519-73-3

Basic information

• Product Name: Triphenylmethane
• Synonyms: 1,1’,1’’-methylidynetris-benzen;Benzene, 1,1',1''-methylidynetris-;Benzene,1,1',1 -methylidynetris-;benzene,1,1’,1’’-methylidynetris-;Benzhydrylbenzene;Methane, triphenyl-;methane,triphenyl-;Triphenylmethan
• CAS NO: 519-73-3
• Molecular Formula: C₁₉H₁₆
• Molecular Weight: 244.33
• EINECS: 208-275-0
• Product Categories: Arenes;Building Blocks;Organic Building Blocks;Aromatics;Diagnostic;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 519-73-3.mol
• Article Data: 292

Chemical Properties

• Melting Point: 92-94 °C(lit.)
• Boiling Point: 358-359 °C754 mm Hg(lit.)
• Flash Point: 358-359°C
• Appearance: Faint yellow/Powder
• Density: 1.014 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.74E-05mmHg at 25°C
• Refractive Index: nD100 1.59546
• Storage Temp.: 2-8°C
• Solubility: dioxane: 0.1 g/mL, clear
• PKA: 31.5(at 25℃)
• Water Solubility: INSOLUBLE
• Stability: Stable; combustible. Incompatible with strong oxidizing agents.
• Merck: 14,9741
• BRN: 1909753
• CAS DataBase Reference: Triphenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: Triphenylmethane(519-73-3)
• EPA Substance Registry System: Triphenylmethane(519-73-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 519-73-3(Hazardous Substances Data)

Usage

Chemical Properties

colorless or light brown powder. soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical).

Uses

Triphenylmethane is a triarylmethane compound used as the backbone of synthetic dyes. Triphenylmethane has also been shown to inhibit 3-methylcholanthrene-induced neoplastic transformation of 10T1/2 cells.

Definition

ChEBI: Triphenylmethane is a triarylmethane in which the three aryl groups are phenyl. It forms the basic skeleton of several synthetic dyes. It has a role as a xenobiotic and an environmental contaminant.

Preparation

Triphenylmethane can be synthesized by Friedel–Crafts reaction from benzene and chloroform with aluminium chloride catalyst: 3 C6H6 + CHCl3 → Ph3CH + 3 HCl

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 5846, 1951 DOI: 10.1021/ja01156a116Organic Syntheses, Coll. Vol. 1, p. 548, 1941Tetrahedron Letters, 21, p. 801, 1980 DOI: 10.1016/S0040-4039(00)71509-7

Purification Methods

Crystallise triphenylmethane from EtOH or *benzene (with one molecule of *benzene of crystallisation which is lost on exposure to air or by heating on a water bath). It can also be sublimed under vacuum. It has been given a preliminary purification by refluxing with tin and glacial acetic acid, then filtered hot through a glass sinter disc, and precipitated by addition of cold water. [Beilstein 5 H 698, 5 IV 2495.]

InChI:InChI=1/C19H16/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,19H

Upstream product

• 110-86-1 pyridine 
• 106-44-5 p-cresol 
• 76-83-5 trityl chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 64-18-6 formic acid 
• 76-84-6 triphenylmethyl alcohol 
• 104-93-8 p-methylanizole 
• 3736-70-7 triphenylphosphonyl dichloride 
• 60-29-7 diethyl ether 
• 75-29-6 isopropyl chloride 
• 4303-71-3 triphenylmethyl sodium 
• 507-20-0 tertiary butyl chloride 
• 67-66-3 chloroform 
• 75-25-2 Bromoform 

Downstream Products

• 76-84-6 triphenylmethyl alcohol 
• 4447-64-7 ethyl 2,2,4-trimethyl-3-oxopentanoate 
• 93-89-0 benzoic acid ethyl ester 
• 971-85-7 triphenylmethyl acetate 
• 3416-62-4 1,1,1,6,6,6-hexaphenyl-hexane 
• 36726-98-4 Dimethyl-<2,2,2-triphenyl-ethyl>-amin 
• 3416-61-3 1,1,1,5,5,5-hexaphenyl-pentane 
• 5467-21-0 methyl 2,2,2-triphenylacetate 
• 32863-87-9 (indol-3-yl)triphenylmethane 
• 68407-94-3 N-1-Tritylbenzotriazole 
• 66365-49-9 N-(triphenylmethyl)succinimide 
• 97990-99-3 (E)-1,1,1-Triphenyl-3-penten-2-ol 
• 40006-86-8 triphenylmethyl anion 
• 67-68-5 dimethyl sulfoxide 

Relevant articles and documents

Supercritical Carbon Dioxide. 3. The Decomposition of Phenylazotriphenylmethane in Supercritical Carbon Dioxide

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Efficient reduction of triphenylmethanol to triphenylmethane by 9,10-dihydro-10-methylacridine in the presence of perchloric acid

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Imidoyl radicals as synthons of unstable acyl radicals

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Synthesis and characterization of a gold vinylidene complex lacking π-conjugated heteroatoms

Abstract Hydride abstraction from the gold (disilyl)ethylacetylide complex [(P)Au{η1-C≡CSi(Me)2CH2CH2SiMe2H}] (P=P(tBu)2o-biphenyl) with triphenylcarbenium tetrakis(pentafluorophenyl)borate at -20 °C formed the cationic gold (β,β-disilyl)vinylidene complex [(P)Au=C=CSi(Me)2CH2CH2Si(Me)2]+B(C6F5)4- with ≥90% selectivity. 29Si NMR analysis of this complex pointed to delocalization of positive charge onto both the β-silyl groups and the (P)Au fragment. The C1 and C2 carbon atoms of the vinylidene complex underwent facile interconversion (ΔG≠=9.7 kcal mol-1), presumably via the gold π-disilacyclohexyne intermediate [(P)Au{η2-C≡CSi(Me)2CH2CH2Si(Me)2}]+B(C6F5)4-. Good as gold: Cationic gold (β,β-disilyl)vinylidene complex 1 was generated by addition of a pendant silylium ion to the C≡C bond of a gold acetylide complex (see scheme, P=PtBu2(o-biphenyl)). The vinylidene C1 and C2 atoms of 1 undergo facile interconversion, presumably via a π-disilacyclohexyne intermediate. 29Si NMR analysis of 1 indicates delocalization of positive charge onto both the β-silyl groups and the (P)Au fragment.

N-Heterocyclic Phosphenium Dihalido-Aurates: On the Borderline between Classical Coordination Compounds and Ion Pairs

2-Bromo- and 2-chloro-1,3,2-diazaphospholenes react with (tht)AuCl to afford isolable N-heterocyclic phosphenium (NHP) dihalido-aurates, which were characterized by analytical and spectroscopic data and in one case by a single-crystal X-ray diffraction study. The T-shaped metal coordination sphere found in the crystal consists of a pseudo-linear AuX2 unit that is perturbed by a weakly bound NHP unit. DFT studies indicate that the subunits interact mainly through electrostatic and dispersion forces, with negligible covalent contributions, and that the phosphenium dibromido-aurate is slightly more stable than an isomeric complex with an intact bromophosphane ligand. NMR studies reveal that the NHP-AuX2 pairs persist in solution but are kinetically labile and readily undergo halide scrambling. The hydride/fluoride exchange reaction between a secondary phosphane-AuCl complex and [Ph3C][BF4] implies that a gold complex with an intact 2-halogeno-1,3,2-diazaphospholene ligand may be more stable than its phosphenium dihalido-aurate isomer when covalent P–X bonding contributions are strengthened.

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Superacid-catalyzed condensation of benzaldehyde with benzene. Study of protonated benzaldehydes and the role of superelectrophilic activation

Under superacid conditions benzaldehyde reacts readily with benzene to give triphenylmethane in high yield. Experimental evidence supports the involvement of diprotonated benzaldehyde in the reaction. Ab initio calculations at the correlated MP2/6-31G* le

Trapping of an NiII Sulfide by a CoI Fulvene Complex

The reaction of [LtBuNiII(SCPh3)] (LtBu = {(2,6-iPr2C6H3)NC(tBu)}2CH) with Cp*2Co yields a NiI cobaltocenium thiolate complex, [LtBuNiI(SCH2Me4C5)Co(Cp*)] (1), along with HCPh3. Formation of this complex is proposed to occur via the reaction of a transient NiII sulfide, [Cp*2Co][LtBuNiII(S)], with a CoI fulvene complex, [CoCp*(C5Me4CH2)]. The latter complex is formed in situ by reaction of [Cp*2Co]+ with [CPh3]?. Control experiments, as well as cyclic voltammetry measurements of 1, are used to support the proposed mechanism.

Evidence for a Silylenium Ion in Solution

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Substituent effects on the reaction of trityl chlorides with Grignard reagents

The result of the substitution of trityl chlorides with Grignard reagents was found to be highly dependent on the solvent and the nature of the substituents on the trityl group. In THF, electron donating substituents were found to give high yields of Grig

Deoxygenation of tertiary and secondary alcohols with sodium borohydride, trimethylsilyl chloride, and potassium iodide in acetonitrile

The deoxygenation of tertiary and secondary alcohols to give the corresponding alkanes is conventionally performed using an organosilane and a strong acid. In this study, a deoxygenation method was developed for tertiary and secondary alcohols, using trimethylsilane and trimethylsilyl iodide generated in situ from sodium borohydride and trimethylsilyl chloride, and trimethylsilyl chloride and potassium iodide, respectively. With our method, tertiary and secondary alcohols, which provided stable carbocations, were converted into the corresponding alkanes. This paper also presents the optimization of the reaction conditions, the reaction mechanism, as well as the scope and limitations of the method.

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki-Miyaura Reactions of Diarylmethyl Esters

The synthesis of triarylmethanes via Pd-catalyzed Suzuki-Miyaura reactions between diarylmethyl 2,3,4,5,6-pentafluorobenzoates and aryl boronic acids is described. The system operates under mild conditions and has a broad substrate scope, including the coupling of diphenylmethanol derivatives that do not contain extended aromatic substituents. This is significant as these substrates, which result in the types of triarylmethane products that are prevalent in pharmaceuticals, have not previously been compatible with systems for diarylmethyl ester coupling. Furthermore, the reaction can be performed stereospecifically to generate stereoinverted products. On the basis of DFT calculations, it is proposed that the oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrate occurs via an SN2 pathway, which results in the inverted products. Mechanistic studies indicate that oxidative addition of the diarylmethyl 2,3,4,5,6-pentafluorobenzoate substrates to (IPr)Pd(0) results in the selective cleavage of the O-C(benzyl) bond in part because of a stabilizing η3-interaction between the benzyl ligand and Pd. This is in contrast to previously described Pd-catalyzed Suzuki-Miyaura reactions involving phenyl esters, which involve selective cleavage of the C(acyl)-O bond, because there is no stabilizing η3-interaction. It is anticipated that this fundamental knowledge will aid the development of new catalytic systems, which use esters as electrophiles in cross-coupling reactions.