403-24-7

Basic information

• Product Name: 2-Fluoro-4-nitrobenzoic acid
• Synonyms: 2-Fluoro-4-nitrobenzotc acid;0083512-Fluoro-4-nitrobenzoicacid;2-Fluoro-4-nitrobenzoic acid 98+%;4-Carboxy-3-fluoronitrobenzene;2-Fluor-4-nitrobenzoic acid;NSC 190361;2-Fluoro-4-nitrobenzoic acid 97%;Benzoicacid, 2-fluoro-4-nitro-
• CAS NO: 403-24-7
• Molecular Formula: C₇H₄FNO₄
• Molecular Weight: 185.11
• EINECS: -0
• Product Categories: Carboxylic Acids;Phenyls & Phenyl-Het;Benzoic acid;Miscellaneous;Carboxylic Acids;Phenyls & Phenyl-Het;intermediate;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 403-24-7.mol
• Article Data: 24

Chemical Properties

• Melting Point: 170 °C
• Boiling Point: 352.5 °C at 760 mmHg
• Flash Point: 167 °C
• Appearance: white to light yellow crystal powder
• Density: 1.568 g/cm³
• Vapor Pressure: 1.41E-05mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.37±0.13(Predicted)
• BRN: 2582091
• CAS DataBase Reference: 2-Fluoro-4-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-4-nitrobenzoic acid(403-24-7)
• EPA Substance Registry System: 2-Fluoro-4-nitrobenzoic acid(403-24-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-37/39-36/37/39-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 403-24-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C7H4FNO4/c8-6-3-4(9(12)13)1-2-5(6)7(10)11/h1-3H,(H,10,11)/p-1

Synthetic route

2-fluoro-4-nitrotoluene (1427-07-2) → 2-fluoro-4-nitrobenzoic acid (403-24-7)

Conditions	Yield
With chromium(VI) oxide; periodic acid In acetonitrile for 1h;	81%
With chromium(VI) oxide; periodic acid In acetonitrile for 1h;	81%
With chromium(VI) oxide; periodic acid In acetonitrile for 1h; Inert atmosphere;	81%

1-(2-fluoro-4-nitrophenyl)ethanone (866579-96-6) → 2-fluoro-4-nitrobenzoic acid (403-24-7)

Conditions	Yield
With copper (II) nitrate tetrahydrate; oxygen In acetonitrile at 180℃; under 18751.9 Torr; for 1.5h; Green chemistry;	69%

2-fluoro-4-nitrotoluene (1427-07-2) + acetic acid (64-19-7) → 2-fluoro-4-nitrobenzoic acid (403-24-7)

Conditions	Yield
With potassium dichromate; sulfuric acid at 90℃; for 3h;	62%

2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-4-aminobenzoic acid (446-31-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; under 760 Torr;	100%
With hydrogen; palladium over charcoal In methanol; acetic acid at 20℃; under 760.051 Torr;	100%
With hydrogen; palladium 10% on activated carbon In methanol	100%
With ammonium hydroxide; iron(II) sulfate
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 16h;

2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-4-nitrobenzoyl chloride (403-23-6)

Conditions	Yield
With thionyl chloride at 80℃; for 3h;	100%
With thionyl chloride In toluene for 3h; Heating;	86%
With thionyl chloride

2-fluoro-4-nitrobenzoic acid (403-24-7) + diazomethyl-trimethyl-silane (18107-18-1) → 2-fluoro-4-nitro-benzoic acid methyl ester (392-09-6)

Conditions	Yield
In methanol; diethyl ether; toluene at 20℃; for 1.5h;	100%
In methanol

2-fluoro-4-nitrobenzoic acid (403-24-7) + N-(tert-butyl)oxycarbonyl-N,N’-trimethyl-1,3-diaminopropane (123183-72-2) → tert-Butyl (3-{[(2-fluoro-4-nitrophenyl)carbonyl](methyl)amino}propyl)methylcarbamate (1246246-94-5)

Conditions	Yield
Stage #1: 2-fluoro-4-nitrobenzoic acid With pivaloyl chloride; triethylamine In dichloromethane at 20℃; for 0.25h; Cooling with ice; Stage #2: N-(tert-butyl)oxycarbonyl-N,N’-trimethyl-1,3-diaminopropane In dichloromethane at 20℃; for 2h; Cooling with ice;	100%

2-fluoro-4-nitrobenzoic acid (403-24-7) + 5-chloro-4-(1-(phenylsulfonyl)-1-indol-3-yl)-N-(piperidin-4-yl)pyrimidin-2-amine → (4-(5-chloro-4-(1-(phenylsulfonyl)-1H-indol-3-yl)pyrimidin-2-ylamino)piperidin-1-yl)(2-fluoro-4-nitrophenyl)methanone

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃;	100%

methanol (67-56-1) + 2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-4-nitro-benzoic acid methyl ester (392-09-6)

Conditions	Yield
With sulfuric acid for 4h; Reflux;	99%
With sulfuric acid Reflux;	98%
With sulfuric acid for 15h; Reflux; Large scale;	95%

2-fluoro-4-nitrobenzoic acid (403-24-7) + methylamine (74-89-5) → 2-(methylamino)-4-nitro-benzoic acid (49565-62-0)

Conditions	Yield
In ethanol at 80℃; for 16h; Sealed tube;	91%

2-fluoro-4-nitrobenzoic acid (403-24-7) + ethyl 5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylate hydrobromide → ethyl 6-(2-fluoro-4-nitrobenzoyl)-5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylate

Conditions	Yield
Stage #1: 2-fluoro-4-nitrobenzoic acid With thionyl chloride In dichloromethane for 2h; Reflux; Stage #2: ethyl 5,6-dihydro-4H-benzo[b]thieno[2,3-d]azepine-2-carboxylate hydrobromide With pyridine In acetonitrile at 20 - 50℃; for 5h;	88%

2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-4-nitrobenzamide (350-32-3)

Conditions	Yield
Stage #1: 2-fluoro-4-nitrobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 25℃; for 4h; Stage #2: With ammonia In water for 0.166667h;	85%
With pyridine; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate	53%
With pyridine; ammonium chloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide	53%

2-fluoro-4-nitrobenzoic acid (403-24-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-fluoro-N-methoxy-N-methyl-4-nitrobenzamide (774239-17-7)

Conditions	Yield
With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 60℃; for 15h;	85%
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;

2-fluoro-4-nitrobenzoic acid (403-24-7) → 4-nitro-2-fluorobenzaldehyde (157701-72-9)

Conditions	Yield
With borane-THF In tetrahydrofuran at 80℃; for 3h;	83%

2-fluoro-4-nitrobenzoic acid (403-24-7) + N,N-dimethylammonium chloride (506-59-2) → 2-fluoro-N,N-dimethyl-4-nitro-benzamide (1187368-66-6)

Conditions	Yield
With ethylene dichloride hydrochloride; benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	81%
Stage #1: 2-fluoro-4-nitrobenzoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: N,N-dimethylammonium chloride With triethylamine In dichloromethane for 1h;	60%

1-methyl-4-aminopiperidine (41838-46-4) + 2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-N-(1-methyl-4-piperidyl)-4-nitro-benzamide (957855-56-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In ISOPROPYLAMIDE at 20℃; for 4h;	78%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 18 - 25℃; for 18h;	59%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 17 - 25℃; for 18h;	59%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 18 - 25℃; for 18h;	59%
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 dichloromethane at 20 - 40℃;

2-fluoro-4-nitrobenzoic acid (403-24-7) → 2-fluoro-4-nitro-1-(trifluoromethyl)benzene (69411-67-2)

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride at 85℃; for 24h; Autoclave; Inert atmosphere;	78%

2-fluoro-4-nitrobenzoic acid (403-24-7) + tert-butyl alcohol (75-65-0) → tert-butyl 2-fluoro-4-nitrobenzoate (157665-46-8)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride at 0℃; for 19h;	75%
With pyridine; p-toluenesulfonyl chloride at 0℃; for 19h;	75%
With pyridine; p-toluenesulfonyl chloride 1.) 15 deg C, 5 min, 2.) RT, 2.5 h; Yield given. Multistep reaction;
With pyridine; p-toluenesulfonyl chloride for 19h;	524 mg

t-butoxycarbonylhydrazine (870-46-2) + 2-fluoro-4-nitrobenzoic acid (403-24-7) → N'-(2-fluoro-4-nitrobenzoyl)hydrazinecarboxylic acid tert-butyl ester (590421-50-4)

Conditions	Yield
With 3-methyl-N-(3-methylbutyl)-1-butanamine; HATU In N,N-dimethyl-formamide at 20℃;	57%
Stage #1: 2-fluoro-4-nitrobenzoic acid With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 20℃; for 0.333333h; Stage #2: t-butoxycarbonylhydrazine In DMF (N,N-dimethyl-formamide) at 20℃;	57%

2-fluoro-4-nitrobenzoic acid (403-24-7) + phenylmethanethiol (100-53-8) → 2-(benzylsulfanyl)-4-nitrobenzoic acid (92163-95-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 65℃; for 35h;	55.5%

(14S,16S,32R,33R,2R,4S,10E,12E,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl methyl-L-alaninate (77668-69-0) + 2-fluoro-4-nitrobenzoic acid (403-24-7) → C39H46ClFN4O12

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℃; for 72h; Inert atmosphere;	35%

Upstream product

• 1427-07-2 2-fluoro-4-nitrotoluene 
• 64-19-7 acetic acid 
• 866579-96-6 1-(2-fluoro-4-nitrophenyl)ethanone 

Downstream Products

• 392-09-6 2-fluoro-4-nitro-benzoic acid methyl ester 
• 157701-72-9 4-nitro-2-fluorobenzaldehyde 
• 363-32-6 2-fluoro-4-nitrobenzoic acid ethyl ester 
• 590421-50-4 N'-(2-fluoro-4-nitrobenzoyl)hydrazinecarboxylic acid tert-butyl ester 
• 660432-43-9 (2-fluoro-4-nitrophenyl)methanol 
• 1289942-66-0 2-((3-fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methyl propanoic acid 
• 915087-24-0 2-fluoro-N-methyl-4-nitro-benzamide 
• 85803-30-1 2'-fluoroaminopterin di-tert-butyl ester 
• 85803-29-8 2'-fluoroaminopterin 
• 191469-57-5 ethyl 2-fluoro-4-[(3'-methoxymethoxy-4-bromo-5',6',7',8'-tetrahydro-5',5',8',8'-tetramethylnaphtalen-2'-yl)carbamoyl]benzoate 
• 73792-06-0 ethyl-4-amino-2-fluorobenzoate 
• 35212-90-9 methyl 3-amino-6-nitro<1>benzothiophene-2-carboxylate 
• 380241-81-6 6-fluoro-2-[2-[(2-methoxyethoxy)methoxy]biphenyl-3-yl]-1H-indole-5-carbonitrile 
• 380241-69-0 (4-cyano-2-iodo-5-fluorophenyl)carbamic acid tert-butyl ester 

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