1,6-二苯基-1,3,5-己三烯 | 1720-32-7

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,6-二苯基-1,3,5-己三烯
• 中文别名: 1,6-二苯基-1,3,5-7己三烯；二肉桂酰
• 英文名称: 1,6-diphenyl-hexa-1,3,5-triene
• 英文别名: DPH；1,6-diphenyl-1,3,5-hexatriene；diphenylhexatriene；1,6-diphenylhexatriene；Benzene, 1,1'-(1,3,5-hexatriene-1,6-diyl)bis-；6-phenylhexa-1,3,5-trienylbenzene
• CAS: 1720-32-7
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: BOBLSBAZCVBABY-UHFFFAOYSA-N

物化性质

• 熔点：
  199-203 °C (lit.)
• 沸点：
  309.49°C (rough estimate)
• 密度：
  1.0479 (estimate)
• 溶解度：
  可溶于氯仿（少许）、二氯甲烷（少许）
• 稳定性/保质期：

  常温常压下稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2902909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	1 6-Diphenyl-1 3 5-Hexatriene 98% Material Safety Data Sheet
Synonym:	Benzene,1,1'-(1,3,5-Hexatriene-1,6-diyl)bis-
CAS:	1720-32-7

Section 1 - Chemical Product MSDS Name:1 6-Diphenyl-1 3 5-Hexatriene 98% Material Safety Data Sheet
Synonym:Benzene,1,1'-(1,3,5-Hexatriene-1,6-diyl)bis-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1720-32-7	Benzene, 1,1'-(1,3,5-hexatriene-1,6-di	98	217-011-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1720-32-7: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: yellow
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 201.50 - 202.50 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C18H16
Molecular Weight: 232.33

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1720-32-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Benzene, 1,1'-(1,3,5-hexatriene-1,6-diyl)bis- - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 1720-32-7: No information available.
Canada
CAS# 1720-32-7 is listed on Canada's NDSL List.
CAS# 1720-32-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1720-32-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

1,6-二苯基六-1,3,5-三烯是一种荧光探针。

反应信息

• 作为反应物：
  描述：

  1,6-二苯基-1,3,5-己三烯 在 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 6-苯基己基苯
  参考文献：
  名称：

  Kuhn; Winterstein, Helvetica Chimica Acta, 1928, vol. 11, p. 113

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-苯基(2-苯乙烯基环丙基)甲醇 以 二甲基亚砜 为溶剂， 反应 5.0h， 以74%的产率得到1,6-二苯基-1,3,5-己三烯
  参考文献：
  名称：

  取代丁二烯和共轭多烯的高度立体选择性合成

  摘要：

  通过环丙基甲醇在二甲亚砜中的热脱水开环，已开发出高度立体选择性的1,3-丁二烯及其高级烯基类似物的合成方法。

  DOI：

  10.1016/s0040-4039(00)77721-5

文献信息

• Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (<i>E</i>)-Stilbenes and (1<i>E</i>,3<i>E</i>)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products
  作者：Zhao Zhang、Dejiang Zhang、Longzhi Zhu、Dishu Zeng、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acs.orglett.1c01532

  日期：2021.7.16

  A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The

  公开了一种通用且有效的钯催化的有机锑与苯乙烯的交叉偶联，以得到 ( E )-烯烃。通过使用有机锑试剂，该方法可以以良好的收率和高E / Z制备不对称的 ( E )-1,2-二芳基乙烯和 (1 E ,3 E )-1,4-二芳基丁二烯-1,3-二烯选择性和良好的官能团耐受性。白藜芦醇和 DMU-212 以高产率合成。该协议可以扩展到 (1 E ,3 E ,5 E )-1,6-diphenylhexa-1,3,5-triene的合成,产率为 40%。产品5e、5f和7a 显示出良好的光致发光量子产率，范围为 72% 至 99%。
• Reductive Coupling of Geminal Dichlorides by Iron(II) Oxalate Dihydrate
  作者：Jitender M. Khurana、Golak C. Maikap、Sanjay Mehta

  DOI：10.1055/s-1990-26998

  日期：——

  A facile procedure for the quantitative conversion of geminal dichlorides to E olefins with iron(II) oxalate dihydrate in refluxing anhydrous dimethylformamide under a nitrogen atmosphere is described. The coupling proceeds via the corresponding vicinal dichlorides.

  本文描述了一种简便的方法，通过在氮气气氛下，以二水合草酸亚铁作为催化剂，在无水二甲基甲酰胺中回流反应，将偕二氯化合物定量转化为E型烯烃。反应过程中经历了相应的邻二氯化物中间体。
• Palladium-Catalyzed Syntheses of Conjugated Trienes
  作者：Akira Kasahara、Taeko Izumi、Naoto Kudou

  DOI：10.1055/s-1988-27677

  日期：——

  Conjugated trienes 3 and 5 have been prepared by the palladium-catalyzed reaction of alkenes 2 with fumaryl chloride (1) and (E)-5-phenyl-2,4-pentadienoyl chloride (4), respectively, in the presence of N-ethylmorpholine.

  通过钯催化的反应，分别在N-乙基吗啉的存在下，以富马酰氯（1）和（E）-5-苯基-2,4-戊二烯酰氯（4）作为原料，制备了共轭三烯3和5。
• A Convenient Method for the Preparation of Conjugated Olefins from Allylic Acetates and Aldehydes. Synthesis of Pellitorine
  作者：Yuhko Tsukahara、Hideki Kinoshita、Katsuhiko Inomata、Hiroshi Kotake

  DOI：10.1246/bcsj.57.3013

  日期：1984.10

  A variety of allylic acetates were treated with sodium bromide and triphenylphosphine in the presence of 5 mol% of [Pd(PPh3)4] to give the phosphonium salts, which were converted to the ylids in situ and allowed to react with various aldehydes to afford the corresponding conjugated olefins in good yields. Furthermore, this procedure was applied to the synthesis of an insecticidal substance, Pellitorine

  在 5 mol% [Pd(PPh3)4] 存在下用溴化钠和三苯基膦处理各种烯丙基乙酸酯，得到鏻盐，将其原位转化为叶立德，并与各种醛反应得到相应的共轭烯烃收率良好。此外，该程序还用于合成杀虫物质 Pellitorine。
• Palladium-Catalyzed Three-Component Reaction of 3-(Tri-<i>n</i>- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ-Substituted Allylic Tin Reagents
  作者：Yoshikazu Horino、Miki Sugata、Hitoshi Abe

  DOI：10.1002/adsc.201501049

  日期：2016.3.31

  (E)‐anti‐homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem‐palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of

  在钯-Xantphos催化剂体系的存在下，3-（三-正丁基锡烷基）烯丙基乙酸酯，醛和三有机硼烷的三组分反应主要产生具有高非对映选择性和良好至高水平的（E）-抗-均芳醇烯烃的立体控制。当使用富含对映体的底物时，观察到有效的手性转移。该反应是通过形成烯丙基宝石钯/锡烷基中间体而引发的，该中间体随后通过烯丙基三丁基锡将醛进行烯丙基化，然后将原位生成的（E）-乙烯基乙酸钯与三有机硼烷偶合。