71026-66-9

Basic information

• Product Name: 4-(TERT-BUTOXYCARBONYLAMINO)ANILINE
• Synonyms: tert-butyl N-(4-aMinophenyl)carbaMate;N-Boc-benzene-1,4-diaMine;Carbamicacid,N-(4-aminophenyl)-,1,1-dimethylethylester;N-Boc-p-phenylenediamine >=97.0% (NT);BOC-1,4-PHENYLENEDIAMINE;(4-AMINO-PHENYL)-CARBAMIC ACID TERT-BUTYL ESTER;4-(TERT-BUTOXYCARBONYLAMINO)ANILINE;N-BOC-P-PHENYLENEDIAMINE
• CAS NO: 71026-66-9
• Molecular Formula: C₁₁H₁₆N₂O₂
• Molecular Weight: 208.26
• EINECS: 275-132-7
• Product Categories: N-BOC
• Mol File: 71026-66-9.mol
• Article Data: 74

Chemical Properties

• Melting Point: 113-115 °C
• Boiling Point: 295.4 °C at 760 mmHg
• Flash Point: 132.5 °C
• Appearance: beige to brownish crystalline powder
• Density: 1.152 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 13.49±0.70(Predicted)
• BRN: 2969618
• CAS DataBase Reference: 4-(TERT-BUTOXYCARBONYLAMINO)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TERT-BUTOXYCARBONYLAMINO)ANILINE(71026-66-9)
• EPA Substance Registry System: 4-(TERT-BUTOXYCARBONYLAMINO)ANILINE(71026-66-9)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 71026-66-9(Hazardous Substances Data)

Usage

Description

4-(TERT-BUTOXYCARBONYLAMINO)ANILINE, also known as N-Boc-p-phenylenediamine, is an organic compound with the chemical formula C10H16N2O2. It is a white crystalline solid that is soluble in organic solvents. 4-(TERT-BUTOXYCARBONYLAMINO)ANILINE is a versatile building block in organic synthesis and has various applications in different industries.

Uses

Used in Dye-Sensitized Solar Cell Applications:
4-(TERT-BUTOXYCARBONYLAMINO)ANILINE is used as a reactant to prepare perylene monoimide-based dyes, which are employed in dye-sensitized solar cell applications. These dyes have high light absorption and charge transfer properties, making them suitable for efficient energy conversion in solar cells.
Used in Hydrogen Fuel Cell Applications:
4-(TERT-BUTOXYCARBONYLAMINO)ANILINE is used as a starting material to synthesize covalent organic frameworks (COFs). These COFs are utilized as proton exchange membranes in hydrogen fuel cell applications. They exhibit high proton conductivity, excellent chemical stability, and good mechanical properties, making them ideal for efficient energy conversion in fuel cells.
Used in Pharmaceutical Applications:
4-(TERT-BUTOXYCARBONYLAMINO)ANILINE is used as a reactant in the synthesis of bestatin-derived hydroxamic acids, which are potent pan-HDAC inhibitors. These inhibitors have potential applications in the treatment of various diseases, including cancer, by modulating the activity of histone deacetylases (HDACs) and regulating gene expression.

InChI:InChI=1/C11H16N2O2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,12H2,1-3H3,(H,13,14)

Upstream product

• 18437-63-3 tert-butyl N-(4-nitrophenyl)carbamate 
• 106-50-3 1,4-phenylenediamine 
• 851651-82-6 tert-butyl (4-(vinylsulfonamido)phenyl)carbamate 
• 179321-49-4 N-(tert-butoxycarbonyl)-4-aminocyclohexanone 
• 54840-15-2 4-N-tert-butoxycarbonylaminophenol 
• 24608-52-4 tert-butyl chloroformate 
• 395639-03-9 bis(1,1-dimethylethyl)(4-nitrophenyl)imidocarbonate 
• 2733-41-7 4-nitrobenzoyl azide 
• 100-01-6 4-nitro-aniline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86031-24-5 O-(tert-butoxycarbonyl)hydroxylamine 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 160291-53-2 tert-butyl N-<4-(7-diethylamino-2-oxo-2H-chromene-3-carboxamido)phenyl>carbamate 
• 183740-30-9 3-[4-(N-BOC-amino)-phenylamino]-2-cyano-3-methylmercapto-acrylonitrile 
• 230645-87-1 Methyl (E)-3-[N-(4-Boc-aminophenyl)-2-carbamoylvinyl]-4,5-dimethylpyrrole-2-carboxylate 
• 457631-47-9 [4-(2-[1,2]dithiolan-3-yl-acetylamino)-phenyl]-carbamic acid tert-butyl ester 
• 912838-01-8 butyl 5-(3-buten-1-yl)-1-{4-[(tert-butoxycarbonyl)amino]phenyl}-1H-1,2,3-triazole-4-carboxylate 
• 936576-80-6 1-(tert-butyloxycarbamido)-4-[2,3-di(isopropylmercapto)benzamido]benzene 

Relevant articles and documents

Combined Intrinsic and Extrinsic Proton Conduction in Robust Covalent Organic Frameworks for Hydrogen Fuel Cell Applications

Developing new materials for the fabrication of proton exchange membranes (PEMs) for fuel cells is of great significance. Herein, a series of highly crystalline, porous, and stable new covalent organic frameworks (COFs) have been developed by a stepwise synthesis strategy. The synthesized COFs exhibit high hydrophilicity and excellent stability in strong acid or base (e.g., 12 m NaOH or HCl) and boiling water. These features make them ideal platforms for proton conduction applications. Upon loading with H3PO4, the COFs (H3PO4?COFs) realize an ultrahigh proton conductivity of 1.13×10?1 S cm?1, the highest among all COF materials, and maintain high proton conductivity across a wide relative humidity (40–100 %) and temperature range (20–80 °C). Furthermore, membrane electrode assemblies were fabricated using H3PO4?COFs as the solid electrolyte membrane for proton exchange resulting in a maximum power density of 81 mW cm?2 and a maximum current density of 456 mA cm?2, which exceeds all previously reported COF materials.

Selective primary aniline synthesis through supported Pd-catalyzed acceptorless dehydrogenative aromatization by utilizing hydrazine

By utilizing hydrazine (N2H4) as the nitrogen source in the presence of a hydroxyapatite-supported Pd nanoparticle catalyst (Pd/HAP), various primary anilines can be selectively synthesized from cyclohexanonesviaacceptorless dehydrogenative aromatization. The strong nucleophilicity of N2H4and the stability of the hydrazone intermediates can effectively suppress the formation of the undesired secondary aniline byproducts.

SARs of a novel series of s-triazine compounds targeting vimentin to induce methuotic phenotype

Herein, we describe the design, synthesis and structure?activity relationships of a series of novel s-triazine compounds can induce methuotic phenotype in various types of cancer cells. (E)-1-(4-Chlorophenyl)-3-(4-((4-morpholino-6-styryl-1,3,5-triazine-2-yl)amino)phenyl)urea, compound V6, exhibited a striking methuotic phenotype with a minimal effective concentration of less than 10 nM in U87 glioblastoma cells. Based on structure?activity relationship studies, we designed and synthesized an active probe P1 that retained the full potential of V6 in inducing the methuotic phenotype in U87 glioblastoma cells. Using this probe following affinity-based proteomic profiling strategy, we identified vimentin as the specific target protein of compound V6. Molecular docking revealed that V6 can form hydrogen bonds with vimentin at 273R and 276Y in its rod domain.