39579-09-4

Basic information

• Product Name: 5-Methylbiphenyl-2-ol
• Synonyms: 5-Methyl-1,1'-biphenyl-2-ol;5-Methylbiphenyl-2-ol
• CAS NO: 39579-09-4
• Molecular Formula: C₁₃H₁₂O
• Molecular Weight: 184.2338
• Mol File: 39579-09-4.mol

Chemical Properties

• Boiling Point: 300.2°Cat760mmHg
• Flash Point: 142.3°C
• Appearance: /
• Density: 1.087g/cm³
• Vapor Pressure: 0.000638mmHg at 25°C
• Refractive Index: 1.594
• CAS DataBase Reference: 5-Methylbiphenyl-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methylbiphenyl-2-ol(39579-09-4)
• EPA Substance Registry System: 5-Methylbiphenyl-2-ol(39579-09-4)

Safety Data

• Hazardous Substances Data: 39579-09-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12O/c1-10-7-8-13(14)12(9-10)11-5-3-2-4-6-11/h2-9,14H,1H3

Upstream product

• 1706-12-3 4-phenoxytoluene 
• 220464-86-8 N-(4-methylphenoxy)phthalimide 
• 71-43-2 benzene 

Downstream Products

• 1020207-89-9 5-methyl-3-[phenyl(pentafluorophenylimino)methyl]biphenyl-2-ol 
• 87682-05-1 5',5''-Dimethyl<1,1':3',1'':3'',1'''-quarterphenyl>-2',2''-diol 

Relevant articles and documents

Reaction of N-phenoxyphthalimide derivatives with aluminum chloride in benzene

N-Phenoxyphthalimides react with AlCl3 in benzene to form products of intramolecular N-C and inter molecular C-C bond formation via aryloxenium ion intermediates. N-Phenoxy derivatives having an electron-withdrawing substituent on the para position react with solvent benzene on the imide carbonyl, assisted by the neighboring oxygen atom, to produce N-(4-substituted phenoxy)-3,3-diphenyl-2,3-dihydroisoindol-1-ones.

Mechanisms of the photochemical rearrangement of diphenyl ethers

The mechanism of the photochemical rearrangement of diphenyl ether (1a) was studied. Irradiation of 1a in ethanol gave 2-phenylphenol (2, 42%) and 4-phenylphenol (3, 11%) as rearrangement products, in addition to phenol (4, 30%) and benzene (5, 25%) as diffusion products. Cross-coupling experiments employing [2H10]1a demonstrated that the formation of 2- and 4-phenylphenol was an intramolecular process. Irradiation of 1a in benzene or in toluene gave biphenyls in good yields. The combined yields of rearrangement products (2 and 3) increased with increase of solvent viscosity, with a concomitant decrease in the formation of 4. All the results can be rationalized in terms of excitation of 1a to the singlet state and dissociation to a radical pair intermediate involving phenoxy and phenyl radicals. Intramolecular recombination of these radicals gives rearrangement products, and escape followed by hydrogen abstraction from the solvent gives diffusion products. When position 4 of 1a was occupied by an electron-donating substituent (1b-e), aryloxy-phenyl bond cleavage to give the corresponding rearrangement products prevailed over phenoxy-aryl bond cleavage. The opposite was the case for substrates with an electron-withdrawing substituent at position 4 (1h,i).