5081-36-7

Basic information

• Product Name: 3-Methoxy-4-nitrobenzoic acid
• Synonyms: 3-METHOXY-4-NITROBENZOIC ACIID;3-METHOXY-4-NITROBENZOIC ACID, 98+%;4-AMino-3-Methoxybenzoic acid (Methyl, ethyl);Benzoic acid, 3-methoxy-4-nitro-;4-Nitro-3-methoxybenzoic acid;3-METHOXY-4-NITROBENZOIC ACID;4-Nitro-m-anisic acid
• CAS NO: 5081-36-7
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14
• EINECS: 225-793-2
• Product Categories: blocks;Carboxes;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 5081-36-7.mol
• Article Data: 15

Chemical Properties

• Melting Point: 233-235 °C(lit.)
• Boiling Point: 334.23°C (rough estimate)
• Flash Point: 198.7 °C
• Appearance: light yellow to beige crystalline powder
• Density: 1.5023 (rough estimate)
• Vapor Pressure: 2.78E-07mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.30±0.10(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 2696042
• CAS DataBase Reference: 3-Methoxy-4-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methoxy-4-nitrobenzoic acid(5081-36-7)
• EPA Substance Registry System: 3-Methoxy-4-nitrobenzoic acid(5081-36-7)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38
• Safety Statements: 24/25
• RIDADR: Cool, dry,tightly closed
• WGK Germany: 3
• Hazardous Substances Data: 5081-36-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to beige crystalline powder

Uses

3-Methoxy-4-nitrobenzoic acid was used in detection of nitroaromatic compounds by CdSe- quantum dots capped with polyamidoamine dendrimer-1,12-diaminododecane core-generation 4 nanocomposites. It was used in the synthesis of vorozole derivatives.

InChI:InChI=1/C8H7NO5/c1-14-7-4-5(8(10)11)2-3-6(7)9(12)13/h2-4H,1H3,(H,10,11)/p-1

Synthetic route

3-methoxy-4-nitrotoluene (38512-82-2) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With potassium permanganate; sodium carbonate In water for 1.5h; Heating;	100%
With potassium permanganate	87%
With potassium permanganate; sodium hydrogencarbonate In water for 4h; Heating;	73%

methanol (67-56-1) + 3-fluoro-4-nitrobenzoic acid (403-21-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Stage #1: methanol With sodium methylate In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: 3-fluoro-4-nitrobenzoic acid In tetrahydrofuran at 0 - 25℃; for 1h; Inert atmosphere;	100%
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 2h;

methyl 3-methoxy-4-nitrobenzoate (5081-37-8) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With water In methanol for 2h; Reflux;	96%
With sodium hydroxide In tetrahydrofuran at 20℃; for 15h;	86%
With sodium hydroxide In methanol for 0.5h; Yield given;
With sodium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 12h;	5.1 g
With lithium hydroxide In methanol; water at 20℃; for 20h;

methyl 3-fluoro-4-nitrobenzoate (185629-31-6) + methanol (67-56-1) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Stage #1: methanol With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Stage #2: methyl 3-fluoro-4-nitrobenzoate In tetrahydrofuran at 0 - 20℃; for 2h;	82%

1-(3-methoxy-4-nitrophenyl)ethanone (22106-39-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With copper (II) nitrate tetrahydrate; oxygen In acetonitrile at 180℃; under 18751.9 Torr; for 1.5h; Green chemistry;	77%

3-hydroxy-4-nitro-benzoic acid (619-14-7) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
durch Methylierung;
Multi-step reaction with 3 steps 1: thionyl chloride / 15 h / 0 - 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C 3: sodium hydroxide / tetrahydrofuran / 15 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 90 °C 2: water / methanol / 2 h / Reflux View Scheme

3-methoxy-4-nitrobenzaldehyde (80410-57-7) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
durch Oxydation;
With potassium permanganate
With silver(l) oxide

3-(3-Methoxy-4-nitrophenyl)-2-propenoic acid (118510-04-6) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With potassium permanganate; sodium carbonate
Multi-step reaction with 2 steps 1: alkali; potassium permanganate / ein wahrscheinlich unreines Praeparat 2: silver oxide View Scheme

3-fluoro-4-nitrobenzoic acid (403-21-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With potassium hydroxide
Multi-step reaction with 2 steps 1.1: methanol; hexane; dichloromethane / 0.67 h / 20 °C 2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C 2.2: 2 h / 0 - 20 °C View Scheme

3-Methoxybenzoic acid (586-38-9) → 3-methoxy-2-nitrobenzoic acid (4920-80-3) + 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With sulfuric acid; nitric acid; acetic anhydride at -10 - -5℃;

3-methoxy-4-nitrobenzamide (92241-87-7) → 3-methoxy-4-nitroanilin (16292-88-9) + 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
at 85℃; Hofmann rearrangement;	A 13 g B 5 g

acetic anhydride (108-24-7) + 3-Methoxybenzoic acid (586-38-9) + HNO3+H2SO4 → 3-methoxy-2-nitrobenzoic acid (4920-80-3) + 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
at -10 - -5℃;

3-methoxy-4-nitrobenzoic acid chloride (67579-92-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: 5 g / 85 °C / Hofmann rearrangement View Scheme

2-nitro-5-methylphenol (700-38-9) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. NaOH / H2O / 80 °C 2: 100 percent / KMnO4, Na2CO3 / H2O / 1.5 h / Heating View Scheme

3-methoxy-benzaldehyde (591-31-1) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid / 0 - 10 °C / Aus Benzol krystallisiert 2-Nitro-3-methoxy-benzaldehyd aus; die beiden anderen Isomeren koennen nach Entfernung des Benzols durch Destillation mit Wasserdampf getrennt werden 2: silver oxide View Scheme

2-fluoro-4-methyl-1-nitrobenzene (446-34-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous potassium permanganate solution 2: methanol. KOH-solution View Scheme

3-methoxy-4-nitrobenzaldehyde (80410-57-7) → 3-methoxy-4-nitrobenzoic acid (5081-36-7) + C8H7(18)FO2 (129841-10-7)

Conditions	Yield
With potassium carbonate; N,N-dimethyl-formamide at 140℃;

3-Bromo-4-nitrobenzoic acid (101420-81-9) + sodium methylate (124-41-4) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
With carbon disulfide at 20℃; for 2h;

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → 3-methoxy-4-nitrobenzoic acid (5081-36-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C 2: sodium hydroxide / methanol; tetrahydrofuran; water / 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C 2: sodium hydroxide / tetrahydrofuran / 15 h / 20 °C View Scheme

3-methoxy-4-nitrobenzoic acid (5081-36-7) → 3-methoxy-4-nitrobenzoic acid chloride (67579-92-4)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran; dichloromethane at 0 - 20℃; for 3h;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 3h;	100%
With thionyl chloride In toluene for 1h; Heating / reflux;	100%

methanol (67-56-1) + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → methyl 3-methoxy-4-nitrobenzoate (5081-37-8)

Conditions	Yield
With thionyl chloride at 0 - 20℃;	100%
With thionyl chloride at 0 - 20℃;	100%
With sulfuric acid Reflux; Inert atmosphere;	95%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + methylamine hydrochloride (593-51-1) → 3-methoxy-N-methyl-4-nitrobenzamide (878160-13-5)

Conditions	Yield
Stage #1: 3-methoxy-4-nitrobenzoic acid; methylamine hydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	100%
With benzotriazol-1-ol In N,N-dimethyl-formamide at 20℃; for 18h;

morpholine (110-91-8) + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → (3-methoxy-4-nitrophenyl)(morpholino)methanone (761440-55-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	100%
Stage #1: 3-methoxy-4-nitrobenzoic acid With thionyl chloride In toluene at 120℃; for 2h; Inert atmosphere; Stage #2: morpholine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 1h;	92%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	88.85%
Stage #1: 3-methoxy-4-nitrobenzoic acid With thionyl chloride In toluene for 2h; Reflux; Stage #2: morpholine With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; for 1h;	75%

Ala-OtBu (21691-50-9) + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → C15H20N2O6 (1147133-55-8)

Conditions	Yield
With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 24h;	95%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + benzyl bromide (100-39-0) → benzyl 3-methoxy-4-nitrobenzoate (190330-62-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 21h; Inert atmosphere;	93.9%

1-methyl-4-aminopiperidine (41838-46-4) + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → 3-methoxy-N-(1-methylpiperidin-4-yl)-4-nitrobenzamide (876126-59-9)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	90%
Stage #1: 3-methoxy-4-nitrobenzoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 1h; Stage #2: 4-Amino-1-methylpiperidine In dichloromethane at 20℃; for 16h; Product distribution / selectivity;
Stage #1: 3-methoxy-4-nitrobenzoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 1h; Stage #2: 4-Amino-1-methylpiperidine In dichloromethane at 20℃; for 16h; Product distribution / selectivity;
Stage #1: 3-methoxy-4-nitrobenzoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 105 - 120℃; for 1.5h; Heating / reflux; Stage #2: 4-Amino-1-methylpiperidine With triethylamine In toluene at 55 - 65℃; for 1h; Stage #3: With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;

C17H18N2O5 + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → C25H23N3O9

Conditions	Yield
Stage #1: 3-methoxy-4-nitrobenzoic acid With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane Reflux; Inert atmosphere; Stage #2: C17H18N2O5 In dichloromethane for 5h; Inert atmosphere; Reflux;	90%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + ethylamine (75-04-7) → C10H12N2O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	87.93%

3-methoxy-4-nitrobenzoic acid (5081-36-7) → 3-methoxy-4-phenylureidophenylacetic acid + 3-methoxy-4-nitrobenzoic acid chloride (67579-92-4)

Conditions	Yield
With thionyl chloride	A 87% B n/a

3-methoxy-4-nitrobenzoic acid (5081-36-7) + tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate 0.5 oxalic acid salt → tert-butyl 7-(3-methoxy-4-nitrobenzoyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	86%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + methylamine (74-89-5) → 3-methoxy-N-methyl-4-nitrobenzamide (878160-13-5)

Conditions	Yield
Stage #1: 3-methoxy-4-nitrobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: methylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h;	83%
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃;	78%

3-methoxy-4-nitrobenzoic acid (5081-36-7) → potassium 3-methoxy-4-nitrobenzoate

Conditions	Yield
With potassium tert-butylate In ethanol for 1h;	83%
With potassium tert-butylate In ethanol for 1h;

3-methoxy-4-nitrobenzoic acid (5081-36-7) + tert-butyl alcohol (75-65-0) → tert-Butyl 3-methoxy-4-nitrobenzoate (123330-91-6)

Conditions	Yield
With pyridine; toluene-4-sulfonic acid In dichloromethane at 40℃; for 16h;	83%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + methylamine (74-89-5) → 3-methylamino-4-nitro-benzoic acid (214778-10-6)

Conditions	Yield
In water at 100℃;	82%
In water at 100 - 105℃;	75%
With hydrogenchloride	73%
With potassium carbonate In methanol; water at 160℃; for 0.0833333h; Microwave irradiation;	68%
With potassium carbonate In methanol; water at 160℃; for 0.0833333h; Irradiation;	68%

4-(4-methoxyphenyl)-1,3-thiazol-2-amine (2104-04-3) + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → 3-methoxy-N-(4-(4-methoxyphenyl)thiazol-2-yl)-4-nitrobenzamide

Conditions	Yield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In acetonitrile at 65℃;	82%

4-fluoropiperidine hydrochloride + 3-methoxy-4-nitrobenzoic acid (5081-36-7) → (4-fluoropiperidin-1-yl)(3-methoxy-4-nitrophenyl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	82%

3-methoxy-4-nitrobenzoic acid (5081-36-7) + (S)-octahydropyrrolo[1,2-a]pyrazine (93643-24-4) → (S)-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)(3-methoxy-4-nitrophenyl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	81%

Upstream product

• 38512-82-2 3-methoxy-4-nitrotoluene 
• 619-14-7 3-hydroxy-4-nitro-benzoic acid 
• 586-38-9 3-Methoxybenzoic acid 
• 92241-87-7 3-methoxy-4-nitrobenzamide 
• 108-24-7 acetic anhydride 
• 700-38-9 2-nitro-5-methylphenol 
• 67-56-1 methanol 
• 403-21-4 3-fluoro-4-nitrobenzoic acid 
• 185629-31-6 methyl 3-fluoro-4-nitrobenzoate 
• 22106-39-4 1-(3-methoxy-4-nitrophenyl)ethanone 
• 713-52-0 methyl 3-hydroxy-4-nitrobenzoate 
• 101420-81-9 3-Bromo-4-nitrobenzoic acid 
• 124-41-4 sodium methylate 
• 80410-57-7 3-methoxy-4-nitrobenzaldehyde 

Downstream Products

• 16292-88-9 3-methoxy-4-nitroanilin 
• 92241-91-3 2-methoxy-4-deuterioaniline 
• 92241-90-2 C₇H₆⁽²⁾HNO₃ 
• 877671-39-1 tert-butyl (3-methoxy-4-nitrophenyl)carbamate 
• 185629-32-7 methyl 4-amino-3-fluorobenzene carboxylate 
• 197369-19-0 methyl 2-[4,5-methylenedioxy-2-(3-methoxy-4-nitrobenzoyl)-phenyl]acetate 
• 67579-92-4 3-methoxy-4-nitrobenzoic acid chloride 
• 426840-15-5 1-(3-methoxy4-nitrophenyl)-7chloro-3,4-dihydroisoquinoline 
• 876126-59-9 3-methoxy-N-(1-methylpiperidin-4-yl)-4-nitrobenzamide 
• 1147133-55-8 C₁₅H₂₀N₂O₆ 
• 878160-13-5 3-methoxy-N-methyl-4-nitrobenzamide 
• 190330-62-2 benzyl 3-methoxy-4-nitrobenzoate 
• 1061358-40-4 4-amino-3-methoxy-N,N-dimethylbenzamide 
• 1356016-31-3 3-methoxy-N,N-dimethyl-4-nitro-benzamide 

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