Tetrametilammonio cloruro

Tetrametilammonio cloruro
Struttura chimica del tetrametilammonio cloruro
Struttura tridimensionale del tetrametilammonio cloruro
Caratteristiche generali
Formula bruta o molecolare	C₄H₁₂NCl
Massa molecolare (u)	109.60 g/mol
Aspetto	Bianco cristallino
Numero CAS	75-57-0
Numero EINECS	200-880-8
PubChem	6379 e 3248084
SMILES	`C[N+](C)(C)C.[Cl-]`
Proprietà chimico-fisiche
Densità (g/cm³, in c.s.)	1.17 g/cm³
Temperatura di fusione	425 °C
Indicazioni di sicurezza
Simboli di rischio chimico

Frasi R	21-25-36/37/38
Frasi S	26-28-36/37-45
Modifica dati su Wikidata · Manuale

Il tetrametilammonio cloruro è un sale di ammonio quaternario con formula chimica [(CH₃)₄N]Cl.

Preparazione e usi di laboratorio

Può essere sintetizzato tramite alchilazione del cloruro di ammonio con dimetilcarbonato^[1]:

{\ce {[NH4^+]Cl- + 2 (CH3O)2CO -> [N(CH3)4^+]Cl- + 2 H2O + 2 CO2}}

È utilizzato nella sintesi organica per metilazione e, talvolta, come agente precipitante^[2].

A basse concentrazioni è utilizzato nella reazione a catena della polimerasi per aumentarne la resa e la specificità. Si è visto che, alla concentrazione di 60 mM, esso aumenta la resa di 5-10 volte, stabilizzando le coppie di basi formate da adenina e timina^[3].

Note

^ Z. et al. Zheng, Jie Wang, Ting Hua Wu e Xiao Ping Zhou, Alkylation of Ammonium Salts Catalyzed by Imidazolium-Based Ionic Liquid Catalysts, in Advanced Synthesis & Catalysis, vol. 349, n. 7, 2007, pp. 1095–1101, DOI:10.1002/adsc.200600451.
^ W. J. Middleton and D. W. Wiley, Tetramethylammonium 1-Propene-1,1,2,3,3-pentacarbonitrile, in Organic Syntheses, n. 5, 1973, p. 1013. URL consultato il 1º luglio 2012 (archiviato dall'url originale il 4 ottobre 2012).
^ Chevet E. et al (1995) “Low concentrations of tetramethylammonium chloride increase yield and specificity of PCR”, “Nucleic Acids Research” 23 (16): 3343-3344

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Altri progetti

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