164596-20-7

Basic information

• Product Name: methyl 4-(tert-butoxycarbonylamino)benzoate
• Synonyms: 4-tert-butoxycarbonylamino-benzoic acid methyl ester;methyl 4-(tert-butoxycarbonylamino)benzoate;Methyl 4-(BOC-aMino)benzoate;Methyl 4-(tert-butoxycarbonylamino)benzenecarboxylate
• CAS NO: 164596-20-7
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.27838
• Mol File: 164596-20-7.mol
• Article Data: 21

Chemical Properties

• Melting Point: 163-166°C
• Appearance: /
• CAS DataBase Reference: methyl 4-(tert-butoxycarbonylamino)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(tert-butoxycarbonylamino)benzoate(164596-20-7)
• EPA Substance Registry System: methyl 4-(tert-butoxycarbonylamino)benzoate(164596-20-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43-52/53
• Safety Statements: 36/37-61
• WGK Germany: 3
• Hazardous Substances Data: 164596-20-7(Hazardous Substances Data)

Usage

Uses

Methyl 4-(Boc-amino)benzoate is an impuriy of α,α-Bis[4-(dimethylamino)phenyl]-4-(methylamino)-benzenemethanol which is a product from degradation of methyl green.

Upstream product

• 226065-30-1 tert-butyl 1-(4-(methoxycarbonyl)phenyl)hydrazinecarboxylate 
• 93-58-3 benzoic acid methyl ester 
• 4248-19-5 tert-butyl carbazate 
• 1613027-54-5 methyl 4-[{(tert-butoxycarbonyl)amino}oxycarbonyl]benzoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 131818-17-2 tert-butyl (4-bromophenyl)carbamate 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 619-45-4 4-methoxycarbonyl aniline 
• 67-56-1 methanol 
• 321527-88-2 tert-Butyl [4-(chlorocarbonyl)phenyl]carbamate 
• 150-13-0 4-amino-benzoic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 5320-91-2 4,4'-bismethoxycarbonylazobenzene 

Downstream Products

• 660432-39-3 4-(N-tert-butoxycarbonyl-N-ethyl-amino)-benzoic acid methyl ester 
• 869108-92-9 Methyl 4-(benzyl-tert-butoxycarbonylamino)benzenecarboxylate 
• 1260650-61-0 methyl 4-((tert-butoxycarbonyl)amino)-3-chlorobenzoate 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 119162-75-3 3-(4-aminophenyl)isoxazol-5-amine 

Relevant articles and documents

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.

Thieme Chemistry Journals Awardees - Where Are They Now? Bis(2-pyridyl)amides as Readily Cleavable Amides under Catalytic, Neutral, and Room-Temperature Conditions

Mild solvolytic cleavage of bis(2-pyridyl)amide under neutral and room-temperature conditions is described. The inherently stable amide was readily activated by catalytic amounts of metal cations to react with alcohols. Based on X-ray crystallographic analysis, the primary driving force was considered to be amide distortion induced by the metal coordination of two pyridyl groups in a bidentate fashion without affecting the amide functionality. The compatibility of the acid/base-sensitive functionalities and the absence of racemization during solvolysis highlight the mildness of the present protocol.

Visible-Light-Driven Carboxylation of Aryl Halides by the Combined Use of Palladium and Photoredox Catalysts

A highly useful, visible-light-driven carboxylation of aryl bromides and chlorides with CO2 was realized using a combination of Pd(OAc)2 as a carboxylation catalyst and Ir(ppy)2(dtbpy)(PF6) as a photoredox catalyst. This carboxylation reaction proceeded in high yields under 1 atm of CO2 with a variety of functionalized aryl bromides and chlorides without the necessity of using stoichiometric metallic reductants.