52988-34-8

Basic information

• Product Name: 4'-Methoxybiphenyl-4-carbaldehyde
• Synonyms: [1,1'-BIPHENYL]-4-CARBOXALDEHYDE, 4'-METHOXY-;AKOS BAR-0060;4'-METHOXY-BIPHENYL-4-CARBALDEHYDE;4'-METHOXY-BIPHENYL-4-CARBOXALDEHYDE;4'-METHOXY[1,1'-BIPHENYL]-4-CARBOXALDEHYDE;4'-METHOXY[1,1'-BIPHENYL]-4-CARBALDEHYDE;4-(4-METHOXYPHENYL)BENZALDEHYDE;4-(4-METHOXY)BENZALDEHYDE
• CAS NO: 52988-34-8
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.24
• Mol File: 52988-34-8.mol

Chemical Properties

• Melting Point: 98-100°C
• Boiling Point: 363.5 °C at 760 mmHg
• Flash Point: >110°(230°F)
• Appearance: /
• Density: 1.114 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Air Sensitive
• CAS DataBase Reference: 4'-Methoxybiphenyl-4-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Methoxybiphenyl-4-carbaldehyde(52988-34-8)
• EPA Substance Registry System: 4'-Methoxybiphenyl-4-carbaldehyde(52988-34-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52988-34-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4'-Methoxybiphenyl-4-carbaldehyde is used as a reagent in the development of aryliden-methyloxazolones, which are reversible inhibitors of the Monoacylglycerol Lipase (MAGL) enzyme. These inhibitors have shown promise in cancer treatment, as they can modulate the endocannabinoid system and potentially lead to the suppression of tumor growth and progression.
Used in Chemical Synthesis:
In the chemical industry, 4'-Methoxybiphenyl-4-carbaldehyde can be utilized as a key intermediate in the synthesis of various compounds, such as dyes, pigments, and other specialty chemicals. Its unique structure and reactivity make it a valuable building block for creating novel molecules with specific properties and applications.

Upstream product

• 1018955-96-8 6-(4-methoxyphenyl)bicyclo[3.2.0]hept-2-en-6-ol 
• 127591-24-6 p-methoxyphenyl(triphenylphosphine)gold(I) 
• 1122-91-4 4-bromo-benzaldehyde 
• 1130440-65-1 [4-(trifluoromethyl)phenyl](triphenylphosphine)gold(I) 
• 87199-17-5 4-formylphenylboronic acid, 
• 29304-87-8 7-(4-methoxyphenyl)cyclohepta-1,3,5-triene 
• 104-92-7 1-bromo-4-methoxy-benzene 

Downstream Products

• 75472-33-2 N,N-bis(p-methoxyphenylbenzylidene)-α,α'-bi-p-toluidine 
• 162755-27-3 (E)-2-<4-(4-methoxyphenyl)benzylidene>-p-menthan-3-one 
• 477726-56-0 3-(2-Amino-6-methyl-pyrimidin-4-yl)-biphenyl-4,4'-diol 
• 1072896-75-3 p-methoxyphenyl (3,5,9-trideoxy-5-glycolamido-9-(4'-methoxy-4-biphenyl)-methylamino-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside 
• 1380049-03-5 (S)-2-{(R)-hydroxy[4'-methoxy-1,1'-biphenyl-4-yl]methyl}cyclopentanone 

Relevant articles and documents

Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement

Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.

Catalytic and stoichiometric reactions of Arylpalladium(II) complexes bearing a trans-chelating dinitrogen ligand with arylboronic acids

Pd(II) complexes with 1,2-bis(2′-pyridylethylnyl)benzene (bpeb) ligand, PdCl2(bpep) and Pd(OAc)2(bpep), catalyze cross-coupling of arylboronic acids and aryl iodide, in spite of the trans-chelation of the ligand. Arylpalladium iodo and trifluoroacetate complexes with bpep ligand, Pd(C6H4X-4)(I)(bpep) (3a-3h, X = OMe, Me, H, COMe, CHO, COOEt, NO2, F), Pd(C6H3F2-2,4)(I)(bpep) (3i), Pd(C6H4X-4)(OCOCF3)(bpep) (4a-4e, X = OMe, Me, H, COMe, CHO) and Pd(C6F5)(OCOCF3)(bpep) (4j), were obtained by ligand exchange of the Pd complexes having tmeda ligand (tmeda = N,N,N′,N′-tetramethylethylenedi-amine). X-ray crystallographic results of arylpalladium(II) trifluoroacetate complex, Pd(C6H4OMe-4)(OCOCF3)(bpeb) (4a), and bis(trifluoroacetate)palladium(II) complex, Pd(OCOCF3)2(bpeb) (5) revealed the structures with two pyridyl groups of bpeb coordinated to Pd(II) in a trans-chelating bidentate mode. 2-Pyridyl hydrogens and an acetate oxygen of 5 are at close positions to each other (2.52 and 2.66 ?). The reaction of (4-MeC6H4)B(OH)2 (7b) with Pd(C6H4OMe-4)(OCOCF3)(bpeb) (4a) in the presence of Ag2O yields Pd(C6H4Me-4)(OCOCF3)(bpeb) (4b) via exchange of the aryl group between the palladium complex and arylboronic acid. The reaction of (4-CHOC6H4)B(OH)2 (7e) yields not only Pd(C6H4CHO-4)(OCOCF3)(bpeb) (4e) but also biaryls, 4-MeOC6H4-C6H4Y-4 (Y = OMe (8a), CHO (8e)). Hammett plots of the reaction exchange suggest higher reactivity of the Pd complex with more electron-donating aryl ligand.

Nickel-catalyzed cross-coupling of organogold reagents

Organogold compounds undergo nickel-catalyzed cross-coupling reactions with aryl and vinyl bromides in high yield under mild conditions. The reaction tolerates both electron-rich and electron-poor organogold complexes, and olefinic bromides undergo cross-coupling with high stereoselectivity. This novel transformation links well-established nickel catalysis with more recent developments in organogold transformations.

An oxidative rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol to 1,1′-biphenyl-carbaldehydes: A mechanistic study

Acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0]heptan-6-ol gave 1,1′-biphenyl and 1,1′-biphenyl-carbaldehydes in small amounts as well as the expected rearrangement products. A detailed study of the reaction mechanism revealed that the conversion occurs via an oxidative process through the consecutive formation of cycloheptadienes, cycloheptatrienes, and 1,1′-biphenyls. The acid-catalyzed rearrangement of 6-phenylbicyclo[3.2.0] hept-2-en-6-ols gave 1- and 2-phenylcycloheptatrienes directly, from which 1,1′-biphenyl and 1,1′-biphenyl-carbaldehydes were obtained by oxidation.