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N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE

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N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE Basic information

Product Name:
N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE
Synonyms:
  • 2,2,5,5-Tetramethyl-3-oxa-4-aza-2,5-disilahexane
  • N,O-Bis-(trimethylsilyl)-hydroxylamin
  • Silanamine, 1,1,1-trimethyl-N-[(trimethylsilyl)oxy]-
  • 1,1,1-trimethyl-N-[(trimethylsilyl)oxy]silylamine
  • N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE, 97 %
  • N,0-Bis(trimethylsilyl)hydroxylamine
  • Bis(trimethylsilyl)hydroxylamine
  • (Trimethylsiloxy)(trimethylsilyl)amine
CAS:
22737-37-7
MF:
C6H19NOSi2
MW:
177.39
EINECS:
245-188-7
Product Categories:
  • Building Blocks
  • Chemical Synthesis
  • Hydroxylamines
  • Hydroxylamines (N-Substituted)
  • Nitrogen Compounds
  • Organic Building Blocks
  • Hydroxylamines (O-Substituted)
  • Si (Classes of Silicon Compounds)
  • Si-N Compounds
  • Trimethylsilylazide, etc.
  • Nitrogen Compounds
  • Organic Building Blocks
Mol File:
22737-37-7.mol
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N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE Chemical Properties

Boiling point:
78-80 °C100 mm Hg(lit.)
Density 
0.83 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.411(lit.)
Flash point:
84 °F
storage temp. 
2-8°C
solubility 
sol THF, ether, pentane, CH2Cl2.
form 
clear liquid
pka
5.94±0.70(Predicted)
color 
Colorless to Almost colorless
Specific Gravity
0.83
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
BRN 
1920452
CAS DataBase Reference
22737-37-7(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,C
Risk Statements 
10-36/37/38-34
Safety Statements 
26-36-45-36/37/39
RIDADR 
UN 1993 3/PG 3
WGK Germany 
3
10-21
TSCA 
No
HazardClass 
3.2
PackingGroup 
III
HS Code 
29319019

MSDS

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N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE Usage And Synthesis

Chemical Properties

Clear colorless liquid

Physical properties

bp 137–139°C, 78–80°C/100 mmHg; d 0.830 g cm?3; flash point 28°C.

Uses

N,O-Bis(trimethylsilyl)hydroxylamine has been used as reagent for the preparation of N-(dialkyl phosphinoyl)hydroxylamines and migration of simple alkyl groups in rearrangement of their O-p-nitrobenzenesulfonates.

Uses

N,O-Bis(trimethylsilyl)hydroxylamine is a protected, lipophilic form of hydroxylamine. It reacts with a variety of electrophiles predominantly by attack on the nitrogen nucleophilic center. Reaction with acid chlorides (1 equiv) in the presence of triethylamine gives N,O-bis(trimethylsilyl)- hydroxamic acids by N-acylation.A related reagent, tris(trimethylsilyl) hydroxylamine, gives the same product in high yields, also by N-acylation.Hydrolysis gives the free hydroxamic acids, whereas thermal fragmentation affords isocyanates (eq 1).

Preparation

N,O-Bis(trimethylsilyl)hydroxylamine can be prepared in 69% yield by treating dry hydroxylamine with equiv chlorotrimethylsilane and equiv triethylamine.A safer preparation, which avoids the use of the explosive solid, hydroxylamine, uses the reaction of hydroxylamine hydrochloride with excess hexamethyldisilazane (71–75% yield).Alternatively, neutralization of hydroxylamine hydrochloride with ethylenediamine followed by addition of chlorotrimethylsilane can be used.

General Description

N,O-Bis(trimethylsilyl)hydroxylamine on reaction with 9-chloro-9-borafluorene yields 10-trimethylsilyloxy-9-aza-10-boraphenanthrene. It reacts with free phenolic steroids during the analysis of conjugated estrogen tablets and injectable formulations by GLC.

N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINESupplier

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