| Identification | Back Directory | [Name]
DI-TERTBUTYLNITROPHENOL | [CAS]
728-40-5 | [Synonyms]
B-28589
BAY-28589
ENT-25569
NSC 81682
Bayer-28589
DI-TERTBUTYLNITROPHENOL
4-Nitro-2,6-di-tert-butylphenol
3,4-Di-tert-butyl-2-nitrophenol
2,6-Bis(1,1-dimethylethyl)-4-nitrophenol
4-Nitro-2,6-bis-(1,1-dimethylethyl)phenol
Phenol, 2,6-bis(1,1-diMethylethyl)-4-nitro- | [EINECS(EC#)]
616-586-1 | [Molecular Formula]
C14H21NO3 | [MOL File]
728-40-5.mol | [Molecular Weight]
251.32 |
| Chemical Properties | Back Directory | [Melting point ]
154-156℃ | [Boiling point ]
307℃ | [density ]
1.078 | [refractive index ]
1.5774 (estimate) | [Fp ]
118℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
7.17±0.40(Predicted) | [color ]
Light Yellow to Yellow | [InChI]
InChI=1S/C14H21NO3/c1-13(2,3)10-7-9(15(17)18)8-11(12(10)16)14(4,5)6/h7-8,16H,1-6H3 | [InChIKey]
FCGKUUOTWLWJHE-UHFFFAOYSA-N | [SMILES]
C1(O)=C(C(C)(C)C)C=C([N+]([O-])=O)C=C1C(C)(C)C | [EPA Substance Registry System]
Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitro- (728-40-5) |
| Hazard Information | Back Directory | [Uses]
2,6-Di-tert-butyl-4-nitrophenol is a potentially powerful uncoupler of ATP-generating oxidative phosphorylation that has been reported to be a contaminant in submarines and indoor spaces, causing a number of objects to turn yellow (even human skin). | [Synthesis]
General procedure for the synthesis of 2,6-di-tert-butyl-4-nitrophenol from 2,6-di-tert-butylphenol: 2,6-di-tert-butylphenol (8 g, 39 mmol) was dissolved in 25 ml of cyclohexane at 10 °C. A mixed acid (5 ml) consisting of nitric acid and acetic acid mixed 1:1 by volume was slowly added dropwise to the reaction system while maintaining the reaction temperature at 10 °C. After the dropwise addition was completed, the reaction mixture was stirred at room temperature for 15 minutes. Upon completion of the reaction, the precipitate formed was collected by filtration and washed sequentially with water and pentane. The resulting crude product of 2,6-di-tert-butyl-4-nitrophenol (6.34 g, 65% yield) was dried in an oven and used in subsequent steps without further purification. The product was a light yellow powder with a melting point of 167-168 °C. 1H NMR (CDCl3, 100 MHz, δ): 1.48 (s, 18H, 2×t-Bu), 5.93 (s, 1H, OH), 8.13 (s, 2H, Ar-H). | [References]
[1] Journal of Chemical Research, 2011, vol. 35, # 2, p. 101 - 103
[2] Organic Letters, 2009, vol. 11, # 18, p. 4172 - 4175
[3] Patent: US6335445, 2002, B1. Location in patent: Page column 91
[4] Patent: US6727239, 2004, B1. Location in patent: Page column 19
[5] Journal of the Chemical Society. Perkin Transactions 2, 2002, # 6, p. 1112 - 1117 |
|
|