Benzenediazonium chloride
- Benzenediazonium chloride
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IUPACName = Benzenediazonium chloride
OtherNames = Phenyldiazonium chloride
Section1 = Chembox Identifiers
CASNo = 100-34-5
PubChem =
SMILES = [Cl-] .N# [N+] c1ccccc1
Section2 = Chembox Properties
Formula = C6H5ClN2
MolarMass = 140.570 g/mol
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Section3 = Chembox Hazards
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Benzenediazonium chloride is the diazonium compound of aniline. It is used in the preparation of azo compounds (e.g. azo dyes). It is synthesised from nitrous acid and aniline. Nitrous acid is prepared "in situ" due to the fact that it is not stable enough to be stored.
Synthesis
Preparation of nitrous acid:
:NaNO2 + HCl → HNO2 + NaCl
The nitrous acid formed is reacted with aniline to give benzenediazonium chloride:
: C6H5NH2 + HNO2 + HCl → [C6H5N+≡N] [Cl−]
The temperature must be kept between 0-5 °C to avoid the product from decomposing to give dinitrogen.
Diazo coupling reactions
Benzenediazonium chloride can react with phenol or aniline, via diazo coupling reactions, to give azo compounds:
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benzenediazonium — ˌbenˌzēnˌdīəˈzōnēəm noun ( s) Etymology: benzene + diaz + onium : a univalent cation C6H5N2+ known best in the form of crystalline explosive salts (as the chloride C6H5N2Cl made by reaction of aniline hydrochloride and nitrous acid) … Useful english dictionary
Diazonium compound — Phenyldiazonium cation Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R N2+ X where R can be any organic residue such alkyl or aryl and X is an inorganic or organic anion such as a… … Wikipedia
triphenylformazan — (|)trī|fenəl, fēn + noun Etymology: triphenyl + formazan : a red insoluble compound C6H5N . NC(C6H5) . NNHC6H5 obtained by reaction of benzaldehyde phenylhydrazone with benzenediazonium chloride or by reduction of triphenyltetrazolium chloride … Useful english dictionary
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diazonium salt — Chem. any of a group of salts of the general formula ArN2X, in which Ar represents an aryl group and X an anion, as benzenediazonium chloride, C6H5N(N)Cl, many of which are important intermediates in the manufacture of azo dyes. [1905 10] * * * ▪ … Universalium
phenylhydrazine — | ̷ ̷ ̷ ̷+ noun Etymology: International Scientific Vocabulary phenyl + hydrazine; originally formed as German phenylhydrazin : a toxic liquid nitrogen base C6H5NHNH2 that is made by reduction of benzenediazonium chloride and that reacts with… … Useful english dictionary
diazonium salt — Chem. any of a group of salts of the general formula ArN2X, in which Ar represents an aryl group and X an anion, as benzenediazonium chloride, C6H5N(N)Cl, many of which are important intermediates in the manufacture of azo dyes. [1905 10] … Useful english dictionary
Nucleophile — A nucleophile is a species that donates an electron pair to an electrophile to form a chemical bond in a reaction. All molecules or ions with a free pair of electrons can act as nucleophiles. Because nucleophiles donate electrons, they are by… … Wikipedia
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