1504-52-5

Basic information

• Product Name: 2,3-diphenylprop-2-en-1-ol
• CAS NO: 1504-52-5
• Molecular Formula: C₁₅H₁₄O
• Molecular Weight: 210.2711
• Mol File: 1504-52-5.mol

Chemical Properties

• Boiling Point: 351.9°C at 760 mmHg
• Flash Point: 150.8°C
• Density: 1.106g/cm³
• Vapor Pressure: 1.47E-05mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 2,3-diphenylprop-2-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-diphenylprop-2-en-1-ol(1504-52-5)
• EPA Substance Registry System: 2,3-diphenylprop-2-en-1-ol(1504-52-5)

Safety Data

• Hazardous Substances Data: 1504-52-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2,3-diphenylprop-2-en-1-ol is used as a reagent in organic chemistry for its unique chemical properties and versatile reactivity, facilitating various chemical transformations.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2,3-diphenylprop-2-en-1-ol is utilized as a key intermediate in the synthesis of various pharmaceuticals, leveraging its potential for diverse chemical reactions to create complex organic compounds with therapeutic applications.

Upstream product

• 2048-32-0 ethyl (Z)-2,3-diphenyl-2-propenoate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 98-80-6 phenylboronic acid 
• 104-54-1 3-Phenylpropenol 
• 91-47-4 2,3-diphenylacrylic acid 
• 67-56-1 methanol 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 13702-35-7 2,3-diphenylprop-2-en-1-al 
• 378240-98-3 (E/Z)-N-(1,3-diphenylallyl)benzenamine 
• 74963-01-2 ((2S,3S)-2,3-diphenyloxiran-2-yl)methanol 
• 88424-61-7 ((2R,3R)-2,3-diphenyloxiran-2-yl)methanol 
• 1794-49-6 3-chloro-1,2-diphenyl-1-propene 

Relevant articles and documents

Allylic alcohol synthesis by Ni-catalyzed direct and selective coupling of alkynes and methanol

Methanol is an abundant and renewable chemical raw material, but its use as a C1 source in C-C bond coupling reactions still constitutes a big challenge, and the known methods are limited to the use of expensive and noble metal catalysts such as Ru, Rh and Ir. We herein report nickel-catalyzed direct coupling of alkynes and methanol, providing direct access to valuable allylic alcohols in good yields and excellent chemo- and regioselectivity. The approach features a broad substrate scope and high atom-, step- and redox-economy. Moreover, this method was successfully extended to the synthesis of [5,6]-bicyclic hemiacetals through a cascade cyclization reaction of alkynones and methanol.

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

Heck transformations of biological compounds catalyzed by phosphine-free palladium

The development and optimization of synthetic methods leading to functionalized biologically active compounds is described. Two alternative pathways based on Heck-type reactions, employing iodobenzene or phenylboronic acid, were elaborated for the arylation of eugenol and estragole. Cinnamyl alcohol was efficiently transformed to saturated arylated aldehydes in reaction with iodobenzene using the tandem arylation/isomerization sequential process. The arylation of cinnamyl alcohol with phenylboronic acid mainly gave unsaturated alcohol, while the yield of saturated aldehyde was much lower. Catalytic reactions were carried out using simple, phosphine-free palladium precursors and water as a cosolvent, following green chemistry rules as much as possible.

Employing Water as the Hydride Source in Synthesis: A Case Study of Diboron Mediated Alkyne Hydroarylation

We present an approach to utilize water as the hydride source via Pd(II)/Pd(0) catalysis. As a case study, we have achieved a diboron mediated Pd(II)-catalyzed hydroarylation of alkynes using arylboronic acids. This approach not only complements conventional reactivity of Pd via Pd(0)/Pd(II) cycle for the hydroarylation but also utilizes water as the hydride source. We believe this would particularly be beneficial in utilizing water as a reagent.

The nitrile functionality as a directing group in the Palladium-catalysed addition of aryl boronic acids to alkynes

The nitrile group is shown to direct the palladium-catalysed hydroarylation of internal alkynes bearing a pendant nitrile with boronic acids.