3-环己基-1-丙炔 | 17715-00-3

• 分子结构分类: 有机化合物 - 乙炔化物
• 中文名称: 3-环己基-1-丙炔
• 中文别名: 2-炔丙基环己烷；3-环己基丙炔
• 英文名称: prop-2-ynylcyclohexane
• 英文别名: prop-2-yn-1-ylcyclohexane；3-cyclohexyl-1-propyne；3-cyclohexylpropyne；3-cyclohexylprop-1-yne；cyclohexyl-1-propyne；2-propynyl cyclohexane
• CAS: 17715-00-3
• 化学式: C₉H₁₄
• mdl: MFCD00041562
• 分子量: 122.21
• InChiKey: UARFKZSJGDQRLF-UHFFFAOYSA-N

物化性质

• 沸点：
  157-158 °C(lit.)
• 密度：
  0.845 g/mL at 25 °C(lit.)
• 闪点：
  95 °F
• 稳定性/保质期：

  常温常压下稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  3
• 安全说明：
  S16,S26,S36
• 危险品运输编号：
  UN 1993 3/PG 3
• WGK Germany：
  3
• 海关编码：
  2902199090
• 危险类别：
  3
• 危险品标志：
  Xn
• 危险类别码：
  R10
• RTECS号：
  UK4725000
• 包装等级：
  III
• 储存条件：
  常温下应密闭避光保存，并放置于通风、干燥处。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 3-Cyclohexyl-1-propyne

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Flammable liquids (Category 3)
Acute toxicity, Oral (Category 4)
Serious eye damage (Category 1)
According to European Directive 67/548/EEC as amended.
Harmful if swallowed. Risk of serious damage to eyes. Flammable.
Label elements
Pictogram
Signal word Danger
Hazard statement(s)
H226 Flammable liquid and vapour.
H302 Harmful if swallowed.
H318 Causes serious eye damage.
Precautionary statement(s)
P280 Wear protective gloves/ eye protection/ face protection.
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)
Xn Harmful
R-phrase(s)
R22 Harmful if swallowed.
R41 Risk of serious damage to eyes.
R10 Flammable.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
S16 Keep away from sources of ignition - No smoking.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C9H14
Molecular Weight : 122,21 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
3-Cyclohexyl-1-propyne
17715-00-3 - - Flam. Liq. 3; Acute Tox. 4; -
Eye Dam. 1; H226, H302,
H318
Xn, R22 - R41 - 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
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. Evacuate personnel to safe areas. 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 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
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
Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and
approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin and body protection
Complete suit protecting against chemicals, 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 157 - 158 °C - lit.
Flash point 35 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 0,845 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 3,06
n-octanol/water

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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

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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 Harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes Causes eye burns.
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: UK4725000

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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. (3-Cyclohexyl-1-propyne)
IMDG
UN-Number: 1993 Class: 3 Packing group: III EMS-No: F-E, S-E
Proper shipping name: FLAMMABLE LIQUID, N.O.S. (3-Cyclohexyl-1-propyne)
Marine pollutant: No
IATA
UN-Number: 1993 Class: 3 Packing group: III
Proper shipping name: Flammable liquid, n.o.s. (3-Cyclohexyl-1-propyne)

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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

化学性质
无色液体，沸点为55℃（2.8 kPa）。

用途
用作有机合成中间体。

生产方法
将细粉状氨基钠与矿物油的悬浮混合物加热至约160℃，搅拌下滴加3-环己基-2-溴丙烯。反应完成后继续加热2小时。冷却后加入乙醚，将混合物倾入碎冰中，并用浓盐酸进行酸化处理。分出醚层后进行干燥和蒸馏，常压蒸馏除去乙醚，再在减压条件下收集115℃（2.67 kPa）以前的馏分。再次蒸馏时收集55-63℃（2.67 kPa）的馏分，得到3-环己基丙炔。

反应信息

• 作为反应物：
  描述：

  3-环己基-1-丙炔 在 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、689.49 kPa 条件下， 反应 24.0h， 以90%的产率得到正丙基环己烷
  参考文献：
  名称：

  纳米粒子负载和可磁回收的镍催化剂：坚固且经济 氢化 和转移 氢化 协议

  摘要：

  磁性 纳米粒子支持的防浸 你 催化剂 可以很容易地由廉价的原料制备，这种原料可以催化各种 氢化 和转移 氢化反应; 高的催化活性 以及使用外部磁场恢复的便捷性是该产品的其他环保特性 催化 系统。

  DOI：

  10.1039/b815058c
• 作为产物：
  描述：

  环己基丙二醇 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到3-环己基-1-丙炔
  参考文献：
  名称：

  通过金属化中间体将烷基和芳基丙二烯转化为 1-炔烃

  摘要：

  摘要：通过将丙二烯 RCH=C=CH2 或乙炔和丙二烯的混合物与正丁基锂在四氢呋喃-己烷中的金属化反应，在室温下重排金属化丙二烯或通过水解反应获得了大量乙炔 RCH2C=CH。回流加热。

  DOI：

  10.1080/00397919708005448

文献信息

• Triazole Ligands Reveal Distinct Molecular Features That Induce Histamine H₄ Receptor Affinity and Subtly Govern H₄/H₃ Subtype Selectivity
  作者：Maikel Wijtmans、Chris de Graaf、Gerdien de Kloe、Enade P. Istyastono、Judith Smit、Herman Lim、Ratchanok Boonnak、Saskia Nijmeijer、Rogier A. Smits、Aldo Jongejan、Obbe Zuiderveld、Iwan J. P. de Esch、Rob Leurs

  DOI：10.1021/jm1013488

  日期：2011.3.24

  a peripheral imidazole group. The imidazole ring posed some problems in the click chemistry putatively due to Cu(II) coordination, but Boc protection of the imidazole and removal of oxygen from the reaction mixture provided effective strategies. Pharmacological studies revealed two monosubstituted imidazoles (6h,p) with <10 nM H4R affinities and >10-fold H4R/H3R selectivity. Both compounds possess

  组胺H 3（H 3 R）和H 4（H 4 R）受体引起了药物化学界的极大兴趣。鉴于它们相对较高的同源性，但治疗前景却大相径庭，因此对两种受体的配体选择性至关重要。我们使用具有[1,2,3]三唑核心的配体询问H 4 R / H 3 R的选择性。Cu（I）辅助的“点击化学”被用来组装各种[1,2,3]三唑化合物（6a - w和7a - f），许多含有外围咪唑基团。咪唑环可能由于Cu（II）配位而在点击化学中造成了一些问题，但是咪唑的Boc保护和从反应混合物中除去氧气提供了有效的策略。药理研究表明，两种单取代的咪唑（6h，p）的亲和力<10 nM H 4 R和H 4 R / H 3 R选择性> 10倍。两种化合物均具有环烷基甲基，并且似乎靶向H 4中的亲脂性口袋R具有很高的空间精度。[1,2,3]三唑支架的使用进一步证明了以下概念，即间隔区长度或外围基团的简单改变可以逆转对H 3 R的选择性。提
• Oxidative Dehydrosulfurative Cross-Coupling of 3,4-Dihydropyrimidine-2-thiones with Alkynes for Access to 2-Alkynylpyrimidines
  作者：Ngoc Son Le Pham、Hyunik Shin、Jun Yong Kang、Jeong-Hun Sohn

  DOI：10.1021/acs.joc.0c00091

  日期：2020.4.3

  (DHPMs) via dehydrosulfurative Sonogashira cross-coupling with concomitant oxidative dehydrogenation using a Pd/Cu catalytic system. Together with the ready availability of DHPMs possessing various substituents at the C4–C6 positions, this transformation offers rapid and general access to diverse 2-alkynylpyrimidine derivatives.

  描述了一种通过Pd / Cu催化体系通过脱硫Sonogashira交叉偶联与伴随的氧化脱氢从3,4-二氢嘧啶-1 H -2-硫酮（DHPM）一步合成2-炔基嘧啶的反应方法。连同在C4–C6位置具有各种取代基的DHPM的现成可用性，这种转变为获得各种2-炔基嘧啶衍生物提供了快速而通用的途径。
• A General Cyclocarbonylation of Aryl Bromides and Triflates with Acetylenes: Palladium-Catalyzed Synthesis of 3-Alkylidenefuran-2-ones
  作者：Xiao-Feng Wu、Basker Sundararaju、Pazhamalai Anbarasan、Helfried Neumann、Pierre H. Dixneuf、Matthias Beller

  DOI：10.1002/chem.201101083

  日期：2011.7.11

  Making use of CO: An improved efficient synthesis of 5‐aryl‐3‐alkylidenefuran‐2‐ones has been developed (see scheme). Starting from readily available (hetero)aryl bromides or aryl triflates and alkynes, furanones were produced in good yields through a double carbonylation process. To illustrate the generality of the method more than 25 furanone derivatives were synthesized, including the permethylated

  利用一氧化碳：已开发出一种改进的5-芳基-3-亚烷基呋喃-2-酮的有效合成方法（参见方案）。从容易获得的（杂）芳基溴化物或芳基三氟甲磺酸酯和炔烃开始，呋喃酮通过双羰基化过程以高收率生产。为了说明该方法的通用性，合成了25种以上的呋喃酮衍生物，包括全甲基化激酶抑制剂BE-23372M。
• 2:1 versus 1:1 Coupling of Alkylacetylenes with Secondary Amines: Selectivity Switching in 8-Quinolinolato Rhodium Catalysis
  作者：Yoshihiko Morimoto、Moe Hamada、Shotaro Takano、Katsufumi Mochizuki、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/acs.orglett.1c00094

  日期：2021.5.21

  Both 2:1 and 1:1 couplings of alkylacetylenes with secondary amines were achieved using 8-quinolinolato rhodium catalysts and CsF. The 2:1/1:1 selectivity was switched by choosing the reaction solvent. In DMA, an unprecedented 2:1 coupling reaction of alkylacetylenes with amines proceeded to give 2-aminodiene products. One-pot 2:1 coupling/reduction provided rapid access to various allylamines, while

  烷基乙炔与仲胺的2：1和1：1偶合均使用8-喹啉基铑催化剂和CsF实现。通过选择反应溶剂来切换2：1/1：1的选择性。在DMA中，前所未有的烷基乙炔与胺的2：1偶联反应进行，得到了2-氨基二烯产物。一锅2：1偶联/还原提供了快速接触各种烯丙胺的功能，而一锅偶联/水解则提供了烯酮类产品。在甲苯中，在相对温和的条件下发生了反马尔可夫尼科夫胺化反应，生成了1：1的偶联产物。
• Synthesis, characterization and catalytic application of some novel PNP-Ni(II) complexes: Regio-selective [2+2+2] cycloaddition reaction of alkyne
  作者：Masilamani Tamizmani、Chinnappan Sivasankar

  DOI：10.1016/j.jorganchem.2017.02.039

  日期：2017.9

  We have also performed alkyne [2+2+2] cycloaddition reaction using Ni(II) complexes and observed high regioselectivity of the products. The observed selectivity is well correlating with the electronic feature of alkynes. The [2+2+2] cycloaddition of electron rich alkynes produced 1,3,5-substituted benzene derivatives as a major product whereas the electron deficient alkynes produced 1,2,4-substituted

  PN（H）P Ph，PN（Me）P iPr和PN（Me）P tBu配体的一些新颖的Ni（II）配合物已通过标准的分析和光谱方法（例如1 H NMR，31 P NMR，元素分析，ESI-MS，紫外可见光谱和单晶X射线晶体学。在三氟甲磺酸银存在下，复合物[PN（H）P Ph NiCl] 2 NiBr 4 （5）在室温下激活二氯甲烷的C-Cl键，得到复合物[PN（H）P Ph NiCl] OTf （6）。我们还使用Ni（II）配合物进行了炔烃[2 + 2 + 2]环加成反应，并观察到了产物的高区域选择性。观察到的选择性与炔烃的电子特征很好地相关。富电子炔烃的[2 + 2 + 2]环加成反应生成1,3,5-取代的苯衍生物作为主要产物，而缺电子炔烃则生成1,2,4-取代的苯衍生物作为主要产物。

表征谱图