6051-41-8

Basic information

• Product Name: Benzamide, 4-formyl-
• Synonyms: Terephthalaldehydamide(8CI); 4-Aminocarbonylbenzaldehyde; 4-Carbamoylbenzaldehyde; 4-Formylbenzamide
• CAS NO: 6051-41-8
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 163.17
• Product Categories: ALDEHYDE;AMIDE
• Mol File: 6051-41-8.mol
• Article Data: 43

Chemical Properties

• Melting Point: 153-158℃
• Boiling Point: 290.25°C (rough estimate)
• Appearance: /
• Density: 1.2021 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• PKA: 15.48±0.50(Predicted)
• CAS DataBase Reference: Benzamide, 4-formyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, 4-formyl-(6051-41-8)
• EPA Substance Registry System: Benzamide, 4-formyl-(6051-41-8)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 6051-41-8(Hazardous Substances Data)

Usage

General Description

4-formyl-benzamide is a chemical compound with the molecular formula C8H7NO2. It is a derivative of benzamide, which is a white solid formed by the condensation of benzoyl chloride and ammonia. 4-formyl-benzamide is commonly used in organic synthesis and medicinal chemistry as a reagent and intermediate. It is a versatile building block for the synthesis of various biologically active compounds and pharmaceuticals. Benzamide, 4-formyl- is also known for its potential application in the development of insecticides and herbicides due to its aromatic properties and chemical reactivity. Additionally, 4-formyl-benzamide has been studied for its potential anti-cancer properties and as a component in the production of fluorescent dyes.

Synthetic route

4-cyanobenzaldehyde (105-07-7) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With manganese(IV) oxide; water In isopropyl alcohol at 100℃; under 5171.62 Torr; for 0.333333h;	99%
With [RuH(tBu-PNP(-))(CO)]; water In tetrahydrofuran; tert-butyl alcohol at 20℃; for 24h;	99%
With sodium perborate In ethanol; water for 0.0333333h; microwave irradiation;	97%

4-formylbenzoyl azide → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With benzyltriethylammonium tetrathiomolybdate In water; acetonitrile at 25℃; for 3h;	88%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + 4-bromo-benzaldehyde (1122-91-4) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3h; Sealed tube;	82%

para-methylbenzamide (619-55-6) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With carbon tetrabromide; oxygen In acetonitrile at 20℃; for 3.5h; Irradiation; Green chemistry;	79%

dicobalt octacarbonyl (15226-74-1, 61091-28-9, 61117-58-6) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3h; Sealed tube;	77%

terephthalaldehyde, (623-27-8) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With tert.-butylhydroperoxide; sodium carbonate; ammonium chloride In acetonitrile at 50℃; for 0.666667h; Inert atmosphere; Green chemistry;	76%

carbon monoxide (201230-82-2) + 4-bromo-benzaldehyde (1122-91-4) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; ammonium carbamate; sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 20h; Inert atmosphere;	65%

4-Carboxybenzaldehyde (619-66-9) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
Stage #1: 4-Carboxybenzaldehyde With 4-methyl-morpholine In dichloromethane at 0℃; Stage #2: With isobutyl chloroformate at 0℃; for 0.5h; Stage #3: With ammonium hydroxide at 0℃; for 1h;	48%
Stage #1: 4-Carboxybenzaldehyde With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at -5 - 0℃; for 0.583333h; Stage #2: With ammonia In tetrahydrofuran; 1,4-dioxane at -5 - 0℃; for 0.616667h;	33%
Stage #1: 4-Carboxybenzaldehyde In tetrahydrofuran at 0℃; for 16h; Stage #2: With ammonia In tetrahydrofuran; water	30%
Multi-step reaction with 2 steps 1: Vilsmeier reagent / tetrahydrofuran / 16 h / 0 °C 2: ammonia / water / Cooling View Scheme

tert-butyl 4-(chloromethyl)benzamide (84545-14-2) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With 4-methylmorpholine N-oxide In tetrahydrofuran at 20℃; for 12h; Reflux;	45%

4-cyanobenzylidene diacetate (36735-42-9) → 4-formylbenzamide (6051-41-8) + 4-cyanobenzaldehyde (105-07-7)

Conditions	Yield
With sulfuric acid

4-dichloromethyl-benzoic acid amide → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With propan-1-ol; calcium carbonate

para-methylbenzonitrile (104-85-8) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3; acetic acid; H2SO4 2: aq.-ethanolic H2SO4 View Scheme

carbon monoxide (201230-82-2) + 4-hydroxy-benzaldehyde (123-08-0) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; Nonafluorobutanesulfonyl fluoride; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; bis[2-(diphenylphosphino)phenyl] ether In acetonitrile at 80℃; under 1500.15 Torr; for 16h; Inert atmosphere; Autoclave;	15 %Chromat.

4-formylbenzoyl chloride (16173-52-7) → 4-formylbenzamide (6051-41-8)

Conditions	Yield
With ammonia In water Cooling;	10.23 g

4-formylbenzamide (6051-41-8) + 1,3-diaminoguanidine hydrochloride (36062-19-8) → C17H17N7O2*ClH

Conditions	Yield
In ethanol for 16h; Reflux;	100%

4-formylbenzamide (6051-41-8) → (4-hydroxymethyl)benzamide (87128-27-6)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.5h;	96%

4-formylbenzamide (6051-41-8) → terephthalamic acid (6051-43-0)

Conditions	Yield
With oxygen; Langlois reagent In acetonitrile at 25℃; under 760.051 Torr; for 12h; Irradiation; Green chemistry;	96%

1-chloro-4-hydrazinophthalazine (51935-42-3, 59275-72-8) + 4-formylbenzamide (6051-41-8) → 4-[(4-Chloro-phthalazin-1-yl)-hydrazonomethyl]-benzamide (87539-68-2)

Conditions	Yield
With hydrogenchloride at 60℃; for 0.166667h;	95%

4-formylbenzamide (6051-41-8) + 1-(4-nitrophenyl)-2-(4-(trifluoromethyl)phenyl)ethane-1,2-dione → 4-(4-(4-nitrophenyl)-5-(4-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)benzamide

Conditions	Yield
With ammonium acetate In neat (no solvent) at 100℃; for 0.45h;	91%

4-formylbenzamide (6051-41-8) + Ac-LYRANA-NHNH2 → C41H61N13O11

Conditions	Yield
Stage #1: 4-formylbenzamide; Ac-LYRANA-NHNH2 With 1,1,1,3',3',3'-hexafluoro-propanol; acetic acid at 37℃; for 1h; Stage #2: With 2-picoline borane complex at 37℃; for 1h;	91%

2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)acetohydrazide (1499151-89-1) + 4-formylbenzamide (6051-41-8) → 4-((2-(2-(4-methyl-5,5-dioxido-3-phenylbenzo[e]pyrazolo[4,3-c][1,2]thiazin-1(4H)-yl)acetyl)hydrazono)methyl)benzamide

Conditions	Yield
With acetic acid In ethanol for 0.05h; Time; Microwave irradiation; Reflux;	86%

4-formylbenzamide (6051-41-8) → 4-cyanobenzamide (3034-34-2)

Conditions	Yield
Stage #1: 4-formylbenzamide With hydroxylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: With potassium hydrogen difluoride; 3-(imidazole-1-sulfonyl)-1-methyl-3H-imidazol-1-ium triflate In water at 20℃; for 3h;	86%

4-formylbenzamide (6051-41-8) + 2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetohydrazide → (E)-N-(4-((2-(2-(6-methyl-1H-pyrazolo[3,4-b]quinolin-1-yl)acetyl)hydrazono)methyl)phenyl)acetamide

Conditions	Yield
With phosphoric acid In ethanol for 2h; Reflux;	86%

methanol (67-56-1) + 4-formylbenzamide (6051-41-8) → 4-(hydroxymethyl)-N-methylbenzamide

Conditions	Yield
With C54H43ClN3P2Ru(1+)*F6P(1-); caesium carbonate In toluene at 140℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;	82%

tryptamine (61-54-1) + (Z)-ethyl 2-hydroxy-4-oxo-4-(pyridin-3-yl)but-2-enoate (778531-36-5) + 4-formylbenzamide (6051-41-8) → 4-(1-(2-(1H-indol-3-yl)ethyl)-4-hydroxy-3-nicotinoyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl)benzamide (1569975-46-7)

Conditions	Yield
With pyridinium p-toluenesulfonate In 1,4-dioxane at 20℃; for 12h;	76%

4-formylbenzamide (6051-41-8) + 1,3-diphenyl-3-[(prop-2-yn-1-yl)amino]prop-2-en-1-one (79893-97-3) → 4-(4,6-diphenyl-2,3-dihydrofuro[2,3-b]pyridin-2-yl)benzamide

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	74%

3-methyl-4,5-dihydro-6-oxopyridazine (5157-08-4) + 4-formylbenzamide (6051-41-8) → 4-[(6-methyl-3-oxo-2,3-dihydropyridazin-4-yl)methyl]benzamide (1444311-58-3)

Conditions	Yield
With potassium hydroxide In ethanol Reflux;	70%

5-hydroxy-2,3-dihydrobenzofuran-3-one (19278-82-1) + 4-formylbenzamide (6051-41-8) → (Z)-5-hydroxy-2-(4-carbamoylbenzylidene)benzofuran-3(2H)-one (1261274-07-0)

Conditions	Yield
With hydrogenchloride In acetic acid at 20℃; for 3h; Aldol condensation;	67%

3-methyl-4-phenylcyclobut-3-ene-1,2-dione (34667-97-5) + 4-formylbenzamide (6051-41-8) → trans-4-<2-(3,4-Dioxo-2-phenyl-1-cyclobuten-1-yl)vinyl>benzamid (81399-64-6)

Conditions	Yield
With sulfuric acid for 96h; Ambient temperature;	64%

4-formylbenzamide (6051-41-8) + diphenyl acetylene (501-65-5) → 2,3,7,8-tetraphenylpyrano[4,3,2-ij]isoquinoline-5-carbaldehyde

Conditions	Yield
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 1-methyl-1-cyclohexanecarboxylic acid; silver trifluoroacetate; magnesium(II) acetate tetrahydrate; silver(l) oxide In 1,2-dichloro-ethane at 85℃; for 12h; Schlenk technique; Inert atmosphere;	58%

4-formylbenzamide (6051-41-8) + tranylcypromine hydrochloride (1986-47-6, 2208-35-7, 2337-86-2, 4548-34-9, 37388-05-9, 54779-58-7, 61-81-4) → 4-((((1S*,2R*)-2-phenylcyclopropyl)amino)methyl)benzamide

Conditions	Yield
Stage #1: 4-formylbenzamide; tranylcypromine hydrochloride With acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane	56%

4-formylbenzamide (6051-41-8) + 1H-indazol-5-ylamine (19335-11-6) + cyclohexanone (108-94-1) → 4-(8,9,10,11-tetrahydro-3H-pyrazolo[4,3-a]phenanthridin-7-yl)benzamide

Conditions	Yield
With hydrogenchloride In ethanol for 12h; Reflux;	50%

H3BNH2(CH2)4NH2 (860026-68-2) + (4-aminobutylamine)-(N-aminobutyl)azanonaborane(11) (484050-03-5) + 4-formylbenzamide (6051-41-8) → NH2OCC6H4CH2NH(CH2)4NH2(B8H11)NH(CH2)4NHCH2C6H4CONH2 (860293-69-2)

Conditions	Yield
In tetrahydrofuran carbonyl compd. was added dropwise to soln. of azanonaborane and H3BNH2(CH2)4NH2 in THF at room temp.; mixt. was stirred for 2 d; filtered; volatiles removed (vac.); chromd. (silica gel, THF/CH2Cl2, 1/2); elem. anal.;	45%

4-formylbenzamide (6051-41-8) + 2-(3,4-diaminophenyl)-1H-benzo[d]imidazole-6-carboximidamide hydrochloride → 4-(6-carbamimidoyl-1H,3'H-[2,5'-bibenzo[d]imidazole]-2'-yl)benzamide hydrochloride

Conditions	Yield
Stage #1: 4-formylbenzamide With sodium metabisulfite In ethanol; water for 1h; Stage #2: 2-(3,4-diaminophenyl)-1H-benzo[d]imidazole-6-carboximidamide hydrochloride In ethanol; water for 24h; Reflux; Stage #3: With hydrogenchloride In methanol; ethanol for 24h;	43%

4-formylbenzamide (6051-41-8) + Anabaseine dihydrochloride → 3-(4-aminocarbonylbenzylidene)-anabaseine

Conditions	Yield
With hydrogenchloride In ethanol at 85℃; for 336h;	15%

Upstream product

• 36735-42-9 4-cyanobenzylidene diacetate 
• 105-07-7 4-cyanobenzaldehyde 
• 104-85-8 para-methylbenzonitrile 
• 619-66-9 4-Carboxybenzaldehyde 
• 201230-82-2 carbon monoxide 
• 1122-91-4 4-bromo-benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 16173-52-7 4-formylbenzoyl chloride 
• 84545-14-2 tert-butyl 4-(chloromethyl)benzamide 
• 623-27-8 terephthalaldehyde, 
• 15226-74-1 dicobalt octacarbonyl 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 619-55-6 para-methylbenzamide 

Downstream Products

• 87539-68-2 4-[(4-Chloro-phthalazin-1-yl)-hydrazonomethyl]-benzamide 
• 81399-64-6 trans-4-<2-(3,4-Dioxo-2-phenyl-1-cyclobuten-1-yl)vinyl>benzamid 
• 72094-45-2 4-{[(E)-4-Chloro-phenylimino]-methyl}-benzamide 
• 113628-64-1 4-(6-Chloro-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-benzamide 
• 87540-31-6 4-(6-Pyrrolidin-1-yl-[1,2,4]triazolo[3,4-a]phthalazin-3-yl)-benzamide 
• 67629-80-5 5-(4-Carbamoyl-benzylamino)-pyridine-2-carboxylic acid 
• 860293-69-2 NH₂OCC₆H₄CH₂NH(CH₂)4NH₂(B₈H₁₁)NH(CH₂)4NHCH₂C₆H₄CONH₂ 
• 1073612-86-8 C₁₈H₁₁F₃N₂O₂S₂ 
• 1177253-14-3 4-[(1-benzyl-1H-tetrazol-5-yl)(4-cyclobutyl-1,4-diazepan-1-yl)methyl]benzamide 
• 1261274-07-0 (Z)-5-hydroxy-2-(4-carbamoylbenzylidene)benzofuran-3(2H)-one 
• 1394355-24-8 C₂₄H₂₇N₃O₃S₂ 

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