119-33-5

Usage

Uses

Used in Chemical Industry:
2-Nitro-p-cresol is used as an intermediate for the synthesis of various chemicals and compounds. Its chemical structure allows it to be a key component in the production of different products, making it valuable in the chemical industry.
Used in Environmental Science:
2-Nitro-p-cresol is used as a chemical marker to characterize secondary organic aerosols from the photooxidation of toluene in hydrocarbon-NOx mixtures. This application helps in understanding the formation and behavior of aerosols in the atmosphere, which is crucial for air quality management and climate research.

Hazard

Toxic by ingestion, inhalation, and skin absorption.

InChI:InChI=1/C7H7NO3/c1-5-2-3-7(9)6(4-5)8(10)11/h2-4,9H,1H3/p-1

Synthetic route

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With (NH4)2Ce(NO3)6 on Ca-bentonite In chloroform at 25℃; for 48h;	98.5%
With toluene-4-sulfonic acid; nickel(II) nitrate In acetone at 20℃; for 0.0166667h;	98%
With dimethylbromosulphonium bromide; tetrabutylammonium nitrite In acetonitrile at 20℃; for 1h; regioselective reaction;	96%

p-cresol (106-44-5) + cuprous nitrate (3251-29-4) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With acetic anhydride In tetrachloromethane; nitric acid	98%

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5) + 4-methyl-5-nitrophenol (2042-14-0)

Conditions	Yield
With nitro acetate; silica gel In chloroform at -20 - 20℃; Nitration;	A 93% B 6%
With copper(II) nitrate/zeolite H-Y for 0.0166667h; Product distribution; Further Variations:; heating mode; times; microwave irradiation;	A 88% B n/a
With tert.-butylnitrite In acetonitrile at 29.84℃; Kinetics; Solvent; Temperature;	A 85% B n/a

4-methoxy-3-nitrotoluene (119-10-8) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -5 - 25℃;	93%

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5) + 2,6-dinitro-p-cresol (609-93-8)

Conditions	Yield
With Yb-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;	A 88% B 3%
With Montmorillonite KSF; nitric acid; hafnium oxychloride In tetrahydrofuran at 20℃; for 16h;	A 81% B 6%
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 6h; Ionic liquid;	A 78% B 16%

(E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-(4-nitrophenyl)acrylate → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	88%

(E)-methyl 3-(4-fluorophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate (1151899-38-5) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	84%

tert.-butylnitrite (540-80-7) + p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With water In tetrahydrofuran at 25℃; for 2.5h; Schlenk technique;	82%

(E)-methyl 3-(4-methoxyphenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate (1151899-28-3) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	79%

(E)-methyl 3-(4-cyanophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	79%

(E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-phenylacrylate (1151898-86-0) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	78%

p-cresol (106-44-5) → 1,4-dimethyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,11-tetraen-10-one + 4-methyl-2-nitrophenol (119-33-5) + 2-(2-hydroxy-5-methyl-3-nitrophenyl)-4-methyl-6-nitrophenol (32039-28-4)

Conditions	Yield
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 12h;	A 10% B 77% C 12%

4-Methylanisole (104-93-8) → p-cresol (106-44-5) + 4-methyl-2-nitrophenol (119-33-5) + 4-methoxy-3-nitrotoluene (119-10-8)

Conditions	Yield
With nitric acid In sulfuric acid at 25℃;	A 7.3% B 28.4% C 73%
With nitric acid In sulfuric acid at 25℃;	A 8.25% B 32.5% C 67.8%
With nitric acid In sulfuric acid at 25℃;	A 8.2% B 32.5% C 67.8%
With nitric acid In sulfuric acid at 25℃; Rate constant; Product distribution; various acid concentrations and molar ratios;	A 8.1% B 31.2% C 64.5%

(E)-methyl 3-(4-bromophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With GLUTATHIONE In aq. phosphate buffer; acetonitrile at 37℃; for 4h; pH=7.4; Kinetics;	73%

p-cresol (106-44-5) + nitro acetate (591-09-3) → 4-methyl-2-nitrophenol (119-33-5) + 4-methyl-4-nitrocyclohexa-2,5-dien-1-one (62622-59-7)

Conditions	Yield
In acetic anhydride at 22℃; Mechanism; NMR-investigation, also with AcO(15)NO2;	A 70% B n/a

2-(4-fluorophenoxy)-4-fluorophenol → p-cresol (106-44-5) + 4-methyl-2-nitrophenol (119-33-5) + 4-methoxy-3-nitrotoluene (119-10-8)

Conditions	Yield
With nitric acid In sulfuric acid at 25℃; Product distribution; various acid concentration;	A 8.1% B 31.2% C 68.8%

4-Methylanisole (104-93-8) → 4-methyl-2-nitrophenol (119-33-5) + 4-methoxy-3-nitrotoluene (119-10-8) + 2,6-dinitro-p-cresol (609-93-8)

Conditions	Yield
With dinitrogen tetraoxide In dichloromethane at -30℃; for 1h; Nitration; demethylation;	A 11% B 61% C 24%
With tetranitromethane; tetrabutylammonium perchlorate In acetonitrile at 25 - 30℃; for 6h; Irradiation; Title compound not separated from byproducts;	A 6 % Spectr. B 55 % Spectr. C 39 % Spectr.

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5) + 2,6-dinitro-p-cresol (609-93-8) + 4-methyl-4-nitrocyclohexa-2,5-dien-1-one (62622-59-7)

Conditions	Yield
With Nitrogen dioxide In dichloromethane at -23℃; for 1h;	A 8% B 60% C 32%

4-Methylanisole (104-93-8) → 4-methyl-2-nitrophenol (119-33-5) + 4-methoxy-3-nitrotoluene (119-10-8)

Conditions	Yield
With air; nitrogen(II) oxide In acetonitrile for 2h; Ambient temperature;	A 16% B 58%
With nitric acid; hydrazine at 25℃; Rate constant;	A 42% B 49%
With tetranitromethane; tetrabutylammonium perchlorate In dichloromethane at 25 - 30℃; for 6h; Irradiation; Title compound not separated from byproducts;	A 39 % Spectr. B 61 % Spectr.
With nitric acid; acetic acid

para-chlorotoluene (106-43-4) → 4-methyl-2-nitrophenol (119-33-5) + 4-chloro-2-nitrotoluene (89-59-8) + 1-chloro-4-methyl-2-nitro-benzene (89-60-1)

Conditions	Yield
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h;	A 9.3% B 39.1% C 31%
With sulfuric acid; nitric acid In water at 25℃; for 3.83333h; Title compound not separated from byproducts;	A 9.3 % Chromat. B 39.1 % Chromat. C 31.0 % Chromat.

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5) + 2-bromo-4-methyl-6-nitrophenol (20039-91-2)

Conditions	Yield
With bromine; silver nitrate In acetonitrile for 2h; Ambient temperature;	A 23% B 39%

p-cresol (106-44-5) → 4-methyl-2-nitrophenol (119-33-5) + 2-iodo-4-methyl-6-nitrophenol (69492-91-7)

Conditions	Yield
With iodine; silver nitrate In acetonitrile for 2h; Ambient temperature;	A 25% B 37%

p-cresol (106-44-5) → 4-methyl resorcinol (496-73-1) + 4-methyl-2-nitrophenol (119-33-5) + 4-methyl-1,2-dihydroxybenzene (452-86-8)

Conditions	Yield
With ammonium cerium(IV) nitrate; dihydrogen peroxide; sodium dodecyl-sulfate In acetic acid for 48h; Ambient temperature;	A 22% B 12% C 30%

copper(II) bis(4-methyl-2-nitrosophenolato) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With polymer-supported thiourea In acetone at 21℃; for 24h; Molecular sieve; Inert atmosphere;	14%

piperidine (110-89-4) + (4-methyl-2-nitro-phenyl)-(2-nitro-phenyl)-ether (60671-88-7) → 1-(2-nitrophenyl)piperidine (15822-77-2) + 4-methyl-2-nitrophenol (119-33-5)

piperidine (110-89-4) + (2,4-dinitro-phenyl)-(4-methyl-2-nitro-phenyl)-ether (6282-16-2) → 4-methyl-2-nitrophenol (119-33-5) + 1-(2,4-dinitrophenyl)piperidine (839-93-0)

pyridine (110-86-1) + p-cresol (106-44-5) + diethyl ether (60-29-7) + ethanol (64-17-5) + hexanitroethane (918-37-6) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
at 0℃;

methanol (67-56-1) + toluene-4-diazonium ; nitrate → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
unter vermindertem Druck;

p-cresol (106-44-5) + tetranitromethane (509-14-8) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With pyridine; ethanol at 0℃;

p-cresol (106-44-5) + hexanitroethane (918-37-6) → 4-methyl-2-nitrophenol (119-33-5)

Conditions	Yield
With pyridine; ethanol

4-methyl-2-nitrophenol (119-33-5) → 3-amino-4-hydroxytoluene (95-84-1)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol at 23℃; for 5h;	100%
Stage #1: 4-methyl-2-nitrophenol With sodium dithionite In aq. phosphate buffer; acetone at 37℃; for 0.5h; pH=7.4; Stage #2: With disodium hydrogenphosphate; sodium dihydrogenphosphate	95%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16h; Inert atmosphere;	93%

4-methyl-2-nitrophenol (119-33-5) + 2-bromoethanol (540-51-2) → 2-(4-methyl-2-nitro-phenoxy)-ethanol (857070-70-3)

Conditions	Yield
With potassium carbonate In acetonitrile for 6h; Heating / reflux;	100%

trifluoromethylsulfonic anhydride (358-23-6) + 4-methyl-2-nitrophenol (119-33-5) → trifluoromethanesulfonic acid 4-methyl-2-nitrophenyl ester (195455-54-0)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 0.5h;	100%
With triethylamine In dichloromethane at 0℃; for 2h;

4-methyl-2-nitrophenol (119-33-5) → 2-bromo-4-methyl-6-nitrophenol (20039-91-2)

Conditions	Yield
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane	99%
With bromine; acetic acid	95%
With aluminium trichloride; bromine In dichloromethane at 20℃;	91%

4-methyl-2-nitrophenol (119-33-5) + acetic anhydride (108-24-7) → 4-methyl-2-nitrophenyl acetate (54646-55-8)

Conditions	Yield
With Zn(N4,N4'-di(pyridin-4-yl)biphenyl-4,4'-dicarboxamide)(5-aminoisophthalate) In dichloromethane at 20℃; for 8h;	99%
With bismuth oxide perchlorate at 20℃; for 1h;	82%
With magnesium(II) perchlorate at 80℃; for 0.5h;	70%

4-methyl-2-nitrophenol (119-33-5) + methyl (Z)-2-(bromomethyl)-3-(4-nitrophenyl)-2-propenoate (137104-37-1) → (E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-(4-nitrophenyl)acrylate

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	99%

4-methyl-2-nitrophenol (119-33-5) + 4-methoxy-benzoyl chloride (100-07-2) → C15H13NO5 (1290636-80-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	98%

4-methyl-2-nitrophenol (119-33-5) + (Z)-methyl 2-(bromomethyl)-3-phenylacrylate (103669-71-2) → (E)-methyl 2-((4-methyl-2-nitrophenoxy)methyl)-3-phenylacrylate (1151898-86-0)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	97%
With potassium carbonate In acetonitrile at 20℃; for 1h;	95%

4-methyl-2-nitrophenol (119-33-5) → 2,6-dinitro-p-cresol (609-93-8)

Conditions	Yield
With Nitrogen dioxide In dichloromethane at -23℃; for 1h;	96%

formaldehyd (50-00-0) + 4-methyl-2-nitrophenol (119-33-5) → 6-bromomethyl-4-methyl-2-nitrophenol (185062-86-6)

Conditions	Yield
With hydrogen bromide; acetic anhydride; acetic acid at 80℃; for 24h;	96%

Cyclohexyl isocyanide (931-53-3) + 4-methyl-2-nitrophenol (119-33-5) + propionaldehyde (123-38-6) + 4-chlorobenzylamine (104-86-9) → 2-(N-(4-chlorobenzyl)-N-(4-methyl-2-nitrophenyl)amino)-N-cyclohexylbutanamide

Conditions	Yield
In methanol at 60℃; for 72h;	96%
In methanol at 60℃; Ugi-Smiles coupling;	96%

methyl (Z)-4-(bromomethyl)-3-(4-fluorophenyl)-2-propenoate (1010396-60-7) + 4-methyl-2-nitrophenol (119-33-5) → (E)-methyl 3-(4-fluorophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate (1151899-38-5)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	96%
With potassium carbonate In acetonitrile at 20℃; for 1h;	90%

4-methyl-2-nitrophenol (119-33-5) + methyl (2Z)-2-(bromomethyl)-3-(4-methoxyphenyl)prop-2-enoate (213999-88-3) → (E)-methyl 3-(4-methoxyphenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate (1151899-28-3)

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	96%
With potassium carbonate In acetonitrile at 20℃; for 1h;	92%

4-methyl-2-nitrophenol (119-33-5) + 1-Bromo-2-chloroethane (107-04-0) → 1-(2-chloro-ethoxy)-4-methyl-2-nitro-benzene (1070770-78-3)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5h;	96%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

4-methyl-2-nitrophenol (119-33-5) + benzyl alcohol (100-51-6) → 5-methyl-2-phenyl-1,3-benzoxazole (7420-86-2)

Conditions	Yield
With Au NCs/TiO2 In toluene at 130℃; for 24h; Inert atmosphere;	96%
With triscarbonyl‐(η4–3,4‐bis(4‐methoxyphenyl)‐2,5‐diphenylcyclopenta‐2,4‐dienone)iron; trimethylamine-N-oxide In o-xylene at 150℃; for 24h; Solvent; Sealed tube; Inert atmosphere;	89%
With 1,1'-bis-(diphenylphosphino)ferrocene In toluene at 150℃; for 24h; Inert atmosphere;	79%

4-methyl-2-nitrophenol (119-33-5) → 2-iodo-4-methyl-6-nitrophenol (69492-91-7)

Conditions	Yield
With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 6h; Ambient temperature;	95%
With iodine; sodium hydrogencarbonate In water at 95℃; for 2.5h;	88%
With Iodine monochloride; acetic acid

4-methyl-2-nitrophenol (119-33-5) + benzoyl chloride (98-88-4) → 4-benzoyloxy-3-nitrotoluene (177179-93-0)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h;	95%
With pyridine
With pyridine at 20℃; for 4h;

4-methyl-2-nitrophenol (119-33-5) + prenyl bromide (870-63-3) → 4-methyl-1-[(3-methylbut-2-en-1-yl)oxy]-2-nitrobenzene

Conditions	Yield
With potassium carbonate In acetone Heating;	95%

4-methyl-2-nitrophenol (119-33-5) + methyl (2Z)-2-(bromomethyl)-3-(2-chlorophenyl)prop-2-enoate (330442-80-3) → C18H16ClNO5 (1151899-32-9)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 1h;	93%

methyl (2Z)-2-(bromomethyl)-3-(4-bromophenyl)prop-2-enoate + 4-methyl-2-nitrophenol (119-33-5) → (E)-methyl 3-(4-bromophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	93%

4-methyl-2-nitrophenol (119-33-5) + benzyl bromide (100-39-0) → 1-(benzyloxy)-4-methyl-2-nitrobenzene (100866-84-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	93%

4-bromoethylbutanoate (2969-81-5) + 4-methyl-2-nitrophenol (119-33-5) → 4-(4-methyl-2-nitrophenoxy)butyric acid ethyl ester (874210-51-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 24h; Heating;	92.3%

4-methyl-2-nitrophenol (119-33-5) + methyl (Z)-2-(bromomethyl)-3-(4-cyanophenyl)prop-2-enoate → (E)-methyl 3-(4-cyanophenyl)-2-((4-methyl-2-nitrophenoxy)methyl)acrylate

Conditions	Yield
With caesium carbonate In acetonitrile at 20℃; Inert atmosphere;	92%

1-bromo-octane (111-83-1) + 4-methyl-2-nitrophenol (119-33-5) → 4-methyl-2-nitro-1-octyloxybenzene (874210-47-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone at 90℃; for 72h;	91%

4-methyl-2-nitrophenol (119-33-5) + methyl (2Z)-2-(bromomethyl)-3-(4-methylphenyl)prop-2-enoate (139413-76-6) → C19H19NO5 (1151899-26-1)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 1h;	91%

4-methyl-2-nitrophenol (119-33-5) + methyl (2Z)-2-(bromomethyl)-3-(4-chlorophenyl)prop-2-enoate (139413-75-5) → C18H16ClNO5 (1151899-36-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 1h;	91%

Upstream product

• 110-89-4 piperidine 
• 60671-88-7 (4-methyl-2-nitro-phenyl)-(2-nitro-phenyl)-ether 
• 6282-16-2 (2,4-dinitro-phenyl)-(4-methyl-2-nitro-phenyl)-ether 
• 110-86-1 pyridine 
• 106-44-5 p-cresol 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 918-37-6 hexanitroethane 
• 104-93-8 p-methylanizole 
• 352-32-9 p-fluorotoluene 
• 612-45-3 4-methyl-2-nitroacetanilide 
• 446-11-7 4-fluoro-3-nitrotoluene 
• 106-49-0 p-toluidine 
• 89-62-3 4-methyl-2-nitroaniline 

Downstream Products

• 85653-54-9 1-ethoxy-4-methyl-2-nitrobenzene 
• 67823-50-1 4-(2,3-epoxy-propoxy)-3-nitro-toluene 
• 861296-09-5 (4-methyl-2-nitro-phenoxy)-acetic acid 
• 6307-98-8 4-methyl-5-carboxymethyl-2-furanone 
• 4743-82-2 4-oxo-2-pentenoic acid 
• 20039-91-2 2-bromo-4-methyl-6-nitrophenol 
• 69492-91-7 2-iodo-4-methyl-6-nitrophenol 
• 177179-93-0 4-benzoyloxy-3-nitrotoluene 
• 35379-88-5 4-hydroxy-5-nitro-toluene-3-sulfonic acid 
• 95-84-1 3-amino-4-hydroxytoluene 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 89-62-3 4-methyl-2-nitroaniline 
• 501357-59-1 carbonic acid ethyl ester-(4-methyl-2-nitro-phenyl ester) 
• 119-10-8 4-methoxy-3-nitrotoluene 

Relevant academic research and scientific papers

Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the nitration of phenols under mild conditions

Nitrophenols can be obtained in moderate to high yields via nitrosation-oxidation of phenols with silica sulfuric acid, NaNO2 and wet SiO2 at room temperature. In situ generation of HNO2 and a radical cation mechanism via the nitrous acid catalyzed (NAC) pathway appear to be applicable to phenol nitration using these reagents.

Cyclodextrin-based artificial oxidases with high rate accelerations and selectivity

Three cyclodextrin derivatives with one to four 2-O-formylmethyl groups attached to the secondary rim were prepared and investigated as catalysts for the oxidation of aminophenols in buffered dilute hydrogen peroxide. The derivatives were found to be Michaelis-Menten catalysts and to give rate accelerations of up to 20,000 for the oxidation of 2-aminophenol to 2-amino-phenoxazin-3-one, and 12,000 for the oxidation of 2-amino-p-cresol to 2-nitro-p-cresol. While a range of differently substituted substrates was oxidized the success of the reaction was highly dependent on the substituent pattern. The ability of one of the new artificial enzymes to oxidize selectively one aminophenol from a mixture of two was investigated giving substrate selectivities of up to 16:1.

Evidence from (15)N Nuclear Polarisation on the Mechanisms of Rearrangement of Nitrocyclohexadienones

Strong (15)N nuclear polarisation is present in both the uncatalysed and acid-catalysed rearrangements of 4-methyl-4-cyclohexa-2,5-dienone but is absent from the rearrangement of 2-methyl-2-nitrocyclohexa-3,5-dienone.

Highly efficient nitration of phenolic compounds by zirconyl nitrate

Zirconyl nitrate was found to be an excellent reagent in the nitration of phenol and substituted phenols to give nitrated phenols. This procedure works efficiently on most of the examples at room temperature yielding nitro derivatives in fair to good yields with high regioselectivity.

Bromodimethylsulfonium bromide/tetrabutylammonium nitrite: An efficient catalyst mixture for the nitration of phenols

Nitrophenols were obtained via direct nitration of phenols with tetrabutylammonium nitrite in the presence of bromodimethylsulfonium bromide at room temperature in high yields under aprotic conditions. TUeBITAK.

p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates

Highly regiospecific mononitration of phenols and substituted phenols is accomplished employing a metal nitrate and a catalytic amount of p-toluenesulfonic acid in acetone. An exclusive ortho-selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o-nitrophenols exclusively in good to excellent yields. The use of p-toluenesulfonic acid is key for the selectivity observed.

Gas-phase reaction of hydroxyl radicals with m-, o- and p-cresol

The gas-phase reaction of oxygenated aromatic compounds m-cresol,o-cresol. and p-cresol with hydroxyl radicals has been studied by GC-MS. Experiments have been performed in a large-volume photoreactor (8000 L) at 294 ± 2 K and atmospheric pressure. The relative kinetic method was used to determine the rate constants for these reactions, with 1,3,5-trimethylbenzene as a reference compound. The rate constants obtained are kOH(m-cresol) = (5.88 ± 0.92) × 10-11 cm3 molecule-1 s-1, kOH(o-cresol) = (4.32 ± 0.52) × 10 -11 cm3 molecule-1 s-1, and k OH(p-cresol) = (4.96 ± 0.75) × 10-11 cm 3 molecule-1 s-1. The degradation products observed and their respective molar yields were methyl-1,4-benzoquinone 12.4 ± 1.2%, 5-methyl-2-nitrophenol 1.5 ± 0.3%, and 3-methyl-2-nitrophenol 1.4 ± 0.3% from m-cresol, methyl-1,4-benzoquinone 5.6 ± 0.9%, and 6-methyl-2-nitrophenol 4.7 ± 0.8% from o-cresol. and 4-methyl-2-nitrophenol 17.2 ± 2.5% from p-cresol. This kinetic and product data are compared with the literature, and the reaction mechanisms are discussed. Our results are in accordance with the previous studies (Atkinson, J Phys Chem Ref Data 1989, Monograph (1), 1-246; Atkinson and Aschmann. Int J Chem Kinet 1990, 22, 59-67; Atkinson et al., Environ Sci Technol 1992, 26, 1397-1403; Atkinson et al., J Phys Chem 1978, 82, 2759-2805; Olariu et al., Atoms Environ 2002, 36, 3685-3697; Semadeni et al., Int J Chem Kinet 1995, 27, 287-304) and confirm the methyl-1,4-benzoquinone yields determined by a different experimental technique (long-path Fourier transform infrared FT-IR (Olariu et al., 2002)).

Silica chloride/NaNO2 as a novel heterogeneous system for the nitration of phenols under mild conditions

Nitrophenols can be obtained via direct nitration of phenols with silica chloride, NANO2, and wet SiO2 at room temperature in moderate to high yields.

Cellulose-supported Ni(NO3)2.6H2O/2,4,6- trichloro-1,3,5-triazine (TCT) as a mild, selective, and biodegradable system for nitration of phenols

Nitration of certain phenols and naphthols in the presence of biodegradable cellulose-supported Ni(NO3)2.6H2O/2,4,6- trichloro-1,3,5-triazine was carried out in acetonitrile at room temperature. Ortho nitrated phenols were obtained regioselectively within a short reaction time with good yields. The reaction condition was mild, and the employed cellulose could be recovered several times for further use. Copyright

KHSO4 as an efficient catalytic system for the regiospecific nitration of phenols with metal nitrates

Highly regiospecific mononitration of phenol and substituted phenols was accomplished employing a metal nitrate and a catalytic amount of KHSO4 in acetonitrile. An exclusive ortho-selectivity was observed with excellent yields. A variety of metal nitrates were used to obtain o-nitrophenols exclusively in good to excellent yields. The use of KHSO4 is key for the selectivity observed.