3422-01-3

Basic information

• Product Name: N-BOC ANILINE
• Synonyms: N-Phenyl-carbaMic Acid 1,1-DiMethylethyl Ester;N-Boc-aniline 97%;Carbanilic acidtert-butyl ester≥ 98% (GC);TIMTEC-BB SBB008371;TERT-BUTYL CARBANILATE;TERT-BUTYL N-PHENYLCARBAMATE;TERT-BUTYL PHENYLCARBAMATE;N-BOC ANILINE
• CAS NO: 3422-01-3
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Product Categories: Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Protected Amines;amine|carboxylic ester;N-BOC;Amines;Aromatics;Miscellaneous Reagents;Building Blocks
• Mol File: 3422-01-3.mol
• Article Data: 202

Chemical Properties

• Melting Point: 133-137 °C(lit.)
• Boiling Point: 235.3 °C at 760 mmHg
• Flash Point: 96.1 °C
• Appearance: White to pale brown/Solid
• Density: 1.082 g/cm³
• Vapor Pressure: 0.0505mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 13.86±0.70(Predicted)
• CAS DataBase Reference: N-BOC ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC ANILINE(3422-01-3)
• EPA Substance Registry System: N-BOC ANILINE(3422-01-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3422-01-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Protected Aniline.

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 1141, 1965 DOI: 10.1021/ja01083a042The Journal of Organic Chemistry, 43, p. 2609, 1978

InChI:InChI=1/C11H15NO2/c1-11(2,3)14-10(13)12-9-7-5-4-6-8-9/h4-8H,1-3H3,(H,12,13)

Upstream product

• 55-21-0 benzamide 
• 75-65-0 tert-butyl alcohol 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 109774-61-0 tert-butyl phenyl(tosyl)carbamate 
• 582-61-6 benzoyl azide 
• 64-10-8 phenyl carbamate 
• 1907-33-1 lithium tert-butoxide 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 185384-36-5 N-(tert-butoxycarbonyl)-N-(prop-2-ynyl)aniline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 65-85-0 benzoic acid 
• 329020-64-6 (4-trimethylstannanylphenyl)carbamic acid tert-butyl ester 
• 95-76-1 m,p-dichloroaniline 

Downstream Products

• 603-23-6 3-phenyl-2,4-(1H,3H)-quinazolinedione 
• 74965-39-2 (2-Phenylthiocarbamoyl-phenyl)-carbamic acid tert-butyl ester 
• 144303-97-9 <2-<(N,N-diethylamino)carbonyl>phenyl>carbamic acid 1,1-dimethylethyl ester 
• 23441-75-0 4-phenyl-1H-quinazolin-2-one 
• 171920-03-9 7-benzyloxy-5-methyl-5H-quino<2,3,4-kl>acridine 
• 1467-21-6 N-phenyl-N'-benzylurea 
• 354583-56-5 (2-diphenylphosphanyl-phenyl)-carbamic acid tert-butyl ester 
• 328956-59-8 tert-butyl N-[2-(trifluoroacetyl)phenyl]carbamate 
• 474088-40-9 (2-amino-phenyl)-(5-chloro-2-methoxy-phenyl)-methanone 
• 474088-45-4 2-chloro-N-[2-(5-chloro-2-methoxy-benzoyl)-phenyl]-acetamide 
• 221112-51-2 3-Amino-4-(5-chloro-2-methoxyphenyl)quinolin-2(1H)-one 
• 154150-19-3 2-Phenylsulfanyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester 
• 622372-88-7 1,1-dimethylethyl {2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}carbamate 
• 1132820-19-9 C₂₄H₂₉F₃N₂O₅ 

Relevant articles and documents

Using hydrogen bonding to control carbamate C-N rotamer equilibria

In chloroform solution, the syn/anti rotamer ratios for AT-(2-pyridyl)carbamates, 3, and JV-phenylcarbamates, 4, are close to 0.05. Addition of the double hydrogen bonding acetic acid moderately stabilizes the syn rotamer of 4, but has no measurable effec

Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines

Thiamin hydrochloride promoted highly efficient and ecofriendly approach has been described for the chemoselective N-tert-butyloxycarbonylation of amines under solvent-free conditions at ambient temperature. The demonstrated approach has been applicable for the N-Boc protection of variety of aliphatic, aryl, heteroaryl amines. The chemoselective protection of amino group occurs in chiral amines and amino alcohol without racemization in high yield. Thiamin hydrochloride is stable, economical, easy to handle and environmentally friendly.

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.