4,4'-二甲氧基芪 | 4705-34-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4,4'-二甲氧基芪
• 中文别名: 4,4-二甲氧基二苯乙烯；4,4’-二甲氧基芪
• 英文名称: 4,4'-dimethoxystilbene
• 英文别名: 1,2-bis(4-methoxyphenyl)ethene；1-methoxy-4-[2-(4-methoxyphenyl)ethenyl]benzene
• CAS: 4705-34-4
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: CAWFCZIEFIQKRV-UHFFFAOYSA-N

物化性质

• 熔点：
  213-215 °C
• 沸点：
  323.02°C (rough estimate)
• 密度：
  1.1228 (rough estimate)
• 溶解度：
  可溶于氯仿（轻微、超声处理）、乙酸乙酯（轻微、超声处理）
• 稳定性/保质期：

  在常温常压下稳定，应避免与不相容材料接触。与强氧化剂反应。

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/38
• 安全说明：
  S24/25
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	4,4'-Dimethoxystilbene, 97% Material Safety Data Sheet
Synonym:	None known.
CAS:	4705-34-4

Section 1 - Chemical Product MSDS Name: 4,4'-Dimethoxystilbene, 97% Material Safety Data Sheet
Synonym: None known.

---

SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4705-34-4	4,4'-Dimethoxystilbene	97	225-189-9

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

---

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.

---

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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:

---

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.

---

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

---

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. Hormones and antibiotics room.

---

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# 4705-34-4: 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.

---

SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Powder
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 211.00 - 213.00 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: C16H16O2
Molecular Weight: 240.30

---

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:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 4705-34-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4,4'-Dimethoxystilbene - Not listed by ACGIH, IARC, or NTP.

---

SECTION 12 - ECOLOGICAL INFORMATION

---

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

---

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.

---

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# 4705-34-4: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 4705-34-4 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 4705-34-4 is not listed on the TSCA inventory. It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #4 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4,4'-二甲氧基芪 在 sodium hydroxide 、 sodium permanganate 作用下， 以 1,4-二氧六环 为溶剂， 生成 二氢茴香偶姻
  参考文献：
  名称：

  烯烃与高锰酸根离子和四氧化反应中的电子效应

  摘要：

  吸引电子的取代基促进了高锰酸根离子对烯烃（脂环族化合物和对苯二甲酸酯）的氧化，但是这些基团阻碍了烯烃与四氧化的反应。对于锑的氧化，获得的近似ρ值：在二恶烷水溶液中的高锰酸盐反应为0·65和在二恶烷中的四氧化反应为–0·55。

  DOI：

  10.1039/j29660000803
• 作为产物：
  描述：

  4-甲氧基苄基三苯基膦溴化盐 在 sodium hydride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以23%的产率得到4,4'-二甲氧基芪
  参考文献：
  名称：

  极性非质子溶剂中碱对烷基三苯基鏻盐的影响

  摘要：

  当芳甲基鏻盐用碱（例如，t-BuOK 或 NaH）处理时，它们均偶合形成对称的 1,2-二芳基乙烯。在某些情况下，稀释和（或）使用过量的碱会导致非常……

  DOI：

  10.1139/v08-056
• 作为试剂：
  描述：

  苯基环丙基甲酮 在 4,4'-二甲氧基芪 、 叠氮化四丁基铵 作用下， 以 乙腈 为溶剂， 生成 phenylcyclopropylketyl anion
  参考文献：
  名称：

  环丙基羰基→酮基自由基阴离子的均烯丙基型开环。结构/反应性关系以及溶剂/抗衡剂重组对内在障碍的贡献

  摘要：

  以下通过Mathivanan，约翰斯顿，和Wayner（开发的协议J.物理学。化学。1995，99，8190-8195），环丙基几个和含有环氧乙烷基-羰基的化合物的自由基阴离子到测量的速率常数的努力产生了用激光闪光光解法测定它们的开环（k o）。将这些实验的结果与从早期电化学研究中获得的结果进行了比较，并且通过使用与逐步解离电子转移有关的Savéant理论（Acc.Chem。 RES。1993年，26，455-461）。与中性自由基的环丙基碳烯基→均烯丙基重排相比，在可比较的驱动力下，自由基阴离子环的开口略慢。速率上的小差异归因于自由基阴离子重排额外的约2 kcal / mol溶剂重组组分的贡献。认为用于这些自由基阴离子的开环的溶剂重组能很小，这是因为在进展反应物→过渡态→产物中负电荷没有明显地移动。

  DOI：

  10.1021/jo047917r

文献信息

• Studies of reduction with dimethoxyborane-transition metal boride systems.
  作者：Atsuko NOSE、Tadahiro KUDO

  DOI：10.1248/cpb.38.1720

  日期：——

  The reductino of a variety of functional groups with new dimethoxyborane-transition metal boride systems was investigated. These systems reduced olefin, aldehyde, ketone and nitrile functionalities to afford the corresponding reduction products under mild conditions. In particular, olefins bearing ketone, carboxylic acid and nitrile functionalities were selectively reduced with the dimethoxyborane-nickel boride system using 1/5mol eq of nickel boride.

  研究了新型二甲氧基硼烷-过渡金属硼化物体系对多种官能团的还原作用。这些体系在温和条件下将烯烃、醛、酮和腈类官能团还原，得到了相应的还原产物。特别是，含有酮、羧酸和腈结构的烯烃在1/5摩尔当量的镍硼化物作用下，通过二甲氧基硼烷-镍硼化物体系选择性地还原。
• Flash vacuum pyrolysis over magnesium. Part 1. Pyrolysis of benzylic, other aryl/alkyl and aliphatic halides
  作者：R. Alan Aitken、Philip K. G. Hodgson、John J. Morrison、Adebayo O. Oyewale

  DOI：10.1039/b108663d

  日期：2002.1.23

  Flash vacuum pyrolysis over a bed of freshly sublimed magnesium on glass wool results in efficient coupling of benzyl halides to give the corresponding bibenzyls. Where an ortho halogen substituent is present further dehalogenation gives some dihydroanthracene and anthracene. Efficient coupling is also observed for halomethylnaphthalenes and halodiphenylmethanes while chlorotriphenylmethane gives 4,4′-bis(diphenylmethyl)biphenyl. By using α,α′-dihalo-o-xylenes, benzocyclobutenes are obtained in good yield, while the isomeric α,α′-dihalo-p-xylenes give a range of high thermal stability polymers by polymerisation of the initially formed p-xylylenes. Other haloalkylbenzenes undergo largely dehydrohalogenation where this is possible, in some cases resulting in cyclisation. Deoxygenation is also observed with haloalkyl phenyl ketones to give phenylalkynes as well as other products. With simple alkyl halides there is efficient elimination of HCl or HBr to give alkenes. For aliphatic dihalides this also occurs to give dienes but there is also cyclisation to give cycloalkanes and dehalogenation with hydrogen atom transfer to give alkenes in some cases. For 5-bromopent-1-ene the products are those expected from a radical pathway but for 6-bromohex-1-ene they are clearly not. For 2,2-dichloropropane and 1,1-dichloropropane elimination of HCl occurs but for 1,1-dichlorobutane, -pentane and -hexane partial hydrolysis followed by elimination of HCl gives E,E-, E,Z- and Z,Z- isomers of the dialk-1-enyl ethers and fully assigned 13C NMR data are presented for these. With 6-chlorohex-1-yne and 7-chlorohept-1-yne there is cyclisation to give methylenecycloalkanes and -cycloalkynes. The behaviour of 1,2-dibromocyclohexane and 1,2-dichlorocyclooctane under these conditions is also examined. Various pieces of evidence are presented that suggest that these processes do not involve generation of free gas-phase radicals but rather surface-adsorbed organometallic species.

  在玻璃棉上覆盖一层新升华的镁,进行闪式真空热解,能有效促使苄基卤化物耦合生成相应的联苄。当有邻位卤素取代基存在时,进一步脱卤生成部分二氢蒽和蒽。卤甲基萘和二苯基甲烷也能高效耦合,而三苯基氯甲烷则生成4,4′-双(二苯甲基)联苯。用α,α′-二卤代邻二甲苯可以获得较高产率的苯并环丁烯,而异构的α,α′-二卤代对二甲苯,通过形成的对二甲苯的聚合,可以得到一系列高热稳定性的聚合物。其他卤代烃苯大体上会脱卤化氢,某些情况下能产生环化反应。同样可以观察到,苯基卤代烷烃脱去羰基生成苯乙炔以及其他产物。简单的烷基卤化物则高效地脱去HCl或HBr生成烯烃。脂肪族二卤化物也会发生这一反应生成二烯,但不发生环化反应生成环烷烃,或在某些情况下发生氢原子转移的脱卤反应生成烯烃。5-溴戊-1-烯的产物符合自由基途径的预期,但6-溴己-1-烯并不符合。2,2-二氯丙烷和1,1-二氯丙烷能脱去HCl,但1,1-二氯丁烷、戊烷和己烷则能部分水解,随后脱去HCl,生成E,E-, E,Z-和Z,Z-异构体二烷-1-烯基醚,并且得到了这些物质的13C NMR全归属数据。6-氯己-1-炔和7-氯庚-1-炔能发生环化反应生成亚甲基环烷烃和环炔烃。本文还考察了1,2-二溴环己烷和1,2-二氯环辛烷在上述条件下的行为。本文给出了众多种证据,表明这些反应过程不涉及气相自由基的形成,而是表面吸附的金属有机物种。
• Synthesis, crystal structure, and catalytic activity of bridged-bis(N-heterocyclic carbene) palladium(II) complexes in selective Mizoroki-Heck cross-coupling reactions
  作者：Waseem Mansour、Rami Suleiman、Wissam Iali、Mohammed Fettouhi、Bassam El Ali

  DOI：10.1016/j.poly.2021.115371

  日期：2021.10

  temperature range 25–120 °C. The catalytic activities of three Pd-bridged bis(NHC) complexes in the Mizoroki-Heck cross-coupling reactions were not found to have a direct correlation with +I effect order of the N-substituents of the ligand. However, a direct correlation was found between the DFT calculated absolute softness of the three complexes with their respective catalytic activity. The highest calculated

  一系列三个 1,3-丙二基桥连双（N-杂环卡宾）钯（II）配合物（Pd-BNH1、Pd-BNH2和Pd-BNH3），配体的N-取代基具有 + I 效应顺序（异丙基 > 苄基 > 甲氧基苯基），是光谱、结构、计算和催化研究的主题。在芳基溴化物与苯乙烯或丙烯酸酯衍生物的 Mizoroki-Heck 偶联反应中评估了双 (NHC)PdBr 2配合物，并显示出生产二芳基乙烯和肉桂酸衍生物的高催化效率。最活跃的钯配合物Pd-BNH3的 X 射线结构表明 Pd(II) 中心与双 (N-杂环卡宾）和顺式位置的两个溴化物配体，导致扭曲的方形平面几何形状。Pd-BNH3的 NMR 数据与溶液中的单椅船刚性构象一致，在 25-120 °C 的温度范围内没有 8 元环钯环的动态行为。未发现在 Mizoroki-Heck 交叉偶联反应中三种 Pd 桥连双 (NHC) 配合物的催化活性与配体N取代基的+I 效应顺序直接相关。然而，发现三种复合物的
• Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes
  作者：Samuel L. Bourne、Matthew O'Brien、Sivarajan Kasinathan、Peter Koos、Päivi Tolstoy、Dennis X. Hu、Roderick W. Bates、Benjamin Martin、Berthold Schenkel、Steven V. Ley

  DOI：10.1002/cctc.201200778

  日期：2013.1

  Two tandem flow chemistry processes have been developed. A single palladium‐catalysed Heck reaction with ethylene gas provides an efficient synthesis for functionalised styrenes. Through further elaboration the catalyst becomes multi‐functional and performs a second Heck reaction providing a single continuous process for the synthesis of unsymmetrical stilbenes. In addition, the continuous, rhodium‐catalysed

  已经开发了两种串联流化学方法。钯与乙烯气体的单催化Heck反应为官能化苯乙烯提供了有效的合成方法。通过进一步的精制，催化剂变为多功能，并进行第二次Heck反应，从而为不对称对苯二甲酸酯的合成提供了一个连续的过程。此外，苯乙烯衍生物与合成气的铑连续催化加氢甲酰化反应可提供具有良好选择性的支链醛。在线水洗和液-液分离相结合，使乙烯Heck反应可伸缩进入加氢甲酰化步骤，从而直接从芳基碘化物中直接合成支链醛。
• Ni-Catalyzed hydrocyanation of alkenes with formamide as the cyano source
  作者：Xiao Shu、Yuan-Yuan Jiang、Lei Kang、Luo Yang

  DOI：10.1039/c9gc04275j

  日期：——

  “CN” generation from formamide dehydration! A novel Ni-catalyzed hydrocyanation of various alkenes to provide aliphatic nitriles is developed by generating hydrocyanic acid in situ from safe and readily available formamide. Excellent linear or branched regio-selectivity, wide substrate scope, cheap and stable nickel salt as a pre-catalyst, a safe cyano source, slow generation of “CN” to obviate catalyst

  甲酰胺脱水生成“ CN”！通过从安全易得的甲酰胺中原位生成氢氰酸，开发了各种烯烃的新型Ni催化氢氰化反应，以提供脂肪族腈。优异的线性或支链区域选择性，广泛的底物范围，廉价且稳定的镍盐作为预催化剂，安全的氰基源，缓慢生成的“ CN”可避免催化剂失活以及方便的实验操作，使得这种氢氰化作用对于实验室合成而言是无活性的脂肪腈。