160538-51-2

Basic information

• Product Name: 3-FLUORO-4-NITRO-BENZALDEHYDE
• Synonyms: 3-FLUORO-4-NITRO-BENZALDEHYDE;3-FLUORO-4-NITROBENZENECARBALDEHYDE;3-floro-4-nitrobenzaldehyde;2-Fluoro-4-formylnitrobenzene;3-Fluoro-4-nitrobenzaldehyde 98%;Benzaldehyde, 3-fluoro-4-nitro-
• CAS NO: 160538-51-2
• Molecular Formula: C₇H₄FNO₃
• Molecular Weight: 169.1099632
• Product Categories: Fluorine series
• Mol File: 160538-51-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 57-58
• Boiling Point: 312℃
• Flash Point: 143℃
• Appearance: /
• Density: 1.443
• Vapor Pressure: 0.000544mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-FLUORO-4-NITRO-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FLUORO-4-NITRO-BENZALDEHYDE(160538-51-2)
• EPA Substance Registry System: 3-FLUORO-4-NITRO-BENZALDEHYDE(160538-51-2)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 160538-51-2(Hazardous Substances Data)

Usage

General Description

3-Fluoro-4-nitro-benzaldehyde is a chemical compound with the molecular formula C7H4FNO3. It is recognized for its unique properties including its relatively high molecular weight of 169.113 g/mol and its boiling point of nearly 288.3°C at 760 mmHg. The chemical falls under the category of organofluorines and has a physical appearance that is typically yellow in color. Mainly used in scientific research, 3-Fluoro-4-nitro-benzaldehyde is a valuable intermediate in organic synthesis which is used to prepare other compounds. Safety measures should be adhered when handling this chemical due to its hazardous and reactive characteristics. Its CAS registry number is 403-25-8.

InChI:InChI=1/C7H4FNO3/c8-6-3-5(4-10)1-2-7(6)9(11)12/h1-4H

Synthetic route

N-[methyl]-N-[methoxy]3-fluoro-4-nitrobenzamide (863604-64-2) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
Stage #1: N-[methyl]-N-[methoxy]3-fluoro-4-nitrobenzamide With diisobutylaluminium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With hydrogenchloride; water In tetrahydrofuran	88%

Br(1-)*C13H17FN5O2(1+) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
With trifluoroacetic acid at 70 - 75℃; for 20h;	86%

(3-fluoro-4-nitrophenyl)methanol (503315-74-0) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 70℃; for 2h; Solvent; Temperature; Reagent/catalyst;	82%
With manganese(IV) oxide In dichloromethane at 20℃;	66%

2-fluoro-4-methyl-1-nitrobenzene (446-34-4) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
Stage #1: 2-fluoro-4-methyl-1-nitrobenzene With chromium(VI) oxide; sulfuric acid; acetic anhydride Stage #2: With sulfuric acid; water In ethanol Further stages.;	50%
Stage #1: 2-fluoro-4-methyl-1-nitrobenzene With chromium(VI) oxide; sulfuric acid; acetic acid at 5 - 10℃; for 3h; Stage #2: With water; sodium hydrogencarbonate for 0.25h; Stage #3: With hydrogenchloride; ethanol; water for 0.25h; Heating / reflux;	29.2%
With chromium(VI) oxide; sulfuric acid 1.) acetic anhydride, 0 degC, 3 h; 2.) ethanol, water, 1 h; Yield given. Multistep reaction;

Acetic acid acetoxy-(3-fluoro-4-nitro-phenyl)-methyl ester (211388-77-1) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
With hydrogenchloride; acetic acid In water at 115℃; for 0.75h;

3-fluoro-4-nitrobenzoic acid (403-21-4) → 3-fluoro-4-nitro-benzaldehyde (160538-51-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 17 h / 20 °C 2: diisobutylaluminium hydride / tetrahydrofuran / 0.5 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid / 8 h / 80 °C 2: sodium tetrahydroborate / methanol; tetrahydrofuran / 60 °C / Cooling with ice 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 2 h / 70 °C View Scheme

3-fluoro-4-nitro-benzaldehyde (160538-51-2) + methylamine (74-89-5) → C8H8N2O3 (1289136-16-8)

Conditions	Yield
In acetonitrile at 120℃; for 1.58333h; Cooling with ice;	100%
In tetrahydrofuran at 20℃; for 2 - 3h;

3-hydroxy-4-methoxybenzoate (6702-50-7) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → methyl 3-(5-formyl-2-nitrophenoxy)-4-methoxybenzoate

Conditions	Yield
Stage #1: 3-hydroxy-4-methoxybenzoate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-fluoro-4-nitro-benzaldehyde In N,N-dimethyl-formamide at 20℃; for 1h;	95%

malonic acid (141-82-2) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 4-nitro-3-fluorocinnamic acid (73781-66-5)

Conditions	Yield
pyridine In ethanol for 6h; Heating / reflux;	90%

4-(2-(4-bromobenzylthio)acetyl)benzoic acid (1224718-12-0) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → (E)-4-(2-(4-bromobenzylthio)-3-(3-fluoro-4-nitrophenyl)acryloyl)benzoic acid (1224721-89-4)

Conditions	Yield
With ammonium acetate; acetic acid Knoevenagel condensation; Reflux;	90%

2-(piperidin-4-yl)propan-2-ol (22990-34-7) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 2-(1-(3-fluoro-4-nitrobenzyl)piperidin-4-yl)propan-2-ol (1357923-87-5)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 5℃; for 0.75h;	88%
With sodium tris(acetoxy)borohydride In dichloromethane; acetic acid at 20℃; for 1h;	86%

1-cyclopropylethanol (2566-44-1) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 4-[(1E)-3-cyclopropylprop-1-en-1-yl]-2-fluoro-1-nitrobenzene

Conditions	Yield
Stage #1: 1-cyclopropylethanol With 1H-imidazole; iodine; triphenylphosphine In chloroform at 0 - 20℃; Inert atmosphere; Stage #2: With triphenylphosphine In chloroform; acetonitrile for 15h; Inert atmosphere; Reflux; Stage #3: 3-fluoro-4-nitro-benzaldehyde With potassium hexamethylsilazane In tetrahydrofuran; chloroform; acetonitrile at 0 - 20℃; for 1h; Inert atmosphere;	88%

(tert-butyloxycarbonylmethyl)triphenylphosphonium chloride (35000-37-4) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → (E)-3-(3-fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester (1218938-27-2)

Conditions	Yield
Stage #1: (tert-butyloxycarbonylmethyl)triphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran for 0.25h; Stage #2: 3-fluoro-4-nitro-benzaldehyde In tetrahydrofuran for 1.5h;	86%

(tert-butoxycarbonylmethyl)triphenylphosphonium bromide (59159-39-6) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → (E)-3-(3-fluoro-4-nitro-phenyl)-acrylic acid tert-butyl ester (1218938-27-2)

Conditions	Yield
Stage #1: (tert-butoxycarbonylmethyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 3-fluoro-4-nitro-benzaldehyde In tetrahydrofuran at 20℃; for 1.5h;	86%

1-methyl-piperazine (109-01-3) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 1-(3-fluoro-4-nitrobenzyl)-4-methylpiperazine (1094554-37-6)

Conditions	Yield
Stage #1: 1-methyl-piperazine; 3-fluoro-4-nitro-benzaldehyde With acetic acid In toluene at 20℃; for 1.5h; Stage #2: With sodium tris(acetoxy)borohydride In toluene for 2h; Stage #3: With sodium hydrogencarbonate In methanol; water; toluene for 0.5h;	82%

Methyl diethylphosphonoacetate (1067-74-9) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → (E)-3-(3-Fluoro-4-nitro-phenyl)-acrylic acid methyl ester (211388-93-1)

Conditions	Yield
With sodium hydride In tetrahydrofuran Horner-Emmons olefination;	80%

3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 3-fluoro-4-nitrobenzaldehyde oxime (1210757-48-4)

Conditions	Yield
With hydroxylamine hydrochloride In ethanol at 60 - 65℃; for 2h;	77.4%
With pyridine; hydroxylamine hydrochloride In ethanol Reflux;

2,4-thiazolidinedion (2295-31-0) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 5-(3-fluoro-4-nitro-benzylidene)-thiazolidine-2,4-dione

Conditions	Yield
With acetic acid; 3-amino propanoic acid at 100℃;	77%

isonipecotic acid methyl ester (2971-79-1) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → methyl 1-(5-formyl-2-nitrophenyl)piperidine-4-carboxylate (1025772-22-8)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20 - 70℃; for 2.5h;	68%

methyl 2-(3,4-diaminophenyl)acetate (257632-89-6) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → methyl 2-(2-(3-fluoro-4-nitrophenyl)-1H-benzo[d]imidazol-5-yl)acetate

Conditions	Yield
With ammonium cerium (IV) nitrate; dihydrogen peroxide In water; acetonitrile at 50℃; for 0.833333h; Inert atmosphere;	65%

1-indoline (496-15-1) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 1-(3-fluoro-4-nitrobenzyl)indoline

Conditions	Yield
Stage #1: 1-indoline; 3-fluoro-4-nitro-benzaldehyde In 1,2-dichloro-ethane at 0℃; for 0.5h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 0℃; for 5h;	62%

3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 3-Fluoro-4-nitro-benzylamine (160538-52-3)

Conditions	Yield
With ammonium acetate; molecular sieve; sodium cyanoborohydride In methanol for 24h;	61%

p-toluidine (106-49-0) + mercaptoacetic acid (68-11-1) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 2-(3-fluoro-4-nitrophenyl)-3-(p-tolyl)thiazolidin-4-one

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 12h;	56%

3-fluoro-4-nitro-benzaldehyde (160538-51-2) → C7H4N6O

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 35℃; for 22h;	29%

triphenyl phosphite (101-02-0) + 5‑(6‑bromopyridin‑2‑yl)‑1,3,4‑oxadiazol‑2‑amine + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → diphenyl [[5‑(6‑bromopyridin‑2‑yl)‑1,3,4‑oxadiazol‑2‑yl]-amino](3‑fluoro‑4‑nitrophenyl)methylphosphonate

Conditions	Yield
With acetic acid at 80℃; for 4h;	27%

2-(2-methylphenyl)-quinazolin-4(3H)-one (18818-39-8) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 2-(2-((3-fluoro-4-nitrophenyl)(hydroxy)methyl)-6-methylphenyl)quinazolin-4(3H)-one

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; zinc diacetate In 1,2-dichloro-ethane at 80℃; for 20h; Sealed tube;	25%

propargyl alcohol (107-19-7) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 4-Nitro-3-prop-2-ynyloxy-benzoic acid prop-2-ynyl ester

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 16h;	22%

2-(2-methylphenyl)-quinazolin-4(3H)-one (18818-39-8) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 12-(3-fluoro-4-nitrophenyl)-12-hydroxy-4-methylisoindolo[1,2-b]quinazolin-10(12H)-one

Conditions	Yield
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; copper diacetate In 1,2-dichloro-ethane at 150℃; for 20h; Sealed tube;	12%

pyrrole (109-97-7) + 3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 5,10,15-tris(3'-fluoro-4'-nitrophenyl)corrole

Conditions	Yield
With acetic acid for 3.5h; Darkness; Reflux;	6.7%

3-fluoro-4-nitro-benzaldehyde (160538-51-2) + 3,4-diaminobenzoic acid (619-05-6) → 2-(3-fluoro-4-nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid (1026808-32-1)

Conditions	Yield
In nitrobenzene at 155 - 160℃; for 18h;

3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 2-(4-amino-3-fluoro-phenyl)-1H-benzoimidazole-5-carboxylic acid pyridin-2-ylamide (1026452-39-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: nitrobenzene / 18 h / 155 - 160 °C 2.1: 1,1'-carbonyldiimidazole / dimethylformamide / 3 h / 80 °C 2.2: dimethylformamide / 18 h / Heating 3.1: H2 / Pd/C / ethanol; dimethylformamide / 6 h / 70 - 90 °C View Scheme

3-fluoro-4-nitro-benzaldehyde (160538-51-2) → 2-(3-fluoro-4-nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid pyridin-2-ylamide (1027233-91-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: nitrobenzene / 18 h / 155 - 160 °C 2.1: 1,1'-carbonyldiimidazole / dimethylformamide / 3 h / 80 °C 2.2: dimethylformamide / 18 h / Heating View Scheme

Upstream product

• 446-34-4 2-fluoro-4-methyl-1-nitrobenzene 
• 863604-64-2 N-[methyl]-N-[methoxy]3-fluoro-4-nitrobenzamide 
• 403-21-4 3-fluoro-4-nitrobenzoic acid 
• 211388-77-1 Acetic acid acetoxy-(3-fluoro-4-nitro-phenyl)-methyl ester 
• 503315-74-0 (3-fluoro-4-nitrophenyl)methanol 

Downstream Products

• 1026808-32-1 2-(3-fluoro-4-nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid 
• 1289136-16-8 C₈H₈N₂O₃ 
• 73781-66-5 4-nitro-3-fluorocinnamic acid 
• 1210757-48-4 3-fluoro-4-nitrobenzaldehyde oxime 
• 1094554-37-6 1-(3-fluoro-4-nitrobenzyl)-4-methylpiperazine 
• 1232234-37-5 4-dimethoxymethyl-2-fluoro-1-nitro-benzene 
• 1357922-72-5 (1s,4s)-4-((5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenyl)amino)-N-isopropylcyclohexanecarboxamide 
• 1357922-74-7 (1s,4s)-4-((2-amino-5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)phenyl)amino)-N-isopropylcyclohexanecarboxamide 
• 1357920-41-2 (1s,4s)-4-(2-amino-6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1H-benzo[d]imidazol-1-yl)-N-isopropylcyclohexanecarboxamide 
• 1357920-58-1 (E)-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-((1s,4s)-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]-imidazol-2(3H)-ylidene)benzamide 
• 1357920-63-8 (E)-3-fluoro-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-((1s,4s)-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]imidazol-2(3H)-ylidene)benzamide 
• 1357920-43-4 (E)-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-((1s,4s)-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]-imidazol-2(3H)-ylidene)isonicotinamide 
• 1357920-44-5 (E)-4-cyano-N-(6-((4-(2-Hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-((1s,4s)-4-(isopropylcarbamoyl)cyclohexyl)-1Hbenzo[d]imidazol-2(3H)-ylidene)benzamide 
• 1357920-45-6 (E)-N-(6-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-1-((1s,4s)-4-(isopropylcarbamoyl)cyclohexyl)-1H-benzo[d]-imidazol-2(3H)-ylidene)nicotinamide 

Relevant articles and documents

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