88920-53-0

Basic information

• Product Name: 9,10-dihydro-10-methylene-α-phenyl-9-anthracenemethanol
• Synonyms: 9,10-dihydro-10-methylene-α-phenyl-9-anthracenemethanol
• CAS NO: 88920-53-0
• Molecular Weight: 298.384
• Mol File: 88920-53-0.mol

Chemical Properties

• CAS DataBase Reference: 9,10-dihydro-10-methylene-α-phenyl-9-anthracenemethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-dihydro-10-methylene-α-phenyl-9-anthracenemethanol(88920-53-0)
• EPA Substance Registry System: 9,10-dihydro-10-methylene-α-phenyl-9-anthracenemethanol(88920-53-0)

Safety Data

• Hazardous Substances Data: 88920-53-0(Hazardous Substances Data)

Upstream product

• 2584-79-4 9-(methoxymethyl)anthracene 
• 24463-19-2 anthracenylmethyl chloride 
• 100-52-7 benzaldehyde 
• 135598-25-3 9-(methoxymethyl)anthracene carbanion 
• 61574-53-6 (anthracen-9-yl)methyl methyl sulfide 

Downstream Products

• 779-02-2 9-methylanthracene 

Relevant articles and documents

GENERATION AND THE AMBIDENT CHARACTER OF 9-ANTHRYLMETHYL CARBANIONS

9-Methoxymethylanthracene, 9-trimethylsilylmethylanthracene and 9-thiomethoxymethylanthracene are converted by butyllithium reagents to α-methoxy-9-anthrylmethyl, α-trimethylsilyl-9-anthrylmethyl and 9-anthrylmethyl carbanions, respectively, which react at their C-10 and C-11 positions with appropriate electrophyles.

Preparative methodology and pyrolytic behavior of anthrylmonocarbenes: Synthesis and chemistry of 1H-cyclobuta[de]anthracene

This study involves (1) the behavior of organolithium reagents (1-6), (2) development of efficient methods for preparing 9(7)- and 1(8)- [methoxy(trimethylsilyl)methyl]anthracenes and their analogues, (3) the intramolecular chemistry of the 9(9)- and 1(10)-anthrylcarbenes generated by pyrolyses of 7 and 8, respectively, and (4) investigation of thermal behavior and bromination of the 1H-cyclobuta[de]anthracene (11) obtained from 9 or 10. α-Methoxy-9-anthrylmethyllithium (1), prepared from 9- (methoxymethyl)anthracene (14) and t-BuLi in TMEDA/Et2O/pentane, reacts at C-10 with D2O, chlorotrimethylsilane, dimethyl sulfate, benzoyl chloride, acetaldehyde, benzaldehyde, and acetone to give, after neutralization, 9,10- dihydro-9-(methoxymethylene)-10-substituted-anthracenes 15 and 21a-f. However, lithiation of 9-(thiomethoxymethyl)anthracene (25) with t- BuLi/TMEDA/Et2O/pentane occurs by an apparent radical-anion displacement process to give 9-anthrylmethyllithium (3), which then reacts with chlorotrimethylsilane to yield 9-(trimethylsilylmethyl)anthracene (28). Similarly, 28 is formed from 25 and from 9- (trimethylsilyloxymethyl)anthracene (29) with lithium and then chlorotrimethylsilane. The electrophiles D2O, dimethyl sulfate, and benzaldehyde react with 3 at its methyl and its C-10 positions. [Methoxy(trimethylsilyl)methyl]arenes 40-42 and 7 are obtained by reactions of their aryllithium and arylmagnesium bromide precursors with bromo(methoxy)methyltrimethylsilane (39). 1-(Methoxymethyl)anthracene (45) is converted conveniently by t-BuLi and chlorotrimethylsilane to 8. Flash- vacuum pyrolyses of 7 and 8 yield 11 preparatively; 11 then thermolyzes to 2H-cyclopenta[jk]fluorene (46). Decomposition of 9-deuterio-10- [methoxy(trimethylsilyl)methyl]anthracene (55) at 650 °C/10-3 mm results in 10(56)- and 1(57)-deuteriocyclobutanthracenes, thus revealing that the 10- deuterio-9-anthrylcarbene inserts to give 56 and also isomerizes extensively before yielding 57. Of note is that 56 isomerizes thermally by C10-D movement to form 2-deuteriocyclopentafluorene 58, 57 rearranges by C10-H movement to yield deuteriocyclopentafluorene 59, and 58 and 59 equilibrate 1,5-sigmatropically. Possible mechanisms for the isomerizations of 56 and 57 are outlined. Further, bromine adds rapidly to 11 to form 9,10-dibromo-9,10- dihydro-1H-cyclobuta[de]anthracene (94), which eliminates HBr on warming to yield 10-bromo-1H-cyclobuta[de]anthracene (95).