1620-30-0

Basic information

• Product Name: Diphenyl(4-pyridyl)methanol
• Synonyms: ALPHA,ALPHA-DIPHENYL-4-PYRIDINEMETHANOL;ALPHA,ALPHA-DIPHENYL-4-PYRIDYLMETHANOL;ALPHA-(4-PYRIDYL)BENZHYDROL;A,A-DIPHENYL-4-PYRIDINEMETHANOL;A-4-PYRIDYLBENZHYDROL;DIPHENYL(4-PYRIDYL)METHANOL;(4-Pyridyl)benzhydrol;α-(4-Pyridyl)benzhydrol
• CAS NO: 1620-30-0
• Molecular Formula: C₁₈H₁₅NO
• Molecular Weight: 261.32
• EINECS: 216-584-7
• Product Categories: Pharmaceutical Intermediates;Heterocyclic Compounds
• Mol File: 1620-30-0.mol

Chemical Properties

• Melting Point: 240 °C
• Boiling Point: 445.268 °C at 760 mmHg
• Flash Point: 223.09 °C
• Appearance: /
• Density: 1.169 g/cm³
• Vapor Pressure: 1.04E-08mmHg at 25°C
• Refractive Index: 1.626
• CAS DataBase Reference: Diphenyl(4-pyridyl)methanol(CAS DataBase Reference)
• NIST Chemistry Reference: Diphenyl(4-pyridyl)methanol(1620-30-0)
• EPA Substance Registry System: Diphenyl(4-pyridyl)methanol(1620-30-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36/37/39-22
• WGK Germany: 3
• Hazardous Substances Data: 1620-30-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 27, p. 1903, 1990 DOI: 10.1002/jhet.5570270711

InChI:InChI=1/C18H15NO/c20-18(15-7-3-1-4-8-15,16-9-5-2-6-10-16)17-11-13-19-14-12-17/h1-14,20H

Upstream product

• 54750-97-9 4-lithiopyridine 
• 119-61-9 benzophenone 
• 55-22-1 pyridine-4-carboxylic acid 
• 1570-45-2 isonicotinic acid ethylester 
• 14548-46-0 4-Benzoylpyridine 
• 591-51-5 phenyllithium 
• 110-91-8 morpholine 
• 100-48-1 pyridine-4-carbonitrile 
• 626-61-9 4-Chloropyridine 
• 100-70-9 2-Cyanopyridine 
• 464-72-2 tetraphenylethane-1,2-diol 
• 7379-35-3 4-chlorpyridine hydrochloride 
• 3881-38-7 1-(4'-pyridyl)-4-pyridone 
• 108-86-1 bromobenzene 

Downstream Products

• 62982-12-1 S-(diphenyl-4-pyridylmethyl)-L-cysteine 
• 64991-61-3 diphenyl(4-pyridyl)methyl chloride hydrochloride 
• 164725-87-5 2-Ethoxycarbonylmethyl-4-(hydroxy-diphenyl-methyl)-2H-pyridine-1-carboxylic acid methyl ester 
• 108229-07-8 acetone diphenyl-4-pyridylmethylhydrazone 
• 90334-44-4 N-Cyclohexylidene-N'-(diphenyl-pyridin-4-yl-methyl)-hydrazine 
• 90334-45-5 N-(Diphenyl-pyridin-4-yl-methyl)-N'-[1-methyl-hept-(Z)-ylidene]-hydrazine 
• 108229-08-9 N-Cyclododecylidene-N'-(diphenyl-pyridin-4-yl-methyl)-hydrazine 
• 108229-09-0 diphenyl-4-pyridylmethylhydrazine dihydrochloride 

Relevant articles and documents

Green synthesis method of polyaryl substituted methanol

The invention relates to a green synthesis method of polyaryl substituted methanol, in particular to a method for efficiently synthesizing polyaryl substituted methanol in a polar aprotic solvent under the condition of an oxidizing agent by taking polyaryl substituted methane as a raw material and alkali as an additive. The method provided by the invention is green and environment-friendly, avoids using expensive metal catalysts, and has the advantages of low cost, few reaction steps, short time, high yield and the like.

Preparation method of alpha, alpha-diphenyl-4-piperidine methanol

The invention discloses a preparation method of alpha, alpha-diphenyl-4-piperidine methanol, which comprises the following steps of by using benzophenone and 4-cyanopyridine as raw materials, carrying out free radical coupling reaction under the action of alkali metal to obtain alpha, alpha-diphenyl-4-piperidine methanol, reacting the obtained alpha, alpha-diphenyl-4-pyridine methanol with a benzylation reagent to generate N-benzyl-alpha, alpha-diphenyl-4-pyridine methanol, carrying out hydroboration reduction on the N-benzyl-alpha, alpha-diphenyl-4-pyridine methanol to obtain (1-benzyl-1, 2, 3, 6-tetrahydropyridine-4-yl)benzhydrol, ane enabling (1-benzyl-1, 2, 3, 6-tetrahydropyridine-4-yl)benzhydrol to be subjected to catalytic hydrogenation and debenzylation protection to obtain alpha, alpha-diphenyl-4-piperidine methanol. The method has the advantages of cheap and accessible raw materials, high reaction yield and high controllability, and is suitable for industrial production requirements.

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

OXAZINE MONOACYLGLYCEROL LIPASE (MAGL) INHIBITORS

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The invention relates to a preparation method of diphenyl(4-pyridyl)methanol. According to the method, benzophenone and 4-cyanopyridine are taken as raw materials to carrying out a one-step reaction to prepare the diphenyl(4-pyridyl)methanol. The preparation method is simple in process, low in cost, high in yield and high in controllability, and is suitable for industrial production.

MELANIN PRODUCTION INHIBITOR

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Direct substitution of hydrogen in C(sp3)-H bonds by 4-pyridine was achieved by employing benzophenone and 4-cyanopyridine in aqueous acetonitrile under photo-irradiating conditions. This simple and mild 4-pyridination proceeds in a highly chemoselective manner especially at benzylic C(sp3)-H bonds without affecting polar functional groups, and enables intermolecular formation of sterically hindered bonds between alkylaromatics and 4-pyridine. The present methodology thus serves as a powerful tool for construction of biologically active and functional molecules with 4-pyridine substructures.

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ortho-ortho hydrogen van der Waals repulsions are the origin of the propeller shape of the triphenylmethyl radical and the main reason for the low bond dissociation enthalpy (BDH) of its dimer 1 (44.8 J mol-1).In order to reduce these steric repulsions (eliminating some aromatic hydrogens), diphenyl(2-, 3- or 4-pyridyl)methyl radicals 2-4 were prepared through reductive dehalogenation of the corresponding triarylchloromethanes 2-4a with silver in benzene.They form α,p-dimers 2-4e exclusively through the pyridine ring.ENDOR spectroscopy shows that the structure of the radicals, does not deviate substantially from that of the parent radical, PH3C-radical.In contrast, the BDH values of the dimers (measured using EPR spectroscopy) show strengthening of the central C-C bond in 2e (88.7 kJ mol-1) and 3e (90.0 kJ mol-2) and a silimar value for 4e (46.4 kJ mol-1) with respect to the trityl dimer 1.This is a consequence of the ground state stabilization of the dimers 2-4e due to relief of strain (elimination of ring hydrogens), whereas in the case of 4e, this stabilization is probably compensated by the formation of a weaker C-N bond with respect to the C-C bond.The above dimers undergo easy 1,5-H-rearrangement, autocatalysed by the basic pyridyl groups themselves.