Triphenylmethyl chloride

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Triphenylmethyl chloride
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Names
Preferred IUPAC name
1,1′,1′′-(Chloromethanetriyl)tribenzene
Other names
(Chloromethanetriyl)tribenzene
[Chloro(diphenyl)methyl]benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.898 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C19H15Cl.C10H10.C8H8/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-3-9-5-7-10(4-2)8-6-9;1-2-8-6-4-3-5-7-8/h1-15H;3-8H,1-2H2;2-7H,1H2 Yes check.svgY
    Key: TXMWQDFQVWGFTQ-UHFFFAOYSA-N Yes check.svgY
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl
Properties
C19H15Cl
Molar mass 278.7754 g/mol
Appearancewhite to yellow solid
Density 1.141 g/cm3
Melting point 109 to 112 °C (228 to 234 °F; 382 to 385 K)
Boiling point 230 °C (446 °F; 503 K)(at 20 mmHg) and 374.3 °C (at 760 mmHg)
Solubility soluble in chloroform, benzene, acetone, [1] ether, THF, hexane [2]
Hazards
Flash point 177.9 °C (352.2 °F; 451.0 K)
Safety data sheet (SDS) Corvine Chemicals MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

Contents

Preparation

Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed. [3]

Reactions

Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium: [4]

(C6H5)3CCl + 2 Na → (C6H5)3CNa + NaCl

Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.

See also

Related Research Articles

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Sodium amide Chemical compound

Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula NaNH2. It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. NaNH2 conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. NaNH2 has been widely employed as a strong base in organic synthesis.

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Triphenylmethane Chemical compound

Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is 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).

Caesium fluoride Chemical compound

Caesium fluoride or cesium fluoride is an inorganic compound with the formula CsF and it is a hygroscopic white salt. Caesium fluoride can be used in organic synthesis as a source of the fluoride anion. Caesium also has the highest electropositivity of all non-radioactive elements and fluorine has the highest electronegativity of all elements.

Oxalyl chloride Chemical compound

Oxalyl chloride is a chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.

Thionyl chloride Chemical compound

Thionyl chloride is an inorganic compound with the chemical formula SOCl
2
. It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.

Permanganate Chemical compound

A permanganate is the general name for a chemical compound containing the manganate(VII) ion, MnO
4
, the conjugate base of permanganic acid. Because the manganese atom is in the +7 oxidation state, the permanganate(VII) ion is a strong oxidizing agent. The ion has tetrahedral geometry. Permanganate solutions are purple in color and are stable in neutral or slightly alkaline media. The exact chemical reaction is dependent upon the organic contaminants present and the oxidant utilized. For example, trichloroethane (C2H3Cl3) is oxidized by permanganate ions to form carbon dioxide (CO2), manganese dioxide (MnO2), hydrogen ions (H+), and chloride ions (Cl).

Phosphorus pentachloride Chemical compound

Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive and moisture-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.

Palladium(II) chloride Chemical compound

Palladium(II) chloride, also known as palladium dichloride and palladous chloride, are the chemical compounds with the formula PdCl2. PdCl2 is a common starting material in palladium chemistry – palladium-based catalysts are of particular value in organic synthesis. It is prepared by the reaction of chlorine with palladium metal at high temperatures.

Triphenylmethanol Chemical compound

Triphenylmethanol is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes.

Sulfur tetrafluoride Chemical compound

Sulfur tetrafluoride is the chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous HF upon exposure to water or moisture. Despite these unwelcome characteristics, this compound is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.

Organomercury

Organomercury refers to the group of organometallic compounds that contain mercury. Typically the Hg–C bond is stable toward air and moisture but sensitive to light. Important organomercury compounds are the methylmercury(II) cation, CH3Hg+; ethylmercury(II) cation, C2H5Hg+; dimethylmercury, (CH3)2Hg, diethylmercury, and merbromin ("Mercurochrome"). Thiomersal is used as a preservative for vaccines and intravenous drugs.

Hexafluorophosphate Anion with the chemical formula PF6–

Hexafluorophosphate is an anion with chemical formula of PF
6
. It is an octahedral species that imparts no color to its salts. PF
6
is isoelectronic with sulfur hexafluoride, SF6, and the hexafluorosilicate dianion, SiF2−
6
, and fluoroantimonate SbF
6
. Being poorly nucleophilic, hexafluorophosphate is classified as a non-coordinating anion.

Triphenylarsine Chemical compound

Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.

Zirconocene dichloride is an organozirconium compound composed of a zirconium central atom, with two cyclopentadienyl and two chloro ligands. It is a colourless diamagnetic solid that is somewhat stable in air.

Sulfenyl chloride

A sulfenyl chloride is a functional group with the connectivity R–S–Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS–N and RS–O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.

Organosodium chemistry is the chemistry of organometallic compounds containing a carbon to sodium chemical bond. The application of organosodium compounds in chemistry is limited in part due to competition from organolithium compounds, which are commercially available and exhibit more convenient reactivity.

Triphenylmethyl hexafluorophosphate Chemical compound

Triphenylmethyl hexafluorophosphate is an organic salt with the formula C
19
H
15
F
6
P
or (C
6
H
5
)
3
CPF
6
, consisting of the triphenylmethyl cation [(C
6
H
5
)
3
C]+
and the hexafluorophosphate anion] [PF
6
]
. The cation is also called triphenylcarbenium, trityl cation, or tritylium.

Triphenylcarbenium

In chemistry, triphenylcarbenium, triphenylmethyl cation, tritylium , or trityl cation is an ion with formula [C
19
H
15
]+
or (C
6
H
5
)
3
C+
, consisting of a carbon atom with a positive charge connected to three phenyl groups. It is a charged version of the triphenylmethyl radical (C
6
H
5
)
3
C
. The name is often abbreviated to triphenylmethyl or trityl in salts, although these names also denote the chemical group in compounds like triphenylmethyl chloride that do not contain the cation.

References

  1. http://www.sciencelab.com/msds.php?msdsId=9925340 [ dead link ]
  2. "Trityl chloride | CAS 76-83-5".
  3. W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Organic Syntheses .{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 3, p. 841.
  4. W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses .; Collective Volume, vol. 2, p. 607