2,4-已二烯 | 5194-50-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 中文名称: 2,4-已二烯
• 英文名称: (E,Z)-2,4-hexadiene
• 英文别名: cis,trans-2,4-hexadiene；(2Z,4E)-hexadiene；cis,trans-Hexa-2,4-diene；(2Z,4E)-hexa-2,4-diene
• CAS: 5194-50-3
• 化学式: C₆H₁₀
• 分子量: 82.1454
• InChiKey: APPOKADJQUIAHP-CIIODKQPSA-N

物化性质

• 熔点：
  -96.1 °C
• 沸点：
  83.5 °C
• 密度：
  0.715±0.06 g/cm3(Predicted)
• 保留指数：
  673;673

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

毒理性

• 副作用

神经毒素 - 急性溶剂综合征

Neurotoxin - Acute solvent syndrome

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• 危险品标志：
  F,Xi
• 危险类别码：
  R11
• 危险品运输编号：
  UN 2458 3
• 海关编码：
  2901299090
• 包装等级：
  II
• 危险类别：
  3.1
• 安全说明：
  S16,S26,S36

SDS

Name:	Cis-2 trans-4-hexadiene Material Safety Data Sheet
Synonym:
CAS:	5194-50-3

Section 1 - Chemical Product MSDS Name:Cis-2 trans-4-hexadiene Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
5194-50-3	cis-2, trans-4-Hexadiene	95%	225-979-3

Hazard Symbols: XI F
Risk Phrases: 11 36/37

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Highly flammable. Irritating to eyes and respiratory system.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Flammable liquid and vapor.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep away from heat, sparks and flame.
Storage:
Keep away from heat, sparks, and flame. Flammables-area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 5194-50-3: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure. Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use. Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Color: Clearlight yellow liquid
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 80.0 - 82.0 deg C @ 760.00mm Hg
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: -7 deg C ( 19.40 deg F)
Explosion Limits, lower: .06 vol %
Explosion Limits, upper: .02 vol %
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .7200g/cm3
Molecular Formula: CH3CH=CHCH=CHCH3
Molecular Weight: 82.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 5194-50-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
cis-2, trans-4-Hexadiene - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: HEXADIENE
Hazard Class: 3
UN Number: 2458
Packing Group: II
IMO
Shipping Name: HEXADIENE
Hazard Class: 3
UN Number: 2458
Packing Group: II
RID/ADR
Shipping Name: HEXADIENES
Hazard Class: 3
UN Number: 2458
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI F
Risk Phrases:
R 11 Highly flammable.
R 36/37 Irritating to eyes and respiratory system.
Safety Phrases:
S 16 Keep away from sources of ignition - No
smoking.
WGK (Water Danger/Protection)
CAS# 5194-50-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 5194-50-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 5194-50-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4-已二烯 在 palladium on activated charcoal 、 焦磷酸硫胺素 氢气 、 氧气 作用下， 以 四氯化碳 为溶剂， 生成 2,5-己二醇
  参考文献：
  名称：

  [4 + 2]-单线态氧与共轭无环己二烯的环加成反应：单线态氧诱导的顺式⇌反式异构化的证据

  摘要：

  将单线态氧加至反式，反式-2,4-己二烯（1）立体定向生成内过氧化物2。然而，与顺式，反式-2,4-己二烯（4）混合使用非对映异构的内过氧化物2 + 5，被观察到。通过4与单线态氧/二氮杂二羧酸二乙酯的竞争Diels-Alder反应，获得了单线态氧诱导的顺式反式异构化的证据。

  DOI：

  10.1016/s0040-4039(00)86254-1
• 作为产物：
  描述：

  2,4-已二烯 以 gas 为溶剂， 生成 2,4-已二烯
  参考文献：
  名称：

  Excited-state rearrangements of 1,3- and 1,5-dienes in a radio frequency plasma

  摘要：

  DOI：

  10.1021/ja00277a036

文献信息

• The<i>in situ</i>-Generated Nickel(0)-catalyzed Homo-coupling of Alkenyl Halides with Zinc Powder. A Specific Outcome in Stereochemistry
  作者：Kentaro Takagi、Harutaka Mimura、Saburo Inokawa

  DOI：10.1246/bcsj.57.3517

  日期：1984.12

  The catalytic activity of nickel(0) generated in situ from nickel(II) salt was examined in a dehalogenative coupling of alkenyl halides with zinc powder. The reaction of alkenyl bromides took place provided that potassium iodide was present to assist the reduction of nickel(II) with zinc powder, and also to convert the alkenyl bromides to the corresponding alkenyl iodides. A speculative view concerning

  在烯基卤化物与锌粉的脱卤偶联中检测了从镍 (II) 盐原位生成的镍 (0) 的催化活性。烯基溴化物的反应发生，前提是存在碘化钾以帮助用锌粉还原镍 (II)，并将烯基溴化物转化为相应的烯基碘化物。为了解释观察到的独特立体化学，提出了关于歧化步骤的推测性观点。
• Stereospecific palladium-catalyzed 1,4-acetoxychlorination of 1,3-dienes
  作者：Jan-E. Bäckvall、Ruth E. Nordberg、Jan-E. Nyström

  DOI：10.1016/s0040-4039(00)87173-7

  日期：1982.1

  Palladium-catalyzed oxidation of 1,3-dienes in acetic acid in the presence of LiCl and LiOAc produces 1-acetoxy-4-chloro-2-alkenes in high selectivity. The 1,4-adducts were stereo- and regioselectively functionalized.

  在LiCl和LiOAc的存在下，钯在乙酸中催化1,3-二烯的氧化可高选择性地生成1-乙酰氧基-4-氯-2-烯烃。1,4-加合物被立体和区域选择性官能化。
• Diels-Alder reactions using supercritical water as an aqueous solvent medium
  作者：Michael B. Korzenski、Joseph W. Kolis

  DOI：10.1016/s0040-4039(97)01274-4

  日期：1997.8

  A variety of Diels-Alder reactions have been performed in supercritical water as a reaction medium. The rapid reaction of Diels-Alder reactions of cyclopentadiene and various electron poor dienophiles such as diethyl fumarate and acrylonitrile is observed in supercritical water, and leads to high yields of clean products without added catalysts.

  在超临界水中作为反应介质已经进行了多种Diels-Alder反应。在超临界水中观察到了环戊二烯与各种电子贫乏的亲二烯体（如富马酸二乙酯和丙烯腈）的狄尔斯-阿尔德反应的快速反应，可在不添加催化剂的情况下获得高产率的清洁产品。
• Reactions of cumulated and conjugated dienes with sulfur trioxide
  作者：Ruud M. Schonk、Bert H. Bakker、Hans Cerfontain

  DOI：10.1002/recl.19931120301

  日期：——

  The reactions of a series of cumulated (1a-5a) and conjugated alkadienes (8a-13a) with sulfur trioxide have been studied in the temperature range of −60 to 25°C using dichloromethane as solvent and 1.5 equiv of dioxane as reactivity moderator. Reaction of tetramethylallene (1a) at low temperature yielded the β-sultone 1b, which at 0°C was slowly converted into 2,4-dimethyl-1,3-pentadiene-3-sulfonic

  在-60至25°C的温度范围内，使用二氯甲烷作为溶剂，使用1.5当量的二恶烷作为反应调节剂，研究了一系列累积的（1a-5a）和共轭链二烯（8a-13a）与三氧化硫的反应。四甲基丙烯烯（1a）在低温下的反应产生β-磺内酯1b，其在0℃下缓慢转化为2，4-二甲基-1，3-戊二烯-3-磺酸（1f）。在另外的SO 3存在下，该共轭二烯磺酸在0℃下迅速转化为不饱和δ-磺内酯1g。1,2-环壬二烯（5a）与SO 3的反应作为通常观察到的不饱和δ-磺内酯g的形成的一个例外，因为在低温下形成2-环壬烯-2，1-磺内酯（5b）和相应的羰基硫酸盐（5d）的1：1混合物。将这些产物在0℃下均转化为相同的链二烯磺酸，即。6。当使用过量的SO 3时，6被迅速转化为3-环壬烯-1，2-磺内酯-3-磺酸（7）。
• NICKEL-CATALYZED ULLMANN-TYPE COUPLING OF ALKENYL HALIDES WITH ZINC POWDER
  作者：Kentaro Takagi、Naomi Hayama

  DOI：10.1246/cl.1983.637

  日期：1983.5.5

  Convenient procedure for an Ullmann-type coupling of alkenyl halides using zinc powder, nickel(II) chloride, and potassium iodide and/or thiourea is presented. One double bond in the produced diene retained the configuration of a starting material, while partial cis–trans isomerization was observed in the second one.

  介绍了一种使用锌粉、氯化镍(II)和碘化钾和/或硫脲的烯基卤化物的Ullmann型偶联反应的简便程序。生成的二烯中，一个双键保持了起始材料的构型，而在第二个双键中观察到了部分的顺-反异构化。

表征谱图