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HomeProduct name listtert-Butyl N-hydroxycarbamate

tert-Butyl N-hydroxycarbamate

Synonym(s):tert-Butyl N-hydroxycarbamate

  • CAS NO.:36016-38-3
  • Empirical Formula: C5H11NO3
  • Molecular Weight: 133.15
  • MDL number: MFCD00002107
  • EINECS: 252-836-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-05-21 09:37:49
tert-Butyl N-hydroxycarbamate Structural

What is tert-Butyl N-hydroxycarbamate?

Chemical properties

White to light pink crystalline powder

The Uses of tert-Butyl N-hydroxycarbamate

tert-Butyl N-hydroxycarbamate is used in the preparation of azridines by cycloaddition of azides with nitroso Diels-Alder adducts.

The Uses of tert-Butyl N-hydroxycarbamate

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.

What are the applications of Application

N-Boc-hydroxylamine is a chemical used in the preparation of azridines

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 955, 1959 DOI: 10.1021/ja01513a049
Tetrahedron Letters, 24, p. 231, 1983 DOI: 10.1016/S0040-4039(00)81372-6

Synthesis

A suspension of NH2OH·HCl (9.7 g, 140mmol) and K2CO3 (9.7 g, 700 mmol) in Et2O (60 mL) and H2O (2 mL)was stirred for about 1 h at r.t. with evolution of CO2 gas. A solution of Boc2O (20.0 g, 92 mmol) in Et2O (40 mL) was then added dropwise at 0 °C, and the suspension was stirred at r.t for 12 h. The organic phase was decanted, and the solid was washed with Et2O (3 × 30 mL). The combined organic layers were concentrated, and the residue was recrystallized from cyclohexane/toluene to afford the desired product tert-butyl N-hydroxycarbamate as a white solid.

Properties of tert-Butyl N-hydroxycarbamate

Melting point: 53-55 °C (lit.)
Boiling point: 245.66°C (rough estimate)
Density  1.2510 (rough estimate)
refractive index  1.4120 (estimate)
storage temp.  2-8°C
solubility  Chloroform, Methanol
pka 9.31±0.23(Predicted)
form  Crystalline Powder
color  White to light pink
Water Solubility  Slightly soluble in water.
Sensitive  Moisture Sensitive
BRN  1756546
InChI InChI=1S/C5H11NO3/c1-5(2,3)9-4(7)6-8/h8H,1-3H3,(H,6,7)
CAS DataBase Reference 36016-38-3(CAS DataBase Reference)

Safety information for tert-Butyl N-hydroxycarbamate

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for tert-Butyl N-hydroxycarbamate

InChIKey DRDVJQOGFWAVLH-UHFFFAOYSA-N
SMILES C(OC(C)(C)C)(=O)NO

tert-Butyl N-hydroxycarbamate manufacturer

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