5-十一炔 | 2294-72-6

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 5-十一炔
• 英文名称: undec-5-yne
• 英文别名: 5-undecyne
• CAS: 2294-72-6
• 化学式: C₁₁H₂₀
• mdl: MFCD00041657
• 分子量: 152.28
• InChiKey: VRQLDBSWBBKOCR-UHFFFAOYSA-N

物化性质

• 熔点：
  -74.1°C
• 沸点：
  78°C 10mm
• 密度：
  0,775 g/cm3
• 保留指数：
  1127

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 安全说明：
  S16
• 危险类别码：
  R10
• 海关编码：
  2901299090
• 危险品运输编号：
  1993

SDS

5-Undecyne Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 5-Undecyne

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 4
Flammable liquids
HEALTH HAZARDS
Category 1
Aspiration hazard
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Hazard statements Combustible liquid
May be fatal if swallowed and enters airways
Precautionary statements:
Keep away from flames and hot surfaces.
[Prevention]
Wear protective gloves and eye/face protection.
IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Do NOT
[Response]
induce vomiting.
Store in a well-ventilated place. Keep cool.
[Storage]
Store locked up.
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 5-Undecyne
Percent: ....
CAS Number: 2294-72-6
Chemical Formula: C11H20

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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.
5-Undecyne

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Section 4. FIRST AID MEASURES
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.
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.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, carbon dioxide.
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:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use extra personal protective equipment (self-contained breathing apparatus). Keep
Personal precautions,
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.
Prevention of secondary Remove all sources of ignition. Fire-extinguishing devices should be prepared in
hazards: case of a fire. Use spark-proof tools and explosion-proof equipment.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent generation of vapour or mist. Keep away from flames and hot surfaces. Take
measures to prevent the build up of electrostatic charge. Use explosion-proof
equipment. Wash hands and face thoroughly after handling.
Use a closed system, ventilation.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a cool, dark and well-ventilated place.
Storage conditions:
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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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
Half or full facepiece respirator, self-contained breathing apparatus(SCBA), supplied
Respiratory protection:
air respirator, etc. Use respirators approved under appropriate government standards
and follow local and national regulations.
Hand protection: Impervious gloves.
5-Undecyne

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Section 8. EXPOSURE CONTROLS / PERSONAL 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.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Colorless - Almost colorless
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: 197°C
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: 0.77
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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

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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

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

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-十一炔 在 氨 、 sodium 作用下， 生成 反式-5-十一碳烯
  参考文献：
  名称：

  A new route to α-trialkylsilyl aldehydes. The first isolation of α-trimethylsilyl aldehydes

  摘要：

  通过溴锂交换和三烷基硅基的 1â3 迁移，从三甲基硅基和三乙基硅基 δ溴烯醇醚 1 中得到δ-三甲基硅基和δ-三乙基硅基醛 6。

  DOI：

  10.1039/c39930001763
• 作为产物：
  描述：

  1,5-二碘戊烷 在 正丁基锂 、 nickel(II) salen 、 tetramethylammonium tetrafluoroborate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 5-十一炔
  参考文献：
  名称：

  二甲基甲酰胺中碳阴极上电生成的镍（I）Salen存在下卤代炔烃的催化还原和分子内环化

  摘要：

  通过[[2,2 ' -[1,2-乙二基双（亚硝甲基））]双[苯酚基]催化还原1-碘-或1-溴-5-癸炔可以方便地制备亚萘基环戊烷，产率高达86％。] -N，N '，O，O '在包含四氟硼酸四甲基铵的二甲基甲酰胺中的碳阴极上电生成的]镍酸酯（I）。该电合成可以在卤代炔是电惰性的电势下完成，并且可以在室温下30分钟内完成。尝试在类似条件下分别由1-卤代4-壬炔和11-卤代5-十一炔合成戊二烯环丁烷和戊二烯环己烷可提供非常低的收率（分别为2％和6％）。衍生自各种卤代炔烃的其他产物是二聚体，炔烃和1-炔烃。由1-卤代4-壬炔和11-卤代5-十一炔产生的二聚体（alkadiynes）的产率为80％至89％，而icosa-5,15-diyne（由1-卤代获得的二聚体）发现-5-decyne）的收率明显较低（≤13％）。炔烃和1-炔烃的产率分别为3-10％和2-3％。提出了一种机制方案，该方案涉及由镍（

  DOI：

  10.1021/jo052007a

文献信息

• The reaction of lithium trialkylalkynylborate with methanesulphinyl chloride
  作者：M. Naruse、K. Utimoto、H. Nozaki

  DOI：10.1016/s0040-4020(01)97353-3

  日期：1974.1

  Treatment of lithium trialkylalkynylborates (1) with methanesulphinyl chloride gives internal acetylenes (2) in good yields. The reaction proceeds via β-methanesulphinylvinylboranes 3, followed by cis elimination of methanesulphinyl group and dialkylboron groups. The reaction mixture of B-alkyl-9-BBN and 1-lithio-1-heptyne has been treated with methanesulphinyl chloride to provide mainly a cyclooctane

  用甲磺酰氯处理三烷基炔基硼酸锂（1），以良好的收率得到内部乙炔（2）。该反应通过β-甲磺酰基乙烯基硼烷3进行，然后顺式消除甲磺酰基和二烷基硼基团。B-烷基-9-BBN和1-lithio-1-庚炔的反应混合物已用甲磺酰氯处理，主要提供了环辛烷衍生物6。根据甲烷磺酰氯方法中的空间因素解释了这一发现。
• Iridium-Catalyzed Carbonylative Synthesis of Halogen-Containing Quinolin-2(1<i>H</i>)-ones from Internal Alkynes and Simple Anilines
  作者：Fengxiang Zhu、Yahui Li、Zechao Wang、Xiao-Feng Wu

  DOI：10.1002/adsc.201600680

  日期：2016.11.3

  straightforward synthesis of halogen‐containing quinolin‐2(1H)‐ones. The reaction proceeds without preactivation and directing groups through direct N–H and C–H bond activation with a broad substrate scope and high efficiency. Halogen functional groups can be well tolerated here. Remarkably, this is the first example of an iridium‐catalyzed carbonylative C–H activation of anilines.

  喹啉2（1 H）-1是重要的化学药品，在制药中有多种应用。在本文中，我们开发了一种新颖且有效的铱催化的带有内部炔烃的简单苯胺的羰基环化反应，可直接合成含卤素的喹啉-2（1 H）-酮。反应在没有预活化的情况下进行，并通过直接的N–H和C–H键活化来引导基团，具有广泛的底物范围和高效率。此处可以很好地耐受卤素官能团。值得注意的是，这是铱催化苯胺的羰基CH活化的第一个例子。
• Stereoselective Synthesis ofanti-1,4-Diols by a BH3⋅THF-Mediated Rearrangement of 1,2-Disubstituted Cyclobutenes
  作者：Kolja M. Knapp、Bernd Goldfuss、Paul Knochel

  DOI：10.1002/chem.200304902

  日期：2003.11.7

  A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1,2-disubstituted cyclobutenes, provides anti-1,4-diols with good-to-excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.

  通过对1,2-二取代的环丁烯进行氢硼化获得的环丁基硼烷的新的立体选择性重排，可提供具有优异至出色非对映选择性的抗1,4-二醇。基于理论计算，讨论了重排的机理。
• A new general synthesis of aliphatic and terminal alkynes: flash vacuum pyrolysis of β-oxoalkylidenetriphenylphosphoranes
  作者：R. Alan Aitken、J. Ian Atherton

  DOI：10.1039/c39850001140

  日期：——

  conditions the thermal elimination of Ph3PO from β-oxoalkylidenetriphenylphosphoranes, previously confined to cases with an α-electron withdrawing group, has been extended to provide a general, high yielding synthesis of aliphatic and terminal alkynes.

  通过使用快速真空条件，从以前局限于具有电子吸电子基团的情况下，从β-氧代亚烷基三苯并三苯膦中消除Ph 3 PO的范围扩大了，从而提供了一种通常的高产率的脂肪族和末端炔烃合成方法。
• Copper-Catalyzed Cross-Coupling of Alkyl and Aryl Grignard Reagents with Alkynyl Halides
  作者：Gérard Cahiez、Olivier Gager、Julien Buendia

  DOI：10.1002/anie.200905816

  日期：——

  Good old copper! A new general procedure to couple aliphatic and aromatic Grignard reagents with alkynyl halides under copper catalysis is described (see scheme; NMP=N‐methylpyrrolidinone). The reaction is chemoselective and allows preparation of a vast array of simple and functionalized internal alkynes in high yields.

  好老铜！描述了在铜催化下将脂肪族和芳香族格氏试剂与卤代炔烃偶联的新通用程序（参见方案； NMP = N-甲基吡咯烷酮）。该反应是化学选择性的，并允许以高收率制备大量简单且官能化的内部炔烃。

表征谱图