3279-07-0

Basic information

• Product Name: 4-tert-Butyl-2-nitrophenol
• Synonyms: Phenol, 4-(1,1-dimethylethyl)-2-nitro;2-NITRO-4-TERT-BUTYLPHENOL;4-T-BUTYL-2-NITROPHENOL;4-TERT-BUTYL-2-NITROPHENOL;2-Nitryl-4-tert-butylphenol;O-NITRO-P-(TERT)BUTYL PHENOL;4-TERT-BUTYL-2-NITROPHENOL 98+%;3279-07-0
• CAS NO: 3279-07-0
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.21512
• EINECS: 221-914-8
• Product Categories: Industrial/Fine Chemicals;Aromatic Phenols;Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 3279-07-0.mol
• Article Data: 34

Chemical Properties

• Melting Point: 27-29 °C(lit.)
• Boiling Point: 97 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.12 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00663mmHg at 25°C
• Refractive Index: 1.5500-1.5530
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 7.37±0.14(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 4-tert-Butyl-2-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-tert-Butyl-2-nitrophenol(3279-07-0)
• EPA Substance Registry System: 4-tert-Butyl-2-nitrophenol(3279-07-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3279-07-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow low melting solid

Uses

4-tert-Butyl-2-nitrophenol may be used for the preparation of (2-hydroxy-3-nitro-5-tert-butylbenzyl)trimethylammonium iodide.

InChI:InChI=1/C10H13NO3/c1-10(2,3)7-4-5-9(12)8(6-7)11(13)14/h4-6,12H,1-3H3

Upstream product

• 540-80-7 tert.-butylnitrite 
• 98-54-4 para-tert-butylphenol 
• 4783-74-8 2-(4-(tert-butyl)phenoxy)pyridine 
• 123324-71-0 p-tert-butylphenylboronic acid 
• 228401-16-9 trifluoro-methanesulfonic acid 4-tert-butyl-2-nitro-phenyl ester 
• 7341-17-5 2-ethylhexane-1-thiol 
• 4459-83-0 Toluene-4-sulfonic acid 4-tert-butyl-2-nitro-phenyl ester 
• 496044-20-3 4-tert-butyl-2-nitrophenyl dimethyl phosphate 
• 769-92-6 4-tert-Butylaniline 
• 544-16-1 n-Butyl nitrite 
• 6310-19-6 4-tert-butyl-2-nitroaniline 

Downstream Products

• 1199-46-8 2-amino-4-tert-butylphenol 
• 91247-60-8 1-methoxy-2-nitro-4-(tert-butyl)benzene 
• 74752-32-2 O-4-tert-Butyl-2-nitrophenyl Dimethylcarbamothioate 
• 33444-53-0 o-Nitro-p-tert-butylphenol-isopropylaether 
• 240131-60-6 1-<2-nitrophenyl(thio)>-5-(4-tert-butyl-2-nitrophenoxy)-3-oxapentane 
• 228401-22-7 5-tert-Butyl-2-(2-hydroxyethoxy)-1-nitrobenzene 
• 228401-10-3 4-tert-butyl-1-(3-tetrahydrofuranyloxy)-2-nitrobenzene 
• 207462-02-0 1,8-bis(4-tert-butyl-2-nitrophenoxy)-3,6-dioxaoctane 
• 33353-60-5 o-Nitro-p-tert-butylphenol-propylaether 
• 1261438-94-1 C₁₇H₁₇NO₄ 
• 5998-51-6 5-(tert-butyl)-2-phenylbenzo[d]oxazole 
• 1541175-16-9 (2-hydroxy-3-nitro-5-tert-butylbenzyl)trimethylammoniumiodide 

Relevant articles and documents

Coumarin synthesis on π-acidic surfaces

Catalysis with anion-π interactions is emerging as an important topic in supramolecular chemistry. Among the reactions explored so far on π-acidic surfaces, coumarin synthesis stands out as a cascade process with several coupled anionic transition states. Increasing π-acidity has been shown in a different context to increase transition-state stabilisation and thus catalytic activity. In this report, we explore the possible use of macrocycles to accelerate coumarin synthesis between two π-acidic surfaces. To our disappointment, we found that compared to monomeric π-acids, coumarin synthesis within divalent macrocycles is clearly slower. Hindered access to an overly confined active site within the macrocycles could possibly account for this loss in activity, but several other explanations are certainly possible. However, operational coumarin synthesis on monomeric π-acidic surfaces is shown to tolerate structural modifications. Best results are obtained with structures that aim for proximity without obstructing transition-state stabilisation on the π-acidic surface.

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

Research on unique masked ortho-benzoquinone, monohemiaminal: Synthesis and reactions

Synthesis of ortho-benzoquinone monohemiaminals via the oxidative dearomatization/O-cyclization cascades of phenols bearing an ortho substituent derived from an amino alcohol with PIDA is described. The cascade reactions of substrates bearing a chiral substituent were found to proceed in a stereoselective manner. The Diels-Alder reactions of the ortho-benzoquinone monohemiaminals proceed in a highly stereoselective manner. The oxidative dearomatization/O-cyclization cascade affording the ortho-benzoquinone monohemiaminal had never been reported; hence, there is still ample scope for further investigation.