3,5-辛二炔 | 16387-70-5

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 3,5-辛二炔
• 英文名称: octa-3,5-diyne
• 英文别名: 3,5-octadiyne
• CAS: 16387-70-5
• 化学式: C₈H₁₀
• mdl: MFCD00041633
• 分子量: 106.167
• InChiKey: LILZEAJBVQOINI-UHFFFAOYSA-N

物化性质

• 熔点：
  27°C (estimate)
• 沸点：
  164 °C
• 密度：
  0.81
• 保留指数：
  972

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2901299090

SDS

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Section I.Chemical Product and Company Identification
Chemical Name 3,5-Octadiyne
Portland OR
Synonym Not available.
Chemical Formula C8H10
CAS Number 16387-70-5

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
3,5-Octadiyne 16387-70-5 Min. Not available. Not available.
98.0%(GC)

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
CARCINOGENIC EFFECTS : Not available.
Chronic Health Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact
In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the
toxic material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Auto-Ignition Not available.
Flammability Flammable.
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO 2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
Flammable liquid.
and Instructions SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use alcohol foam, water spray or fog. Cool containing vessels with water jet in order to prevent pressure
build-up, autoignition or explosion. Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
3,5-Octadiyne

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Section VI. Accidental Release Measures
Spill Cleanup Flammable liquid.
Instructions Keep away from heat. Mechanical exhaust required. Stop leak if without risk. Absorb with DRY earth, sand or other
non-combustible material. DO NOT touch spilled material. Prevent entry into sewers, basements or confined areas; dike
if needed. Consult federal, state, and/or local authorities for assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage FLAMMABLE. Keep away from heat. Mechanical exhaust required. Avoid excessive heat and light. Do not breathe
gas/fumes/ vapor/spray.
Information
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their
respective threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Personal Protection Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. Suggested protective clothing might not be sufficient;
consult a specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Solubility
Physical state @ 20°C Liquid. (Clear, Colorless.) Not available.
0.81(water=1)
Specific Gravity
Molecular Weight 106.16 Partition Coefficient Not available.
Boiling Point 164°C (327.2°F) Vapor Pressure Not available.
Melting Point Not available. Vapor Density Not available.
Not available. Volatility Not available.
Refractive Index
Critical Temperature Not available. Odor Not available.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number Not available.
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Toxicity Data Not available.
Chronic Toxic Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Continued on Next Page
3,5-Octadiyne

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification DOT Class 3: Flammable liquid
PIN Number
Proper Shipping Name
Hydrocarbons, liquid, n.o.s.
Packing Group (PG) III
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements R10- Flammable.
R18- In use, may form flammable/explosive vapor-air mixture.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-辛二炔 在 1,2-二溴乙烷 、 copper(I) bromide 、 lithium bromide 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 cis,cis-3,5-octadiene
  参考文献：
  名称：

  活化锌粉对区域和立体特异性还原共轭和非共轭三键

  摘要：

  在无水乙醇中，用1,2-二溴乙烷活化的锌粉，以及依次用二溴乙烷和溴化铜（I）活化的锌粉，进行了多种炔属衍生物的区域还原和立体特异性还原。与第二种试剂相比，第一种试剂的功能更弱，选择性更高。

  DOI：

  10.1039/c39840000735
• 作为产物：
  描述：

  1-丁炔 在 吡啶 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到3,5-辛二炔
  参考文献：
  名称：

  A Procedure for the Oxidative “Dimerization” of Aliphatic 1-Alkynes

  摘要：

  Aliphatic 1-alkynes RC = CH (R = alkyl) are readily converted into diynes R = CC = CR, by introducing oxygen into a mixture of the acetylene and pyridine using copper(I)bromide as a catalyst and 1,8-diazabicyclo[5.4.0] undec-7-ene as a co-catalyst.

  DOI：

  10.1080/00397919108020801

文献信息

• Rhodium-Catalyzed Oxidative Annulation of (2-Arylphenyl)boronic Acids with Alkynes: Selective Synthesis of Phenanthrene Derivatives
  作者：Tetsuya Satoh、Masahiro Miura、Tomoya Nagata、Yuji Nishii

  DOI：10.1055/s-0035-1561940

  日期：——

  A rhodium-catalyzed annulative coupling of (2-arylphenyl)boronic acids with alkynes has been developed for the facile construction of phenanthrene frameworks. The reaction proceeded without external bases, and dioxygen worked as a terminal oxidant. Deuterium-labeling experiments indicated the involvement of five-membered rhodacycle intermediates.

  已经开发了铑催化的（2-芳基苯基）硼酸与炔烃的环状偶联，以方便地构建菲骨架。反应在没有外部碱的情况下进行，双氧作为末端氧化剂。氘标记实验表明五元红环中间体的参与。
• Synthesis of 1<i>H</i>-Inden-1-ol Derivatives via Rhodium-catalyzed Annulation of<i>o</i>-Acylphenylboronic Acids with Alkynes
  作者：Takanori Matsuda、Masaomi Makino、Masahiro Murakami

  DOI：10.1246/cl.2005.1416

  日期：2005.10

  A rhodium-catalyzed annulation reaction of o-formylphenylboronic acid with alkynes occurred regioselectively at room temperature to give substituted 1H-inden-1-ol derivatives. o-Acetylphenylboronic acid also underwent the annulation reaction at 80 °C to afford 1-methyl-1H-inden-1-ols.

  一种以铑为催化剂的环化反应在室温下选择性地将邻甲酰基苯硼酸与炔烃反应，生成取代的1H-inden-1-醇类衍生物。邻乙酰基苯硼酸在80 °C下也发生了环化反应，生成1-甲基-1H-inden-1-醇。
• Oxidative addition of 1,3-diynes at triosmium clusters with cleavage of the central carbon–carbon bond: X-ray crystal structure of [Os₃(µ₃,η²-C₂Ph)(µ-C₂Ph)(CO)₉] derived from 1,4-diphenylbuta-1,3-diyne
  作者：Antony J. Deeming、Mark S. B. Felix、Paul A. Bates、Michael B. Hursthouse

  DOI：10.1039/c39870000461

  日期：——

  The diyne clusters [Os3(µ3,η2-RCCCCR)(CO)10](R = Me, Et, Ph, But, SiMe3) in hydrocarbon solvent at 120 °C decarbonylate to give the nonacarbonyl clusters [Os3(µ3,η2-C2R)(µ-C2R)(CO)9] when R = Ph, But, or SiMe3, [Os3H(µ3,σ,η2,η2-EtCC–CCCHMe)(CO)9] when R = Et, and [Os3(C4Me2)(CO)9] of known structure when R = Me; the µ-C2Ph ligand in [Os3(µ3, η2-C2Ph)(µ-C2Ph)(CO)9](X-ray structure) is unusual in bridging

  的二炔簇[O的3（μ 3，η 2 -RC CC CR）（CO）10 ]（R =甲基，乙基，PH，卜吨，森达3）中在120℃下脱羰烃溶剂，得到nonacarbonyl簇[O的3（μ 3，η 2 -C 2 R）（μ-C 2 R）（CO）9 ]当R = PH，卜吨，或森达3，[O的3 H（μ 3，σ，η 2，η 2 -EtC C-C ç CHME）（CO）9 ]当R =的Et和[O的3当R ＝ Me时，具有已知结构的（C 4 Me 2）（CO）9 ]；的μ-C 2在pH为配体[O的3（μ 3，η 2 -C 2 PH）（μ-C 2 PH）（CO）9 ]（X射线结构）是不对称桥接异常仅通过一个碳原子。
• Chromium-Mediated Synthesis of Polycyclic Aromatic Compounds from Halobiaryls
  作者：Ken-ichiro Kanno、Yuanhong Liu、Atsushi Iesato、Kiyohiko Nakajima、Tamotsu Takahashi

  DOI：10.1021/ol052214x

  日期：2005.11.1

  [reaction: see text] Reaction of 2,2'-dihalobiphenyl with butyllithium followed by the addition of chromium(III) chloride and alkynes afforded the corresponding phenanthrene derivatives via formal [4 + 2] cycloaddition. A variety of alkynes could be used for this reaction, such as alkyl, aryl, silyl, and alkoxycarbonyl alkynes. Repetitive process of the reaction gave more extended polycyclic compounds

  [反应：见正文] 2,2'-二卤代联苯与丁基锂反应，然后加入氯化铬（III）和炔烃，通过正式的[4 + 2]环加成反应提供了相应的菲衍生物。多种炔烃可用于该反应，例如烷基，芳基，甲硅烷基和烷氧羰基炔烃。重复该反应过程得到了更多的延伸多环化合物，例如苯并[g]]和氮杂环戊二烯衍生物。
• Carbon−Carbon Bond Formation Reaction of Zirconacyclopentadienes with Alkynes in the Presence of Ni(II)-complexes
  作者：Tamotsu Takahashi、Fu-Yu Tsai、Yanzhong Li、Kiyohiko Nakajima、Martin Kotora

  DOI：10.1021/ja990750c

  日期：1999.12.1

  tetrahydroisoquinoline derivatives in good to high yields. This procedure was also used for the selective preparation of benzene derivatives from three different alkynes. The use of trimethylsilyl-substituted alkyne as the first, second or third alkyne afforded desilylated benzene derivatives. The reaction of zirconacyclopentadienes with allenes gave benzene derivatives as a mixture of two isomers.

  由两个炔烃或二炔制备的氧化锆环戊二烯与烷基、三甲基甲硅烷基或烷氧基取代的第三炔以及具有吸电子基团的炔在化学计量的 NiBr2(PPh3)2 存在下反应，得到以良好的收率得到苯衍生物。含杂原子的二炔如二炔丙基苄胺和炔丙基-高炔丙基苄胺以良好至高产率得到异二氢吲哚和四氢异喹啉衍生物。该程序还用于从三种不同的炔烃中选择性制备苯衍生物。使用三甲基甲硅烷基取代的炔作为第一、第二或第三炔提供去甲硅烷基化的苯衍生物。锆并环戊二烯与丙二烯的反应得到苯衍生物，为两种异构体的混合物。

表征谱图