4-叔-丁基苯基乙炔 | 772-38-3

• 物质功能分类: 化学试剂 - 有机试剂 - 炔烃
• 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: 4-叔-丁基苯基乙炔
• 中文别名: 4-叔丁基苯基乙炔
• 英文名称: 4-tert-Butylphenylacetylene
• 英文别名: 4-tert-butylphenylethyne；1-(tert-butyl)-4-ethynylbenzene；p-tert-butylphenylacetylene；4-(Tert-butyl)phenylacetylene；1-tert-butyl-4-ethynylbenzene
• CAS: 772-38-3
• 化学式: C₁₂H₁₄
• 分子量: 158.243
• InChiKey: ZSYQVVKVKBVHIL-UHFFFAOYSA-N

物化性质

• 沸点：
  70 °C2 mm Hg(lit.)
• 密度：
  0.877 g/mL at 25 °C(lit.)
• 闪点：
  180 °F
• 溶解度：
  氯仿（微溶）、己烷（微溶）
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  9
• 危险品标志：
  Xi,N
• 安全说明：
  S36/37,S60,S61
• 危险类别码：
  R50/53
• WGK Germany：
  3
• 海关编码：
  2902909090
• 危险品运输编号：
  UN 3082 9/PG 3
• 危险标志：
  GHS07,GHS09
• 危险性描述：
  H319,H410
• 危险性防范说明：
  P273,P305 + P351 + P338,P501
• 包装等级：
  III
• 危险类别：
  9
• 储存条件：
  请将容器密封保存，并储存在阴凉、干燥的地方。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 4-tert-Butylphenylacetylene

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Eye irritation (Category 2)
Acute aquatic toxicity (Category 1)
Chronic aquatic toxicity (Category 1)
According to European Directive 67/548/EEC as amended.
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H319 Causes serious eye irritation.
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
P501 Dispose of contents/container to an approved waste disposal plant.
Hazard symbol(s)
N Dangerous for the environment
R-phrase(s)
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S36/37 Wear suitable protective clothing and gloves.
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety data
sheets.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C12H14
Molecular Weight : 158,24 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
4-tert-Butylphenylacetylene
772-38-3 - - Eye Irrit. 2; Aquatic Acute 1; -
Aquatic Chronic 1; H319,
H410
N, R50/53
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. FIRST AID MEASURES
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
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

---

Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Keep in suitable, closed containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
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
Safety glasses with side-shields conforming to EN166
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 colourless
Safety data
pH no data available
Melting point no data available
Boiling point 70 °C at 3 hPa - lit.
Flash point 82,2 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 0,877 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 4,394
n-octanol/water

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides

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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
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.
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
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.

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Section 13. DISPOSAL CONSIDERATIONS
Product
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: 3082 Class: 9 Packing group: III
Proper shipping name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (4-tert-
Butylphenylacetylene)
IMDG
UN-Number: 3082 Class: 9 Packing group: III EMS-No: F-A, S-F
Proper shipping name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (4-tert-
Butylphenylacetylene)
Marine pollutant: No
IATA
UN-Number: 3082 Class: 9 Packing group: III
Proper shipping name: Environmentally hazardous substance, liquid, n.o.s. (4-tert-Butylphenylacetylene)

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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
Aquatic Acute Acute aquatic toxicity
Aquatic Chronic Chronic aquatic toxicity
Eye Irrit. Eye irritation
H319 Causes serious eye irritation.
H410 Very toxic to aquatic life with long lasting effects.
N Dangerous for the environment
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
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

4-叔丁基苯基乙炔主要用于作为研究用化合物。

反应信息

• 作为反应物：
  描述：

  4-叔-丁基苯基乙炔 在 吡啶 、 macroporous carbonate resin 、 zinc(II) chloride 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 23.25h， 生成 Carbonic acid (2R,3S,6S)-6-(4-tert-butyl-phenylethynyl)-2-ethoxycarbonyloxymethyl-3,6-dihydro-2H-pyran-3-yl ester ethyl ester
  参考文献：
  名称：

  通过糖基支架的环收缩探索骨骼多样性。

  摘要：

  芳基醚C-糖苷支架已由C-糖基化，然后由Pd（0）介导的苯酚进行烯丙基取代，由三-O-乙酰基-D-葡糖醛制备。使芳基醚经历[3,3]-σ重排以产生3-吡喃基-酚或Au（III）介导的环收缩以产生高度取代的四氢呋喃。[结构：见文字]

  DOI：

  10.1021/ol0618252
• 作为产物：
  描述：

  2-(4-叔丁基苯)乙醇 在 硫酰氟 、 potassium carbonate 、 二甲基亚砜 、 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 4-叔-丁基苯基乙炔
  参考文献：
  名称：

  SO2F2 介导的氧化脱氢和醇脱水生成炔

  摘要：

  通过 SO2F2 促进的脱水和脱氢过程，以高产率（超过 40 个实例，高达 95% 的产率）实现了从廉价、丰富的醇直接合成炔烃。sp3-sp3 (CC) 键向 sp-sp (C≡C) 键的这种直接转变只需要在温和条件下廉价且容易获得的试剂（无过渡金属）。粗炔烃足够不含杂质，可以直接用于进一步的转化，如区域选择性 Huisgen 炔烃 - 叠氮化物与 PhN3 环加成反应所示，得到 1,4-取代的 1,2,3-四唑（16 个例子，高达 92%产率）和 Sonogashira 偶联（10 个例子，产率高达 77%）。

  DOI：

  10.1021/jacs.8b10069
• 作为试剂：
  描述：

  3,3-二甲基丁胺 在 4-叔-丁基苯基乙炔 、 iron(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以125 mg的产率得到
  参考文献：
  名称：

  Syntheses and characterizations of α-iminopyridine compounds (alkylNCHpy)2Fe(L/Xn), and an assessment of redox non-innocence

  摘要：

  Treatment of cis-(Me3P)(4)FeMe2 with two equiv (neo)PeN=CH(2-py) afforded {kappa-N,N'-(neo)PeN=CH(2-pyridy1))(2)FeMe2 (2-P). Reductions of FeCl2 with Na/Hg in the presence of (neo)PeN=CH(2-pyridyl) or (neo)HexN=CH(2-pyridyl) and L (H2C=CHCO2Me, PhCCPh, PMe3) gave tentative evidence of [kappa-N,N'-(neo)PeN=CH(2-pyridy1)}(2)Fe(H2C=CHCO2Me) (2-P), but (x-N,N'-(neo)PeN=CH(2-pyridyI)}(2)Fe(PhCCPh) (5-P), (kappa-N,N'-neoHexN=CH(2-pyridy1)}(2)Fe(PhCCPh) (5-H), and {kappa-N,N'-(neo)HexN=CH(2-pyridy1))(2-)Fe(PMe)}(2-) (6-H) were all isolated in good yield. Phosphine complex 6-H could be alkylated with CH3I or CH3OTf to afford {kappa-N,N'-(neo)HexN=CH(2-pyridyl)}(2-)Fe(PMe3)Me]I-+(-) (7-H-I) or {kappa-N,N'-(neo)HexN=CH(2-pyridyl)}(2-)Fe(PMe3)Me]I-+(-) OTf- (7-H-OTf) center dot [{kappa-N,N'-RN=CH(2-pyridyl)}(3-)Fe][OTf](2) (R = (neo)Pe, 8-P-OTf; (neo-)Hex, 8-H-OTf) omplexes were also prepared from Fe(OTO)(2) in order to identify potential byproducts in certain reactions. Compounds 2-P and 7-H-0Tf were tested for ethylene oligomerization activity, to no avail. Complexes 2-P, 5-H, 6-H, and 7-H-OTf were structurally characterized and evaluated by Mossbauer spectroscopy, and 5-H was shown to possess a redox non-innocent alkyne ligand, while the alpha-alkyliminopyridine ligands of 6-H were classified as radical anions, rendering all compounds describable as Fe(ll). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.08.060

文献信息

• 醇供氢钯催化炔烃半还原选择性合成顺、反式烯烃的方法
  申请人：南通大学

  公开号：CN109776253B

  公开（公告）日：2022-07-15

  本发明提供了一种醇供氢钯催化炔烃半还原选择性合成顺、反式烯烃的方法，包括如下步骤：将TEOA、NaOAc、催化剂、醇与炔烃于有机溶剂中进行炔烃的还原反应，反应生成顺式烯烃；将配体、催化剂、醇与炔烃于有机溶剂中进行炔烃的还原反应，反应生成反式烯烃；还原反应的反应器为密封的耐压反应器，还原反应的温度为120～150℃，还原反应的时间为20～48h；催化剂的用量为炔烃摩尔用量的5～20％，醇的用量为炔烃摩尔用量的10～100倍；R,R‑DIPAMP的用量为炔烃摩尔用量的0.5～5倍。本发明中，催化剂体系具有极高的化学反应和立体选择性，能高产率合成顺式或者反式烯烃产物；催化体系对底物的普适性强，含各种官能团的炔烃都能高效地进行高选择性地还原反应。
• Rhodium( <scp>II</scp> )‐Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)‐Aurantioclavine
  作者：Shengguo Duan、Bing Xue、Hui Meng、Zihang Ye、Ze‐Feng Xu、Chuan‐Ying Li

  DOI：10.1002/cjoc.202000657

  日期：2021.5

  rhodium(II)‐catalyzed [4+3] cyclization reaction of 1‐sulfonyl‐1,2‐3‐triazoles and indoles was developed. Azepino[5,4,3‐ cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good to excellent yields. In addition, the total synthesis of (±)‐aurantioclavine was completed in four steps from the known compound 1a adopting this [4+3] cyclization as a key step

  开发了有效的铑（II）催化的1-磺酰基-1,2-3-3三唑和吲哚的[4 + 3]环化反应。可以以良好或极好的收率获得阿斯皮诺[5,4,3- cd ]吲哚，广泛分布在具有各种生物活性的麦角生物碱中。此外，采用这种[4 + 3]环化作为关键步骤，从已知化合物1a的四个步骤中完成了（±）-金葡糖醇的总合成。
• Discovery of Quinazolin-4(3<i>H</i>)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation
  作者：Mohd Abdullaha、Shabber Mohammed、Mehboob Ali、Ajay Kumar、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1021/acs.joc.9b00138

  日期：2019.5.3

  NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C–C triple/double bond and the release of formaldehyde. The reaction relies

  NLRP3炎性小体是许多人类疾病的重要治疗靶标。本文中，使用碘催化的芳基炔烃（或苯乙烯）与O-氨基苯甲酰胺的偶联反应，合成了一系列计算设计的喹唑啉4（3 H）-1 。此转变的关键事件涉及C–C三键/双键的氧化裂解和甲醛的释放。该反应取决于在无金属条件下C–N键的形成以及C–C键的裂解。硝基取代的喹唑啉-4（3 H）-1 2k通过抑制从ATP刺激的J774A.1细胞中释放的IL-1β抑制NLRP3炎性小体（IC 50 5μM）。
• Diethylzinc-Mediated Radical 1,2-Addition of Alkenes and Alkynes
  作者：Xin Li、Songtao He、Qiuling Song

  DOI：10.1021/acs.orglett.1c00669

  日期：2021.4.16

  A novel diethylzinc-mediated radical 1,2-addition of perfluoroalkyl iodides to unactivated alkenes and alkynes is presented, which demonstrates a novel way to generate an ethyl difluoroacetate radical. This method is highly efficient and gives full conversions of the substrates, high yields of the products, and negligible byproducts and requires no column chromatography purifications. The mild conditions

  提出了一种新颖的由二乙基锌介导的全氟烷基碘与非活化烯烃和炔烃进行的1,2-基自由基加成反应，这表明了一种生成二氟乙酸乙酯基团的新方法。该方法非常高效，可实现底物的完全转化，产物的高收率和可忽略的副产物，并且不需要柱色谱法纯化。温和的条件使该协议能够表现出出色的官能团兼容性。
• Platinum(II) Diphosphinamine Complexes for the Efficient Hydration of Alkynes in Micellar Media
  作者：Francesco Trentin、Andrew M. Chapman、Alessandro Scarso、Paolo Sgarbossa、Rino A. Michelin、Giorgio Strukul、Duncan F. Wass

  DOI：10.1002/adsc.201100326

  日期：2012.4.16

  Highly active monomeric bis‐cationic platinum(II) catalysts bearing small bite angle diphosphinamine [N,N‐bis(diarylphosphino)amine] ‘PNP’ ligands efficiently catalyze Markovnikov hydration of terminal and internal alkynes to the corresponding ketones in water. Catalyst solubilization in water is achieved via ion pairing with anionic micelles formed by surfactant addition. The micelles ensure dissolution

  带有小咬合角二膦胺[ N，N-双（二芳基膦基）胺]'PNP'配体的高活性单体双阳离子铂（II）催化剂可有效催化末端炔烃和内部炔烃的马尔可夫尼科夫水合反应生成水中相应的酮。催化剂在水中的溶解是通过与表面活性剂添加形成的阴离子胶束进行离子配对而实现的。胶束确保非极性炔烃的溶解并促进试剂与催化剂之间的紧密接触，而在没有表面活性剂的有机水介质中，反应缓慢。可以通过用非极性溶剂萃取来分离水合产物，保留在水相中的催化剂可以循环使用四次，而不会损失催化活性。