131818-17-2

Basic information

• Product Name: TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE
• Synonyms: N-(TERT-BUTOXYCARBONYL)-4-BROMOANILINE;N-BOC-4-BROMOANILINE;TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE;TERT-BUTYL 4-BROMOPHENYLCARBAMATE;tert-butyl 5-bromopyrazin-2-ylcarbamate;N-BOC-4-bromoaniline, 95+%;4-Bromoaniline, N-BOC protected;(4-Bromophenyl)carbamic acid tert-butyl ester
• CAS NO: 131818-17-2
• Molecular Formula: C₁₁H₁₄BrNO₂
• Molecular Weight: 272.14
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Protected Amines;amine|alkyl bromide| carboxylic ester
• Mol File: 131818-17-2.mol
• Article Data: 96

Chemical Properties

• Melting Point: 103-106 °C(lit.)
• Boiling Point: 281.126 °C at 760 mmHg
• Flash Point: 124℃
• Appearance: Beige/Powder
• Density: 1.398
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• PKA: 12.99±0.70(Predicted)
• CAS DataBase Reference: TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE(131818-17-2)
• EPA Substance Registry System: TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE(131818-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 131818-17-2(Hazardous Substances Data)

Usage

General Description

N-(tert-Butoxycarbonyl)-4-bromoaniline is an N-(tert-butyloxycarbonyl) [N-BOC] protected 4-bromo aniline. Due to the presence of BOC protection, it serves as an ideal substrate for Suzuki coupling reactions. It affords biaryls via reaction with pyridine or 3-benzaldehyde boronic acids.

InChI:InChI=1/C11H14BrNO2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 106-40-1 4-bromo-aniline 
• 193533-92-5 4-methyl-1,2,3-trifluorobenzene 
• 540-37-4 p-aminoiodobenzene 
• 1239374-02-7 tert-butyl 4-bromophenyl(3-perfluorooctylpropoxy)carbamate 
• 586-76-5 4-Bromobenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 4248-19-5 tert-butyl carbazate 
• 589-87-7 1,4-bromoiodobenzene 
• 2617-78-9 N-(4-bromophenyl)formamide 
• 2493-02-9 4-bromophenyl isocyanate 
• 3422-01-3 tert-butyl phenylcarbamate 
• 108-86-1 bromobenzene 
• 110-05-4 di-tert-butyl peroxide 

Downstream Products

• 870703-82-5 tert-butyl (2'-formyl-[1,1'-biphenyl]-4-yl)carbamate 
• 197435-52-2 [4-(pyridin-4-yl)phenyl]carbamic acid tert-butyl ester 
• 147696-69-3 (4-Amino-phenyl)-pyridin-3-yl-methanone 
• 6278-73-5 2-(4-aminophenyl)benzothiazole 
• 43036-17-5 2-(4-aminophenyl)-6-methoxybenzothiazole 
• 937737-95-6 thioacetic acid S-(4-tert-butoxycarbonylaminophenyl) ester 
• 312760-48-8 3-{[5-(4-amino-phenyl)-thiophene-2-carbonyl]-amino}-2-benzenesulfonylamino-propionic acid tert-butyl ester 
• 312760-49-9 C₃₅H₄₅N₅O₉S₂ 

Relevant articles and documents

A mild and green method for the N-BOC protection of amines without assistant of catalyst under solvent-free conditions

A facile, green and versatile method for the Boc protection of amines has been developed by a treatment with (Boc)2O without any additive at room temperature. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines. The advantages of this method are green, simplicity, short reaction times and excellent yields.

Equilibration of Imine-Linked Polymers to Hexagonal Macrocycles Driven by Self-Assembly

Macrocycles based on directional bonding and dynamic covalent bond exchange can be designed with specific pore shapes, sizes, and functionality. These systems retain many of the design criteria and desirable aspects of two-dimensional (2D) covalent organi

The synthesis of a rigid conjugated viologen and its cucurbituril pseudorotaxanes

A linear viologen (bis[4-(4-pyridinyl)phenyl] viologen, BPPV) characterized by a fully-conjugated structure was synthesized through Zinke reaction. BPPV consists of a unique linear sexiaryl structure and is apt to be encapsulated by cucurbit[n]uril (CB[n]

Efficient N-Boc protection of amines by a reusable heterogeneous solid acid nanocatalyst at room temperature

An efficient and rapid protocol for chemoselective N-Boc protection of various structurally different aryl, aliphatic, and heterocyclic amines is reported with (Boc)2O using mesoporous silica phenylsulfonic acid (SBA-15-Ph-SO3H) as a recyclable and heterogeneous solid acid nanocatalyst under solvent-free condition at ambient temperature. The catalyst can be easily recovered and reused for ten reaction cycles for protection of amines without considerable loss of activity. The advantages of this green method are simplicity, easy workup, chemoselectivity, short reaction time, and excellent yield.

Fenton chemistry enables the catalytic oxidative rearrangement of indoles using hydrogen peroxide

Oxidative rearrangement of indoles is an important transformation to yield 2-oxindoles and spirooxindoles, which are present in many pharmaceutical agents and bioactive natural products. Previous oxidation methods show either broad applicability or greenness but rarely achieve both. Reported is the discovery of Fenton chemistry-enabled green catalytic oxidative rearrangement of indoles, which has wide substrate scope (42 examples) and greenness (water as the only stoichiometric byproduct) at the same time. Detailed mechanistic studies revealed that the Fenton chemistry generated hydroxyl radicals that further oxidize bromide to reactive brominating species (RBS: bromine or hypobromous acid). Thisin situgenerated RBS is the real catalyst for the oxidative rearrangement. Importantly, the RBS is generated under neutral conditions, which addresses a long-lasting problem of many haloperoxidase mimics that require a strong acid for the oxidation of bromide with hydrogen peroxide. It is expected that this new catalytic Fenton-halide system will find wide applications in organic synthesis.

Visible light-induced mono-bromination of arenes with BrCCl3

A highly efficient and regioselective bromination of electron-rich arenes and heteroarenes using commercially available BrCCl3as a “Br” source has been developed. The reaction was performed in air under mild conditions with photocatalyst Ru(bpy)3Cl2·6H2O, avoiding the usage of strong acids and strong oxidants. Mono-brominated products were obtained with medium to excellent yields (up to 94%). This strategy has shown good compatibility and highpara-selectivity, which will facilitate the complicated synthesis.