tert-Butyl N-hydroxycarbamate Chemical Properties

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)

InChIKey

DRDVJQOGFWAVLH-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)NO

CAS DataBase Reference

36016-38-3(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

21

HS Code 

29280090

MSDS

• Language:English Provider:N-Boc-hydroxylamine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

tert-Butyl N-hydroxycarbamate Usage And Synthesis

Chemical Properties

White to light pink crystalline powder

Uses

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.

Uses

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

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.

tert-Butyl N-hydroxycarbamate(36016-38-3)Related Product Information

• Buprofezin
• Butyl acetate
• tert-Butyl glycinate
• tert-Butyl 4-aminobenzoate
• Butyl formate
• n-Butyl carbamate
• tert-Butanol
• 2-Butoxyethanol
• Hydroxylamine hydrochloride
• Hydroxylamine sulfate
• tert-Butyl carbazate
• Urethane
• tert-Butyl peroxybenzoate
• 4-Aminobenzoic acid
• N-Carbobenzyloxyglycine
• 4-Hydroxybenzoic acid
• Cyhalofop-butyl
• Methylparaben