Di-tert-butyl nitroxide

Base Information

• Chemical Name: Di-tert-butyl nitroxide
• CAS No.: 2406-25-9
• Deprecated CAS: 13285-32-0,154520-96-4
• Molecular Formula: C8H18 N O
• Molecular Weight: 146.253
• European Community (EC) Number: 219-298-0
• DSSTox Substance ID: DTXSID60873272
• Nikkaji Number: J458.406F
• Mol file: 2406-25-9.mol

Synonyms:di-t-butyl nitroxide;di-tert-butyl-nitroxyl;DTBN-spin

Chemical Property of Di-tert-butyl nitroxide

Chemical Property:

• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 74-75 °C34 mm Hg(lit.)
• Flash Point: 114 °F
• PSA: 3.24000
• Density: 0.877g/cm³
• LogP: 2.23090
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 144.138839198
• Heavy Atom Count: 10
• Complexity: 93.4

Purity/Quality:

98%,99%, ^*data from raw suppliers

Di-tert-butyl nitroxide technical grade, 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 10-22-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)N(C(C)(C)C)[O]
• Uses: Di-tert-butyl Nitroxide is a spin labeled compound that has been used in localization of lipid microdomains and thermal phenomena in murine stratum corneum.

Technology Process of Di-tert-butyl nitroxide

There total 74 articles about Di-tert-butyl nitroxide 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:

2,2,6,6-Tetramethyl-1-piperidinyloxy free radical (2564-83-2,45842-10-2,126517-51-9,25657-03-8,26933-82-4,54637-06-8,64104-42-3) + N,N-di-tert-butylhydroxylamine (10531-39-2) → 2,2,6,6-tetramethylpiperidin-1-ol (7031-93-8) + di-tert-butyl nitroxide (2406-25-9,44871-19-4)

Guidance literature:

In [D₃]acetonitrile; at 24.84 ℃; Solvent; Temperature; Equilibrium constant; Inert atmosphere;

DOI:10.1021/ja904400d

Reference yield:

t-butylnitrite (917-95-3) → tetramethyl-2,2,3,3 butane (594-82-1) + di-tert-butyl nitroxide (2406-25-9,44871-19-4)

Guidance literature:

In decane; Quantum yield; Ambient temperature; Irradiation; photolysis;

Reference yield:

t-butylnitrite (917-95-3) + N,N-dimethyl acetamide (127-19-5,116057-81-9) → di-tert-butyl nitroxide (2406-25-9,44871-19-4) + C8H17N2O2 (1367367-88-1)

Guidance literature:

In acetonitrile; at -10.16 ℃; Inert atmosphere; Photolysis;

DOI:10.1016/j.tet.2012.01.066

upstream raw materials:

2-Methyl-2-nitropropane

tert.-butyl lithium

2,2,4,4-tetramethyl-pentan-3-one O-(1-tert-butyl-2,2-dimethyl-1-nitroso-propyl)-oxime

piperidine

Downstream raw materials:

t-butylnitrite

N-2'-furoyl-O-2''-furoyl-N-t-butylhydroxylamine

isobutene

N,N-di-t-butyl-O-benzylhydroxylamine

Refernces

• 1、 Hoffmann et al.. "". . p. 4675. Retrieved 1961.
• 2、 Knauer,Napier. "". . p. 4395,4396, 4397. Retrieved 1976.
• 3、 Hoffmann et al.. "". . p. 4671. Retrieved 1961.
• 4、 Morosov,Shabatina,Batyuk,Sergeev. "Kinetic model of radical reaction in plastic crystals". . p. 117 - 123. Retrieved 1994.
• 5、 Aretz, Christopher D.,McPeak, Joseph E.,Eaton, Gareth R.,Eaton, Sandra S.,Cowen, Bryan J.. "Mechanism of SmI2 Reduction of 5-Bromo-6-oxo-6-phenylhexyl Methanesulfonate Studied by Spin Trapping with 2-Methyl-2-nitrosopropane". . p. 10688 - 10692. Retrieved 2018.
• 6、 Aurich,H.G.,Stork,K.. "". . p. 555 - 559. Retrieved 1972.
• 7、 Wang, Fan,Lei, Liandi,Wu, Longmin. "NO spin trapping and EPR studies on the photochemistry of aliphatic aldehydes". . p. 156 - 165. Retrieved 2005.
• 8、 Levin et al.. "". . . Retrieved 1975.
• 9、 Xu, Zhengbao,Hang, Zhaojia,Chai, Li,Liu, Zhong-Quan. "A Free-Radical-Promoted Site-Specific Cross-Dehydrogenative-Coupling of N-Heterocycles with Fluorinated Alcohols". supporting information. p. 4662 - 4665. Retrieved 2016/09/28.