N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE Property

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)

Safety

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

F 

10-21

TSCA 

No

HazardClass 

3.2

PackingGroup 

III

HS Code 

29319019

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE Chemical Properties,Usage,Production

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.