3R4或代表C1-卤代烷基取代的C3-C6-环烷基，C3-C6-炔基或C1-C4-氰基，其中 R1、R2、R3和R4如描述中所定义， 以及它们的制备方法，包括它们的制备的新中间体，以及将通式（I）的化合物用作除草剂。
• 一种嘧啶衍生物的制备方法
  申请人：杰达维（上海）医药科技发展有限公司

  公开号：CN106008362B

  公开（公告）日：2018-08-10

  本发明提供一种新型嘧啶衍生物的制备方法，所述嘧啶衍生物为[4‑(1‑氟‑1‑甲基‑乙基)‑嘧啶]‑5‑甲胺盐酸盐。其是一种新的医药中间体，为新药研发筛选所用。可以用于治疗糖尿病、脱发症等各种慢性疾病的新药研发筛选上，这种化合物的合成方法还具有操作简单、高效，原料成本低的优点，这种合成路线有工艺简单方便、适合工厂放大生产的优点。
• Substituted 2,4-diamino-1,3,5-triazine and their use as herbicides
  申请人：Bayer Aktiengesellschaft

  公开号：US06348435B1

  公开（公告）日：2002-02-19

  The invention relates to novel substituted 2,4-diamino-1,3,5-triazines of the formula (I) in which R1 represents, for exampe, H or C1-C6-alkyl, R2 represents, for example, H, C1-C6-alkyl or —CO—R6, R3 represents, for example, H, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl or C3-C6-cycloalkyl, R4 represents, for example, H, C1-C6-alkyl or C3-C6-cycloalkyl, R5 represents one of the groupings below, where R6 represents, for example, C1-C6-alkyl, C1-C6-alkoxy or C2-C6-alkenyl, R7 to R12 represents, for example, H or certain organic radicals and Q represents O or S, to processes and novel intermediates for their preparation and to their use as herbicides.

  该发明涉及化学式(I)中的新型取代2,4-二氨基-1,3,5-三嗪，其中R1代表例如H或C1-C6-烷基，R2代表例如H、C1-C6-烷基或—CO—R6，R3代表例如H、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基或C3-C6-环烷基，R4代表例如H、C1-C6-烷基或C3-C6-环烷基，R5代表下面的一种基团，其中R6代表例如C1-C6-烷基、C1-C6-烷氧基或C2-C6-烯基，R7到R12代表例如H或某些有机基团，Q代表O或S，以及它们的制备方法和新型中间体，以及它们作为除草剂的用途。