4/10/2018 SciFinder - Reaction Answer Set

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[Step 2.1]
~88
~101

~33

Overview
Steps/Stages Notes

p
1.1 R: -MeC6H4SO3H, R:NaNO2, S:H2O, S:MeCN, 60 min, 2) phosphate buffered solution used (stage 1),
cooled regioselective (stage 2), Reactants: 2, Reagents: 3,
2.1 S:H2O, S:MeCN, 0°C, pH 9 Solvents: 2, Steps: 2, Stages: 4, Most stages in any
2.2 5 min, 0°C one step: 3
2.3 R:NaN3, S:H2O
References

Genetic Incorporation of a 2-Naphthol Group into

Proteins for Site-Specific Azo Coupling
Quick View Other Sources
By Chen, Shuo and Tsao, Meng-Lin
From Bioconjugate Chemistry, 24(10), 1645-1649; 2013

Experimental Procedure

Step 1
IV. Azo coupling of p-cresol and 2-naphthol with diazotized aniline derivatives The
stock solution of a series of diazonium salts were prepared by mixing the followings: pre-cooled
100 μL of 0.84 M aqueous p-toluenesulfonic acid, 100 μL of 0.45 M aqueous sodium nitrite, and
200 μL of 0.15 M acetonitrile solution of aniline derivatives such as sulfanilic acid, 4-nitroaniline,
4-aminobenzonitrile, aniline, ptoluidine and 4'-aminoacetanilide, respectively. The reaction
mixtures were kept under an ice bath for 60 min. Final product.
Step 2
General/Typical Procedure: To the 600 μL of 0.2 M phosphate buffered solution (pH 7.0 and pH
p
9.0, respectively), 200 μL of either 30 mM -cresol or 2-naphthol in acetonitrile was added at
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4/10/2018 SciFinder - Reaction Answer Set

0°C. Next, 100 μL of a fresh prepared diazonium stock solution was added. After letting the
reaction mixture sit on an ice bath for 5 min, 20 μL of 1.5 M aqueous sodium azide was added
to quench the reaction by deactivating the remaining diazonium compound. Similar reactions
were carried out for tryptophan, histidine, phenylalanine, and dNTPs (deoxyribonucleotide
triphosphate mixtures). Photos for the formation of the colorful azo adducts were taken as
shown in Figure S2 and Figure S3. Yield 88%. λmax (nm) 492.

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