The Bromo-2-nitrobenzoic Acids

Erickson, J. L. E.; Dechary, J. M.; Pullig, Tillman Rupert

doi:10.1021/ja01142a025

Cited by 8 publications

(7 citation statements)

References 1 publication

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“…We, therefore, prepared the acid by Sandmeyer reaction [ 35 , 36 ] of 4-amino-2-chlorobenzoic acid ( 18 ). However, this reaction also gave an unidentified high-melting side product, and the desired product was obtained in 52% yield only after tedious chromatographic purification.…”

Section: Resultsmentioning

confidence: 99%

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A Simple, Safe and Efficient Synthesis of Tyrian Purple (6,6′-Dibromoindigo)

Wolk

Frimer

2010

Molecules

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6,6’-Dibromoindigo is a major component of the historic pigment Tyrian purple, arguably the most famous dye of antiquity. Over the last century, chemists have been interested in developing practical syntheses of the compound We describe herein a new, reasonably simple and efficient synthesis of Tyrian purple which opens the way to the production of large quantities of the dye with minimal hazards and at low cost.

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Section: Resultsmentioning

confidence: 99%

“…4-Bromo-2-chlorobenzoic acid ( 15 ) [ 35 , 36 ]. 4-amino-2-chlorobenzoic acid ( 18 , Aldrich, 2.50 g, 0.0146 mol) was placed in a 250 mL 3-necked R.B.…”

Section: Methodsmentioning

confidence: 99%

A Simple, Safe and Efficient Synthesis of Tyrian Purple (6,6′-Dibromoindigo)

Wolk

Frimer

2010

Molecules

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“…Unless otherwise indicated, materials were obtained from commercial suppliers and were used without further purification. 4-Bromo-2nitrobenzoic acid and 5-fluoro-2-nitrobenzoic acid were prepared as previously described (Erickson et al, 1952). N-Alkyl amino esters were prepared from alkylamines and methyl bromoacetate .…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Herbicidal Activity of 1H-1,4-Benzodiazepine-2,5-diones

Karp¹,

Manfredi²,

Guaciaro³

et al. 1997

J. Agric. Food Chem.

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A series of 1H-1,4-benzodiazepine-2,5-diones, which have been found to inhibit photosystem II electron transport, were evaluated for their herbicidal activity. Many of the analogues tested exhibited moderate to good herbicidal activity both preemergence and postemergence. The structure-activity relationships were probed by substitution in both the benzene and diazepine ring. Among the variations investigated, it was found that maximal herbicidal activity was obtained by substitution at C-7 and C-9 in the aromatic portion and by bulky aliphatic substitution at N-4 while leaving N-1, C-6, and C-8 unsubstituted.

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“…The starting bromonitroaniline 34 has been prepared by a number of methods, but the most popular are 1) nitration of p -bromoaniline or its derivatives [ 50 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 ], and 2) bromination of o -nitroaniline or its derivatives, usually with bromine in acetic acid [ 95 , 96 , 97 , 98 , 99 , 100 , 101 , 102 , 103 , 104 , 105 , 106 , 107 ]. Here, too, each of these methods has its shortcomings.…”

Section: Preparation Tyrian Purple From 4-bromo-2-nitrobenzaldehydmentioning

confidence: 99%

“…Bromination of o -nitroaniline can likewise lead to formation of the dibrominated product [ 98 , 102 , 103 , 104 , 107 ], unless less than one equivalent of bromine is used [ 106 ]. However, newer, milder synthetic reagents have made the bromination of o -nitroaniline ( 39 ) an attractive route to the required bromonitroaniline 34 .…”

Section: Preparation Tyrian Purple From 4-bromo-2-nitrobenzaldehydmentioning

confidence: 99%