2-乙基丁烯醛 | 19780-25-7

• 物质功能分类: 有机原料 - 醛类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙基丁烯醛
• 中文别名: 2-乙基巴豆醛；2-乙基丁醛-3-烯
• 英文名称: 2-ethylcrotonaldehyde
• 英文别名: 2-ethyl-2-butenal；2-ethylbut-2-enal
• CAS: 19780-25-7
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: IQGZCSXWIRBTRW-UHFFFAOYSA-N

物化性质

• 熔点：
  -78°C (estimate)
• 沸点：
  59 °C / 55mmHg
• 密度：
  0,86 g/cm3
• 闪点：
  31°C
• LogP：
  1.597 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  2
• 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

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  F,Xn
• 安全说明：
  S16,S26,S36,S36/37
• 危险类别码：
  R10
• RTECS号：
  GQ0350000
• 海关编码：
  2912190090
• 危险品运输编号：
  UN 1989
• 储存条件：
  在密封的贮藏器中存放，并将其置于阴凉、干燥处。

SDS

2-Ethylcrotonaldehyde Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2-Ethylcrotonaldehyde

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS
Category 3
Flammable liquids
HEALTH HAZARDS
Category 5
Acute toxicity (Oral)
Acute toxicity (Dermal) Category 3
Category 2
Skin corrosion/irritation
Serious eye damage/eye irritation Category 2A
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Danger
Flammable liquid and vapour
Hazard statements
May be harmful if swallowed
Toxic in contact with skin
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.
Wash hands thoroughly after handling.
Wear protective gloves and eye/face protection.
[Response] 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.
Remove/Take off immediately all contaminated clothing.
Wash contaminated clothing before reuse.
Call a POISON CENTER or doctor/physician if you feel unwell.
2-Ethylcrotonaldehyde

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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: 2-Ethylcrotonaldehyde
>95.0%(GC)
Percent:
CAS Number: 19780-25-7
2-Ethyl-2-butenal
Synonyms:
Chemical Formula: C6H10O

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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.
Call a POISON CENTER or doctor/physician if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Call a POISON CENTER or doctor/physician.
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.
Call a POISON CENTER or doctor/physician if you feel unwell. 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.
2-Ethylcrotonaldehyde

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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 under inert gas.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Air-sensitive
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 - Slightly pale yellow
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
59°C/7.3kPa
Boiling point/range:
Flash point: 31°C
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
Relative density: 0.86
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
orl-rat LD50:2600 uL/kg
Acute Toxicity:
skn-rbt LD50:500 uL/kg
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
2-Ethylcrotonaldehyde

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Section 11. TOXICOLOGICAL INFORMATION
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:
RTECS Number: GQ0350000

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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
Bioaccumulative No data available
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: 1988
Proper shipping name: Aldehydes, flammable, 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

制备方法与用途

制备2-乙基丁烯醛涉及一种α,β-不饱和醛。通过乙醛与正丁醛的反应可以得到β-不饱和醛的混合物，其中主产物即为2-乙基丁烯醛。由于其浓郁的香味、独特的结构以及丰富的化学反应性，α,β-不饱和醛引起了化学家们的极大兴趣。

反应信息

• 作为反应物：
  描述：

  2-乙基丁烯醛 在 platinum(IV) oxide 、 对甲苯磺酸 吡啶 、 三乙烯二胺 、 sodium tetrahydroborate 、 氢气 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Regio-specific total synthesis of (±)-2-hydroxyaklavinone

  摘要：

  DOI：

  10.1016/s0040-4039(01)81382-4
• 作为产物：
  描述：

  1,5-己二烯-3,4-二醇 在 硫酸 作用下， 生成 2-乙基丁烯醛
  参考文献：
  名称：

  Tiffeneau; Weill, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 204, p. 591

  摘要：

  DOI：

文献信息

• Nickel Catalyzed Intermolecular Carbonyl Addition of Aryl Halide
  作者：Seima Ishida、Hiroyuki Suzuki、Seiichiro Uchida、Eiji Yamaguchi、Akichika Itoh

  DOI：10.1002/ejoc.201901367

  日期：2019.12.8

  Nickel‐catalyzed carbonyl arylation reaction employing aldehydes with aryl and allyl halides was demonstrated. Various aryl, α,β‐unsaturated aldehyde and aliphatic aldehydes can be converted into their corresponding secondary alcohols in moderate‐to‐high yields under the reductive coupling condition.

  证明了使用醛与芳基和烯丙基卤化物进行镍催化的羰基芳基化反应。在还原偶联条件下，各种芳基，α，β-不饱和醛和脂肪族醛可以中等至高收率转化为相应的仲醇。
• The mechanism of ozone-alkene reactions in the gas phase. A mass spectrometric study of the reactions of eight linear and branched-chain alkenes
  作者：Richard I. Martinez、John T. Herron、Robert E. Huie

  DOI：10.1021/ja00403a031

  日期：1981.7

  The stable products of the low-pressure (4-8 torr (1 torr = 133.33 Pa)) gas-phase reactions of ozone with ethene, propene, 2-methylpropene, cis-2-butene, trans-2-butene, trans-2-pentene, 2,3-dimethyl-2-butene, and 2-ethyl- 1 -butene have been identified by using a photoionization mass spectrometer coupled to a stirred-flow reactor. The products observed are characteristic of (i) a primary Criegee split

  臭氧与乙烯、丙烯、2-甲基丙烯、顺-2-丁烯、反-2-丁烯、反- 2-戊烯、2,3-二甲基-2-丁烯和2-乙基-1-丁烯已通过使用耦合到搅拌流反应器的光电离质谱仪进行鉴定。观察到的产物具有以下特征：（i）初级 Criegee 分裂成氧代烷烃（醛或酮）和 Criegee 中间体，（ii）反应
• Unusual Coupling Reactions of Aldehydes and Alkynes: A Novel Preparation of Substituted Phthalic Acid Derivatives by Automated Synthesis
  作者：Axel Jacobi von Wangelin、Helfried Neumann、Dirk Gördes、Stefan Klaus、Haijun Jiao、Anke Spannenberg、Thomas Krüger、Christian Wendler、Kerstin Thurow、Norbert Stoll、Matthias Beller

  DOI：10.1002/chem.200204668

  日期：2003.5.23

  Based upon a highly versatile multicomponent methodology, a new one-pot synthesis of substituted phthalic acid derivatives from alpha,beta-unsaturated aldehydes was developed. The reaction involves the intermediacy of an acetamidodiene species which undergoes Diels-Alder addition to diethyl acetylenedicarboxylate. The resultant acetamidocyclohexadiene is subject to elimination of acetamide under the

  基于高度通用的多组分方法，开发了一种新的由一锅合成的α，β-不饱和醛取代邻苯二甲酸衍生物。该反应涉及乙酰胺二烯物质的中间体，该乙酰胺二烯物质经过乙炔二羧酸二乙酯的Diels-Alder加成反应。在反应条件下，将所得的乙酰氨基环己二烯除去乙酰胺，以高收率得到取代的邻苯二甲酸二乙酯。该多米诺缩合-环加成-消除序列已应用于多种α，β-不饱和醛。此外，我们证明了平行和自动化合成技术的开发可用于快速筛选反应条件和组成。
• Use of defined cyclohexenones as agents for the superadditive enhancement of an olfactory impression and fragrance and/or flavor material composition
  申请人：Symrise AG

  公开号：US10045551B2

  公开（公告）日：2018-08-14

  A compound of Formula (I) or of a mixture comprising two, three, four, five, six or a plurality of different compounds of Formula (I) for the superadditive enhancement of an olfactory impression. The invention also relates to novel fragrance and/or flavor material compositions which, in addition to a compound of Formula (I) or a mixture thereof, further contains one, two, three or a plurality of further fragrance and/or flavor materials, the fragrance and/or flavor material or the further fragrance and/or flavor materials not being compound of Formula (I).

  公式(I)的化合物或包含两个、三个、四个、五个、六个或多个不同的公式(I)化合物的混合物，用于超加强嗅觉印象。该发明还涉及新的香味和/或风味材料组合，除了包含公式(I)的化合物或其混合物之外，还进一步含有一种、两种、三种或多种其他香味和/或风味材料，这些香味和/或风味材料或其他香味和/或风味材料不是公式(I)的化合物。
• ２，３−ジメチル−２−シクロペンテノンの製造方法
  申请人：ＪＮＣ株式会社

  公开号：JP2020015673A

  公开（公告）日：2020-01-30

  【課題】２，３−ジメチル−２−シクロペンテノンの工業的な製造方法を提供する。【解決手段】式（１）で示される化合物とアセトンを、塩基の存在下に反応させて、式（２）で示される化合物を得る第一工程、さらに、式（２）で示される化合物から第二工程、第三工程、第四工程を経て、式（６）で示される化合物を得る。さらに、酸または塩基の存在下に反応させて、式（７）で示される２，３−ジメチル−２−シクロペンテノンを製造する。【選択図】なし

  提供工业生产2,3-二甲基-2-环戊烯酮的方法。将式（1）中所示的化合物与丙酮在碱的存在下反应，得到式（2）中所示的化合物作为第一步骤，然后通过从式（2）中所示的化合物经过第二步骤、第三步骤和第四步骤，得到式（6）中所示的化合物。然后，在酸或碱的存在下反应，制备2,3-二甲基-2-环戊烯酮，如式（7）所示。【选择图】无

表征谱图