3712-40-1

Basic information

• Product Name: tert-Butyl N-cyclohexylcarbaMate
• Synonyms: tert-Butyl N-cyclohexylcarbaMate
• CAS NO: 3712-40-1
• Molecular Formula: C₁₁H₂₁NO₂
• Molecular Weight: 199.28994
• Mol File: 3712-40-1.mol
• Article Data: 71

Chemical Properties

• Boiling Point: 289°Cat760mmHg
• Flash Point: 128.6°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.00226mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: tert-Butyl N-cyclohexylcarbaMate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl N-cyclohexylcarbaMate(3712-40-1)
• EPA Substance Registry System: tert-Butyl N-cyclohexylcarbaMate(3712-40-1)

Safety Data

• Hazardous Substances Data: 3712-40-1(Hazardous Substances Data)

Usage

General Description

Tert-butyl N-cyclohexylcarbamate, also known as tBu-N-Cbz, is a carbamate compound with the chemical formula C11H21NO2. It is commonly used in organic synthesis as a protective group for amines, as it can be easily removed under mild conditions. tert-Butyl N-cyclohexylcarbaMate is stable and can be stored without decomposition under normal conditions. It is soluble in organic solvents, such as acetone and dichloromethane, and is often used as a reagent in chemical reactions to selectively protect amine groups in a molecule. Furthermore, tBu-N-Cbz has found applications in the pharmaceutical industry for the synthesis of various drugs and pharmaceutical intermediates.

InChI:InChI=1/C11H21NO2/c1-11(2,3)14-10(13)12-9-7-5-4-6-8-9/h9H,4-8H2,1-3H3,(H,12,13)

Upstream product

• 57022-34-1 tert-butyl cyanoformate 
• 108-91-8 cyclohexylamine 
• 1122-56-1 cyclohexylcarboxamide 
• 75-65-0 tert-butyl alcohol 
• 507-40-4 tert-butylhypochlorite 
• 3173-53-3 Cyclohexyl isocyanate 
• 98-89-5 Cyclohexanecarboxylic acid 
• 1088-01-3 tricyclohexylborane 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 104272-92-6 2-t-butoxycarbonyloxy-3,6-diisopropylpyrazine 
• 104272-95-9 t-butyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate 
• 153789-13-0 tert-butyl 7-azabicyclo<4.1.0>heptane-7-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 19573-22-9 cyclohexyl azide 

Downstream Products

• 57883-84-8 3-Cyclohexyl-1,1-diisopropylurea 
• 886-59-9 N-cyclohexyl-N'-phenylurea 
• 25855-24-7 N-benzyl-N'-cyclohexylurea 
• 56805-21-1 N-cyclohexyl-5-phenyloxazolidin-2-one 
• 6589-48-6 2-cyclohexylamino-1-phenylethanol 
• 777946-66-4 2-cyclohexylamino-1-pyrrolidin-1-yl-ethanethione 
• 753501-09-6 cyclohexyl-(2-oxo-2-piperidin-1-yl-ethyl)-carbamic acid tert-butyl ester 
• 166739-13-5 N-(tert-butoxycarbonyl)-D-cyclohexylglycine 
• 1321591-62-1 (E)-tert-butyl cyclohexyl(1,3-diphenylallyl)carbamate 
• 885280-38-6 (3-oxo-cyclohexyl)-carbamic acid tert-butyl ester 
• 1396514-87-6 tert-butyl cyclohexyl{(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl}carbamate 
• 1397275-19-2 potassium tert-butyl cyclohexyl{(trifluoroborato)methyl}carbamate 
• 1396518-01-6 tert-butyl cyclohexyl(4-methoxybenzyl)carbamate 
• 904816-62-2 tert-butyl (1-cyanocyclohexyl)carbamate 

Relevant articles and documents

Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions

Nickel boride catalyst prepared in situ from NiCl2 and sodium borohydride allowed, in the presence of an aqueous solution of TEMPO-oxidized nanocellulose (0.01 wt%), the reduction of a wide range of nitroarenes and aliphatic nitro compounds. Here we describe how the modified nanocellulose has a stabilizing effect on the catalyst that enables low loading of the nickel salt pre-catalyst. Ni-B prepared in situ from a methanolic solution was also used to develop a greener and facile reduction of organic azides, offering a substantially lowered catalyst loading with respect to reported methods in the literature. Both aromatic and aliphatic azides were reduced, and the protocol is compatible with a one-pot Boc-protection of the obtained amine yielding the corresponding carbamates. Finally, bacterial crystalline nanocellulose was chosen as a support for the Ni-B catalyst to allow an easy recovery step of the catalyst and its recyclability for new reduction cycles.

Metal-free Photocatalytic Intermolecular anti-Markovnikov Hydroamination of Unactivated Alkenes

The development of photocatalytic intermolecular hydroamination reaction between N-aminated dihydropyridines and unactivated alkenes is reported. Metal-free co-catalysts, rhodamine 6G and thiophenol, in presence of visible light are used to initiate the process. The transformation shows a broad substrate scope, both alkenes and amidyl radical can act as coupling partners. The radical strategy provides excellent anti-Markovnikov selectivity and regioselectivity in diene substrates.

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.