344762-21-6

Basic information

• Product Name: bis(3-hydroxy-4-methoxyphenyl)methane
• Synonyms: bis(3-hydroxy-4-methoxyphenyl)methane
• CAS NO: 344762-21-6
• Molecular Weight: 260.29
• Mol File: 344762-21-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: bis(3-hydroxy-4-methoxyphenyl)methane(CAS DataBase Reference)
• NIST Chemistry Reference: bis(3-hydroxy-4-methoxyphenyl)methane(344762-21-6)
• EPA Substance Registry System: bis(3-hydroxy-4-methoxyphenyl)methane(344762-21-6)

Safety Data

• Hazardous Substances Data: 344762-21-6(Hazardous Substances Data)

Upstream product

• 50-00-0 formaldehyd 
• 553-17-3 bis(2-methoxy-phenyl)carbonate 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 90-05-1 2-methoxy-phenol 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 613-70-7 2-methoxyphenyl acetate 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 
• 78504-28-6 2-Benzyloxy-4-bromo-1-methoxybenzene 

Downstream Products

• 108622-12-4 bis-(3-ethoxy-4-methoxy-phenyl)-methane 
• 854734-53-5 4,4'-dibromo-6,6'-dimethoxy-3,3'-methanediyl-di-phenol 
• 41634-67-7 bis-(2-bromo-4,5-dimethoxy-phenyl)-methane 
• 110049-32-6 3,3'-diethoxy-4,4'-dimethoxy-benzophenone 

Relevant articles and documents

Regioselective synthesis, isomerisation, in vitro oestrogenic activity, and copolymerisation of bisguaiacol F (BGF) isomers

Bisguaiacol F (BGF), a potentially safer and renewable bisphenol A (BPA) replacement made from lignin-derivable vanillyl alcohol (p-VA), is a promising building block for future aromatic biopolymers. Unfortunately, like BPA synthesis, this electrophilic condensation reaction is also prone to regioselectivity issues, giving rise to m,p′- and o,p′-BGF byproducts. In this work, the hitherto unconsidered influence of m,p′-BGF, viz. the main isomeric byproduct of p,p′-BGF synthesis, on the physicochemical properties of poly(BGF carbonate) (BGF-PC) was systematically investigated by random copolymerisation with different fractions of pure m,p′-BGF (25, 50 and 75 wt%). To do so, the elusive m,p′-isomer was made in unparalleled regioselectivity (72%) by alkylation condensation of isovanillyl alcohol (m-VA) with guaiacol. Surprisingly, no isomeric scrambling due to acid-catalysed isomerisation was encountered for pure BGF isomers, which strongly facilitates their synthesis in contrast to petrochemical bisphenol F (BPF). Furthermore, to ensure safer chemical design, an in vitro human oestrogen receptor α (hERα) transactivation assay was performed. Both pure m,p′- and p,p′-BGF displayed a significantly reduced oestrogenic potency (～426-457 times lower affinity than BPA) and oestrogenic efficacy (～39-50% of BPA's maximum induction). Interestingly, mutual comparison between p,p′-BPF and p,p′-BGF reveals and proves for the first time the direct link between ortho-methoxy substitution and reduced in vitro oestrogenic activity (for transactivation of hERα). In contrast to o,p′-BPA, viz. the main byproduct of p,p′-BPA synthesis, m,p′-BGF was proven suitable for utilization in thermoplastics, thereby avoiding time-consuming and labour-intensive (re)crystallizations to obtain regioisomerically pure p,p′-BGF.