5779-74-8

Basic information

• Product Name: Benzaldehyde, 3,4,5-trimethyl-
• CAS NO: 5779-74-8
• Molecular Formula: C10H12O
• Molecular Weight: 148.205
• Mol File: 5779-74-8.mol

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 3,4,5-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 3,4,5-trimethyl-(5779-74-8)
• EPA Substance Registry System: Benzaldehyde, 3,4,5-trimethyl-(5779-74-8)

Safety Data

• Hazardous Substances Data: 5779-74-8(Hazardous Substances Data)

Upstream product

• 39126-11-9 3,4,5-trimethylbenzyl alcohol 
• 527-53-7 1,2,3,5-Tetramethylbenzene 
• 57498-46-1 3,4,5-trimethyl-benzoyl chloride 
• 1076-88-6 3,4,5-trimethylbenzoic acid 
• 2047-21-4 3,4,5-trimethylacetophenone 
• 13061-96-6 dihydroxy-methyl-borane 
• 188112-49-4 trifluoromethanesulfonic acid 4-formyl-2,6-dimethylphenyl ester 
• 576-26-1 2.6-dimethylphenol 

Downstream Products

• 32156-17-5 1-methyl-2-(3,4,5-trimethyl-phenyl)-ethylamine 
• 36321-76-3 2,6-Dinitro-3,4,5-trimethyl-benzaldehyd 
• 99060-33-0 2-Nitro-3,4,5-trimethyl-benzaldehyd 
• 100061-17-4 3,4,5-Trimethyl-2,β-dinitro-styrol 
• 103565-14-6 2-Nitro-3,4,5-trimethyl-phenyl-acetaldoxim 
• 1436413-96-5 (E)-2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N'-(3,4,5-trimethylbenzylidene)acetohydrazide 
• 1531637-46-3 C₂₂H₂₃NO₂ 
• 1531637-48-5 C₂₇H₂₅NO₂ 
• 1593978-40-5 (Z)-methyl α-acetamido-3-(3,4,5-trimethylphenyl)acrylate 

Relevant articles and documents

A convenient synthesis of tri- and tetramethylbenzaldehydes from readily available phenols

This letter describes a convenient synthesis of the six isomeric tri- and tetramethylbenzaldehydes, which are not readily available from major chemical suppliers. Formylation of readily available phenols via electrophilic aromatic substitution provides compounds containing the correct aromatic substitution pattern. ?Suzuki cross-coupling of the corresponding trifluoromethanesulfonates with methylboronic acid then provides the benzaldehydes as single isomers. Georg Thieme Verlag Stuttgart. New York.

Photochemical nitration by tetranitromethane. Part XXXIII. Adduct formation in the photochemical reactions of 1,2,4,5- and 1,2,3,5-tetramethylbenzene

The photolysis of the charge-transfer complex of tetranitromethane and 1,2,4,5-tetramethylbenzene in dichloromethane or acetonitrile gives the epimeric 1,3,4,6-tetramethyl-3-nitro-6-trinitromethylcyclohexa-1,4-dienes 8 and 9, in addition to products of nuclear nitration 12 and side-chain modification 10, 11, and 13-18. Similar reactions of 1,2,3,5-tetramethylbenzene gave trans-1,3,5,6-tetramethyl-6-nitro-3-trinitromethylcyclohexa-1,4-diene 30 and two isomeric 'double' adducts 31 and 32, in addition to products of nuclear nitration 27 and side-chain modification 26, 28 and 29. The eliminative rearrangements of adducts 8 and 30 to give re-aromatized products in acetonitrile or [2H3] acetonitrile and in [2H] chloroform are reported. The photolysis of the charge-transfer complexes of tetranitromethane with either 1,2,4,5-tetramethylbenzene or 1,2,3,5-tetramethylbenzene in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFP) gives a marked increase in the yields of ring-nitration products 12 or 27, respectively, reactions presumed to proceed via a nitrosation-oxidation sequence. Reaction of 1,2,4,5-tetramethylbenzene with excess nitrogen dioxide in HFP also results in extensive ring nitration to give 12 and 2,3,5,6-tetramethyl-1,4-dinitrobenzene (25); the latter compound is seen as arising via the 2,3,5,6-tetramethyl-1,4-dinitrosobenzene (34). Similar reaction of 1,2,3,5-tetramethylbenzene gives ring-nitration product 27 as the major product. X-Ray crystal structures are reported for 2,4,6-trimethyl-1-(2′,2′,2′-trinitroethyl)benzene (26) and trans-1,3,5,6-tetramethyl-6-nitro-3-trinitromethyl-cyclohexa-1,4-diene (30). Acta Chemica Scandinavica 1996.

THE PHENYLCARBENE REARRANGEMENT REVISITED

The evolution of mechanistic ideas about the phenylcarbene rearrangement has been reviewed, and three closely linked problems have been identified toward whose solution this research has been aimed: 1.Why do the ratios of the stable end products from the rearrangements of o-, m- and p-tolylmethylene differ when all three reactions have been thought to pass through a common intermediate? 2.Why does the rearrangement of 2-methylcycloheptatrienylidene lead to exclusive formation of styrene? 3.What is the mechanism of styrene formation from o-tolylmethylene? New mechanisms have been proposed in which m- and p-tolylmethylene can rearrange to styrene without necessarily being converted to o-tolylmethylene.The formation of a small amount of 2,6-dimethylstyrene from the rearrangement of 3,4,5-trimethylphenylmethylene is viewed as evidence for such a mechanism, and a set of interconverting norcaradienylidenes are believed to be the crucial intermediates.Other alternatives are considered and rejected on the basis of the rearrangement products of 3,5-dimethyl- and 3,4,5-trimethylphenylmethylene.

Nitration of 2,3,4,6-Tetramethylphenol and 1,2,3,5-Tetramethylbenzene

Nitration of 1,2,3,5-tetramethylbenzene (2a) with fuming nitric acid gives the tetramethylnitrobenzene (22), products of side-chain modification (23)-(27), the rearranged 6,6-dimethylcyclohexenones (8), (28), (29) and (30), and 2,3,4,6-tetramethyl ketone