2-乙炔基-α,α,α-三氟甲苯 | 704-41-6

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟甲苯系列
• 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: 2-乙炔基-α,α,α-三氟甲苯
• 中文别名: 2-(三氟甲基)苯基乙稀；2-乙炔基-ALPHAALPHAALPHA-三氟甲苯；2-乙炔基三氟甲苯；2-乙炔基-ALPHA ALPHA ALPHA-三氟甲苯
• 英文名称: 1-ethynyl-2-(trifluoromethyl)benzene
• 英文别名: 2-(trifluoromethyl)phenylacetylene；2-ethynyl-α,α,α-trifluorotoluene；o-trifluoromethylphenylacetylene；o-(trifluoromethyl)ethynylbenzene；1-trifluoromethyl-2-ethynylbenzene；[2-(trifluoromethyl)phenyl]ethyne；2-trifluoro phenyl acetylene
• CAS: 704-41-6
• 化学式: C₉H₅F₃
• 分子量: 170.134
• InChiKey: OOZKONVIIMFOKW-UHFFFAOYSA-N

物化性质

• 沸点：
  45 °C8 mm Hg(lit.)
• 密度：
  1.222 g/mL at 25 °C(lit.)
• 闪点：
  78 °F
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 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：
  S26,S36/37/39
• 危险类别码：
  R10
• WGK Germany：
  3
• 海关编码：
  2903999090
• 危险品运输编号：
  UN 1993 3/PG 3
• 储存条件：
  常温、避光、存于通风干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
: 2-Ethynyl-α,α,α-trifluorotoluene
Product name

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Flammable liquids (Category 3)
According to European Directive 67/548/EEC as amended.
Flammable.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H226 Flammable liquid and vapour.
Precautionary statement(s) none
Hazard symbol(s) none
R-phrase(s)
R10 Flammable.
S-phrase(s) none
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Synonyms : 1-Ethynyl-2-trifluoromethylbenzene
Formula : C9H5F3
Molecular Weight : 170,13 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
2-Ethynyl-α ,α ,α-trifluorotoluene
704-41-6 - - Flam. Liq. 3; H226 -
R10
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
Flush eyes with water as a precaution.
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
Avoid breathing vapors, mist or gas. Remove all sources of ignition. Beware of vapours accumulating to form
explosive concentrations. Vapours can accumulate in low areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains.
Methods and materials for containment and cleaning up
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place
in container for disposal according to local regulations (see section 13).

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
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
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. Store in cool place.

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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
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without
touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves
after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Eye protection
Face shield and safety glasses Use equipment for eye protection tested and approved under appropriate
government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
impervious clothing, Flame retardant antistatic protective clothing, The type of protective equipment must
be selected according to the concentration and amount of the dangerous substance at the specific
workplace.
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 colourless
Safety data
pH no data available
Melting point no data available
Boiling point 45 °C at 11 hPa - lit.
Flash point 25 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 1,222 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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not 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. Offer surplus and non-recyclable solutions to a licensed disposal company.
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. (2-Ethynyl-α ,α ,α-trifluorotoluene)
IMDG
UN-Number: 1993 Class: 3 Packing group: III EMS-No: F-E, S-E
Proper shipping name: FLAMMABLE LIQUID, N.O.S. (2-Ethynyl-α ,α ,α-trifluorotoluene)
Marine pollutant: No
IATA
UN-Number: 1993 Class: 3 Packing group: III
Proper shipping name: Flammable liquid, n.o.s. (2-Ethynyl-α ,α ,α-trifluorotoluene)

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Flam. Liq. Flammable liquids
H226 Flammable liquid and vapour.
R10 Flammable.
Further information
Copyright 2010 Co. License granted to make unlimited paper copies for internal use only.
The above information is believed to be correct but does not purport to be all inclusive and shall be used
only as a guide. The information in this document is based on the present state of our knowledge and is
applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee
of the properties of the product. Co., shall not be held liable for any damage resulting from
handling or from contact with the above product. See reverse side of invoice or packing slip for additional
terms and conditions of sale.

制备方法与用途

用途

2-乙炔基-α,α,α-三氟甲苯用作研究用化合物。

反应信息

• 作为反应物：
  描述：

  2-乙炔基-α,α,α-三氟甲苯 在 氢气 作用下， 以 甲苯 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以90%的产率得到2-(三氟甲基)苯乙烯
  参考文献：
  名称：

  双金属Cu-Pd纳米粒子促进的末端炔烃选择性半加氢

  摘要：

  摘要 在温和的反应条件下（H 2气球，110°C），由负载在介孔结构二氧化硅（MCM）上的铜和钯纳米粒子组成的双金属纳米催化剂（重量比为5：1）促进了末端炔烃的选择性半氢化反应-48）。事实证明，Cu-PdNPS @ MCM-48催化剂对炔烃官能团具有高度化学选择性，可以很容易地从商业原料中制备，并且可以在热处理后在H 2气氛下还原后进行回收和再利用。 在温和的反应条件下（H 2气球，110°C），由负载在介孔结构二氧化硅（MCM）上的铜和钯纳米粒子组成的双金属纳米催化剂（重量比为5：1）促进了末端炔烃的选择性半氢化反应-48）。事实证明，Cu-PdNPS @ MCM-48催化剂对炔烃官能团具有高度化学选择性，可以很容易地从商业原料中制备，并且可以在热处理后在H 2气氛下还原后进行回收和再利用。

  DOI：

  10.1055/s-0037-1610318
• 作为产物：
  描述：

  邻溴三氟甲苯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 2.4h， 生成 2-乙炔基-α,α,α-三氟甲苯
  参考文献：
  名称：

  Preparation of Fluorine-Containing Phenylacetylenes by the Method of Introduction of the Ethynyl Group Using 1,1-Dichloro-2,2-difluoroethene

  摘要：

  具有氟或三氟甲基取代基的苯乙炔（ArC≡CH）（邻、间、对位氟；邻、间、对位CF3；2,4-、2,5-、2,6-、3,5-双(CF3)2）已通过溴苯（ArBr）和苯（ArH）与1,1-二氯-2,2-二氟乙烯（1）的两步路线制备得到：ArLi或ArMgBr→ArCF=CCl2→ArC≡CLi。在-70°C下仔细处理时，邻氟苯基锂以良好产率生成邻FC6H4CF=CCl2，同时伴随苯炔衍生的产物，如邻(邻FC6H4)C6H4CF=CCl2。在0°C下对间双(三氟甲基)苯进行9小时（24小时）的锂化，随后用溴处理，分别以35（38）%、31（36）%和8（6）%的产率得到1-溴-2,4-、2,6-和3,5-双(三氟甲基)苯。

  DOI：

  10.1246/bcsj.61.1625
• 作为试剂：
  描述：

  甲醇 、 异戊醛 在 2-乙炔基-α,α,α-三氟甲苯 作用下， 反应 24.0h， 生成 1,1-二甲氧基-3-甲基丁烷
  参考文献：
  名称：

  末端炔烃作为均相催化剂进行缩醛化和酯化的新应用

  摘要：

  在这项研究中，进行了理论研究，重点研究了可能使用低分子量的单端和多功能末端炔烃作为两个反应的催化剂，已知这两个反应通常是酸催化的-缩醛化和酯化。多功能末端炔烃[（二乙炔基苯，三乙炔基苯和四（4-乙炔基苯基）]甲烷]的活性明显高于单官能团（环丙基乙炔，苯基乙炔，3-环己基丙-1-炔，1-乙炔基-2-氟苯，1-乙炔基） -4-氟苯，4-乙炔基甲苯，4-叔-丁基苯基乙炔和2-乙炔基-α，α，α-三氟甲苯），这一事实可以部分由每个炔烃分子中较高的乙炔基基团来解释。我们证实，低分子量炔烃中的乙炔基末端可以成功地充当缩醛化和酯化的酸催化中心。

  DOI：

  10.1016/j.tet.2019.04.013

文献信息

• Cyclopenta[<i>b</i>]annulation of Heteroarenes by Organocatalytic γ′[C(sp³)−H] Functionalization of Ynones
  作者：Moluguri Raghu、Jagdeep Grover、S. S. V. Ramasastry

  DOI：10.1002/chem.201604562

  日期：2016.12.19

  to the designed ynones triggers γ′[C(sp3)−H] functionalization, leading to the formation of heteroaryl‐based ortho‐quinodimethane (oQDM) intermediates that undergo carbocyclization to provide cyclopentannulated heteroarenes in good yields and excellent stereoselectivities. Deuterium‐labeling experiments substantiated the proposed reaction mechanism as well as the speculated epimerization.

  对于环戊二烯并[一种新方法b通过金属和无定向基团的γ'[C（SP杂芳烃的]环3）-H]官能化和ynones的分子内加氢烷基化得到了发展。在史无前例的事件中，将有机膦亲核加成到设计的炔酮上会触发γ'[C（sp 3）-H]功能化，导致形成杂芳基邻喹啉二甲烷（oQDM）中间体，该中间体经过碳环化作用以提供环戊环杂芳烃具有良好的收率和出色的立体选择性。氘标记实验证实了拟议的反应机理以及推测的差向异构。
• Selective Syntheses of <i>Z</i>-Alkenes via Photocatalyzed Decarboxylative Coupling of <i>N</i>-Hydroxyphthalimide Esters with Terminal Arylalkynes
  作者：Guo-Li Dai、Shu-Zhen Lai、Zhuangzhu Luo、Zhen-Yu Tang

  DOI：10.1021/acs.orglett.9b00558

  日期：2019.4.5

  A novel, efficient Z-alkene synthesis via photocatalyzed decarboxylative couplings between terminal aryl alkynes and alkyl N-hydroxyphthalimide (NHPI) esters, which are derived from aliphatic carboxylic acids, is described. A wide range of primary, secondary, and tertiary carboxylates as well as α-amino acid and α-oxyacid-derived esters were employed as suitable substrates. The mild reaction conditions

  描述了通过末端芳基炔烃和衍生自脂族羧酸的烷基N-羟基邻苯二甲酰亚胺（NHPI）酯之间的光催化脱羧偶联的新颖，有效的Z-烯烃合成。各种各样的伯，仲和叔羧酸盐以及α-氨基酸和α-含氧酸衍生的酯被用作合适的底物。温和的反应条件，广泛的底物范围，官能团耐受性和操作简便性使得该脱羧偶联反应成为有机合成中的重要方法。
• Photoredox synthesis of functionalized quinazolines <i>via</i> copper-catalyzed aerobic oxidative C_sp2–H annulation of amidines with terminal alkynes
  作者：Vaibhav Pramod Charpe、Ayyakkannu Ragupathi、Arunachalam Sagadevan、Kuo Chu Hwang

  DOI：10.1039/d1gc01493e

  日期：——

  We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2–H annulation (Friedel–Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copper(I)-phenylacetylide catalyzed photo-oxidative Csp2–H annulation of amidines at RT, which is very challenging and complementary to the conventional transition

  我们开发了一种可见光诱导的光氧化还原铜催化氧化 C sp 2 -H 环化（Friedel-Crafts 型环化）与末端炔烃在室温下合成功能化喹唑啉。我们报告了铜（I）-苯乙炔在室温下催化的脒的光氧化 C sp 2 -H 环化，这是非常具有挑战性的，并且与传统的过渡金属催化的热环化反应互补。我们已经通过合成抗癌化合物证明了这种方法的应用。此外，绿色化学指标（E-factor 比报道的热方法好 1.9 倍）和 Eco-Scale（尺度 55.4，显示可接受的合成）评估表明该方法是生态友好和环境可行的。
• [EN] ANTIBACTERIAL BENZOIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDES BENZOIQUES ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2004018428A1

  公开（公告）日：2004-03-04

  The invention provides antimicrobial agents and methods of using the agents for sterilization, sanitation, antisepsis, disinfection, and treatment of infections in mammals.

  这项发明提供了抗菌剂和使用这些剂进行哺乳动物的消毒、卫生、防腐、消毒和治疗感染的方法。
• Amphipathic monolith-supported palladium catalysts for chemoselective hydrogenation and cross-coupling reactions
  作者：Yasunari Monguchi、Fumika Wakayama、Shun Ueda、Ryo Ito、Hitoshi Takada、Hiroshi Inoue、Akira Nakamura、Yoshinari Sawama、Hironao Sajiki

  DOI：10.1039/c6ra24769e

  日期：——

  functions (sulfonic acid moieties) (Pd/CM) was developed. It was used as a catalyst for hydrogenation and ligand-free cross-coupling reactions, such as the Suzuki–Miyaura, Mizoroki–Heck, and copper- and amine-free Sonogashira-type reactions, together with a palladium catalyst supported on monolithic polymer (Pd/AM) bearing basic anion exchange functions (ammonium salt moieties), which has been in practical

  开发了固定在具有强酸性阳离子交换功能（磺酸基团）（Pd / CM）的两亲且整体的聚苯乙烯-二乙烯基苯聚合物上的钯催化剂。它用作加氢和无配体交叉偶联反应的催化剂，例如铃木-宫浦，Mizoroki-Heck以及无铜和胺的Sonogashira型反应，以及负载在整体聚合物上的钯催化剂（ Pd / AM）具有基本的阴离子交换功能（铵盐部分），在超纯水生产过程中已被实际用于分解作为副产物产生的过氧化氢。尽管Pd / CM作为氢化催化剂具有很高的活性，并且可以还原各种可还原的官能团，但Pd / AM的使用却导致了独特的化学选择性氢化。N -Cbz基团可以顺利加氢裂化。使用任何一种催化剂，交叉偶联反应均很容易进行。在Sonogashira型反应中从未观察到从Pd / CM浸出到反应介质中的钯，由于钯种类与炔烃具有良好的亲和力，其他钯负载的多相催化剂很难做到这一点。