713-52-0

Basic information

• Product Name: Methyl 3-hydroxy-4-nitrobenzoate
• Synonyms: RARECHEM AL BF 0673;TIMTEC-BB SBB002401;METHYL 3-HYDROXY-4-NITROBENZOATE;3-HYDROXY-4-NITROMETHYLBENZOATE;3-HYDROXY-4-NITROBENZOIC ACID METHYL ESTER;4-Nitro-3-hydroxybenzoic acid methyl ester;Benzoic acid, 3-hydroxy-4-nitro-, Methyl ester;Methyl3-hydroxy-4-nitrobenzoate,98%
• CAS NO: 713-52-0
• Molecular Formula: C₈H₇NO₅
• Molecular Weight: 197.14
• Product Categories: blocks;Carboxes;NitroCompounds;Aromatic Esters
• Mol File: 713-52-0.mol
• Article Data: 50

Chemical Properties

• Melting Point: 90-91°C
• Boiling Point: 346.4 °C at 760 mmHg
• Flash Point: 163.3 °C
• Appearance: /
• Density: 1.432 g/cm³
• Vapor Pressure: 2.88E-05mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.05±0.13(Predicted)
• BRN: 2583832
• CAS DataBase Reference: Methyl 3-hydroxy-4-nitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-hydroxy-4-nitrobenzoate(713-52-0)
• EPA Substance Registry System: Methyl 3-hydroxy-4-nitrobenzoate(713-52-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 713-52-0(Hazardous Substances Data)

Usage

General Description

Methyl 3-hydroxy-4-nitrobenzoate, also known as methyl 3-hydroxy-4-nitrobenzoate, is a chemical compound with the molecular formula C8H7NO5. It is a yellow crystalline solid that is commonly used in the production of pharmaceuticals and organic synthesis. Methyl 3-hydroxy-4-nitrobenzoate is an ester of methyl alcohol and 3-hydroxy-4-nitrobenzoic acid, and it is often used as a building block for the synthesis of various other organic compounds. Methyl 3-hydroxy-4-nitrobenzoate has potential applications in the pharmaceutical industry due to its pharmacological properties, and it is also used as an intermediate in the manufacturing of dyes and pigments. Additionally, it is important to handle and store this compound carefully, as it can be hazardous if not properly managed.

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

Synthetic route

methanol (67-56-1) + 3-hydroxy-4-nitro-benzoic acid (619-14-7) → methyl 3-hydroxy-4-nitrobenzoate (713-52-0)

Conditions	Yield
With sulfuric acid at 65℃; for 17h;	100%
With thionyl chloride at 0℃; for 12h; Reflux; Inert atmosphere;	100%
With thionyl chloride at 0℃; for 17h; Reflux; Inert atmosphere;	100%

methyl 4-nitro-3-(prop-2-en-1-yloxy)benzoate (326799-92-2) → methyl 3-hydroxy-4-nitrobenzoate (713-52-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol at 20℃; for 6h;	95%

3-hydroxy-4-nitro-benzoic acid (619-14-7) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 3-hydroxy-4-nitrobenzoate (713-52-0)

Conditions	Yield
In methanol; diethyl ether; toluene at 0℃; for 0.5h; Inert atmosphere;	90%

3-hydroxy-4-nitro-benzoic acid (619-14-7) → methyl 3-hydroxy-4-nitrobenzoate (713-52-0)

Conditions	Yield
	85%
With hydrogenchloride; methanol In water Heating / reflux;
With sulfuric acid In methanol

3-hydroxy-4-nitro-benzoic acid (619-14-7) + acetyl chloride (75-36-5) → methyl 3-hydroxy-4-nitrobenzoate (713-52-0)

Conditions	Yield
In methanol

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → 3-hydroxy-4-aminobenzoic acid methyl ester (63435-16-5)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol under 760.051 Torr; for 4h;	100%
With hydrogen; palladium on activated charcoal In ethanol for 6h;	98%
With hydrogenchloride; tin(ll) chloride
With palladium on carbon; hydrogen In ethanol
With hydrogenchloride; tin(ll) chloride

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + benzyl bromide (100-39-0) → methyl 3-(benzyloxy)-4-nitrobenzoate (209528-69-8)

Conditions	Yield
With potassium carbonate In acetone at 56℃; for 17h;	100%
With potassium carbonate In acetone at 56℃; for 17h; Inert atmosphere;	100%
With potassium carbonate In acetone Heating;	93%

Cyclopentyl bromide (137-43-9) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 3-cyclopentyloxy-4-nitrobenzoate

Conditions	Yield
With sodium chloride; potassium carbonate In N,N-dimethyl-formamide	100%
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 4h;

1-Iodooctane (629-27-6) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 3-(octyloxy)-4-nitrobenzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	100%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Reflux; Inert atmosphere;	83.7%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 2-Bromoethyl methyl ether (6482-24-2) → methyl 3-(2-methoxyethoxy)-4-nitrobenzoate (1176327-21-1)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20 - 70℃;	100%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + cyclopropylcarbinyl bromide (7051-34-5) → methyl 3-(cyclopropylmethoxy)-4-nitrobenzoate (1239278-72-8)

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	100%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;	95%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	81%
Stage #1: methyl 3-hydroxy-4-nitrobenzoate With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: cyclopropylcarbinyl bromide In N,N-dimethyl-formamide at 20℃;	26.3%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; for 6h; Inert atmosphere;

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 3-isopropyloxy-4-nitrobenzoate (159783-41-2)

Conditions	Yield
In tetrahydrofuran; toluene at 20℃; for 17h; Inert atmosphere;	100%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + bromoacetic acid methyl ester (96-32-2) → methyl 3-(2-methoxy-2-oxo-ethoxy)-4-nitrobenzoate (138035-71-9)

Conditions	Yield
With potassium carbonate In acetone for 4h; Heating;	99%
With caesium carbonate In acetone for 48h; Heating / reflux;

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + ethyl bromoacetate (105-36-2) → C12H13NO7

Conditions	Yield
Stage #1: methyl 3-hydroxy-4-nitrobenzoate With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Further stages.;	99%

[13C2,D6]dimethyl sulfate + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → [methoxy-13C,D3]methyl 3-methoxy-4-nitrobenzoate (1130037-27-2)

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 17h;	99%

tiglyl bromide (57253-30-2) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → (E)-methyl 3-((2-methylbut-2-en-1-yl)oxy)-4-nitrobenzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;	99%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 2-chloromethylpyridine hydrochloride (6959-47-3) → methyl 4-nitro-3-(pyridin-2-ylmethoxy)benzoate

Conditions	Yield
Stage #1: methyl 3-hydroxy-4-nitrobenzoate With potassium carbonate In N,N-dimethyl-formamide for 0.333333h; Stage #2: 2-chloromethylpyridine hydrochloride In N,N-dimethyl-formamide at 100℃; for 5h;	99%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + allyl bromide (106-95-6) → methyl 4-nitro-3-(prop-2-en-1-yloxy)benzoate (326799-92-2)

Conditions	Yield
With potassium carbonate In acetone Heating / reflux;	98.8%
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide	97%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;	92%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + isobutyraldehyde (78-84-2) → 6-carbomethoxy-2-isopropylbenzoxazole

Conditions	Yield
With poly(ethylene glycol)-bound sulphonic acid In chloroform at 50 - 60℃;	98%
Stage #1: methyl 3-hydroxy-4-nitrobenzoate With chromium dichloride; manganese; chloro-trimethyl-silane In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: isobutyraldehyde In N,N-dimethyl-formamide at 20℃; for 18h; Further stages.;	57%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 1-(bromomethyl)-4-(1,1-dimethylethyl)benzene (18880-00-7) → methyl 3-((4-(tert-butyl)benzyl)oxy)-4-nitrobenzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	98%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + isopropyl alcohol (67-63-0) → methyl 3-isopropyloxy-4-nitrobenzoate (159783-41-2)

Conditions	Yield
Stage #1: methyl 3-hydroxy-4-nitrobenzoate; isopropyl alcohol With triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Mitsunobu Displacement; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 15h; Mitsunobu Displacement; Inert atmosphere;	97%
Stage #1: methyl 3-hydroxy-4-nitrobenzoate; isopropyl alcohol With triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Mitsunobu Displacement; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 15h; Mitsunobu Displacement;	93%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 15h; Mitsunobu Displacement;	92%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 2-bromomethylnaphthyl bromide (939-26-4) → methyl 3-((2-naphthylmethyl)oxy)-4-nitrobenzoate (1006030-78-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃;	97%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 12h; Inert atmosphere;

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 2-ethyl-1-bromobutane (3814-34-4) → C14H19NO5 (1318208-80-8)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	97%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + propargyl bromide (106-96-7) → methyl 4-nitro-3-(prop-2-ynyloxy)benzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere;	97%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;
With potassium carbonate In toluene; acetonitrile at 70℃; Inert atmosphere;

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + sodium thiomethoxide (5188-07-8) → methyl 3-hydroxy-4-(methylthio)benzoate (159782-91-9)

Conditions	Yield
With potassium iodide In N,N-dimethyl-formamide at 0 - 20℃;	97%

2-methylmercapto-ethanol (5271-38-5) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → C11H13NO5S

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 30℃; for 16h;	97%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + 4-(2-chloroethyl)morpholine hydrochride (3647-69-6) → methyl 3-(2-morpholinoethoxy)-4-nitrobenzoate

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 80℃;	96.6%

1-bromo dodecane (112-29-8) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 3-decyloxy-4-nitrobenzoate (630765-11-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h;	96%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + isopropyl bromide (75-26-3) → methyl 3-isopropyloxy-4-nitrobenzoate (159783-41-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 70℃;	96%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 6h; Inert atmosphere;	95%
With potassium carbonate In N,N-dimethyl-formamide Heating;	71%

2-Methylbutyraldehyde (96-17-3, 57456-98-1) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 2-(butan-2-yl)-1,3-benzoxazole-6-carboxylate

Conditions	Yield
With poly(ethylene glycol)-bound sulphonic acid In chloroform at 50 - 60℃;	95%
Stage #1: methyl 3-hydroxy-4-nitrobenzoate With chromium dichloride; manganese; chloro-trimethyl-silane In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 2-Methylbutyraldehyde In N,N-dimethyl-formamide at 20℃; for 18h; Further stages.;	62%

(4-(tert-butoxy)phenyl)methanol (51503-08-3) + methyl 3-hydroxy-4-nitrobenzoate (713-52-0) → methyl 3-((4-(tert-butoxy)benzyl)oxy)-4-nitrobenzoate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere;	95%

methyl 3-hydroxy-4-nitrobenzoate (713-52-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → methyl 3-(2,2-diethoxyethoxy)-4-nitrobenzoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 14h;	94.2%

Upstream product

• 67-56-1 methanol 
• 619-14-7 3-hydroxy-4-nitro-benzoic acid 
• 326799-92-2 methyl 4-nitro-3-(prop-2-en-1-yloxy)benzoate 
• 75-36-5 acetyl chloride 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 61161-83-9 5-(hydroxymethyl)-2-nitrophenol 
• 136663-23-5 methyl 2-methyl-1,3-benzoxazole-6-carboxylate 
• 63435-16-5 3-hydroxy-4-aminobenzoic acid methyl ester 
• 209528-69-8 methyl 3-(benzyloxy)-4-nitrobenzoate 
• 131035-57-9 methyl 3-hydroxy-4-(2,2,2-trifluoroacetamido)benzoate 
• 131035-58-0 Methyl 3-hydroxy-2-nitro-4-N-trifluoroacetylaminobenzoate 
• 159783-41-2 methyl 3-isopropyloxy-4-nitrobenzoate 
• 457098-18-9 methyl 4-nitro-3-(pyridin-3-ylmethoxy)benzoate 
• 196103-66-9 methyl 4-nitro-3-(((trifluoromethyl)sulfonyl)oxy)benzoate 
• 183430-73-1 methyl 3-(2-hydroxyethoxy)-4-nitrobenzoate 
• 1157849-32-5 methyl 3-(difluoromethoxy)-4-nitrobenzoate 
• 1096816-13-5 methyl 4-amino-3-(difluoromethoxy)benzoate 
• 1351762-28-1 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoic acid 
• 1351762-27-0 methyl 4-(5-chloro-4-(methylamino)pyrimidin-2-ylamino)-3-(difluoromethoxy)benzoate 

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