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A Colorful Grignard Reaction: Preparation of the Triarylmethane Dyes from 4-Bromo-N,N-Dimethylaniline

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Douglass F. Taber , Robert P. Meagley and Danielle Supplee

University of Delaware, Newark, DE 19716

J. Chem. Educ., 1996, 73 (3), p 259

DOI: 10.1021/ed073p259

Publication Date (Web): March 1, 1996

Section:

History, Education, and Documentation

Abstract

The Grignard reagent is readily prepared from 4-bromo-N,N-dimethylaniline. Addition of this Grignard reagent to diethyl carbonate, followed by acid hydrolysis gives the triarylmethane dye Crystal Violet. Addition of the Grignard reagent to methyl benzoate, followed by acid hydrolysis gives the dye Malachite Green. A procedure suitable for an undergraduate laboratory course is presented.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Dyes / Pigments

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions
James V. McCullagh and Kelly A. Daggett
Journal of Chemical Education2007 84 (11), 1799
- Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions
  James V. McCullagh and Kelly A. Daggett
  Journal of Chemical Education2007 84 (11), 1799
  The synthesis of dyes has long been a popular topic in organic chemistry laboratory experiments because it allows students to see first hand that reactions learned in class can be used to make compounds with useful applications. In this experiment ...
  Abstract | Hi-Res PDF | PDF w/ Links
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment
Roy D. Pointer , Michael A. G. Berg
Journal of Chemical Education2007 84 (3), 483
- Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment
  Roy D. Pointer , Michael A. G. Berg
  Journal of Chemical Education2007 84 (3), 483
  A commercially available Grignard reagent (3.0 M solution of phenyl magnesium bromide in ether) was used in a convenient Grignard synthesis in a second-year organic chemistry laboratory without any of the typical failures associated with the Grignard ...
  Abstract | Hi-Res PDF | PDF w/ Links