8-十六炔 | 19781-86-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 8-十六炔
• 英文名称: hexadec-8-yne
• 英文别名: 8-hexadecyne
• CAS: 19781-86-3
• 化学式: C₁₆H₃₀
• mdl: MFCD00041664
• 分子量: 222.414
• InChiKey: YSDKMBBHKZXPME-UHFFFAOYSA-N

物化性质

• 熔点：
  17.51°C (estimate)
• 沸点：
  115-6°C 0,5mm
• 密度：
  0.80

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2901299090
• 储存条件：
  | 室温 干燥 |

SDS

8-Hexadecyne Revision number: 5
SAFETY DATA SHEET

---

Section 1. IDENTIFICATION
Product name: 8-Hexadecyne

Revision number: 5

---

Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Aspiration hazard Category 1
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Hazard statements
May be fatal if swallowed and enters airways
Precautionary statements:
[Response] IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Do NOT
induce vomiting.
[Storage] Store locked up.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government.

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 8-Hexadecyne
Percent: >99.0%(GC)
CAS Number: 19781-86-3
Chemical Formula: C16H30

---

Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
8-Hexadecyne

---

Section 4. FIRST AID MEASURES
Ingestion: Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT
induce vomiting.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

---

Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, carbon dioxide.
Suitable extinguishing
media:
Unsuitable extinguishing Water (It may scatter and spread fire.)
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use extra personal protective equipment (self-contained breathing apparatus). Keep
protective equipment and people away from and upwind of spill/leak. Ensure adequate ventilation. Entry to non-
emergency procedures: involved personnel should be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Absorb spilled material in a suitable absorbent (e.g. rag, dry sand, earth, saw-dust).
containment and cleaning In case of large amount of spillage, contain a spill by bunding. Adhered or collected
up: material should be promptly disposed of, in accordance with appropriate laws and
regulations.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent generation of vapour or mist. Wash hands and face thoroughly after
handling.
Use a closed system if possible. Use a ventilation, local exhaust if vapour or aerosol
will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

---

Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Half or full facepiece respirator, self-contained breathing apparatus(SCBA), supplied
air respirator, etc. Use respirators approved under appropriate government standards
and follow local and national regulations.
Impervious gloves.
Hand protection:
Eye protection: Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Colorless - Very pale yellow
Colour:
8-Hexadecyne

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 0.80
Solubility(ies):
[Water] No data available
[Other solvents] No data available

---

Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

---

Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

---

Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

---

Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to burn in a chemical
incinerator equipped with an afterburner and scrubber system. Observe all federal, state and local regulations when
disposing of the substance.

---

Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
8-Hexadecyne

---

Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  8-十六炔 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三环己基膦 、 甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 以90%的产率得到正十六烷
  参考文献：
  名称：

  用羧酸和第 10 族过渡金属配合物对炔烃进行简便的区域和立体选择性加氢金属化：用甲酸对炔烃进行选择性加氢

  摘要：

  通过炔烃、羧酸和零价族 10 过渡金属络合物 M(PEt(3))(4) (M =镍、钯、铂）。一项机理研究表明，氢金属化不是通过炔烃与由羧酸与 Pt(PEt(3))(4) 质子化产生的氢化金属反应进行的，而是通过炔烃配位金属络合物与酸。这一发现阐明了长期以来提出的反应机制，该机制通过生成烯基钯中间体和随后在由 Brφnsted 酸和 Pd(0) 配合物的组合催化的各种反应中转化该配合物来进行。

  DOI：

  10.1021/ja2069246
• 作为产物：
  描述：

  1-溴代庚烷 、 乙炔钠 在 sodium amide 作用下， 以 氨 为溶剂， 生成 8-十六炔
  参考文献：
  名称：

  Synthesis of 1,2-dialkylcyclopropenes, methyl malvalate, and sterculate

  摘要：

  DOI：

  10.1021/jo00986a012
• 作为试剂：
  描述：

  3,5-diphenyl-1-tosyl-2,3-dihydro-1H-pyrrole 在 silver hexafluoroantimonate 、 copper(II) acetate monohydrate 、 bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)] 、 8-十六炔 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 4-methyl-N-(4-oxo-2,4-diphenylbutyl)benzenesulfonamide
  参考文献：
  名称：

  铑（III）催化[3 + 2]通过C（sp2）与内部炔烃一起生成5-芳基-2,3-二氢-1H-吡咯的环状结构？H /烯烃功能化

  摘要：

  这项研究描述了一种新的铑（III）催化的[3- + 2] 5-芳基-2,3-二氢-1H-吡咯与内部炔烃的反应，该反应使用Cu（OAc）2氧化剂构建螺环系统，包括芳基C（SP的官能化2） H成烯烃CC键的键和加法/质子分解。该方法适用于广泛的5-芳基-2,3-二氢-1H-吡咯和内部炔烃，并能以良好的收率合成螺[indene-1,2'-吡咯烷]结构，并获得优异的收率。区域选择性。

  DOI：

  10.1002/anie.201407175

文献信息

• PROCESS FOR PRODUCTION OF FUSED RING COMPOUND
  申请人：Miura Masahiro

  公开号：US20090156832A1

  公开（公告）日：2009-06-18

  It is an object of the present invention to provide a method for manufacturing a fused ring compound, with which a fused ring compound that has excellent charge transport property and that has excellent solubility in solvents can be obtained efficiently. The method of the present invention for manufacturing a fused ring compound involves reacting a compound expressed by the following General Formula (1a) and a compound expressed by the following General Formula (1b) in the presence of an amine and a metal complex catalyst: (where Ar 11 and Ar 12 are each independently an atom group constituting an aromatic ring or a heterocyclic ring; X 11 and X 12 are each independently a hydrogen atom or a halogen atom, and at least one is a halogen atom; and R 11 and R 12 are each independently a hydrogen atom, an all group, an alkoxy group, an alkylthio group, an alkylamino group, an alkoxycarbonyl group, an aryl group, a heterocyclic group, or a cyano group, provided that at least one of R 11 and R 12 is not a hydrogen atom).

  本发明的目的是提供一种制造融环化合物的方法，通过该方法可以高效地获得具有优异电荷传输性能和在溶剂中具有优异溶解性的融环化合物。本发明的制造融环化合物的方法涉及在胺和金属络合催化剂存在下，使下述通用式（1a）表示的化合物与下述通用式（1b）表示的化合物发生反应： （其中Ar11和Ar12分别独立地是构成芳香环或杂环的原子团；X11和X12分别独立地是氢原子或卤素原子，至少一个是卤素原子；R11和R12分别独立地是氢原子、烷基、烷氧基、烷基硫基、烷基氨基、烷氧羰基、芳基、杂环基或氰基，但R11和R12中至少一个不是氢原子）。
• Syngas‐Free Highly Regioselective Rhodium‐Catalyzed Transfer Hydroformylation of Alkynes to α,β‐Unsaturated Aldehydes
  作者：Guangying Tan、Yimin Wu、Yang Shi、Jingsong You

  DOI：10.1002/anie.201902553

  日期：2019.5.27

  fundamental and important reaction in both academic research and industry. Conventional methods focus on the conversion of alkynes, CO, and H2 into α,β‐unsaturated aldehydes, but they often suffer from problems associated with operation, regioselectivity, and chemoselectivity. Herein, we disclose an operationally simple, mild, and syngas‐free rhodium‐catalyzed reaction for the hydroformylation of alkynes

  炔烃的加氢甲酰化是学术研究和工业中的基本且重要的反应。常规方法着重于将炔烃，CO和H 2转化为α，β-不饱和醛，但它们经常遇到与操作，区域选择性和化学选择性相关的问题。本文中，我们公开了一种操作简单，温和且无合成气的铑催化的反应，可通过烷基醛中的甲酰基和氢化物转移进行炔烃的加氢甲酰化反应。该合成方法使用廉价且易于手柄Ñ-丁醛可克服传统方法中使用合成气带来的挑战，并使用市售的催化剂和配体将各种内部炔烃（尤其是含炔基的复杂分子）转化为通用的立体定义的α，β-不饱和醛，具有出色的化学，区域和立体选择性。
• Iodomesitylene-Catalyzed Oxidative Cleavage of Carbon−Carbon Double and Triple Bonds Using <i>m</i>-Chloroperbenzoic Acid as a Terminal Oxidant
  作者：Kazunori Miyamoto、Yoshihisa Sei、Kentaro Yamaguchi、Masahito Ochiai

  DOI：10.1021/ja808829t

  日期：2009.2.4

  Transition metal-catalyzed oxidative cleavage of carbon-carbon multiple bonds has emerged as a powerful tool in organic synthesis. High-valent oxometals, mostly of Ru, Os, Mn, Mo, W, and Re, were used catalytically as reactive oxygen transfer agents to the multiple bonds. Reported here for the first time are the organocatalytic versions of the oxidative cleavage reactions. Our method involves use of

  过渡金属催化的碳-碳多键氧化裂解已成为有机合成中的有力工具。高价含氧金属，主要是 Ru、Os、Mn、Mo、W 和 Re，被用作催化多键的活性氧转移剂。这里首次报道了氧化裂解反应的有机催化版本。我们的方法涉及使用碘代三甲苯作为有效的有机催化剂，在无金属条件下生成活性芳基（羟基）-λ（3）-碘烷 5 和间氯过苯甲酸（m-CPBA）作为末端氧化剂。环状和无环烯烃以及脂肪族和芳香族炔烃在有机催化条件下顺利裂解为羧酸。
• Palladium-catalysed carboformylation of alkynes using acid chlorides as a dual carbon monoxide and carbon source
  作者：Yong Ho Lee、Elliott H. Denton、Bill Morandi

  DOI：10.1038/s41557-020-00621-x

  日期：2021.2

  Hydroformylation, a reaction that installs both a C–H bond and an aldehyde group across an unsaturated substrate, is one of the most important catalytic reactions in both industry and academia. Given the synthetic importance of creating new C–C bonds, the development of carboformylation reactions, wherein a new C–C bond is formed instead of a C–H bond, would bear enormous synthetic potential to rapidly

  加氢甲酰化是一种在不饱和底物上同时安装 C-H 键和醛基的反应，是工业界和学术界最重要的催化反应之一。鉴于创造新的 C-C 键的合成重要性，发展碳甲酰化反应，其中形成新的 C-C 键而不是 C-H 键，将具有巨大的合成潜力，可以在有价值的合成中迅速增加分子的复杂性醛类。然而，利用外源 CO 源的四组分反应固有的苛刻复杂性使得直接碳甲酰化反应的发展成为一项艰巨的挑战。在这里，我们描述了一种钯催化策略，该策略使用现成的芳酰氯作为碳亲电试剂和 CO 源，与空间拥挤的氢硅烷串联，进行炔烃的立体选择性碳甲酰化。将该协议扩展到四种化学发散性羰基化，进一步突出了该策略在羰基化化学中提供的创造性机会。
• Synthesis of Alkylated Benzo[2,1-<i>b</i>:3,4-<i>b</i>′]dithiophenes by Annulative Coupling and Their Direct Arylation under Palladium Catalysis
  作者：Hiroyuki Watanabe、Jun Kumagai、Hayato Tsurugi、Tetsuya Satoh、Masahiro Miura

  DOI：10.1246/cl.2007.1336

  日期：2007.11.5

  The annulative coupling of 3,3′-diiodo-2,2′-bithiophene with internal alkynes efficiently proceeds in the presence of a palladium catalyst to afford the corresponding benzo[2,1-b:3,4-b′]dithiophene derivatives. The dithiophenes also undergo palladium-catalyzed direct arylation with aryl bromides at the 2- and 7-positions selectively.

  在钯催化剂的存在下，3,3'-二碘-2,2'-双噻吩与内部炔烃的累积耦合反应高效进行，得到了相应的苯并[2,1-b:3,4-b']二噻吩衍生物。这些二噻吩还能在钯催化下直接与溴代芳烃在2位和7位选择性地发生芳基化反应。

表征谱图