9-十一碳炔-1-醇 | 177961-61-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 9-十一碳炔-1-醇
• 中文别名: 9-十一炔-1-醇
• 英文名称: undec-9-yn-1-ol
• 英文别名: 9-undecyn-1-ol；9-undecynoyl
• CAS: 177961-61-4
• 化学式: C₁₁H₂₀O
• mdl: MFCD04116376
• 分子量: 168.279
• InChiKey: YSDWKSIWEWYTEF-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C/0.03 mmHg
• 密度：
  0.866 g/mL at 25 °C
• 闪点：
  110 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn,N
• 危险类别码：
  R22
• 危险品运输编号：
  UN 3082 9/PG 3
• 安全说明：
  S26
• WGK Germany：
  3
• 危险标志：
  GHS07,GHS09
• 危险性描述：
  H302,H319,H400
• 危险性防范说明：
  P273,P305 + P351 + P338

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 9-Undecyn-1-ol

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Acute toxicity, Oral (Category 4)
Eye irritation (Category 2)
Acute aquatic toxicity (Category 1)
According to European Directive 67/548/EEC as amended.
Harmful if swallowed. Irritating to eyes. Very toxic to aquatic organisms, may cause long-term adverse effects
in the aquatic environment.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
H400 Very toxic to aquatic life.
Precautionary statement(s)
P273 Avoid release to the environment.
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
N Dangerous for the environment
R-phrase(s)
R22 Harmful if swallowed.
R36 Irritating to eyes.
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety data
sheets.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C11H20O
Molecular Weight : 168,28 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
9-Undecyn-1-ol
177961-61-4 - - Acute Tox. 4; Eye Irrit. 2; -
Aquatic Acute 1; H302, H319,
H400
Xn, N, R22 - R36 - R50/53
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
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
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.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Evacuate personnel to safe areas.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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.

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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.
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.
Recommended storage temperature: 2 - 8 °C

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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
Face shield and safety glasses 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, 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 92 - 93 °C at 0,04 hPa
Flash point > 110 °C - closed cup
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Density 0,866 g/cm3 at 25 °C
Water solubility no data available
Partition coefficient: log Pow: 3,481
n-octanol/water

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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

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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 serious 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

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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
Very toxic to aquatic life.

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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.

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Section 14. TRANSPORT INFORMATION
ADR/RID
UN-Number: 3082 Class: 9 Packing group: III
Proper shipping name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (9-Undecyn-1-ol)
IMDG
UN-Number: 3082 Class: 9 Packing group: III EMS-No: F-A, S-F
Proper shipping name: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, LIQUID, N.O.S. (9-Undecyn-1-ol)
Marine pollutant: Marine pollutant
IATA
UN-Number: 3082 Class: 9 Packing group: III
Proper shipping name: Environmentally hazardous substance, liquid, n.o.s. (9-Undecyn-1-ol)
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination packagings
containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Acute Tox. Acute toxicity
Aquatic Acute Acute aquatic toxicity
Eye Irrit. Eye irritation
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
H400 Very toxic to aquatic life.
N Dangerous for the environment
Xn Harmful
R22 Harmful if swallowed.
R36 Irritating to eyes.
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic
environment.
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：

  9-十一碳炔-1-醇 在 Lindlar's catalyst 重铬酸吡啶 、 hexacarbonyl molybdenum 、 氢气 、 对氯苯酚 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 氧杂环十三烷-2-酮
  参考文献：
  名称：

  Fürstner, Alois; Guth, Oliver; Rumbo, Antonio, Journal of the American Chemical Society, 1999, vol. 121, # 48, p. 11108 - 11113

  摘要：

  DOI：

文献信息

• Photo-organocatalytic synthesis of acetals from aldehydes
  作者：Nikolaos F. Nikitas、Ierasia Triandafillidi、Christoforos G. Kokotos

  DOI：10.1039/c8gc03605e

  日期：——

  developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied.

  已经开发出用于醛的高效缩醛化的温和绿色光有机催化方案。利用噻吨酮作为光催化剂，使用廉价的家用灯作为光源，已将各种芳族和脂族醛高产率地转化为无环和环状缩醛。反应机理得到了广泛的研究。
• Synthesis by Ring-Closing Alkyne Metathesis with Selective Hydrogenation, and Olfactory Comparison of (7<i>E</i>)- and (7<i>Z</i>)-Cyclohexadec-7-enone (<i>Aurelione</i>^®)
  作者：Marion Mathys、Philip Kraft

  DOI：10.1002/cbdv.201400011

  日期：2014.10

  synthesized via cyclohexadec‐7‐ynol (16) by ring‐closing alkyne metathesis of icosa‐2,18‐diyn‐9‐ol (15), employing an in situ‐formed catalyst from Mo(CO)6 and 4‐(trifluoromethyl)phenol. Pyridinium chlorochromate (PCC) oxidation and subsequent Lindlar hydrogenation afforded the (7Z)‐configured isomer (7Z)‐6, while hydrosilylation of the intermediate cyclohexadec‐7‐ynone (17), followed by desilylation, provided

  环十六-7-烯酮（6，Aurelione®）的两种CC-键异构体都是通过环十六-7-炔醇（16）通过icosa-2,18-diyn-9-ol的闭环炔复分解选择性合成的（ 15)，采用由 Mo(CO)6 和 4-(三氟甲基)苯酚原位形成的催化剂。氯铬酸吡啶 (PCC) 氧化和随后的 Lindlar 氢化得到 (7Z) 构型的异构体 (7Z)-6，而中间体环十六烷-7-炔酮 (17) 的氢化硅烷化，然后脱甲硅烷基化，提供 (7E) 构型的环十六烷‐7-烯酮 ((7E)‐6)。炔复分解反应的底物由环庚酮 (7) 通过氯甲基卡宾环加成到其三甲基甲硅烷基烯醇醚 8 上制备，随后加合物 9 在重排为 2-甲基环辛基-2-烯酮 (10) 下环扩大，其经过 WeitzScheffer 环氧化和 Eschenmoser Ohloff 裂解成非 7-ynal (12)。它与 11-bromoundec-2-yne
• Robust Alkyne Metathesis Catalyzed by Air Stable d² Re(V) Alkylidyne Complexes
  作者：Mingxu Cui、Wei Bai、Herman H. Y. Sung、Ian D. Williams、Guochen Jia

  DOI：10.1021/jacs.0c06581

  日期：2020.8.5

  We report in this communication the first example of catalytic alkyne metathesis reactions mediated by well-defined non-d0 alkylidyne complexes. The air-stable d2 Re(V) alkylidyne complex Re4, bearing two PO-chelating ligands and a labile pyridine ligand, could catalyze homo-metathesis of internal alkynes with a broad substrate scope, including alcohols, amines and even carboxylic acids. The catalyst

  我们在此通讯中报告了由明确定义的非 d0 烷炔配合物介导的催化炔复分解反应的第一个例子。空气稳定的 d2 Re(V) 亚烷基配合物 Re4，带有两个 PO 螯合配体和一个不稳定的吡啶配​​体，可以催化具有广泛底物范围的内炔的均位复分解，包括醇、胺甚至羧酸。该催化剂在固体和溶液状态下都可以耐受加热、空气和水分，催化复分解反应可以在湿溶剂中正常进行。
• Hexafluoroisopropanol‐Promoted or Brønsted Acid‐Mediated Photochemical [2+2] Cycloadditions of Alkynes with Maleimides
  作者：Ierasia Triandafillidi、Nikolaos F. Nikitas、Petros L. Gkizis、Nikoleta Spiliopoulou、Christoforos G. Kokotos

  DOI：10.1002/cssc.202102441

  日期：2022.2.18

  Photochemistry: A systematic study for the development of a mild, metal-free, and easy-to-execute protocol for the photochemical [2+2] cycloaddition of alkynes with maleimides is presented.

  光化学：提出了一项系统研究，用于开发一种温和、无金属且易于执行的方案，用于炔烃与马来酰亚胺的光化学 [2+2] 环加成反应。
• Using stereoretention for the synthesis of <i>E</i>-macrocycles with ruthenium-based olefin metathesis catalysts
  作者：Tonia S. Ahmed、T. Patrick Montgomery、Robert H. Grubbs

  DOI：10.1039/c8sc00435h

  日期：——

  The synthesis of E-macrocycles is achieved using stereoretentive, Ru-based olefin metathesis catalysts supported by dithiolate ligands. Kinetic studies elucidate marked differences in activity among the catalysts tested, with catalyst 4 providing meaningful yields of products in much shorter reaction times than stereoretentive catalysts 2 and 3. Macrocycles were generated with excellent selectivity

  E-大环的合成是使用二硫醇盐配体负载的立体保持性，Ru基烯烃复分解催化剂来实现的。动力学研究阐明了所测试的催化剂之间活性的显着差异，其中催化剂4在比立体保持催化剂2和3短得多的反应时间内提供了有意义的产物收率。大环以优异的选择性（> 99％E）和中等至高收率（47-80％收率）从带有两种E-构型烯烃的二烯原料中生成。构建了各种环，范围从12到18元的大环化合物，包括抗生素回收苯环内酯。