22737-37-7 Usage
Uses
Used in Organic Synthesis:
N,O-Bis(trimethylsilyl)hydroxylamine is used as a reagent for the preparation of N-(dialkyl phosphinoyl)hydroxylamines and migration of simple alkyl groups in the rearrangement of their O-p-nitrobenzenesulfonates. This makes it a valuable tool in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Chemical Reactions:
N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE is utilized in reactions with acid chlorides in the presence of triethylamine, resulting in the formation of N,O-bis(trimethylsilyl)-hydroxamic acids through N-acylation. Additionally, a related reagent, tris(trimethylsilyl)hydroxylamine, can produce the same product in high yields.
Used in Hydrolysis:
N,O-Bis(trimethylsilyl)hydroxylamine can undergo hydrolysis to yield free hydroxamic acids, which are important intermediates in the synthesis of various organic compounds.
Used in Thermal Fragmentation:
Thermal fragmentation of N,O-Bis(trimethylsilyl)hydroxylamine affords isocyanates, which are valuable building blocks in the synthesis of pharmaceuticals, agrochemicals, and polymers.
Used in Analytical Chemistry:
N,O-BIS(TRIMETHYLSILYL)HYDROXYLAMINE is used in the analysis of conjugated estrogen tablets and injectable formulations by gas-liquid chromatography (GLC). It reacts with free phenolic steroids, providing a means to analyze and quantify these compounds in pharmaceutical products.
Physical Properties:
N,O-Bis(trimethylsilyl)hydroxylamine has a boiling point of 137-139°C and a reduced pressure boiling point of 78-80°C/100 mmHg. It also has a flash point of 28°C, indicating its flammability and the need for proper handling and storage conditions.
Chemical Properties:
As a clear colorless liquid, N,O-Bis(trimethylsilyl)hydroxylamine is stable under normal conditions but should be handled with care due to its reactivity with electrophiles and its potential to form isocyanates upon thermal fragmentation.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 22737-37-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,7,3 and 7 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 22737-37:
(7*2)+(6*2)+(5*7)+(4*3)+(3*7)+(2*3)+(1*7)=107
107 % 10 = 7
So 22737-37-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H19NOSi2/c1-9(2,3)7-8-10(4,5)6/h7H,1-6H3
22737-37-7Relevant academic research and scientific papers
Electrophilic amination of catecholboronate esters formed in the asymmetric hydroboration of vinylarenes
Knight, Frances I.,Brown, John M.,Lazzari, Dario,Ricci, Alfredo,Blacker, A. John
, p. 11411 - 11424 (2007/10/03)
(S)-(4-Methoxyphenyl)-ethyl-1,3,2-benzodioxaborole, (S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole and (S)-1-indanyl-1,3,2-benzodioxaborole, intermediates in the catalytic asymmetric hydroboration of 4-chloro- and 4-methoxystyrene, were isolated as pure oils in 75%, 84% and 49% yield respectively. For the first example, amination with N-chloromagnesio-N-methyl-O-trimethylsilylhydroxylamine gave a mixture of (S)-1-(4-methoxyphenyl)-N- methylethylamine in 33% yield, 88% e.e. and (S)-1-(4-methoxyphenyl) ethanol in 31% yield, 86% e.e.. Related results were obtained in the other cases, and the steps of catalytic hydroboration and amination could be combined in a single sequence without isolation of the intermediate Numerous variants were carried out in the amination procedure with only marginal improvements in chemoselectivity. An investigation of the mechanism was carried out using low temperature heteronuclear NMR on 13C-1-(S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole. The dual pathway is a result of an irreversible and unselective initial step.
EXPEDIENT SYNTHESIS OF MONO-TRIMETHYLSILYL HYDROXYLAMINE AND BIS-TRIMETHYLSILYL HYDROXYLAMINE
Bottaro, Jeffrey C.,Bedford, Clifford D.,Dodge, Allen
, p. 1333 - 1336 (2007/10/02)
Mono and Bis-trimethylsilylhydroxylamine are conveniently prepared by similar procedures on an arbitrarily large scale, without risk or undue effort on the part of the experimenter.
Investigation of Thermally Induced α-Deoxysilylation of Organosilylated Hydroxylamine Derivatives as a General Method for Nitrene Production
Chang, Young Hwan,Chiu, Fang-Ting,Zon, Gerald
, p. 342 - 354 (2007/10/02)
A variety of organosilylated hydroxylamine derivatives have been synthesized and studied as possible nitrene generators by thermally induced α-deoxysilylation: GN(OR')SiR3 GN + R'OSiR3, where G = EtO2C, ArCO, ArSO2, Me, H, and Ph2PO.The methods used to assess nitrene formation include trapping product characterization, substitutent variation, kinetic activation parameter measurements, Hammett studies, and solvent effects.While the latter two types of precursors were only briefly investigated because of their marked resistance to fragmentation, the combined data for the remaining compounds are consistent with the intermediacy of a nitrene.The existence of alternative deoxysilylation pathways is discussed in some cases, and for comparison with the nitrogen systems reported herein, kinetic activation parameters for α-deoxysilylation about carbon and silicon have been determined.
