1-苯基-1-己炔-3-醇 | 1817-51-2

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物 - 环醇
• 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-苯基-1-己炔-3-醇
• 英文名称: 1-phenyl-1-hexyn-3-ol
• 英文别名: 1-phenylhex-1-yn-3-ol
• CAS: 1817-51-2
• 化学式: C₁₂H₁₄O
• mdl: MFCD00046687
• 分子量: 174.243
• InChiKey: HGUIQUVFOYTZNC-UHFFFAOYSA-N

物化性质

• 密度：
  0.949 g/mL at 25 °C
• 闪点：
  110 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906299090
• WGK Germany：
  3
• 储存条件：
  存储条件：室温、密封、干燥

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 1-Phenyl-1-hexyn-3-ol

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a dangerous substance according to GHS.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
This substance is not classified as dangerous according to Directive 67/548/EEC.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C12H14O
Molecular Weight : 174,24 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
1-Phenyl-1-hexyn-3-ol
1817-51-2 - - - -

---

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
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.

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed
containers for disposal.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Normal measures for preventive fire protection.
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.

---

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
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, 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.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form liquid
Colour colourless
Safety data
pH no data available
Melting point no data available
Boiling point no data available
Flash point > 110 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 0,949 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 3,454
n-octanol/water

---

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

---

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
Prolonged or repeated exposure may cause allergic reactions in certain sensitive individuals.
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: Not available

---

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

---

Section 13. DISPOSAL CONSIDERATIONS
Product
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.

---

Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

---

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

---

Section 16. OTHER INFORMATION
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.

反应信息

• 作为反应物：
  描述：

  1-苯基-1-己炔-3-醇 在 氧气 、 特戊醛 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到1-苯基己-1-炔-3-酮
  参考文献：
  名称：

  钴（III）复合催化炔丙醇的好氧氧化

  摘要：

  在新戊醛的存在下，在分子氧的大气压下，邻苯二（N'-甲基草酰胺酸酯）钴（III）配合物可作为一种有效的催化剂，用于将炔丙醇氧化为相应的 α,β-炔属羰基化合物.

  DOI：

  10.1055/s-2007-990804
• 作为产物：
  描述：

  1-苯基-1-己炔 在 氧气 、 溶剂黄146 、 potassium iodide 作用下， 生成 1-苯基-1-己炔-3-醇
  参考文献：
  名称：

  Chirko,A.I. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 1887 - 1890

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-phenyl-1-hexyn-3-yl 1-pyrrolidinecarboximidate 在 1-苯基-1-己炔-3-醇 作用下， 以 xylene 为溶剂， 反应 20.0h， 以45%的产率得到3-ethyl-6-phenyl-2(1H)-pyridinone
  参考文献：
  名称：

  Preparation of substituted 2-pyridones by thermal rearrangement of propargylic pyrrolidine pseudoureas

  摘要：

  DOI：

  10.1021/ja00522a052

文献信息

• [(NHC)AuI]-Catalyzed Formation of Conjugated Enones and Enals: An Experimental and Computational Study
  作者：Nicolas Marion、Peter Carlqvist、Ronan Gealageas、Pierre de Frémont、Feliu Maseras、Steven P. Nolan

  DOI：10.1002/chem.200700134

  日期：2007.7.27

  or absence of water in the reaction mixture was found to be crucial. From the same phenylpropargyl acetates, anhydrous conditions led to the formation of indene compounds via a tandem [3,3] sigmatropic rearrangement/intramolecular hydroarylation process, whereas simply adding water to the reaction mixture produced enone derivatives cleanly. Several mechanistic hypotheses, including the hydrolysis of

  描述了由炔丙基乙酸酯的[（NHC）AuI]催化的（NHC = N-杂环卡宾）形成的α，β-不饱和羰基化合物（烯酮和烯醛）。该反应在[（NHC）AuCl]和AgSbF6等摩尔混合物的存在下于60摄氏度在8小时内发生，并以高收率生产共轭烯酮和烯醛。优化研究表明，该反应对溶剂，NHC敏感，并且在较小程度上对所用的银盐敏感，从而导致在THF中使用[（ItBu）AuCl] / AgSbF6作为有效的催化体系。事实证明，这种转变具有广阔的范围，能够以极大的结构多样性立体选择性地形成（E）-烯和-烯。研究了炔丙基和炔基位置的取代作用，以及芳基取代对肉桂基酮形成的影响。发现反应混合物中水的存在或不存在是至关重要的。从相同的苯基炔丙基乙酸酯中，无水条件通过串联[3,3]σ重排/分子内氢芳基化过程导致茚化合物的形成，而仅向反应混合物中加水则干净地生成了烯酮衍生物。研究了几种机械学假说，包括烯丙醇酯中间体的水解
• Highly regioselective gold-catalyzed formal hydration of propargylic <i>gem</i>-difluorides
  作者：Jean-Denys Hamel、Tatsuru Hayashi、Mélissa Cloutier、Paul R. Savoie、Olivier Thibeault、Meggan Beaudoin、Jean-François Paquin

  DOI：10.1039/c7ob02406a

  日期：——

  Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility

  在本文中，我们报道了炔丙基宝石-二氟化物的高度区域选择性金催化的正式水合。这种转化不仅提供了难以或几乎不可能预先获得的多用途氟化结构单元的途径，而且还代表了内部炔烃具有高度区域选择性的金催化加氢烷氧基化的罕见情况，并提出了二氟亚甲基单元的实用性。催化中的指导基团。
• Hydrogen-Bond-Promoted Friedel–Crafts Reaction of Secondary Propargylic Fluorides: Preparation of 1-Alkyl-1-aryl-2-alkynes
  作者：Jean-Denys Hamel、Meggan Beaudoin、Mélissa Cloutier、Jean-François Paquin

  DOI：10.1055/s-0036-1589057

  日期：2017.12

  We report that aromatic propargylation is achievable with secondary propargylic fluorides, thus affording 1-alkyl-1-aryl-2-alkynes. In the present case, hydrogen bonding is responsible for the activation of the C–F bond. A large excess of arene nucleophile is shown to be necessary to achieve good yields.

  我们报告说，芳族炔丙基化可以用仲炔丙基氟化物实现，从而提供 1-烷基-1-芳基-2-炔烃。在目前的情况下，氢键负责激活 C-F 键。大量过量的芳烃亲核试剂被证明是获得良好收率所必需的。
• Synthesis of Arylnaphthalene Lignan Scaffold by Gold-Catalyzed Intramolecular Sequential Electrophilic Addition and Benzannulation
  作者：Vanajakshi Gudla、Rengarajan Balamurugan

  DOI：10.1021/jo201918d

  日期：2011.12.16

  an arylnaphthalene lignan scaffold in high yields is presented. It involves a sequential intramolecular electrophilic attack of carbonyl on arylalkyne followed by benzannulation catalyzed by gold salt. AuCl3 in combination with AgSbF6 works better to effect this transformation. Selected products have been converted into arylnaphthalene lactone natural products such as justicidin E, taiwanin C, and

  提出了一种以高产率产生包含芳基萘木脂体骨架的化合物的分子内方法。它涉及羰基对芳基炔的连续分子内亲电攻击，然后由金盐催化苯环化。AuCl 3与AgSbF 6结合使用效果更好。某些产品已被转化为芳基萘内酯天然产品，例如司法正义素E，黄花青素C和逆转录调节素B。
• Cationic Rhodium(I)/Bisphosphane Complex-Catalyzed Isomerization of Secondary Propargylic Alcohols to α,β-Enones
  作者：Ken Tanaka、Takeaki Shoji、Masao Hirano

  DOI：10.1002/ejoc.200700071

  日期：2007.6

  alcohols to α,β-enones. A kinetic resolution of secondary propargylic alcohols proceeded with moderate selectivity with [Rh((R)-BINAP)]OTf as a catalyst. Mechanistic studies revealed that the isomerization proceeds through intramolecular 1,3- and 1,2-hydrogen migration pathways. The isomerization of propargylic diol derivatives was also investigated, which revealed that 1,4-diketones, furans, and α,β-enones

  我们已经确定氢化阳离子 Rh(I)/双膦配合物是用于将仲炔醇异构化为 α,β-烯酮的高活性催化剂。仲炔醇的动力学拆分以 [Rh((R)-BINAP)]OTf 作为催化剂以中等选择性进行。机理研究表明，异构化通过分子内 1,3- 和 1,2- 氢迁移途径进行。还研究了炔二醇衍生物的异构化，结果表明 1,4-二酮、呋喃和 α,β-烯酮是从 2-butyn-1,4-diol、1-methoxy-2-butyn-4- ol 和 1-acetoxy-2-butyn-4-ol 衍生物，分别。此外，研究了炔二醇异构化的化学选择性，并观察到炔丙基羟基的优先氧化。