851789-43-0

Basic information

• Product Name: 2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol
• Synonyms: 2-(3-Hydro-1-phenyl-propyl)-4-methyl-phenol;2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol;3-(2-Hydroxy-5-methylphenyl)-3-phenylpropanol;2-Hydroxy-5-Methyl-γ-phenylbenzenepropanol (Tolterodine IMpurity);2-(3-Hydro-1-phenyl-propyl)-4-Methyl-4Methyl-phenol
• CAS NO: 851789-43-0
• Molecular Formula: C₁₆H₁₈O₂
• Molecular Weight: 242.31
• Product Categories: Medicine intermediate;Aromatics;Impurity;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 851789-43-0.mol
• Article Data: 11

Chemical Properties

• Melting Point: 118-120°C
• Boiling Point: 414.8°C at 760 mmHg
• Flash Point: 197°C
• Appearance: /
• Density: 1.128
• Vapor Pressure: 1.26E-07mmHg at 25°C
• Refractive Index: 1.595
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.18±0.48(Predicted)
• CAS DataBase Reference: 2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol(851789-43-0)
• EPA Substance Registry System: 2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol(851789-43-0)

Safety Data

• Hazardous Substances Data: 851789-43-0(Hazardous Substances Data)

Usage

Description

2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol is an organic compound that serves as an important intermediate in the synthesis of various pharmaceuticals and chemicals. It is characterized by its unique molecular structure, which consists of a phenol group with a hydroxyl group attached to a phenylpropyl chain and a methyl group on the para position.

Uses

Used in Pharmaceutical Industry:
2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol is used as a key intermediate in the efficient synthesis of Tolterodine, a medication used for the treatment of overactive bladder and urinary incontinence. Its unique structure allows for the formation of specific chemical bonds and reactions that are crucial for the production of Tolterodine.
Used in Chemical Synthesis:
2-(3-Hydroxy-1-phenylpropyl)-4-methylphenol is also used in the synthesis of various other chemicals and compounds, owing to its reactive functional groups and versatile chemical properties. Its ability to participate in a wide range of chemical reactions makes it a valuable building block in the development of new materials and products.

InChI:InChI=1/C16H18O2/c1-12-7-8-16(18)15(11-12)14(9-10-17)13-5-3-2-4-6-13/h2-8,11,14,17-18H,9-10H2,1H3

Upstream product

• 40546-94-9 6-methyl-4-phenyl-3,4-dihydrocoumarin 
• 108-18-9 diisopropylamine 
• 828933-86-4 (4R)-6-methyl-4-phenylchroman-2-ol 
• 827007-19-2 (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one 
• 98-80-6 phenylboronic acid 
• 92-48-8 6-methylcoumarin 
• 140-10-3 (E)-3-phenylacrylic acid 
• 106-44-5 p-cresol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 349547-18-8 (S)-6-methyl-4-phenylchroman-2-one 

Downstream Products

• 894773-88-7 3-(2-(ethanesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-ethanesulfonate 
• 851789-45-2 3-(2-(p-toluenesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-p-toluenesulfonate 
• 124937-52-6 tolterodine tartrate 
• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 894773-87-6 3-(2-(benzenesulfonyloxy)-5-methylphenyl)-3-phenylpropyl-benzenesulfonate 
• 854306-68-6 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropanol 

Relevant articles and documents

Computationally-Led Ligand Modification using Interplay between Theory and Experiments: Highly Active Chiral Rhodium Catalyst Controlled by Electronic Effects and CH–π Interactions

A chiral ligand for the rhodium-catalyzed asymmetric 1,4-addition of an arylboronic acid to a coumarin substrate that could markedly reduce catalyst loading was developed using interplay between theoretical and experimental approaches. Evaluation of the transition states for insertion and for hydrolysis of intermediate complexes (which were emphasized in response to the experimental results) using DFT calculations at the B97D/6-31G(d) level with the LANL2DZ basis set for rhodium revealed that: (i) the electron-poor nature of the ligands and (ii) CH–π interactions between the ligand and coumarin substrates played significant roles in both acceleration of insertion and inhibition of ArB(OH)2 decomposition (protodeboronation). The computationally-designed ligand, incorporating the above information, enabled a decrease in the catalyst loading to 0.025 mol% (S/C=4,000), which is less than one one-hundredth relative to past catalyst loadings of typically 3 mol%, with almost complete enantioselectivity. Furthermore, the gram-scale synthesis of the urological drug, (R)-tolterodine (l)-tartrate, was demonstrated without the need of intermediate purification. (Figure presented.).

Synthesis and Antioxidant Properties of New Substituted 8-Methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide Derivatives

A new route for the synthesis of substituted 8-methyl-6-phenyl-5,6-dihydro-4H-1,3,2-benzodioxaphosphocine-2-oxide derivatives has been developed by using cinnamic acid and p-cresol via condensation, reduction, and followed by phosphorylation steps. The ti

Co-catalyzed mild and chemoselective reduction of phenyl esters with NaBH4: a practical synthesis of (R)-tolterodine

CoCl2 catalyzes effectively the chemoselective reduction of phenyl carboxylic esters to the corresponding saturated alcohols in high yields using NaBH4 at ambient conditions. By employing this methodology, the synthesis of (R)-tolterodine, a muscarinic receptor antagonist, has been achieved in high yield and optical purity.