7072-00-6

Basic information

• Product Name: 10-METHYLANTHRACENE-9-CARBOXALDEHYDE
• Synonyms: 9-METHYL-10-ANTHRALDEHYDE;10-METHYLANTHRACENE-9-CARBOXALDEHYDE;10-Methyl-9-anthracenecarbaldehyde;9-Anthracenecarboxaldehyde, 10-methyl-;10-methylanthracene-9-carbaldehyde;10-METHYLANTHRACENE-9-CARBOXALDEHYDE, 96 %;10-Methylanthracene-9-carboxaldehyde,99%;10-Methylanthracene-9-carboxaldehyde 96%
• CAS NO: 7072-00-6
• Molecular Formula: C₁₆H₁₂O
• Molecular Weight: 220.27
• EINECS: 230-366-9
• Product Categories: Aldehydes;C10 to C21;Carbonyl Compounds;Building Blocks;C13-C60;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 7072-00-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 169-171.5 °C(lit.)
• Boiling Point: 321.21°C (rough estimate)
• Flash Point: 269.2°C
• Appearance: /
• Density: 1.0588 (rough estimate)
• Vapor Pressure: 3.24E-07mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• CAS DataBase Reference: 10-METHYLANTHRACENE-9-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 10-METHYLANTHRACENE-9-CARBOXALDEHYDE(7072-00-6)
• EPA Substance Registry System: 10-METHYLANTHRACENE-9-CARBOXALDEHYDE(7072-00-6)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• WGK Germany: 3
• Hazardous Substances Data: 7072-00-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H12O/c1-11-12-6-2-4-8-14(12)16(10-17)15-9-5-3-7-13(11)15/h2-10H,1H3

Upstream product

• 779-02-2 9-methylanthracene 
• 93-61-8 N-methyl-N-phenylformamide 
• 781-43-1 9,10-dimethylanthracene 
• 696-33-3 iodoxybenzene 
• 10025-87-3 trichlorophosphate 
• 25891-31-0 triformylamine 
• 642-31-9 9-anthracene aldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 4444-44-4 1a,10b-dihydro-6H-dibenzo[3,4:6,7]cyclohepta[1,2-b]oxiren-6-one 
• 2222-33-5 dibenzosuberenon 
• 18259-45-5 5-hydroxy-5-methyl-5H-dibenzocycloheptene 
• 10354-00-4 5H-dibenzo[a,d]cyclohepten-5-ol 

Downstream Products

• 781-43-1 9,10-dimethylanthracene 
• 71339-55-4 9-(hydroxymethyl)-10-dimethylanthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 184962-83-2 (S)-2-(Benzhydrylidene-amino)-3-(10-cyano-anthracen-9-yl)-propionic acid tert-butyl ester 
• 17104-31-3 10-hydroxy-10-methylanthracen-9(10H)-one 

Relevant articles and documents

Substituted 9-Anthraldehydes from Dibenzocycloheptanol Epoxides via Acid-Catalyzed Epoxide Opening/Semipinacol Rearrangement

Starting from benzaldehyde derivatives, the corresponding dibenzocycloheptenol could be prepared in five steps. Under both substrate (secondary vs tertiary alcohol and the substituents on the aromatic ring(s)) and condition control, the subsequent epoxidation and acid-catalyzed epoxide opening/semipinacol rearrangement/aromatization afforded the corresponding 9-anthraldehydes in good yields, up to 88% over two steps. The presence of the electron-withdrawing group(s) on the aromatic ring(s) suppressed the rate of the epoxidation while the subsequent semipinacol rearrangement step required heating; the presence of the electron-donating group(s), on the other hand, frequently led to the decomposition during the epoxidation. From the mechanistic studies, the semipinacol rearrangement of the epoxide could precede the ionization at the bisbenzylic position, yielding the aldehyde intermediate. The ensuing dehydrative aromatization led to the formation of 9-anthraldehyde. Conversely, nucleophilic addition to the aldehyde and dehydrative aromatization with concomitant loss of formic acid led to anthracene.

Orthoamides. LIII. A New Synthesis for Aromatic Aldehydes of Wide Scope

Diformamide (1) reacts with activated aromatic compounds like toluene, anisole, m-xylene, 1,2-dimethoxybenzene in the presence of AlCl3 to give N-(diarylmethyl)-formamides 2a-d, the corresponding aromatic aldehydes 3-6 are formed as by-products in low yields. From N,N-dimethylaniline and 1/AlCl3 the triphenylmethane derivative 7 can be obtained. The reaction of anisole with N-methyl-diformamide (9) affords the formamide 10. The mixture of formamide, P4O10 and AlCl3 reveals to be a reagent which is capable to formylate toluene and anisole, resp. Triformamide (14)/AlCl3 is an effective formylating system which allows the preparation of aromatic aldehydes (e.g. 3,4,17-32) from the corresponding aromatic hydrocarbons. Aluminiumchloride can be replaced by borontrichloride. The yields of the formylation reactions depend strongly from the reaction conditions (molar ratio: aromatic hydrocarbon/ AlCl3/14; solvent, reaction temperature). The scope of the reaction covers nearly complete those of the Gattermann-Koch-, Gattermann- and Vilsmeier-Haack-reaction.

Dramatic Solvent and Stereoelectronic Effects in a Biomimetic Oxidation: 9,10-Dialkylanthracenes

-