1-乙炔基-3-氟苯 | 2561-17-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-乙炔基-3-氟苯
• 中文别名: 3-氟苯乙炔
• 英文名称: 1-ethynyl-3-fluoro-benzene
• 英文别名: 3-fluorophenylacetylene；m-fluorophenylacetylene；(3-fluorophenyl)ethyne；meta-fluorophenylacetylene；1-fluoro-3-ethynylbenzene；1-ethynyl-3-fluorobenzene
• CAS: 2561-17-3
• 化学式: C₈H₅F
• 分子量: 120.126
• InChiKey: PTRUTZFCVFUTMW-UHFFFAOYSA-N

物化性质

• 沸点：
  138 °C (lit.)
• 密度：
  1.039 g/mL at 25 °C (lit.)
• 闪点：
  90 °F
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，未有已知危险发生。

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

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,R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 1993 3/PG 3
• 海关编码：
  2903999090
• 包装等级：
  III
• 危险类别：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H225,H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Fluorophenylacetylene
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H226: Flammable liquid and vapour
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluorophenylacetylene
CAS number: 2561-17-3

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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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H5F
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
UN Number: UN1993 Class: 3 Packing group: III
Proper shipping name: FLAMMABLE LIQUIDS, N.O.S. (3-Fluorophenylacetylene)

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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

3-氟苯乙炔是烃类衍生物，属于端炔。端炔的加成反应广泛应用于药物、农药和有机功能材料的合成中，这类反应之所以重要，是因为产物中含有一个炔键，可以进一步进行功能化，因此是一类重要的有机合成中间体。

用途

3-氟苯乙炔可用作医药合成中间体，是一种端炔。

反应信息

• 作为反应物：
  描述：

  1-乙炔基-3-氟苯 在 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 、 5,5'-二(三氟甲基)-2,2'-联吡啶 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 反应 8.0h， 以77%的产率得到3-氟苯乙醛
  参考文献：
  名称：

  炔烃常温抗Markovnikov水合反应的广谱催化剂

  摘要：

  抗马尔科夫尼科夫炔烃水合为醛的合成提供了有价值的途径。由5,5'-双（三氟甲基）-2,2'-联吡啶连接的半三明治钌络合物对于该转化非常有效。在2mol％金属的存在下，在环境温度下高产率地将多种官能化的脂族和芳族炔烃水合。

  DOI：

  10.1002/anie.201404320
• 作为产物：
  描述：

  3-氟苯乙烯 在 dipotassium peroxodisulfate 、 2,2,6,6-四甲基哌啶氧化物 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 25.0h， 生成 1-乙炔基-3-氟苯
  参考文献：
  名称：

  MOF 触发的亚纳米 Ag02 团簇和 Fe3+ 单原子的合成：异质化导致高效和协同的一锅催化反应

  摘要：

  金属有机骨架 (MOF) 通道内定义明确的 Fe 3+孤立单金属原子和 Ag 2亚纳米金属簇的组合首次通过单晶 X 射线衍射进行了报道和表征。所得杂化材料，分子式为[Ag 0 2 (Ag 0 ) 1.34 Fe III 0.66 ]@Na I 2 {Ni II 4 [Cu II 2 (Me 3 mpba) 2 ] 3 }·63H 2 O ( Fe 3+银0 2 @MOF)，能够在一锅中催化苯乙烯前所未有地直接转化为苯乙炔。特别是，Fe 3+ Ag 0 2 @MOF——可以很容易地以克规模获得——对苯乙烯与苯砜的无 TEMPO 氧化交叉偶联表现出优异的催化活性，以产生乙烯基砜，产率高达 >99 %，最终原位转化为相应的苯乙炔产物。这里展示的结果构成了一个典型的例子，说明在明确定义的固体催化剂中合成不同的金属物种，结合溶液中有机反应的真正金属催化剂的物种形成，允许设计一个新的具有挑战性的反应。

  DOI：

  10.1021/jacs.3c02155
• 作为试剂：
  描述：

  1-乙炔基-3-氟苯 、 3-氨基-2-溴-4,6-二甲基吡啶 在 1-乙炔基-3-氟苯 作用下， 以72的产率得到2-[2-(3-氟苯基)乙炔基]-4,6-二甲基吡啶-3-胺
  参考文献：
  名称：

  [EN] NOVEL AMINOPYRIDINE DERIVATIVES AS mGIuR5 ANTAGONISTS
  [FR] DERIVES NOUVEAUX D'AMINOPYRIDINE UTILES COMME ANTAGONISTES DE MGLUR5

  摘要：

  本发明涉及一种新型氨基吡啶衍生物，其化学式为(I)，其中R1为甲基，R4和氨基NR6R7，R5形成芳基炔基或杂芳基炔基基团。该化合物在预防或治疗中枢神经系统疾病以及其他受mGIuR5受体调节的疾病方面具有用途。

  公开号：

  WO2004078728A1

文献信息

• Copper-Catalyzed One-Pot Synthesis of Substituted Benzimidazoles
  作者：Hongwei Jin、Xiaoliang Xu、Jianrong Gao、Jianhua Zhong、Yanguang Wang

  DOI：10.1002/adsc.200900706

  日期：2010.2.15

  A copper-catalyzed one-pot synthesis of functionalized benzimidazoles has been developed. The procedure combines the copper-catalyzed three-component cascade reaction of sulfonyl azides, alkynes and 2-bromoaniline and the copper-catalyzed intramolecular N-arylation of sulfonamides in one sequence, which afforded the products in moderate to good yields.

  已经开发了铜催化的一锅合成功能化的苯并咪唑。该程序将铜催化的磺酰叠氮化物，炔烃和2-溴苯胺的三组分级联反应与铜催化的磺酰胺的分子内N-芳基化反应结合在一起，从而以中等到良好的产率提供了产物。
• Synthesis of 3-Pyrrolin-2-ones by Rhodium-Catalyzed Transannulation of 1-Sulfonyl-1,2,3-triazole with Ketene Silyl Acetal
  作者：Rui-Qiao Ran、Jun He、Shi-Dong Xiu、Kai-Bing Wang、Chuan-Ying Li

  DOI：10.1021/ol501514b

  日期：2014.7.18

  α-Imino rhodium carbenoids generated from 1-sulfonyl 1,2,3-triazole were applied to the 3 + 2 cycloaddition with ketene silyl acetal, offering a novel and straightforward synthesis of biologically interesting compound 3-pyrrolin-2-one with broad substrate scope.

  由1-磺酰基1,2,3-三唑生成的α-氨基铑类胡萝卜素与乙烯酮甲硅烷基缩醛应用于3 + 2环加成反应，提供了一种新颖而直接的合成方法，可合成具有广泛底物的生物学上令人感兴趣的化合物3-吡咯啉-2-酮范围。
• Rhodium-Catalyzed Denitrogenative Transannulation of <i>N</i>-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused <i>N</i>-Glycosides
  作者：Jingjing Bi、Qiang Tan、Hao Wu、Qingfeng Liu、Guisheng Zhang

  DOI：10.1021/acs.orglett.1c02141

  日期：2021.8.20

  with exclusive regioselectivity and stereoselectivity. Functional application of such a resultant product by oxidative addition and epoxidation is also explored. Notably, the treatment of a pyrroline-fused N-glycoside (3a) with TMSOTf efficiently leads to an interesting unexpected C-nucleoside (9) via a TMSOTf-inducing ring opening/acetyl migration/ring closing reaction sequence.

  这里描述的是通过铑催化的N-磺酰基-1,2,3-三唑与聚糖的脱氮环化反应选择性合成 2,3-二氢吡咯稠合的N-糖苷。一系列吡咯啉稠合的N-糖苷以中等至极好的收率提供，具有独特的区域选择性和立体选择性。还探索了这种通过氧化加成和环氧化得到的产物的功能应用。值得注意的是，通过 TMSOTf 诱导的开环/乙酰基迁移/闭环反应序列，用 TMSOTf处理吡咯啉稠合的N-糖苷（3a）有效地导致有趣的意外C-核苷（9）。
• Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids
  作者：Wei Hou、Zhi Luo、Guanjun Zhang、Danhui Cao、Di Li、Haoqiang Ruan、Benfang Helen Ruan、Lin Su、Hongtao Xu

  DOI：10.1016/j.ejmech.2017.07.049

  日期：2017.9

  exhibited obviously improved IC50 values ranging from 0.7 to 1.2 μM against a panel of tested cancer cells, but also showed very weak cytotoxicity on normal cells. Preliminary mechanism studies indicated that compound 24 could induce apoptosis in MDA-MB-231 cells and was worth developing into a novel natural product-like anticancer lead by proper structure modification.

  已经建立了一种简洁有效的合成方法，以中到高收率容易地获得一系列新颖的C-14 1,2,3-三唑系绳的脱氢松香酸衍生物。体外抗增殖活性评估表明，大多数杂种在低微摩尔至亚微摩尔IC 50值的多种癌细胞系中均表现出有效的抑制活性。进一步的研究表明，一些这些类似物如20，21，和24也针对在低浓度以剂量依赖性方式耐阿霉素MCF-7克隆有效。值得注意的是，最有效的化合物24具有3-（叔-丁氧基羰基氨基）苯基取代的三唑部分不仅对一组经过测试的癌细胞表现出明显改善的IC 50值，范围为0.7至1.2μM，而且对正常细胞的毒性也很弱。初步的机理研究表明，化合物24可以诱导MDA-MB-231细胞凋亡，通过适当的结构修饰，值得发展为新型的天然产物样抗癌药。
• Oxone^®/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro- and β-Iodonitro-Substituted Alkenes
  作者：Sornsiri Hlekhlai、Natthapol Samakkanad、Tassaporn Sawangphon、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram、Thaworn Jaipetch、Chutima Kuhakarn

  DOI：10.1002/ejoc.201402750

  日期：2014.11

  Oxone® (2KHSO5·KHSO4·K2SO4) was used to promote the nitration of alkenes and alkynes with sodium nitrite (NaNO2) and potassium iodide (KI). This stable, easy-to-handle, and environmentally benign oxidant was used under mild conditions (room temperature) and provided short reaction times. Styrene derivatives that did not contain electron-donating groups afforded the corresponding nitro alkenes in moderate

  Oxone® (2KHSO5·KHSO4·K2SO4) 用于促进烯烃和炔烃与亚硝酸钠 (NaNO2) 和碘化钾 (KI) 的硝化反应。这种稳定、易于处理且对环境无害的氧化剂在温和条件（室温）下使用，反应时间短。不含给电子基团的苯乙烯衍生物以中等至良好的产率提供相应的硝基烯烃，而脂肪族烯烃和缺电子烯烃不是很好的底物。在类似的反应条件下，芳基炔烃生成 β-碘硝基烯烃。