36016-38-3

Basic information

• Product Name: tert-Butyl N-hydroxycarbamate
• Synonyms: N-(T-BUTOXYCARBONYL)-HYDROXYLAMINE;N-T-BOC HYDROXYLAMINE;N-HYDROXYCARBAMIC ACID TERT-BUTYL ESTER;N-BOC-HYDROXYLAMINE;N-Boc-hydroxylamine, >=98%;N-tert-Butoxycarbonylhydroxylamine, 98+%;N-(tert-Butoxycarbonyl)hydroxylamine~tert-ButylN-hydroxycarbamate;TERT-BUTYL N-HYDROXYCARBAMATE 99.0%
• CAS NO: 36016-38-3
• Molecular Formula: C₅H₁₁NO₃
• Molecular Weight: 133.15
• EINECS: 252-836-2
• Product Categories: INTERMEDIATESOFMEROPENAM;API intermediates;Hydroxylamines;Hydroxylamines (N-Substituted);Naphthyridine,Quinoline
• Mol File: 36016-38-3.mol
• Article Data: 50

Chemical Properties

• Melting Point: 53-55 °C(lit.)
• Boiling Point: 245.66°C (rough estimate)
• Flash Point: 105.2 °C
• Appearance: White to light pink/Crystalline Powder
• Density: 1.2510 (rough estimate)
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.4120 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: 9.31±0.23(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 1756546
• CAS DataBase Reference: tert-Butyl N-hydroxycarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl N-hydroxycarbamate(36016-38-3)
• EPA Substance Registry System: tert-Butyl N-hydroxycarbamate(36016-38-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 36016-38-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 36016-38-3 differently. You can refer to the following data:
1. tert-Butyl N-hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts.
2. N-Boc-hydroxylamine is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts. It acts as a reagent for the synthesis of hydroxylamine derivatives t-butyl-N-(acyloxy)carbamates and N,O-diacylated N-hydroxyarylsulfonamides.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 955, 1959 DOI: 10.1021/ja01513a049Tetrahedron Letters, 24, p. 231, 1983 DOI: 10.1016/S0040-4039(00)81372-6

InChI:InChI=1/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7)

Upstream product

• 24608-52-4 tert-butyl chloroformate 
• 38965-26-3 3,3-Dimethylbuttersaeureanhydrid 
• 31583-38-7 tert-butyl 1,4-dioxo-1,4-dihydro-3H-benzo[d][1,2]oxazine-3-carboxylate 
• 105340-85-0 (benzyloxy)carbamic acid 1,1-dimethylethyl ester 
• 870-46-2 t-butoxycarbonylhydrazine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5470-11-1 hydroxylamine hydrochloride 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 24424-95-1 di-tert-butyl tricarbonate 

Downstream Products

• 85006-25-3 N,N-di(tert-butoxycarbonyl)hydroxylamine 
• 99768-83-9 (acetyloxy)carbamic acid 1,1-dimethyl ethyl ester 
• 35657-40-0 tert-butyl (pivaloyloxy)carbamate 
• 38100-27-5 t-Butyl-N-(2,6-dinitrophenoxy)-carbamat 
• 33543-54-3 N-Boc-O-(4-nitrophenyl)hydroxylamine 
• 19689-97-5 N-(tert-butoxycarbonyl)-N-methylhydroxylamine 
• 58377-44-9 N-(tert-butoxycarbonyl)-O-methylhydroxylamine 
• 58377-43-8 tert.-Butyl-N-p-tert-butylphenyl-methoxycarbamat 
• 36016-39-4 N-(tert-butoxycarbonyl)-O-(mesitylsulfonyl)hydroxylamine 
• 1013036-52-6 tert-butyl 2-(benzyloxy)-1-(phenylsulfonyl)ethyl-N-hydroxycarbamate 
• 1013036-55-9 tert-butyl 1-cyclohex-2-enyl-1-(phenylsulfonyl)methyl-N-hydroxycarbamate 
• 952151-38-1 5-benzyl-2-(tert-butyl) 1,2,5-oxadiazepane-2,5-dicarboxylate 
• 870300-80-4 tert-butyl 3-phenyl-1-(phenylsulfonyl)propyl-N-hydroxycarbamate 
• 619333-95-8 1,1-dimethylethyl [[bis(4-methoxyphenyl)phosphinyl]oxy]carbamate 

Relevant articles and documents

High-throughput protein glycomics: Combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry

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Enantioselective Diels-Alder reaction with an α-chloronitroso dienophile derived from 5-O-acetyl-2,3-isopropylidenedioxy-D-ribose

Crystalline 5-O-acetyl-2,3-isopropylidenedioxy-D-ribonolactone oxime (8) was synthesised from D-ribose in 40% overall yield. The chloronitroso dienophile 3b was obtained from 8 by oxidation with t-BuOCl and underwent asymmetric Diels-Alder reaction with cyclic and acyclic dienes 10-13 to give crystalline adducts 14a-17a in good yield and excellent enantiomeric excess (93-99%).

Alternating Current Electrolysis as Efficient Tool for the Direct Electrochemical Oxidation of Hydroxamic Acids for Acyl Nitroso Diels–Alder Reactions

The acyl nitroso Diels–Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted. A mixture of triethylamine/hexafluoroisopropanol served as supporting electrolyte in dichloromethane, thus giving products of high purity after evaporation of the volatiles without further purification. The optimised reaction conditions were applied to various 1,3-dienes and hydroxamic acids, giving up to 96 % isolated yield.

An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation

The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).

Palladium-Catalyzed Synthesis of Indolines from Aroyloxycarbamates through a Tandem Decarboxylative Amination/Heck/Annulation Reaction

A novel synthesis of functionalized indolines via a Pd-catalyzed tandem decarboxylative amination/Heck/annulation reaction has been developed. This process features operational simplicity, mild conditions, and the use of a readily available and environmentally friendly starting material, namely carboxylic acid. Furthermore, the reaction shows good functional group tolerance and chemical selectivity. (Figure presented.).