4428-13-1

Basic information

• Product Name: 1,1,2-triphenylethanol
• Synonyms: 1,1,2-triphenylethanol;α,α-Diphenylbenzeneethanol
• CAS NO: 4428-13-1
• Molecular Formula: C₂₀H₁₈O
• Molecular Weight: 274.35632
• EINECS: 224-614-5
• Mol File: 4428-13-1.mol

Chemical Properties

• Melting Point: 89.5°C
• Boiling Point: 377.34°C (rough estimate)
• Flash Point: 153.1 °C
• Appearance: /
• Density: 1.0338 (rough estimate)
• Vapor Pressure: 4.81E-07mmHg at 25°C
• Refractive Index: 1.4880 (estimate)
• CAS DataBase Reference: 1,1,2-triphenylethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2-triphenylethanol(4428-13-1)
• EPA Substance Registry System: 1,1,2-triphenylethanol(4428-13-1)

Safety Data

• Hazardous Substances Data: 4428-13-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
1,1,2-Triphenylethanol is used as a chiral auxiliary in asymmetric synthesis reactions for its ability to induce selectivity and improve the yield of enantioselective reactions.
Used in Pharmaceutical Industry:
1,1,2-Triphenylethanol is used as a versatile building block for the construction of various biologically active molecules, contributing to the development of new drugs and therapeutic agents.
Used in Cosmetic Industry:
1,1,2-Triphenylethanol is used for its potential antioxidant and antibacterial properties, making it a promising candidate for applications in skincare and personal care products.
Used in Chemical Research and Development:
1,1,2-Triphenylethanol is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, playing a significant role in advancing chemical research and development.

InChI:InChI=1/C20H18O/c21-20(18-12-6-2-7-13-18,19-14-8-3-9-15-19)16-17-10-4-1-5-11-17/h1-15,21H,16H2

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 119-61-9 benzophenone 
• 1589-82-8 phenylmagnesium bromide 
• 2785-29-7 benzyl potassium 
• 882-59-7 1,1-diphenyloxirane 
• 591-51-5 phenyllithium 
• 4479-98-5 2,2,3-triphenyloxirane 
• 7716-70-3 acetic acid-(1,1,2-triphenyl-ethyl ester) 
• 101-97-3 Ethyl 2-phenylethanoate 
• 108-88-3 toluene 
• 6921-34-2 benzylmagnesium chloride 
• 100-44-7 benzyl chloride 
• 591-50-4 iodobenzene 
• 770-09-2 benzyltrimethylsilane 

Downstream Products

• 58-72-0 Triphenylethylene 
• 34131-92-5 nitro-tris-(4-nitro-phenyl)-ethene 
• 5670-70-2 nitro-triphenyl-ethene 
• 29240-44-6 2-bromo-1,1,2-triphenyl-ethanol 
• 55682-86-5 1,1,2-tricyclohexyl-ethane 
• 6973-87-1 1-chloro-1,1,2-triphenyl-ethane 
• 1520-42-9 1,1,2-triphenylethane 
• 119-61-9 benzophenone 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 74064-34-9 1,2-dibromo-1,1,2-triphenyl-ethane 
• 1733-63-7 1,2,2-triphenylethan-1-one 
• 4479-98-5 2,2,3-triphenyloxirane 
• 1485636-32-5 (1-azidoethane-1,1,2-triyl)tribenzene 

Relevant articles and documents

Evidence for Electron-transfer Process in Abnormal Gringard Reactions. Enolization and α-Diketone Formation

The effect of 2,6-dimethyl groups on enolization vs. addition in the reaction of PhMgBr with PhCH2COPh, and also the formation of α-diketone from 2,4,6-Me3C6H2COCl by the treatment with MeMgX and i-PrMgX in the presence of CoCl2, were studied.The results were discussed on the basis of electron-transfer mechanism.

O-H...?(arene) Intermolecular Hydrogen Bonding in the Structure of 1,1,2-Triphenylethanol

The 1,1,2-triphenylethanol molecule, Ph2(PhCH2)COH (I), forms centrosymmetric dimers in the solid state.The shortest O...O separation, 5.837(3) Angstroem, is too long for any O-H...O hydrogen-bond formation.Instead, there are O-H...?(arene) interactions between the hydroxyl group of one molecule and a phenyl group of acentrosymmetrically related molecule.The O...C and H...C distances between the hydroxyl group and the closest phenyl-ring C atom are 3.525(4) and 2.73(4) Angstroem, respectively.These intermolecular contacts are the only driving force towards dimer formation in the solid state.

Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone

A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Paternò-Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.

Hydrogen bonding in ferrocene derivatives: crystal structure of racemic ferrocenyl(phenyl)methanol

A single-cristal X-ray diffraction study has been carried out on racemic ferrocenyl(phenyl)methanol.There are two independent chiral molecules A and B in the asymmetric unit, and the molecules are linked by OH...O hydrogen bonds into zigzag chains characterized by the motif -S(A)-R(B)-R(A)-S(B)-; within these chains the two independent hydrogen-bonded O...O distances are 3.059(2) and 3.150(2) Angstroem.Key words: Ferrocene; Hydrogen bonding; Crystal structure

Iron-catalysed 1,2-aryl migration of tertiary azides

1,2-Aryl migration of α,α-diaryl tertiary azides was achieved by using the catalytic system of FeCl2/N-heterocyclic carbene (NHC) SIPr·HCl. The reaction generated aniline products in good yields after one-pot reduction of the migration-resultant imines.

Iron-Catalyzed Nucleophilic Addition Reaction of Organic Carbanion Equivalents via Hydrazones

Earth-abundant and well-defined iron complexes are found to be cheap and effective catalysts for a series of "umpolung" nucleophilic additions of hydrazones. The new catalytic system not only maintains the broad substrate scope of an earlier expensive ruthenium system but also attains chemoselectivity of different kinds of carbonyl groups. Furthermore, the iron catalyst enables this reaction at ambient temperature.

Photocatalytic Barbier reaction-visible-light induced allylation and benzylation of aldehydes and ketones

We report a photocatalytic version of the Barbier type reaction using readily available allyl or benzyl bromides and aromatic aldehydes or ketones as starting materials to generate allylic or benzylic alcohols. The reaction proceeds at room temperature under visible light irradiation with the organic dye 3,7-di(4-biphenyl)1-naphthalene-10-phenoxazine as a photocatalyst and DIPEA as sacrificial electron donor. The proposed cross-coupling mechanism of a ketyl- and an allyl or benzyl radical is supported by spectroscopic investigations and cyclic voltammetry measurements.

Aldehydes as alkyl carbanion equivalents for additions to carbonyl compounds

Nucleophilic addition reactions of organometallic reagents to carbonyl compounds for carbon-carbon bond construction have played a pivotal role in modern chemistry. However, this reaction's reliance on petroleum-derived chemical feedstocks and a stoichiometric quantity of metal have prompted the development of many carbanion equivalents and catalytic metal alternatives. Here, we show that naturally occurring carbonyls can be used as latent alkyl carbanion equivalents for additions to carbonyl compounds, via reductive polarity reversal. Such 'umpolung' reactivity is facilitated by a ruthenium catalyst and diphosphine ligand under mild conditions, delivering synthetically valuable secondary and tertiary alcohols in up to 98% yield. The unique chemoselectivity exhibited by carbonyl-derived carbanion equivalents is demonstrated by their tolerance to protic reaction media and good functional group compatibility. Enantioenriched tertiary alcohols can also be accessed with the aid of chiral ligands, albeit with moderate stereocontrol. Such carbonyl-derived carbanion equivalents are anticipated to find broad utility in chemical bond formation.

α-Alkylidene-γ-butyrolactone synthesis via one-pot C-H insertion/olefination: substrate scope and the total synthesis of (±)-cedarmycins A and B

Abstract A system for the synthesis of α-alkylidene-γ-butyrolactones via a one-pot C-H insertion/olefination sequence is described. The process is based on the rhodium catalysed C-H insertion reaction of α-diazo-α-(diethoxyphosphoryl)acetates. The mild reaction conditions, operational simplicity and ready availability of starting materials are all key features. A wide range of successful reaction systems are reported (41 examples) highlighting the generality of the method. The application of this method in the total synthesis of the natural products (±)-cedarmycins A and B is also described.

Benzyllithiums bearing aldehyde carbonyl groups. A flash chemistry approach

Reductive lithiation of benzyl halides bearing aldehyde carbonyl groups followed by reaction with subsequently added electrophiles was successfully accomplished without affecting the carbonyl groups by taking advantage of short residence times in flow microreactors.