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

Description

TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE, also known as N-(tert-Butoxycarbonyl)-4-bromoaniline, is an N-(tert-butyloxycarbonyl) [N-BOC] protected 4-bromo aniline. It is a chemical compound that is commonly used as a substrate in Suzuki coupling reactions due to the presence of the BOC protecting group.

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its reactivity in Suzuki coupling reactions allows for the formation of biaryls, which are important structural motifs in many drug molecules.
Used in Chemical Synthesis:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a starting material for the synthesis of various organic compounds. Its BOC protection group can be selectively removed under mild conditions, allowing for further functionalization and modification of the molecule.
Used in Research and Development:
TERT-BUTYL N-(4-BROMOPHENYL)-CARBAMATE is used as a research compound in the development of new synthetic methods and reaction conditions. Its unique reactivity and protecting group make it a valuable tool for exploring new chemical transformations and applications.

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 
• 586-76-5 4-Bromobenzoic acid 
• 75-65-0 tert-butyl alcohol 
• 108-86-1 bromobenzene 
• 4248-19-5 tert-butyl carbazate 
• 586-78-7 para-nitrophenyl bromide 
• 51779-32-9 iminodicarboxylic acid di-tert-butyl ester 
• 110-05-4 di-tert-butyl peroxide 
• 33554-73-3 1-bromo-4-isocyanobenzene 
• 3422-01-3 tert-butyl phenylcarbamate 
• 2493-02-9 4-bromophenyl isocyanate 
• 2617-78-9 N-(4-bromophenyl)formamide 
• 589-87-7 1,4-bromoiodobenzene 

Downstream Products

• 197435-52-2 [4-(pyridin-4-yl)phenyl]carbamic acid tert-butyl ester 
• 147696-69-3 (4-Amino-phenyl)-pyridin-3-yl-methanone 
• 43036-17-5 2-(4-aminophenyl)-6-methoxybenzothiazole 
• 693792-98-2 tert-butyl benzyl(4-bromophenyl)carbamate 
• 639520-70-0 4-(N-tert-butyloxycarbonyl-N-methylamino)phenyl bromide 
• 197073-43-1 4-(tert-butyloxycarbonylamino)cinnamic acid 
• 1009083-69-5 tert-butyl 4-(4-hydroxy-tetrahydro-2H-thiopyran-4-yl)phenylcarbamate 
• 106-40-1 4-bromo-aniline 
• 1333415-86-3 tert-butyl N-{4-[(trifluoromethyl)sulfanyl]phenyl}carbamate 
• 18437-68-8 tert-butyl N-(4-methoxyphenyl)carbamate 
• 1448366-58-2 tert-butyl (4-trideuteriomethoxyphenyl)carbamate 
• 220741-56-0 tert-butyl 4-(benzoyloxycarbonylamido)phenylcarbamate 
• 1593267-90-3 tert-butyl (4-(3-(4-(tert-butyl)phenyl)prop-2-ynoyl)phenyl)carbamate 
• 654056-96-9 tert-butyl (4-(benzo[b]thiophen-2-yl)phenyl)carbamate 

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.

Nanoceria as an efficient and green catalyst for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions

Nanocerium oxide mediated an efficient and green protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at ambient temperature. Various aliphatic, aromatic and heteroaromatic amines were protected using developed protocol and several functional groups such as alcohol, phenol and ester were well tolerated under these conditions. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.