1-乙炔基-3,5-二氟苯 | 151361-87-4

• 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-3,5-二氟苯
• 中文别名: 1-乙炔-3,5-二氟苯
• 英文名称: 1-ethynyl-3,5-difluorobenzene
• 英文别名: 3,5-difluorophenylacetylene
• CAS: 151361-87-4
• 化学式: C₈H₄F₂
• mdl: MFCD04039982
• 分子量: 138.117
• InChiKey: OTDGZDMGSFBZLI-UHFFFAOYSA-N

物化性质

• 沸点：
  123-124 °C (lit.)
• 密度：
  1.163 g/mL at 25 °C (lit.)
• 闪点：
  78 °F
• 稳定性/保质期：
  在常温常压下稳定，应避免与强氧化剂接触，并远离热源、火花和火焰。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 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：
  2

安全信息

• 危险等级：
  3
• 危险品标志：
  Xi
• 安全说明：
  S16
• 危险类别码：
  R10
• WGK Germany：
  3
• 危险品运输编号：
  UN 1993 3/PG 3
• 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：
  密封存储于阴凉、干燥的库房。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 1-Ethynyl-3,5-difluorobenzene

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Flammable liquids (Category 3)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
According to European Directive 67/548/EEC as amended.
Flammable. Irritating to eyes, respiratory system and skin.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
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.
Hazard symbol(s)
Xi Irritant
R-phrase(s)
R10 Flammable.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S16 Keep away from sources of ignition - No smoking.
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C8H4F2
Molecular Weight : 138,11 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
1-Ethynyl-3,5-difluorobenzene
151361-87-4 - - Flam. Liq. 3; Skin Irrit. 2; Eye -
Irrit. 2; STOT SE 3; H226,
H315, H319, H335
Xi, R10 - R36/37/38
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. FIRST AID MEASURES
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing give artificial respiration Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Do NOT induce vomiting. Never give anything by mouth to an unconscious person. Rinse mouth with water.
Consult a physician.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires,
apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spray;
solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Beware of vapours accumulating to form explosive concentrations. Vapours
can accumulate in low areas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with non-combustible absorbent material, (e.g. sand, earth, diatomaceous
earth, vermiculite) and place in container for disposal according to local / national regulations (see section
13). Keep in suitable, closed containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid inhalation of vapour or mist.
Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic
charge.
Conditions for safe storage
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with
multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to
engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Hand protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Handle with gloves.
Eye protection
Face shield and safety glasses
Skin and body protection
Choose body protection according to the amount and concentration of the dangerous substance at the
work place.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Colour light yellow
Safety data
pH no data available
Melting point no data available
Boiling point 123 - 124 °C - lit.
Flash point 33 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,163 g/cm3 at 25 °C
Water solubility no data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
Heat, flames and sparks.
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides, Hydrogen fluoride

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: no data available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as
this material is highly flammable. This combustible material may be burned in a chemical incinerator
equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
ADR/RID
UN-Number: 1993 Class: 3 Packing group: III
Proper shipping name: FLAMMABLE LIQUID, N.O.S. (1-Ethynyl-3,5-difluorobenzene)
IMDG
UN-Number: 1993 Class: 3 Packing group: III EMS-No: F-E, S-E
Proper shipping name: FLAMMABLE LIQUID, N.O.S. (1-Ethynyl-3,5-difluorobenzene)
Marine pollutant: No
IATA
UN-Number: 1993 Class: 3 Packing group: III
Proper shipping name: Flammable liquid, n.o.s. (1-Ethynyl-3,5-difluorobenzene)

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

1-乙炔基-3,5-二氟苯用作研究用化合物。

反应信息

• 作为反应物：
  描述：

  1-乙炔基-3,5-二氟苯 在 4-二甲氨基吡啶 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以58%的产率得到3,5-difluoro-1-(iodoethynyl)benzene
  参考文献：
  名称：

  Serendipity and the Search for Short N---I Halogen Bonds

  摘要：

  The X-ray structure of the complex formed between N,N-dimethylaminopyridine (DMAP) and 1,2-bis(iodoethynyl)benzene is reported. The N---I halogen bond lengths are 2.654 and 2.662 angstrom, approximately 7596 of the sum of the van der Waals radii. On the basis of literature precedent and electrostatic potential calculations, a series of fluorosubstituted iodophenylacetylenes were prepared and individually complexed with dimethylaminopyridine in a search for shorter halogen bonds. A N---I halogen bond distance of 2.680 angstrom was observed in the DMAP complex with 3,5-difluoro(iodoethynyl)benzene, and halogen bond distances of 2.622, 2.676, 2.700, and 2.705 angstrom were observed in the complex of 4-fluoro(iodoethynyl)benzene with DMAP. These N---I bond distances range from 74.3 to 76.6% of the sum of the van der Waals radii.

  DOI：

  10.1021/cg401243h
• 作为产物：
  描述：

  1-溴-3,5-二氟苯 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 1-乙炔基-3,5-二氟苯
  参考文献：
  名称：

  Novel 3-phenylprop-2-ynylamines as inhibitors of mammalian squalene epoxidaseElectronic supplementary information (ESI) available: Proton NMR spectra for the intermediate piperidines 56–60 and acetylenes 63-81 and 85,86. See http://www.rsc.org/suppdata/ob/b2/b209165h/

  摘要：

  报道了一种新型3-苯基丙-2-炔基胺系列化合物的合成，这些化合物是选择性哺乳动物角鲨烯环氧化酶抑制剂。构效关系研究表明，化合物19，即1-[3-(3,5-二氯苯基)丙-2-炔基]-3-甲基哌啶盐酸盐，对大鼠肝脏角鲨烯环氧化酶的IC50值为2.8 ± 0.6 µM。化合物19对23株真菌角鲨烯环氧化酶未显示出活性。

  DOI：

  10.1039/b209165h

文献信息

• Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluoride (SASF) Hubs
  作者：Christopher J. Smedley、Gencheng Li、Andrew S. Barrow、Timothy L. Gialelis、Marie‐Claire Giel、Alessandra Ottonello、Yunfei Cheng、Seiya Kitamura、Dennis W. Wolan、K. Barry Sharpless、John E. Moses

  DOI：10.1002/anie.202003219

  日期：2020.7.20

  Diversity Oriented Clicking (DOC) is a unified click‐approach for the modular synthesis of lead‐like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease” , by combining classic C−C π‐bond click chemistry with recent developments in connective SuFEx‐technologies. We showcase 2‐Substituted‐Alkynyl‐1‐Sulfonyl Fluorides

  面向多样性的点击 (DOC) 是一种统一的点击方法，用于通过应用广泛的点击转换家族来模块化合成类先导结构。DOC 从实现“轻松实现多样性”的概念演变而来，将经典的 C−C π 键点击化学与连接性 SuFEx 技术的最新发展相结合。我们展示了 2-取代的- A炔基-1-磺酰基F氟化物（SASFs）作为一类新的连接枢纽，与多种点击环加成过程相结合。通过具有一系列偶极子和环状二烯的 SASF 的选择性 DOC，我们以最少的合成步骤报告了 173 种独特功能分子的多样化点击库。SuFExable 库包含 10 个离散的杂环核心结构，这些核心结构源自 1,3- 和 1,5- 偶极子；而与环状二烯的反应会产生几种三维双环 Diels-Alder 加合物。通过对 96 孔板中的磺酰氟侧基进行 SuFEx 点击衍生化，可以通过后期修饰将文库增加到 278 种离散化合物——证明了 DOC 方法在快速合成不同功能结构方面的多功能性。
• Cu-Catalyzed Photoredox Chlorosulfonation of Alkenes and Alkynes
  作者：Murat Alkan-Zambada、Xile Hu

  DOI：10.1021/acs.joc.9b00238

  日期：2019.4.5

  Visible-light photoredox chlorosulfonation of alkenes and alkynes is achieved using a Cu photocatalyst. The reactions occur under mild conditions, have broad scope, and have high functional group tolerance.

  使用铜光催化剂实现烯烃和炔烃的可见光光氧化还原氯磺化。反应在温和的条件下发生，范围广，对官能团的耐受性高。
• [EN] FUSED HETEROCYCLIC COMPOUNDS AS S1P MODULATORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS À TITRE DE MODULATEURS DE S1P
  申请人：ABBVIE INC

  公开号：WO2017036978A1

  公开（公告）日：2017-03-09

  The invention relates to heterocyclic compounds as S1P modulators, pharmaceutical compositions comprising such compounds, and uses thereof in the treatment, alleviation or prevention of diseases or disorders mediated by an S1P receptor.

  这项发明涉及杂环化合物作为S1P调节剂，包括这种化合物的药物组合物，以及在治疗、缓解或预防由S1P受体介导的疾病或紊乱中的用途。
• [EN] PYRIDAZINONE COMPOUNDS AND THEIR USE AS DAAO INHIBITORS<br/>[FR] COMPOSÉS DE PYRIDAZINONE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA DAAO
  申请人：TAKEDA PHARMACEUTICAL

  公开号：WO2013027000A1

  公开（公告）日：2013-02-28

  The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1 and R2 are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式（I）的化合物及其药用盐，其中R1和R2如规范中定义，其制备方法，含有它们的药物组合物以及它们在治疗中的用途。
• CARBON LINKED MODULATORS OF gamma-SECRETASE
  申请人：HO Chih Yung

  公开号：US20090105288A1

  公开（公告）日：2009-04-23

  The present invention relates to compounds of Formula I as shown below, wherein the definitions of A, X, R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are provided in the specification. Compounds of Formula I are useful for the treatment of diseases associated with γ-secretase activity, including Alzheimer's disease.

  本发明涉及如下所示的公式I的化合物，其中规定了A、X、R1、R3、R4、R5、R6、R7、R8和R9的定义。公式I的化合物可用于治疗与γ-分泌酶活性相关的疾病，包括阿尔茨海默病。