bis(4-methoxy-2-methylphenyl)methane | 5191-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(4-methoxy-2-methylphenyl)methane
• 英文别名: 2,2'-Dimethyl-4,4'-dimethoxy-diphenylmethan；Bis-(4-methoxy-2-methyl-phenyl)-methan；4-methoxy-1-[(4-methoxy-2-methylphenyl)methyl]-2-methylbenzene
• CAS: 5191-69-5
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: YZONBQYKAOXXFY-UHFFFAOYSA-N

物化性质

• 熔点：
  66 °C
• 沸点：
  215-216 °C(Press: 12 Torr)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(4-methoxy-2-methylphenyl)methane 在 铬酸 作用下， 生成 bis(4-methoxy-2-methylphenyl)methanone
  参考文献：
  名称：

  Quelet et al., Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 1092,1095

  摘要：

  DOI：
• 作为产物：
  描述：

  methylenebis(2-methoxy-4-methyl-5,1-phenylene) bis(trifluoromethanesulfonate) 在 1,1'-双(二苯基膦)二茂铁 、 甲酸 、 palladium diacetate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以76.9%的产率得到bis(4-methoxy-2-methylphenyl)methane
  参考文献：
  名称：

  Effects of o-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins

  摘要：

  Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4'-(ethane-1,1'-diy1)bis-(1-cyanato-3-methylbenzene) (17), and 4,4'-(propane-1,1'-diy1)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 degrees C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 degrees C higher. The T-g's of thermosets generated from the deoxygenated resins ranged from 267 to 283 degrees C, up to 30 degrees C higher than the oxygenated resins, while the onset of thermal degradation was 50-80 degrees C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet T(g)s up to 37 degrees C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16-18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16-18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.

  DOI：

  10.1021/acs.macromol.5b00496

文献信息

• Quelet, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934, vol. 198, p. 102
  作者：Quelet

  DOI：——

  日期：——
• US4275906A
  申请人：——

  公开号：US4275906A

  公开（公告）日：1981-06-30
• Quelet et al., Bulletin de la Societe Chimique de France, 1937, vol. <5> 4, p. 1092,1095
  作者：Quelet et al.

  DOI：——

  日期：——
• Effects of <i>o</i>-Methoxy Groups on the Properties and Thermal Stability of Renewable High-Temperature Cyanate Ester Resins
  作者：Benjamin G. Harvey、Andrew J. Guenthner、William W. Lai、Heather A. Meylemans、Matthew C. Davis、Lee R. Cambrea、Josiah T. Reams、Kevin R. Lamison

  DOI：10.1021/acs.macromol.5b00496

  日期：2015.5.26

  Renewable phenols derived from biomass sources often contain methoxy groups that alter the properties of derivative polymers. To evaluate the impact of o-methoxy groups on the performance characteristics of cyanate ester resins, three bisphenols derived from the renewable phenol creosol were deoxygenated by conversion to ditriflates followed by palladium-catalyzed elimination and hydrolysis of the methoxy groups. The deoxygenated bisphenols were then converted to the following cyanate ester resins: bis(4-cyanato-2-methylphenyl)methane (16), 4,4'-(ethane-1,1'-diy1)bis-(1-cyanato-3-methylbenzene) (17), and 4,4'-(propane-1,1'-diy1)bis(1-cyanato-3-methylbenzene) (18). The physical properties, cure chemistry, and thermal stability of these resins were evaluated and compared to those of cyanate esters derived from the oxygenated bisphenols. 16 and 18 had melting points 37 and >95 degrees C lower, respectively, than the oxygenated versions, while 17 had a melting point 14 degrees C higher. The T-g's of thermosets generated from the deoxygenated resins ranged from 267 to 283 degrees C, up to 30 degrees C higher than the oxygenated resins, while the onset of thermal degradation was 50-80 degrees C higher. The deoxygenated resins also exhibited water uptakes up to 43% lower and wet T(g)s up to 37 degrees C higher than the oxygenated resins. TGA-FTIR of thermoset networks derived from 16-18 revealed a different decomposition mechanism compared to the oxygenated resins. Instead of a low-temperature pathway that resulted in the evolution of phenolic compounds, 16-18 had significantly higher char yields and decomposed via evolution of small molecules including isocyanic acid, CH4, CO2, and NH3.