79364-92-4

Basic information

• Product Name: Benzaldehyde, 2-[(4-methoxyphenyl)methyl]-
• Synonyms: 2-(4-Methoxy-benzyl)-benzaldehyde
• CAS NO: 79364-92-4
• Molecular Formula: C15H14O2
• Molecular Weight: 226.275
• Mol File: 79364-92-4.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 2-[(4-methoxyphenyl)methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 2-[(4-methoxyphenyl)methyl]-(79364-92-4)
• EPA Substance Registry System: Benzaldehyde, 2-[(4-methoxyphenyl)methyl]-(79364-92-4)

Safety Data

• Hazardous Substances Data: 79364-92-4(Hazardous Substances Data)

Upstream product

• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 6630-33-7 ortho-bromobenzaldehyde 
• 100-66-3 methoxybenzene 
• 529-20-4 2-methylphenyl aldehyde 
• 696-62-8 para-iodoanisole 

Downstream Products

• 1187591-29-2 tert-butyl 2-(hydroxy(2-(4-methoxybenzyl)phenyl)methyl)phenylcarbamate 
• 42298-28-2 2-methoxyanthracene 

Relevant articles and documents

Regiodivergent CDC reactions of aromatic aldehydes with unactivated arenes controlled by transient directing strategy

The regiodivergent catalytic dehydrogenative cross-coupling reactions at both sp2and sp3hybridized carbons of aromatic compounds are particularly challenging. Herein, we report the finding of transient directing group controlled regiodivergent C(sp3)-C(sp2) and C(sp2)-C(sp2) cross-coupling in theo-methyl benzaldehyde frameworks. Catalyzed by palladium, using K2S2O8or [F+] reagents as by-standing oxidants and unactivated arenes as substrates/solvents, various benzyl benzaldehydes or phenyl benzaldehydes were prepared. A mechanism study indicated that the regiospecificity is dominated by the [5,6]-fused palladacycle or [6,5]-fused palladacycle intermediates, which are generated from Pd-chelation with specified transient directing groups and further C-H activations.

Palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehydes

The palladium-catalyzed benzylic C(sp3)–H arylation of o-alkylbenzaldehyde derivatives was achieved utilizing 2-dimethylaminoethylamine as a novel transient directing group. The γ-C(sp3)–H arylation reaction efficiently afforded a variety of arylated o-alkylbenzaldehydes and polycyclic aromatic hydrocarbons (PAHs) in one pot, exhibiting high functional group tolerance with broad substrate scope. The aliphatic diamine auxiliary represents a simple, inexpensive, readily available, and removable directing group for C–H activation. The resultant o-benzylbenzaldehyde products could be diversely transformed into potentially important synthetic intermediates under mild conditions.

Semicarbazide: A Transient Directing Group for C(sp3)?H Arylation of 2-Methylbenzaldehydes

Semicarbazide as an effective transient directing group for C(sp3)?H arylation of 2-methylbenzaldehydes is described. Various substituted 2-benzylbenzaldehydes are efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive transient directing group, wide scope of substrates with good functional group compatibility, up to 98% yield, and applicability to gram scale. (Figure presented.).