3-己炔-2-酮 | 1679-36-3

• 物质功能分类: 化学试剂 - 有机试剂 - 脂肪酮(含烯醇)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-己炔-2-酮
• 中文别名: 3-己炔基-2-酮；3-己炔-2-酮,97%
• 英文名称: 3-hexyn-2-one
• 英文别名: hex-3-yn-2-one
• CAS: 1679-36-3
• 化学式: C₆H₈O
• mdl: MFCD00041627
• 分子量: 96.1289
• InChiKey: LTAPKZGQTMVYMX-UHFFFAOYSA-N

物化性质

• 沸点：
  68 °C (50 mmHg)
• 密度：
  0.878
• 闪点：
  39 °C
• 稳定性/保质期：

  常温常压下稳定，避免氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  3
• 危险品标志：
  T+
• 安全说明：
  S23,S24/25
• 危险类别码：
  R10
• 海关编码：
  2914190090
• 包装等级：
  III
• WGK Germany：
  3
• 危险品运输编号：
  UN 1224
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

3-Hexyn-2-one Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 3-Hexyn-2-one

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 3
Flammable liquids
HEALTH HAZARDS
Category 3
Acute toxicity (Oral)
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Hazard statements Flammable liquid and vapour
Toxic if swallowed
Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
[Prevention]
Keep container tightly closed.
Use explosion-proof electrical/ventilating/lighting equipment. Take precautionary
measures against ignition by the static discharge and the spark.
Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
[Response] IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse
mouth.
IF IN EYES: 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.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.
3-Hexyn-2-one

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Section 2. HAZARDS IDENTIFICATION
[Storage] Store in a well-ventilated place. Keep cool.
Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 3-Hexyn-2-one
>95.0%(GC)
Percent:
CAS Number: 1679-36-3
1-Butynyl Methyl Ketone
Synonyms:
Chemical Formula: C6H8O

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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.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. 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.
Immediately call a POISON CENTER or doctor/physician. Rinse mouth.
Ingestion:
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
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: Keep containers cool by
spraying with water. Eliminate all ignition sources if safe to do so.
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
equipment for firefighters:

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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 dry sand or inert absorbent before recovering it into an
containment and cleaning airtight container. In case of large amount of spillage, contain a spill by bunding.
up: Adhered or collected 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
case of a fire. Use spark-proof tools and explosion-proof equipment.
hazards:

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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. Keep away from heat/sparks/open flame/hot
surfaces. -No smoking. Take measures to prevent the build up of electrostatic
charge. Use explosion-proof equipment. Wash hands and face thoroughly after
handling.
3-Hexyn-2-one

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Section 7. HANDLING AND STORAGE
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, dark and well-ventilated place.
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
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.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Liquid
Form: Clear
Colorless - Reddish yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
77°C/10kPa
Boiling point/range:
Flash point: 39°C
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
0.88
Relative density:
Solubility(ies):
No data available
[Water]
[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:
Conditions to avoid: Spark, Open flame, Static discharge
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
3-Hexyn-2-one

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Section 11. TOXICOLOGICAL INFORMATION
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
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):

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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: 3: Flammable liquid.
Subsidiary risk: 6.1: Toxic substance.
UN-No: 1992
Proper shipping name: Flammable liquid, toxic, n.o.s.
Packing group: III

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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：

  3-己炔-2-酮 在 recombinant Cyclocybe aegerita ene/yne-reductase CaEnR₁ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 生成 2-己酮
  参考文献：
  名称：

  使用新型的Cyclocybe aegerita烯/炔还原酶扩展生物催化工具箱

  摘要：

  这项研究引入了一种新的来自Cyclocybe aegerita的烯/炔还原酶，具有广泛的底物范围，包括脂肪族和芳香族烯烃/炔烃，其中脂肪族C8烯酮，C8烯烃和芳香族硝基烯是首选的底物。通过比较烯烃和炔烃，观察到向炔烃的转化率降低了约2倍。此外，可以表明，炔烃的还原是通过将炔烃缓慢还原为烯烃，然后快速还原为相应的烷烃来进行的。没有观察到烯烃的积累。此外，在α，β，γ，δ-的α，β位的双键区域选择性还原发生了不饱和的烯基。这以及不同的脂族和芳族炔烃首次生物催化还原为烷烃，突显了这种生物催化剂的新颖性。因此，通过对新的烯还原酶CaeEnR1的研究，揭示了一种有前途的底物范围，该范围可能描述了此类反应在化学领域内的广泛发生。

  DOI：

  10.1002/cctc.202002011
• 作为产物：
  描述：

  1-己烯-3-炔 在 氢氧化钾 、 硫酸 、 对苯二酚 作用下， 生成 3-己炔-2-酮
  参考文献：
  名称：

  Petrow; Porfir'ewa, Doklady Akademii Nauk SSSR, 1953, vol. 90, p. 561,562,563

  摘要：

  DOI：

文献信息

• [5.5]-<i>P</i>-Spirocyclic Chiral Triaminoiminophosphorane-Catalyzed Asymmetric Hydrophosphonylation of Aldehydes and Ynones
  作者：Daisuke Uraguchi、Takaki Ito、Yuto Kimura、Yumiko Nobori、Makoto Sato、Takashi Ooi

  DOI：10.1246/bcsj.20170040

  日期：2017.5.15

  Development of highly efficient and enantioselective hydrophosphonylations of aldehydes and ynones mediated by [5.5]-P-spirocyclic chiral triaminoiminophosphoranes as base catalysts is described. T...

  描述了由 [5.5]-P-螺环手性三氨基亚氨基正膦作为碱催化剂介导的醛和炔酮的高效和对映选择性氢膦酰化的开发。天...
• Fused bicyclic systems through a ni-mediated intermolecular cyclopentenone annulation
  作者：Francisco Camps、Amadeu Llebaria、Josep M. Moretó、Lluís Pagès

  DOI：10.1016/s0040-4039(00)77686-6

  日期：1992.1

  The extension of the Ni(CO)4 promoted carbonylative cycloaddition of acetylenes and allyl halides to the 5–8 membered 3-halocycloolefins leads efficiently to the formation of the corresponding 4–5 fused 2-cyclopentenones with high regio and stereoselectivities.

  Ni（CO）4的扩展促进了乙炔和烯丙基卤的羰基化环加成反应生成5-8元的3-卤代环烯烃，从而有效地形成了具有高区域和立体选择性的相应的4-5稠合的2-环戊烯酮。
• Controlled Single and Double Iodofluorination of Alkynes with DIH- and HF-Based Reagents
  作者：Lukas Pfeifer、Véronique Gouverneur

  DOI：10.1021/acs.orglett.8b00321

  日期：2018.3.16

  terminal alkynes using 1,3-diiodo-5,5,-dimethylhydantoin and HF-based reagents is disclosed. This approach is used to prepare a fluorinated tamoxifen derivative in two steps from commercially available starting materials. A facile method enabling controlled regioselective double iodofluorination of terminal alkynes is also presented.

  公开了使用1，3-二碘-5，5，-二甲基乙内酰脲和基于HF的试剂进行内部和末端炔的区域和立体选择性碘氟化的新方案。该方法用于从市售原料中分两步制备氟化他莫昔芬衍生物。还提出了一种可控制末端炔烃的区域选择性双碘氟化的简便方法。
• Copper(I)-Catalyzed Enantioselective Incorporation of Ketones to Cyclic Hemiaminals for the Synthesis of Versatile Alkaloid Precursors
  作者：Shi-Liang Shi、Xiao-Feng Wei、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/ja308872z

  日期：2012.10.17

  A general catalytic enantioselective method that can produce five-, six-, and seven-membered N-heterocycles possessing various ketone moieties starting from stable and easily available cyclic hemiaminals and ketones was developed. The method involves three successive steps in one pot (aldol addition, dehydration, and enantioselective intramolecular aza-Michael reaction), all of which are promoted by

  开发了一种通用的催化对映选择性方法，该方法可以从稳定且易于获得的环状半胺醛和酮开始生产具有各种酮部分的五元、六元和七元 N-杂环。该方法包括三个连续步骤（醛醇加成、脱水和对映选择性分子内氮杂-迈克尔反应），所有这些都由手性铜（I）-共轭 Brønsted 碱催化剂促进。该方法可用于快速获取用于合成药物铅生物碱的通用手性构件。
• Formation of Reactive π-Conjugated Frustrated N/B Pairs by Borane-Induced Propargyl Amine Rearrangement
  作者：Tongdao Wang、Constantin G. Daniliuc、Christian Mück-Lichtenfeld、Gerald Kehr、Gerhard Erker

  DOI：10.1021/jacs.7b11958

  日期：2018.3.14

  substituted alkenyl-bridged frustrated N/B Lewis pairs 5. Their structures and spectroscopic features indicate a pronounced participation of the mesomeric s-trans-iminium/borata-alkene resonance form. The compounds are thought to be formed in a stepwise addition/rearrangement process which is initiated by a trans-1,2-amine/borane FLP addition to the carbon-carbon triple bond to generate a reactive zwitterionic

  N-炔丙基四甲基哌啶与一系列反式-烯基-B(C6F5)2 化合物反应，得到取代的烯基桥连的受挫 N/B 路易斯对 5。它们的结构和光谱特征表明中间体 s-反式亚胺鎓的显着参与/硼酸烯烃共振形式。这些化合物被认为是在逐步加成/重排过程中形成的，该过程由反式-1,2-胺/硼烷 FLP 加成到碳-碳三键引发，生成反应性两性离子氮丙啶鎓/链烯基硼酸盐中间体。随后的烯基硼酸盐攻击导致活化的三元杂环打开，并形成产物 5a-c。用 B( )3 处理炔丙基-TMP 底物给出了这种氮丙啶鎓/硼酸甜菜碱的稳定实例，该实例已被分离并充分表征。产品 5a-c 是有源 N/B FLP。他们在温和条件下异裂二氢，得到相应的 NH+/BH- 产物 9a-c。这些包含 Z 构型的核心 C=C 双键，这表明在该反应过程中围绕 5a-c 的中心 CC 键的旋转平衡。通过 DFT 计算分析了 5c 系统的结构和化学特征。