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Triphenylmethane

 

 
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Triphenylmethane
 
 
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Triphenylmethane, or triphenyl methane, is the hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents, but not water. Triphenylmethane has the basic skeleton of many synthetic dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s called triarylmethane dyes, many of them are pH indicator
PH indicator

A pH indicator is a halochromism chemical chemical compound that is added in small amounts to a solution so that the pH of the solution can be determined easily....
s, and some display fluorescence
Fluorescence

Fluorescence is a luminescence that is mostly found as an optical phenomenon in cold bodies, in which the molecular absorption of a photon triggers the emission of a photon with a longer wavelength....
. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g.






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Triphenylmethane, or triphenyl methane, is the hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
 with the formula
Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
 (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents, but not water. Triphenylmethane has the basic skeleton of many synthetic dye
Dye

A dye can generally be described as a colored substance that has an Chemical affinity to the Wiktionary:substrate to which it is being applied....
s called triarylmethane dyes, many of them are pH indicator
PH indicator

A pH indicator is a halochromism chemical chemical compound that is added in small amounts to a solution so that the pH of the solution can be determined easily....
s, and some display fluorescence
Fluorescence

Fluorescence is a luminescence that is mostly found as an optical phenomenon in cold bodies, in which the molecular absorption of a photon triggers the emission of a photon with a longer wavelength....
. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride
Triphenylmethyl chloride

Triphenylmethyl chloride or trityl chloride is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group....
 — trityl chloride.

Preparation

Triphenylmethane can be synthesized by Friedel-Crafts reaction
Friedel-Crafts reaction

The Friedel-Crafts reactions are a set of organic reaction developed by Charles Friedel and James Crafts in 1877. There are two main types of Friedel-Crafts reactions: alkylation reactions and acylation reactions....
 from benzene
Benzene

Benzene, or benzol, is an organic compound chemical compound and a known carcinogen with the molecular formula Carbon6Hydrogen6....
 and chloroform
Chloroform

Chloroform, also known as trichloromethane and methyl trichloride, is a chemical compound with chemical formula CarbonHydrogenChlorine3....
 with aluminium chloride
Aluminium chloride

Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
 catalyst:

3 C6H6 + CHCl3 → Ph3CH + 3 HCl


Alternatively, benzene may react with carbon tetrachloride
Carbon tetrachloride

Carbon tetrachloride, also known by many other names is the organic compound with the chemical formula CCl4. It is a reagent in organic synthesis chemistry and was formerly widely used in fire extinguishers, as a precursor to refrigerations, and a cleaning agent....
 using the same catalyst to obtain the trityl chloride-aluminium chloride
Aluminium chloride

Aluminium chloride is a chemical compound of aluminium and chlorine. The solid has a low melting and boiling point, and is Covalent bond. It sublimation at 178 ?Celsius....
 adduct, which is hydrolyzed with dilute acid:

3 C6H6 + CCl4 + AlCl3 → Ph3CCl·AlCl3
Ph3CCl·AlCl3 + HCl → Ph3CH


Synthesis from benzylidene chloride, prepared from benzaldehyde
Benzaldehyde

Benzaldehyde is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds....
 and phosphorus pentachloride, is used as well.

Acidity

The pKa
PKA

PKA or pKa may be:* Protein kinase A, a cAMP activated protein kinase* pKa, the symbol for Acid dissociation constant...
 of the hydrogen on the central carbon is around 31. Triphenylmethane is significantly more acidic than most other hydrocarbons because the planar trityl anion is stabilized by extensive delocalization over three phenyl rings. The trityl anion absorbs strongly in the visible region, making it red. This colour can be used as an indicator when maintaining anhydrous conditions with calcium hydride
Calcium hydride

Calcium hydride is the chemical compound with the formula CaH2. This grey powder reacts vigorously with water liberating hydrogen gas....
; the hydride reagent reacts with water to form solid calcium hydroxide, while it is also a strong enough base to generate the trityl anion. If the hydride is used up then the solution will turn colourless. The sodium salt can be prepared also from the chloride: 3CCl + 2 Na ? (C6H5)3CNa + NaCl Before the popularization of butyllithium and related strong bases, trityl sodium was often used as a strong, non-nucleophilic base.

Triarylmethane dyes

Examples of triarylmethane dyes are bromocresol green
Bromocresol green

Bromocresol Green is a dye of the triphenylmethane family , which is used as a pH indicator and as a tracking dye for DNA agarose gel electrophoresis....
:
Bromocresol Green
or malachite green
Malachite green

Malachite green, also called aniline green, basic green 4, diamond green B, or victoria green B, IUPAC name:4-[-phenyl-methyl]-N,N-dimethyl-aniline is a toxin chemical primarily used as a dye....
: