2-氟丙烯酸甲酯 | 2343-89-7

• 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-氟丙烯酸甲酯
• 中文别名: Alpha-氟丙烯酸甲酯；2-氟代丙烯酸甲酯
• 英文名称: methyl 2-fluoroprop-2-enoate
• 英文别名: methyl 2-fluoroacrylate；2-fluoroacrylic acid methyl ester
• CAS: 2343-89-7
• 化学式: C₄H₅FO₂
• 分子量: 104.081
• InChiKey: ZTZJVAOTIOAZGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  41°C
• 密度：
  1,114 g/cm3
• LogP：
  0.931 at 25℃ and pH6.3
• 表面张力：
  71.5mN/m at 1g/L and 20.4℃

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 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
• 危险品标志：
  Xi
• 安全说明：
  S16,S26,S36
• 危险类别码：
  R10
• 海关编码：
  2916190090
• 危险品运输编号：
  UN 1993
• 包装等级：
  II
• 危险类别：
  3,6.1
• 危险性防范说明：
  P273,P260,P210,P370+P378,P391,P301+P310+P330
• 危险性描述：
  H301,H372,H411,H225
• 储存条件：
  温度范围：0-10°C；请勿加热。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 2-fluoroacrylate, BHT stablized
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H224: Extremely flammable liquid and vapour
H301: Toxic if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P210: Keep away from heat/sparks/open flames/hot surfaces. No smoking
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P405: Store locked up

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Section 3. Composition/information on ingredients.
Ingredient name: Methyl 2-fluoroacrylate, BHT stablized
CAS number: 2343-89-7

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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.
Storage: Store in closed vessels, refrigerated.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H5FO2
Molecular weight: 104.1

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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
UN Number: UN1993 Class: 3 Packing group: II
Proper shipping name: FLAMMABLE LIQUIDS, N.O.S. (Methyl 2-fluoroacrylate, BHT stablized)

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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

简介

含氟高分子光纤材料的性能在很大程度上取决于单体结构。全氟丙烯酸酯类单体虽然具有很高的商业价值，但生产成本高昂且聚合难度大；主要的可商用产品包括2-位氟代和酯基上的全氟代聚合物。因此，2-氟丙烯酸甲酯成为含氟高分子光纤材料的关键单体，而合成此关键单体的重要中间体则是2-氟丙酸酯。

用途

2-氟丙烯酸甲酯在医药、材料工业中具有重要用途，它是合成多种有用化合物如医药品、涂料和半导体光刻胶材料的中间体。随着工业需求的增长，其产量逐年提高。

制备

如图所示，将1000毫升三口瓶中加入200.1克（1摩尔，理论产量）上步反应浓干产物，300毫升正戊烷，31.5克多聚甲醛（1.05摩尔），以及1.0克对苯二酚（克莱森钠盐质量的0.5%）。在25~30℃下控制温度反应10小时后停止。向反应液中加入300毫升水破坏，搅拌0.5小时后分液。有机相用水洗至中性后，进行常压蒸馏（30~36℃）以除去正戊烷，再通过减压蒸馏（30-40℃，P=-0.6MPa~—O.7MPa)得到无色液体2-氟丙烯酸甲酯47.5克。收率为42.4%，其中GC主含量为97.5577%。

反应信息

• 作为反应物：
  描述：

  2-氟丙烯酸甲酯 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 水 、 sodium sulfate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以70%的产率得到2-氟烯丙醇
  参考文献：
  名称：

  使用构象柔性手性超分子催化剂，具有异常内/外选择性的对映选择性Diels-Alder反应

  摘要：

  交换选择性：使用量身定制的催化剂会导致环戊二烯与不同丙烯醛的Diels-Alder反应异常的内/外选择性和高对映选择性（请参阅方案）。这些超分子催化剂在原位制备由手性二醇，芳基硼酸，和三（五氟苯基）硼烷，并且可以区分重新/ SI的亲二烯体的面以及所述内切/外切二烯的方法。

  DOI：

  10.1002/anie.201106497
• 作为产物：
  描述：

  2,3-Dichlor-2-fluor-propansaeuremethylester 在 硫酸 、 水 、 锌 作用下， 以52%的产率得到2-氟丙烯酸甲酯
  参考文献：
  名称：

  合成vonα-Fluoracrylsäure和Derivaten

  摘要：

  Three new routes to derivatives of alpha-fluoracrylic acid, including a laboratory synthesis and a large-scale method, are reported. The processes are (i) addition of elementary fluorine to acrylic esters and subsequent elimination of HF; (ii) addition of difluorocarbene to isopropenyl methyl ether, oxidation via ring opening and dehalogenation; and (iii) 'nitrofluorination' of 2,3-dichloropropene, hydrolysis and dechlorination.

  DOI：

  10.1016/s0022-1139(00)80116-5

文献信息

• [EN] ANTIESTROGENS FOR CANCER THERAPY<br/>[FR] ANTI-ŒSTROGÈNES DE THÉRAPIE DU CANCER DU SEIN
  申请人：UNIV ILLINOIS

  公开号：WO2018175965A1

  公开（公告）日：2018-09-27

  1, 1-Diarylmethylcycloalkanylidenes are antiestrogens having utility in the treatment of cancer, including recurrent breast cancer and estrogen receptor-positive, endocrine therapy-sensitive tumors or endocrine therapy resistant tumors.

  1,1-二芳基甲基环烷基亚甲基化合物是抗雌激素化合物，在治疗癌症中具有实用价值，包括复发性乳腺癌和雌激素受体阳性、内分泌治疗敏感性肿瘤或内分泌治疗耐药性肿瘤。
• Minimization of Back‐Electron Transfer Enables the Elusive sp ³ C−H Functionalization of Secondary Anilines
  作者：Huaibo Zhao、Daniele Leonori

  DOI：10.1002/anie.202100051

  日期：2021.3.29

  Anilines are some of the most used class of substrates for application in photoinduced electron transfer. N,N‐Dialkyl‐derivatives enable radical generation α to the N‐atom by oxidation followed by deprotonation. This approach is however elusive to monosubstituted anilines owing to fast back‐electron transfer (BET). Here we demonstrate that BET can be minimised by using photoredox catalysis in the presence

  苯胺是光诱导电子转移中最常用的一类底物。 N,N-二烷基衍生物能够通过氧化然后去质子化使 N 原子产生自由基 α。然而，由于快速反电子转移（BET），这种方法对于单取代苯胺来说难以捉摸。在这里，我们证明了在外源烷基胺存在的情况下使用光氧化还原催化可以最大限度地减少 BET。这种方法协同帮助苯胺 SET 氧化，然后加速随后的去质子化。通过这种方式，现在可以生成 α-苯胺烷基自由基，并且这些物质可以在一般意义上用于实现不同的 sp 3 C−H 官能化。
• α-Tetrasubstituted Aldehydes through Electronic and Strain-Controlled Branch-Selective Stereoselective Hydroformylation
  作者：Josephine Eshon、Floriana Foarta、Clark R. Landis、Jennifer M. Schomaker

  DOI：10.1021/acs.joc.8b01431

  日期：2018.9.7

  high conversions and yields of tetrasubstituted aldehydes (e.g., 13:1 regioselectivity, 85% ee, and <1% hydrogenation for 1-fluoromethyl acrylate). The scope also encompasses both acyclic 1,1′-disubstituted and trisubstituted, electron-poor alkenes as well as di- and trisubstituted alkenes composed of small rings with exocyclic and endocyclic unsaturation. For example, 1-methylene-β-lactam furnished

  加氢甲酰化利用二氢，一氧化碳和催化剂将烯烃转化为醛。这项工作将手性双二氮杂膦烷（BDP）和双膦酰氨基乙烷连接的铑络合物应用于各种烯烃的加氢甲酰化反应，以生产手性四取代的醛。带有吸电子取代基的1,1'-二取代丙烯酸酯在温和条件下（1摩尔％的催化剂/ BDP配体，150 psig气体，60°C）以高转化率和四取代醛（例如13：1区域选择性）收率进行加氢甲酰化，1-85％ee和小于1％的氢化反应（对于丙烯酸1-氟甲基丙烯酸酯）。该范围还涵盖无环的1,1'-二取代和三取代的贫电子烯烃，以及由具有环外和环内不饱和键的小环组成的二和三取代的烯烃。例如，1-亚甲基-β-内酰胺为四取代的醛提供了98％的选择性和高达83％的ee。值得注意的是，手性三取代双环亚甲基氮丙啶以> 50催化剂周转/小时的速率以> 99％的区域选择性和> 19：1的非对映选择性转化为四取代的醛。HRh（BDP）（CO）非催化反应的N
• [EN] IMMUNOPROTEASOME INHIBITORS<br/>[FR] INHIBITEURS D'IMMUNOPROTÉASOME
  申请人：PRINCIPIA BIOPHARMA INC

  公开号：WO2019099582A1

  公开（公告）日：2019-05-23

  Provided herein are compounds, such as a compound of Formula (I), or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

  本文提供了化合物，例如式（I）的化合物，或其药用可接受的盐，这些化合物是免疫蛋白酶体（如LMP2和LMP7）抑制剂。本文描述的化合物可用于治疗通过抑制免疫蛋白酶体可治疗的疾病。本文还提供了含有这些化合物的药物组合物和制备这些化合物的方法。
• Protected Chloroethyl and Chloropropyl Amines as Conformationally Unrestricted Annulating Reagents
  作者：Qing Shi、Mariah C. Meehan、Michael Galella、Hyunsoo Park、Purnima Khandelwal、John Hynes、T. G. Murali Dhar、David Marcoux

  DOI：10.1021/acs.orglett.7b03548

  日期：2018.1.19

  The purpose of this letter is to document the use of protected chloroethyl and chloropropyl amines as conformationally unrestricted ambiphilic reagents that undergo annulation reactions with Michael acceptors. This reaction is wide in scope and utilizes reagents that are commercially available, inexpensive, and stable. Furthermore, this reaction is easy to execute and proceeds rapidly.

  这封信的目的是证明使用受保护的氯乙基和氯丙基胺作为构象不受限制的双歧试剂，该试剂与迈克尔受体发生环化反应。该反应的范围很广，并且使用了可商购的，廉价的和稳定的试剂。此外，该反应易于进行并且迅速进行。