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 
• 65-85-0 benzoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 62-53-3 aniline 
• 101137-67-1 tert-butyl N-phenyl-N-formylcarbamate 
• 109774-61-0 tert-butyl phenyl(tosyl)carbamate 
• 106-96-7 propargyl bromide 
• 583-04-0 vinyl benzoate 
• 142-04-1 aniline hydrochloride 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 226065-37-8 N-phenyl-hydrazine carboxylic acid tert-butyl ester 
• 329020-64-6 (4-trimethylstannanylphenyl)carbamic acid tert-butyl ester 
• 95-76-1 m,p-dichloroaniline 

Downstream Products

• 74965-36-9 4-(4-chlorophenyl)-2,4-dihydro-1H-3,1-benzoxazin-2-one 
• 74965-35-8 {2-[(4-Chloro-phenyl)-hydroxy-methyl]-phenyl}-carbamic acid tert-butyl ester 
• 155302-10-6 {2-[N-(tert-butyloxycarbonyl)amino]phenyl}[1-(tert-butyloxycarbonyl)-4,4-dimethylpiperidin-2-yl]methanol 
• 195044-92-9 {2-[N-(tert-butyloxycarbonyl)amino]phenyl}[(2R,S)-1-(tert-butyloxycarbonyl)-4,4-dimethylpiperidin-2-yl]methanone 
• 212652-20-5 [2-(6-Chloro-hexanoyl)-phenyl]-carbamic acid tert-butyl ester 
• 62-53-3 aniline 
• 185384-39-8 2,3-dimethoxy-4-hydroxy-4-{3-[N-(tert-butoxycarbonyl)-N-phenylamino]-1-propynyl}-2-cyclobuten-1-one 
• 14465-74-8 N-phenyl-N-prop-2-ynylamine 
• 588-47-6 N-isobutylaniline 
• 156115-84-3 2-Diazo-N-phenyl-N-prop-2-ynylmalonamic acid ethyl ester 
• 156115-81-0 2-Diazo-N-isobutyl-N-phenylmalonamic acid ethyl ester 
• 115377-94-1 2-(tert-butoxycarbonylamino)phenylboronic acid 
• 1132910-26-9 benzyl 2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,3'-piperidine]-1'-carboxylate 
• 1132910-35-0 benzyl 3-(2-(tert-butoxycarbonylamino)phenyl)-3-hydroxypiperidine-1-carboxylate 

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

Integrating Hydrogen Production and Transfer Hydrogenation with Selenite Promoted Electrooxidation of α-Nitrotoluenes to E-Nitroethenes

Developing an electrochemical carbon-added reaction with accelerated kinetics to replace the low-value and sluggish oxygen evolution reaction (OER) is markedly significant to pure hydrogen production. Regulating the critical steps to precisely design electrode materials to selectively synthesize targeted compounds is highly desirable. Here, inspired by the surfaced adsorbed SeOx2? promoting OER, NiSe is demonstrated to be an efficient anode enabling α-nitrotoluene electrooxidation to E-nitroethene with up to 99 % E selectivity, 89 % Faradaic efficiency, and the reaction rate of 0.25 mmol cm?2 h?1 via inhibiting side reactions for energy-saving hydrogen generation. The high performance can be associated with its in situ formed NiOOH surface layer and absorbed SeOx2? via Se leaching-oxidation during electrooxidation, and the preferential adsorption of two -NO2 groups of intermediate on NiOOH. A self-coupling of α-carbon radicals and subsequent elimination of a nitrite molecule pathway is proposed. Wide substrate scope, scale-up synthesis of E-nitroethene, and paired productions of E-nitroethene and hydrogen or N-protected aminoarenes over a bifunctional NiSe electrode highlight the promising potential. Gold also displays a similar promoting effect for α-nitrotoluene transformation like SeOx2?, rationalizing the strategy of designing materials to suppress side reactions.

Ultrasound promoted environmentally benign, highly efficient, and chemoselective N-tert-butyloxycarbonylation of amines by reusable sulfated polyborate

The sulfated polyborate catalyzed an efficient and chemoselective N-tert-butyloxycarbonylation of amines under ultrasonic irradiation is developed. A broad substrate scope has been demonstrated for N-Boc protection of various primary/secondary amines. It allows converting several aliphatic/aryl/heteroaryl amines, amino alcohol, aminoester, and chiral amines to their N-Boc-protected derivatives under solvent-free conditions with excellent yields. The protocol has several advantages such as easy catalyst, and product isolation, short reaction time, excellent yields, outstanding chemoselectivity, and catalyst recyclability, among others. This makes the process practicable, economical, and environmentally benign.