ChemicalBook CAS DataBase List Tetramethylbenzidine

Tetramethylbenzidine synthesis

7synthesis methods

Product Name:Tetramethylbenzidine
CAS Number:54827-17-7
Molecular formula:C16H20N2
Molecular Weight:240.34

Synthesis of 3,3',5,5'-Tetramethylbenzidine: Using 2,6-dimethylaniline as raw material, through activation, oxidative coupling and purification, pure 3,3,5,5-tetramethylbenzidine was obtained Methylbenzidine, the total yield is 65%.

2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

1004761-68-5
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$66.00/100mg

24596-19-8 Synthesis

24596-19-8
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$8.00/10g

54827-17-7
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$6.00/250mg

Yield:54827-17-7 210 g

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;caesium carbonate in 1,4-dioxane at 75; for 16 h;Inert atmosphere;

Steps:

1.2

2) 250 g of 2,6-dimethylaniline (5) and3L N, N- dimethylformamide solution was added to 5L three reaction flask,1 L of 246 g N-bromosuccinimide was slowly added dropwise at about 0 ° CN, N-dimethylformamide, and the mixture was stirred at room temperature for 2 hours.The reaction mixture was introduced into 30 L of water, extracted with 3 L of ethyl acetate twice,The organic phase was washed with 2 L saturated brine, dried over anhydrous sodium sulfate, filtered,Dried to afford 350 g of 2,6-dimethyl-4-bromoaniline (6) as a yellow solid.Next, 350 g of the product (6), 268 g of potassium acetate,364 g of bis (pinacolato) diboron, 50 g[1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride,4L1,4 - dioxane, 400mL water was added 5L three-necked flask, nitrogen protection,Heated to 80 stirring continued 15h. After falling to room temperature, filtration,Dried to give 414g brown solid boric acid ester (7);332 g of product (6),414 g product (7) 667 g cesium carbonate,50 g of [1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride,4L 1,4-dioxane was added 5L three-necked flask, a nitrogen atmosphere,Heat to 75 ° C and continue stirring for 16h. After falling to room temperature, filtration,The filtrate was washed with 2 L of water, dried over anhydrous sodium sulfate, filtered and spun dry.Recrystallized from 2 L ethyl acetate: petroleum ether = 1: 4 (volume ratio) solution,The solid was filtered off to give 210 g of white crystals2,2 ', 6,6'-tetramethylbiphenylenediamine(8).

References:

CN106810506,2017,A Location in patent:Paragraph 0039