306937-14-4

Basic information

• Product Name: tert-Butyl N-(4-bromo-2-methylphenyl)carbamate
• Synonyms: 3-Chloroperoxybenzoic acid, balance 3-Chlorobenzoic acid and water;Carbamic acid, (4-bromo-2-methylphenyl)-, 1,1-dimethylethyl ester (9CI);1,1-Dimethylethyl (4-bromo-2-methylphenyl)carbamate;N-BOC 4-Bromo-2-methylaniline;tert-Butyl 4-bromo-2-methylphenylcarbamate;4-Bromo-2-methylaniline, N-BOC protected;4-Bromo-N-(tert-butoxycarbonyl)-2-methylaniline, tert-Butyl (4-bromo-2-methylphenyl)carbamate;tert-Butyl (4-bromo-2-methylphenyl)
• CAS NO: 306937-14-4
• Molecular Formula: C12H16BrNO2
• Molecular Weight: 286.16
• Product Categories: N-BOC
• Mol File: 306937-14-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 294.7 °C at 760 mmHg
• Flash Point: 132 °C
• Appearance: /
• Density: 1.356 g/cm³
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Room temperature.
• PKA: 13.00±0.70(Predicted)
• CAS DataBase Reference: tert-Butyl N-(4-bromo-2-methylphenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl N-(4-bromo-2-methylphenyl)carbamate(306937-14-4)
• EPA Substance Registry System: tert-Butyl N-(4-bromo-2-methylphenyl)carbamate(306937-14-4)

Safety Data

• Hazardous Substances Data: 306937-14-4(Hazardous Substances Data)

Usage

General Description

Tert-Butyl N-(4-bromo-2-methylphenyl)carbamate is a chemical compound with the molecular formula C13H18BrNO2. It is a tert-butyl carbamate derivative with a bromo-methylphenyl group attached to the nitrogen atom. It is commonly used as a reagent in organic synthesis, particularly in the preparation of pharmaceutical compounds and agrochemicals. tert-Butyl N-(4-bromo-2-methylphenyl)carbamate is known for its role as a carbamate protectant group in the synthesis of various biologically active compounds. It is a colorless, odorless solid that is soluble in organic solvents and has a relatively high melting point, making it useful for a wide range of chemical reactions.

InChI:InChI=1/C12H16BrNO2/c1-8-7-9(13)5-6-10(8)14-11(15)16-12(2,3)4/h5-7H,1-4H3,(H,14,15)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 583-75-5 4-Bromo-2-methylaniline 

Relevant articles and documents

Nonsolvent application of ionic liquids: Organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency

1-Alkyl-3-methylimidazolium cation based ionic liquids efficiently catalyze N-tert-butyloxycarbonylation of amines with excellent chemoselectivity. The catalytic role of the ionic liquid is envisaged as "electrophilic activation" of di-tert-butyl dicarbonate (Boc2O) through bifurcated hydrogen bond formation with the C-2 hydrogen of the 1-alkyl-3-methylimidazolium cation and has been supported by a downfield shift of the imidazolium C-2 hydrogen of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2]) from δ 8.39 to 8.66 in the presence of Boc2O in the 1H NMR and a drastic reduction of the catalytic efficiency with 1-butyl-2,3-dimethylimidazolium ionic liquids that are devoid of the C-2 hydrogen. The differential time required for reaction with aromatic and aliphatic amines has offered means for selective N-t-Boc formation during inter and intramolecular competitions. Preferential N-t-Boc formation with secondary aliphatic amine has been achieved in the presence of primary aliphatic amine. Comparison of the catalytic efficiency for N-t-Boc formation with a common substrate revealed that [bmim][NTf2] is superior to the reported Lewis acid catalysts.

Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature

Commercially available copper(II) tetrafluoroborate hydrate was found to be a highly efficient catalyst for chemoselective N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions and at room temperature. Various aromatic amines were protected as their N-tert-butyl carbamates in high yields and in short times. No competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation was observed. Chemoselective N-tert-butoxycarbonylation was achieved with substrates bearing OH and SH groups. Chiral α-amino acid esters afforded the corresponding N-t-Boc derivatives in excellent yields.

Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water

Catalyst-free N-tert-butyloxycarbonylation of amines in water is reported. The N-t-Boc derivatives were formed chemoselectively without any isocyanate, urea, N,N-di-t-Boc, and O/S-t-Boc as side products. Chiral amines, esters of α-amino acids, and β-amino alcohol afforded optically pure N-t-Boc derivatives. Amino alcohol and 2-aminophenol afforded the N-t-Boc derivative without oxazolidinone formation. Selectivity was observed during competition of aromatic amine vs aliphatic amine, amine vs amino acid ester, amine vs amino alcohol, and primary amine vs secondary amine.