N,O-Bis(trimethylsilyl)hydroxylamine

Base Information

• Chemical Name: N,O-Bis(trimethylsilyl)hydroxylamine
• CAS No.: 22737-37-7
• Molecular Formula: C6H19NOSi2
• Molecular Weight: 177.394
• Hs Code.: 29319019
• European Community (EC) Number: 245-188-7
• DSSTox Substance ID: DTXSID50177276
• Nikkaji Number: J286.289A
• Wikidata: Q83047592
• Mol file: 22737-37-7.mol

Synonyms:N,O-Bis(trimethylsilyl)hydroxylamine;22737-37-7;[dimethyl-(trimethylsilyloxyamino)silyl]methane;1,1,1-Trimethyl-N-((trimethylsilyl)oxy)silylamine;EINECS 245-188-7;Silanamine, 1,1,1-trimethyl-N-[(trimethylsilyl)oxy]-;1,1,1-trimethyl-N-[(trimethylsilyl)oxy]silylamine;MFCD00008266;C6H19NOSi2;SCHEMBL484827;Hydroxylamine, 2TMS derivative;C6-H19-N-O-Si2;DTXSID50177276;N,O-bis-trimethylsilylhydroxylamine;N,O-Bis(trimethylsilyl)hydroxylamin;n,o-bis-trimethylsilyl hydroxylamine;AKOS004115285;N,O-Bis-(trimethylsilyl)-hydroxylamin;BS-44095;N,O-Bis(trimethylsilyl)hydroxylamine, 97%;B1825;FT-0638248;T70598;J-014833;2,2,5,5-Tetramethyl-3-oxa-4-aza-2,5-disilahexane #;N,O-Bis(trimethylsilyl)hydroxylamine, purum, >=97.0% (GC)

Chemical Property of N,O-Bis(trimethylsilyl)hydroxylamine

Chemical Property:

• Appearance/Colour: Clear colorless liquid
• Vapor Pressure: 6.33mmHg at 25°C
• Refractive Index: n20/D 1.411(lit.)
• Boiling Point: 139.8 °C at 760 mmHg
• PKA: 5.94±0.70(Predicted)
• Flash Point: 38.3 °C
• PSA: 21.26000
• Density: 0.828 g/cm³
• LogP: 2.56830
• Storage Temp.: 2-8°C
• Solubility.: sol THF, ether, pentane, CH2Cl2.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 177.10051730
• Heavy Atom Count: 10
• Complexity: 103

Purity/Quality:

99.5% ^*data from raw suppliers

N,O-bis(Trimethylsilyl)hydroxylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,C
• Statements: 10-36/37/38-34
• Safety Statements: 26-36-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[Si](C)(C)NO[Si](C)(C)C
• 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 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). 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.

Technology Process of N,O-Bis(trimethylsilyl)hydroxylamine

There total 3 articles about N,O-Bis(trimethylsilyl)hydroxylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → N,O-bis(trimethylsilyl)hydroxylamine (22737-37-7)

Guidance literature:

With hydroxylamine hydrochloride; In tetrahydrofuran; pentane; for 24h; Heating;

DOI:10.1021/jo00315a024

Reference yield: 70.0%

chloro-trimethyl-silane (75-77-4) → N,O-bis(trimethylsilyl)hydroxylamine (22737-37-7)

Guidance literature:

With hydroxylamine hydrochloride; In dichloromethane; ethylenediamine; for 24h;

Reference yield:

→ N,O-bis(trimethylsilyl)hydroxylamine (22737-37-7)

Guidance literature:

R3SiONH2, Ph2CCNSiR3;

DOI:10.1016/S0022-328X(00)95128-3

upstream raw materials:

chloro-trimethyl-silane

1,1,1,3,3,3-hexamethyl-disilazane

Downstream raw materials:

O-(2,4,6-trimethylphenylsulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine

tris-trimethylsilyl-hydroxylamine

C₁₃H₂₆FNOSi₃

C₁₂H₂₃F₂NOSi₃

Refernces

• 1、 Knight, Frances I.,Brown, John M.,Lazzari, Dario,Ricci, Alfredo,Blacker, A. John. "Electrophilic amination of catecholboronate esters formed in the asymmetric hydroboration of vinylarenes". . p. 11411 - 11424. Retrieved 2007/10/03.
• 2、 Chang, Young Hwan,Chiu, Fang-Ting,Zon, Gerald. "Investigation of Thermally Induced α-Deoxysilylation of Organosilylated Hydroxylamine Derivatives as a General Method for Nitrene Production". . p. 342 - 354. Retrieved 2007/10/02.