2581-34-2

Basic information

• Product Name: 3-Methyl-4-nitrophenol
• Synonyms: 3-methyl-4-nitro-pheno;4-Nitro-1-hydroxy-3-methylbenzene;4-Nitro-3-phenylphenol;4-nitro-5-methylphenol;4-nitro-m-creso;5-Methyl-4-nitrophenol;m-Cresol, 4-nitro-;Phenol, 3-methyl-4-nitro-
• CAS NO: 2581-34-2
• Molecular Formula: C₇H₇NO₃
• Molecular Weight: 153.14
• EINECS: 219-952-5
• Product Categories: Aromatic Phenols;Phenoles and thiophenoles
• Mol File: 2581-34-2.mol
• Article Data: 51

Chemical Properties

• Melting Point: 125-130 °C(lit.)
• Boiling Point: 200℃（分解）
• Flash Point: 110℃
• Appearance: yellowish to beige crystalline powder
• Density: 1.2744 (estimate)
• Vapor Pressure: 0.000472mmHg at 25°C
• Refractive Index: 1.5744 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.39±0.10(Predicted)
• Water Solubility: Soluble in water(1.34g/L).
• BRN: 1868105
• CAS DataBase Reference: 3-Methyl-4-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-4-nitrophenol(2581-34-2)
• EPA Substance Registry System: 3-Methyl-4-nitrophenol(2581-34-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37-37/39-36-24/25
• RIDADR: UN 2446 6.1/PG 3
• WGK Germany: 3
• RTECS: GP2625000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2581-34-2(Hazardous Substances Data)

Usage

Chemical Properties

YELLOWISH TO BEIGE CRYSTALLINE POWDER

Uses

3-Methyl-4-nitrophenol is a biochemical used in the preparation of phosphorothioamidate analogues as antimalarial agents. 3-methyl-4-nitrophenol has anti-androgenic activity. PNMC significantly inhibits basal and hCG-stimulated testosterone production in rats.

Definition

ChEBI: A C-nitro compound in which the nitro group is attached at C-4 of m-cresol.

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

Synthetic route

3-methyl-phenol (108-39-4) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Microwave irradiation;	92%
With potassium hydrogensulfate; potassium metaperiodate; sodium nitrite In water; acetonitrile at 30 - 35℃; for 15h; Reagent/catalyst; Solvent;	78%
With ferric nitrate; 1,3-di-n-butyl-imidazolium tetrafluoroborate at 30℃; for 1.5h;	76%

3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With silica supported Al(NO3)3*9H2O In acetone at 20℃; for 0.416667h; regioselective reaction;	A 87% B 5%
With tert.-butylnitrite In acetonitrile at 29.84℃; Kinetics; Solvent; Temperature;	A n/a B 80%
With 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imide at 20℃; for 2h; Ionic liquid;	A 34% B 63%

danishefsky's diene (54125-02-9) + ((Z)-1-Nitro-prop-1-ene-2-sulfinyl)-benzene (112825-86-2) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
In benzene at 25℃; for 24h;	73%

3-methyl-4-nitroso-phenol (615-01-0) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In water at 25 - 40℃; for 3h;	58%
With nitric acid at 40℃;

3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8)

Conditions	Yield
With Eu-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;	A 25% B 53% C 9%
With Yb-Mo-modified montmorillonite HKSF; nitric acid In tetrahydrofuran at 20℃; for 12h;	A 26% B 52% C 13%
With nitro acetate; silica gel In chloroform at -20 - 20℃; Nitration;	A 50% B 20% C 30%

3-methyl-1,4-benzoquinone 4-oxime (13362-34-0) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

4-nitro-3-methylaniline (611-05-2) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sulfuric acid Diazotization.Kochen der Diazoniumsalz-Loesung nach erneutem Zusatz von H2SO4;

2-methyl-4-methoxynitrosobenzene (69745-35-3) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With nitric acid at 40℃;

bis(m-cresyl) carbonate (620-52-0) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sulfuric acid; nitric acid at 12 - 15℃; zuletzt Behandeln bei 5grad, und Kochen des Reaktionsprodukts mit 10 prozentig. wss. Na2CO3-Loesung;

3-hydroxy-6-nitro-toluene-4-sulfonic acid (861774-24-5) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With hydrogenchloride at 170℃; im Rohr;

nitro acetate (591-09-3) + acetic anhydride (108-24-7) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
at -5℃;

nitro acetate (591-09-3) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With acetic anhydride at -5℃;

nitro acetate (591-09-3) + 3-methyl-phenol (108-39-4) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With acetic anhydride at -5℃;

diethyl ether (60-29-7) + 3-methyl-phenol (108-39-4) + isopentyl nitrite (110-46-3) → 3-methyl-4-nitrophenol (2581-34-2)

3-methyl-phenol (108-39-4) + isopentyl nitrite (110-46-3) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With diethyl ether

1-methoxy-3-methyl-benzene (100-84-5) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With nitrosylsulfuric acid; acetic acid at 0℃;
Multi-step reaction with 2 steps 1: glacial acetic acid; nitrosylsulfuric acid / -15 - -10 °C 2: diluted aqueous HNO3 / 40 °C View Scheme

5-methoxy-2-nitrotoluene (5367-32-8) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sodium hydroxide; tert-butyl alcohol In water Quantum yield; Irradiation;

3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8) + 2-Methyl-1,4-benzoquinone (553-97-9)

Conditions	Yield
With hydrogenchloride; sodium nitrate; sulfuric acid; sodium nitrite In diethyl ether for 0.133333h; Title compound not separated from byproducts;	A 27.9 % Chromat. B 41.0 % Chromat. C 22.5 % Chromat. D 7.3 % Chromat.
With hydrogenchloride; sodium nitrate; sulfuric acid; sodium nitrite In diethyl ether for 0.133333h; Product distribution; two phase nitration of 3-substituted phenols with or without NaNO2 and urea;	A 27.9 % Chromat. B 41.0 % Chromat. C 22.5 % Chromat. D 7.3 % Chromat.
With sulfuric acid; nitric acid; sodium nitrite In diethyl ether Mechanism; Product distribution; 2-phase nitration; further 3-alkylphenoles;
With hydrogenchloride; sodium nitrate; sulfuric acid; sodium nitrite In diethyl ether for 0.133333h; Title compound not separated from byproducts;	A 27.9 % Chromat. B 41.0 % Chromat. C 22.5 % Chromat. D 7.3 % Chromat.

(4-nitrophenyl)ethanone (100-19-6) + 3-Methyl-4-nitro-phenol (58864-63-4) → 3-methyl-4-nitrophenol (2581-34-2) + p-nitroacetophenone anion radical (100-19-6)

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

N,N,N',N'-Tetramethyl-acridine-3,6-diamine; compound with 3-methyl-4-nitro-phenol → 3-methyl-4-nitrophenol (2581-34-2) + acridine orange (494-38-2) + N,N,N',N'-Tetramethyl-acridine-3,6-diamine; compound with 3-methyl-4-nitro-phenol

Conditions	Yield
In benzonitrile at 25℃; Equilibrium constant; ionic strength 0.1 M (var.);

tri-m-cresyl phosphate (563-04-2) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sulfuric acid; nitric acid

2,6-difluorophenol (28177-48-2) + Toluene-4-sulfonate1-methyl-4-(3-methyl-4-nitro-phenoxycarbonyl)-pyridinium; → 3-methyl-4-nitrophenol (2581-34-2) + 4-(2,6-Difluoro-phenoxycarbonyl)-1-methyl-pyridinium

Conditions	Yield
With 2,6-dimethylpyridine In water at 25℃; Rate constant;

MEP (122-14-5) → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
With sodium hydroxide; β‐cyclodextrin at 25℃; Kinetics; Further Variations:; Reagents; Hydrolysis;
With water; mercury dichloride In methanol at 25℃; pH=5.5; Kinetics; Further Variations:; pH-values; Hydrolysis;
With ethanol; sodium methylate; zinc trifluoromethanesulfonate at 25℃; Kinetics;

acetic acid (64-19-7) + 1-methoxy-3-methyl-benzene (100-84-5) + nitrosylsulfuric acid → 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
at 0 - 20℃;

chloroform (67-66-3) + nitric acid (7697-37-2) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2)

Conditions	Yield
at 35℃;

nitric acid (7697-37-2) + acetic acid (64-19-7) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2)

3-methyl-phenol (108-39-4) + benzene (71-43-2) + nitrogen dioxide + gasolyne → 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8)

water (7732-18-5) + nitric acid (7697-37-2) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8)

Conditions	Yield
at 25℃;

nitric acid (7697-37-2) + acetic acid (64-19-7) + 3-methyl-phenol (108-39-4) → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8)

3-methyl-phenol (108-39-4) + benzene (71-43-2) + N2O3 → 2-nitro-5-methylphenol (700-38-9) + 3-methyl-4-nitrophenol (2581-34-2) + 3-methyl-2-nitrophenol (4920-77-8)

3-methyl-4-nitrophenol (2581-34-2) + acetic anhydride (108-24-7) → 3-methyl-4-nitrophenyl acetate (79139-40-5)

Conditions	Yield
With magnesium(II) perchlorate at 80℃; for 0.5h;	100%

allyl iodid (556-56-9) + 3-methyl-4-nitrophenol (2581-34-2) → 4-(allyloxy)-2-methyl-1-nitrobenzene (120106-18-5)

Conditions	Yield
With caesium carbonate In acetone for 24h; Ambient temperature;	99%

3-methyl-4-nitrophenol (2581-34-2) + benzyl bromide (100-39-0) → 5-benzyloxy-2-nitrotoluene (22424-58-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	99%
With potassium carbonate In acetone for 5h; Heating;	99%
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2h;	91%

3-methyl-4-nitrophenol (2581-34-2) + 9-(3-iodopropyl)anthracene (556809-41-7) → 9-[3-(3-methyl-4-nitrophenoxy)propyl]anthracene (556809-42-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2h;	99%

3-methyl-4-nitrophenol (2581-34-2) + propyl bromide (106-94-5) → 2-methyl-4-propoxy-1-nitrobenzene (52177-07-8)

Conditions	Yield
Stage #1: 3-methyl-4-nitrophenol With potassium carbonate In butanone for 0.0833333h; Inert atmosphere; Reflux; Stage #2: propyl bromide In butanone for 18h; Inert atmosphere;	99%

1-bromo-butane (109-65-9) + 3-methyl-4-nitrophenol (2581-34-2) → 4-butoxy-2-methyl-1-nitrobenzene

Conditions	Yield
Stage #1: 3-methyl-4-nitrophenol With potassium carbonate In butanone for 0.0833333h; Inert atmosphere; Reflux; Stage #2: 1-bromo-butane In butanone for 18h; Inert atmosphere;	99%

3-methyl-4-nitrophenol (2581-34-2) → 2,6-dibromo-3-methyl-4-nitro-phenol (14401-03-7)

Conditions	Yield
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane	98%
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane at 0 - 20℃; for 0.5 - 0.666667h;	93%
durch Bromieren;
With bromine; acetic acid at 15 - 20℃;

3-methyl-4-nitrophenol (2581-34-2) + isopropyl bromide (75-26-3) → 4-isopropoxy-2-methyl-1-nitrobenzene (52177-08-9)

Conditions	Yield
Stage #1: 3-methyl-4-nitrophenol With potassium carbonate In butanone for 0.0833333h; Inert atmosphere; Reflux; Stage #2: isopropyl bromide In butanone for 18h; Inert atmosphere;	98%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 22h; Inert atmosphere;	96%
With potassium carbonate In acetone	58.5%
With potassium carbonate In acetone for 5h; Heating;

3-methyl-4-nitrophenol (2581-34-2) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → O-(3-methyl-4-nitrophenyl)dimethylcarbamothioate (83086-54-8)

Conditions	Yield
Stage #1: 3-methyl-4-nitrophenol With 1,4-diaza-bicyclo[2.2.2]octane In 1-methyl-pyrrolidin-2-one at 50℃; Stage #2: N,N-Dimethylthiocarbamoyl chloride In 1-methyl-pyrrolidin-2-one at 50℃; for 2.5h;	98%

diethyl sulfate (64-67-5) + 3-methyl-4-nitrophenol (2581-34-2) → 4-ethoxy-2-methyl-1-nitrobenzene (52177-06-7)

Conditions	Yield
With potassium carbonate In butanone at 70℃; for 2h; Inert atmosphere;	97%
With alkaline solution
With potassium carbonate In butanone at 110℃; for 2h; Williamson Ether Synthesis; Inert atmosphere;

3-methyl-4-nitrophenol (2581-34-2) + benzyl chloride (100-44-7) → 5-benzyloxy-2-nitrotoluene (22424-58-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 1h;	97%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;	93%
With ethanol; sodium ethanolate
With sodium hydroxide
With sodium hydroxide In ethanol; water

3-methyl-4-nitrophenol (2581-34-2) → 2,6-diiodo-3-methyl-4-nitrophenol (25755-15-1)

Conditions	Yield
With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 6h; Ambient temperature;	95%

3-methyl-4-nitrophenol (2581-34-2) + allyl bromide (106-95-6) → 4-(allyloxy)-2-methyl-1-nitrobenzene (120106-18-5)

Conditions	Yield
With potassium carbonate In acetone for 6h; Heating;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;

3-methyl-4-nitrophenol (2581-34-2) → 5-methoxy-2-nitrotoluene (5367-32-8)

Conditions	Yield
	93%
(methylation);

3-methyl-4-nitrophenol (2581-34-2) + potassium carbonate (584-08-7) + ethyl iodide (75-03-6) → 4-ethoxy-2-methyl-1-nitrobenzene (52177-06-7)

Conditions	Yield
In ethyl acetate; butanone	93%

4,6-dichloropyrimidine (1193-21-1) + 3-methyl-4-nitrophenol (2581-34-2) → 4-chloro-6-(3-methyl-4-nitrophenoxy)pyrimidine (1231749-99-7)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	93%
Stage #1: 3-methyl-4-nitrophenol With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: 4,6-dichloropyrimidine In acetonitrile Reflux;	62%

3-methyl-4-nitrophenol (2581-34-2) + 1-dodecylbromide (143-15-7) → C19H31NO3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 23h;	92.9%

3-methyl-4-nitrophenol (2581-34-2) + N,N-diethylcarbamyl chloride (88-10-8) → Diethyl-carbamic acid 3-methyl-4-nitro-phenyl ester (135983-09-4)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	92%

3-methyl-4-nitrophenol (2581-34-2) + (2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) → (S)-glycidyl 3-methyl-4-nitrophenyl ether (250778-99-5)

Conditions	Yield
Stage #1: 3-methyl-4-nitrophenol With cesium fluoride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: (2s)-(+)-glycidyl 3-nitrobenzenesulfonate In N,N-dimethyl-formamide at 20℃; for 24h;	92%

3-methyl-4-nitrophenol (2581-34-2) + 3,4-Dichlorophenylmethyl chloride (102-47-6) → 1,2-dichloro-4-[(3-methyl-4-nitrophenoxy)methyl]benzene (1335101-86-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50 - 100℃;	91%

3-methyl-4-nitrophenol (2581-34-2) + 2-fluoroethyl tosylate (383-50-6) → 4-(2-fluoroethoxy)-2-methyl-1-nitrobenzene (132837-96-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h;	91%

3-methyl-4-nitrophenol (2581-34-2) → 2,6-dichloro-3-methyl-4-nitrophenol (37693-15-5)

Conditions	Yield
With sulfuryl dichloride In acetic acid at 90℃; for 3h;	90%
With benzyltrimethylazanium tetrachloro-λ3-iodanuide In acetic acid at 70℃; for 18h;	70%
With benzyltrimethylazanium tetrachloro-λ3-iodanuide; acetic acid at 70℃; for 18h;	64%
With hydrogenchloride; potassium chlorate
With chlorine; acetic acid

formaldehyd (50-00-0) + 3-methyl-4-nitrophenol (2581-34-2) + diethylamine (109-89-7) → 2,6-bis(diethylaminomethyl)-3-methyl-4-nitrophenol (133394-06-6)

Conditions	Yield
In ethanol at 90 - 95℃; for 65h;	90%

3-methyl-4-nitrophenol (2581-34-2) + chlorophosphoric acid diphenyl ester (2524-64-3) → Phosphoric acid 3-methyl-4-nitro-phenyl ester diphenyl ester (176842-49-2)

Conditions	Yield
With triethylamine In diethyl ether at 25℃; for 4h;	90%

3-methyl-4-nitrophenol (2581-34-2) + 4,5-dichloro-2-chloromethyl-pyridazin-3(2H)-one (51356-03-7) → 4-chloro-5-(3-methyl-4-nitrophenoxy)-2-[(3-methyl-4-nitrophenoxy)methyl]pyridazin-3(2H)-ome (1174278-29-5)

Conditions	Yield
With potassium carbonate In methanol for 0.333333h; Reflux;	90%

3-methyl-4-nitrophenol (2581-34-2) + dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate → 4-(fluoromethoxy)-2-methyl-1-nitrobenzene

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 0.5h; Schlenk technique; Inert atmosphere;	90%

3-methyl-4-nitrophenol (2581-34-2) + 4-fluoro-1-nitro-2-(prop-2-yn-1-yloxy)benzene → 2-methyl-1-nitro-4-(4-nitro-3-(2-propyn-1-oxy)phenoxy)benzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 3h;	90%

3-methyl-4-nitrophenol (2581-34-2) + Bromocyclobutane (4399-47-7) → 4-cyclobutoxy-2-methyl-1-nitrobenzene

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 14h; Inert atmosphere;	89%

3-methyl-4-nitrophenol (2581-34-2) + t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → 1-tert-butyloxycarbonyl-4-(4-nitro-3-methylphenyloxy)piperidine (138227-74-4)

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 1h;	88%

Upstream product

• 69745-35-3 2-methyl-4-methoxynitrosobenzene 
• 54125-02-9 danishefsky's diene 
• 112825-86-2 ((Z)-1-Nitro-prop-1-ene-2-sulfinyl)-benzene 
• 5367-32-8 5-methoxy-2-nitrotoluene 
• 64-19-7 acetic acid 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 67-66-3 chloroform 
• 7697-37-2 nitric acid 
• 108-39-4 3-methyl-phenol 
• 71-43-2 benzene 
• 7732-18-5 water 
• 122-14-5 MEP 
• 861774-24-5 3-hydroxy-6-nitro-toluene-4-sulfonic acid 
• 620-52-0 bis(m-cresyl) carbonate 

Downstream Products

• 52177-06-7 4-ethoxy-2-methyl-1-nitrobenzene 
• 14401-03-7 2,6-dibromo-3-methyl-4-nitro-phenol 
• 2835-99-6 4-amino-3-methylphenol 
• 40130-97-0 2-chloro-5-methyl-4-nitro-phenol 
• 88062-27-5 2-Chlor-3-methyl-4-nitrophenol 
• 14401-60-6 2-bromo-5-methyl-4-nitrophenol 
• 3096-68-2 4-Amino-2-chlor-3-methyl-phenol 
• 37693-15-5 2,6-dichloro-3-methyl-4-nitrophenol 
• 34694-06-9 C₁₄H₂₁N₂O₄PS 
• 34705-06-1 C₁₃H₁₉N₂O₄PS 
• 34704-66-0 C₁₃H₁₉N₂O₆P 
• 28372-51-2 Thiophosphoric acid O-(2-methoxy-ethyl) ester O'-methyl ester O''-(3-methyl-4-nitro-phenyl) ester 
• 28253-45-4 Thiophosphoric acid O-ethyl ester O'-(2-methoxy-ethyl) ester O''-(3-methyl-4-nitro-phenyl) ester 
• 23745-47-3 (4-Trifluoromethyl-phenyl)-carbamic acid 3-methyl-4-nitro-phenyl ester 

Relevant articles and documents

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3-(Ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium cation: A green alternative to tert-butyl nitrite for synthesis of nitro-group-containing arenes and drugs at room temperature

Due to their remarkable properties, task-specific ionic liquids have turned out to be progressively popular over the last few years in the field of green organic synthesis. Herein, for the first time, we report that a new task-specific nitrite-based ionic liquid such as 3-(ethoxycarbonyl)-1-(5-methyl-5-(nitrosooxy)hexyl)pyridin-1-ium bis(trifluoromethanesulfonyl)imides (TS-N-IL) derived from biodegradable ethyl nicotinate indeed acted as an efficient and eco-friendly reagent for the synthesis of highly valuable nitroaromatic compounds and drugs including nitroxynil, tolcapone, niclofolan, flutamide, niclosamide and nitrazepam. The bridging of an ionic liquid with nitrite group not only increases the yield and rate of direct C[sbnd]N bond formation reaction but also allows easy product separation and recyclability of a byproduct. Nonvolatile nature, easy synthesis, merely stoichiometric need and mildness are a portion of the extra focal points of TS-N-IL while contrasted with tert-butyl nitrite an outstanding and highly-flammable reagent utilized largely in organic synthesis.

Sodium perborate/NaNO2/KHSO4-triggered synthesis and kinetics of nitration of aromatic compounds

Sodium perborate (SPB) was used as efficient green catalyst for NaNO2/KHSO4-mediated nitration of aromatic compounds in aqueous acetonitrile medium. Synthesis of nitroaromatic compounds was achieved under both conventional and solvent-free microwave conditions. Reaction times were comparatively shorter in the microwave-assisted than conventional reaction. The reaction kinetics for nitration of phenols in aqueous bisulfate and acetonitrile medium indicated first-order dependence on [Phenol], [NaNO2], and [SPB]. Reaction rates accelerated with introduction of electron-donating groups but retarded with electron-withdrawing groups. Kinetic results did not fit well quantitatively with Hammett’s equation. Observed deviations from linearity were addressed in terms of exalted Hammett’s constants (σˉ or σeff), para resonance interaction energy (ΔΔGp) parameter, and Yukawa–Tsuno parameter (r). This term provides a measure of the extent of resonance stabilization for a reactive structure that builds up charge (positive) in its transition state. The observed negative entropy of activation (?ΔS#) suggests greater solvation and/or cyclic transition state before yielding products.