N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Base Information

• Chemical Name: N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 1218791-23-1
• Molecular Formula: C16H25BN2O4
• Molecular Weight: 320.196
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70682236
• Wikidata: Q82606543
• Mol file: 1218791-23-1.mol

Synonyms:1218791-23-1;N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-(N-t-Butylamino)-3-nitrophenylboronic acid, pinacol ester;N-tert-butyl-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;SCHEMBL14852810;DTXSID70682236;MFCD13195754;AKOS022172794;AS-74397;Benzenamine, N-(1,1-dimethylethyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;CS-0175387;D92874;4-(N-t-Butylamino)-3-nitrophenylboronic acid,pinacol ester;4-(N-tert-butylamino)-3-nitrophenylboronic acid pinacol ester;4-(N-tert-Butylamino)-3-nitrophenylboronic acid, pinacol ester;tert-butyl-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-amine

Chemical Property of N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Chemical Property:

• Boiling Point: 429.7±40.0 °C(Predicted)
• PKA: -0.90±0.50(Predicted)
• PSA: 76.31000
• Density: 1.10±0.1 g/cm3(Predicted)
• LogP: 3.70060
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 320.1907374
• Heavy Atom Count: 23
• Complexity: 440

Purity/Quality:

97% ^*data from raw suppliers

4-(N-t-Butylamino)-3-nitrophenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)NC(C)(C)C)[N+](=O)[O-]

Technology Process of N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

There total 2 articles about N-(tert-Butyl)-2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 51.0%

4-bromo-N-(tert-butyl)-2-nitroaniline (1135351-95-9) + bis(pinacol)diborane (73183-34-3) → tert-butyl-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (1218791-23-1)

Guidance literature:

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 110 ℃; for 4h; Inert atmosphere;

Reference yield:

4-Bromo-1-fluoro-2-nitrobenzene (364-73-8) → tert-butyl-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (1218791-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 16 h / 60 °C

2: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4 h / 110 °C / Inert atmosphere

With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane;

Reference yield: 86.0%

5-bromo-4-methoxypyrimidine-2-ylamine (36082-45-8) + tert-butyl-[2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]amine (1218791-23-1) → 5-(4-tert-butylamino-3-nitrophenyl)-4-methoxypyrimidin-2-ylamine (1310532-18-3)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 110 ℃; for 18h; Sealed; Inert atmosphere;

upstream raw materials:

4-Bromo-1-fluoro-2-nitrobenzene

4-bromo-N-(tert-butyl)-2-nitroaniline

bis(pinacol)diborane

Downstream raw materials:

5-(4-tert-butylamino-3-nitrophenyl)-4-methoxypyrimidin-2-ylamine

5-[1-tert-butyl-2-(2-1,2,4-triazol-1-ylphenyl)-1H-benzimidazol-5-yl]-4-methoxypyrimidin-2-ylamine

4-(2-amino-4-methoxypyrimidin-5-yl)-N₁-tert-butylbenzene-1,2-diamine

2-amino-5-[1-tert-butyl-2-(2-1,2,4-triazol-1-ylphenyl)-1H-benzimidazol-5-yl]-3H-pyrimidin-4-one