Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction; | 100% |
With NiRh3; hydrogen In ethyl acetate at 20℃; for 12h; Mechanism; Reagent/catalyst; Solvent; chemoselective reaction; | 99% |
With hydrogen In ethanol; water at 25℃; under 11251.1 Torr; for 6h; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With silica-supported Jones reagent In dichloromethane for 0.00269444h; | 100% |
With aluminum oxide In N,N-dimethyl-formamide at 120℃; for 10h; Inert atmosphere; | 96% |
With sulfuric acid; dihydrogen peroxide; sodium bromide In 1,4-dioxane; water at 70℃; Flow reactor; Green chemistry; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-nitrobenzyl chloride With potassium sulfate; lead dioxide at 37℃; for 1.5h; Stage #2: With nickel dichloride In cyclohexane at 9 - 56℃; for 5.66667h; Temperature; | 98.8% |
With sodium sulfide | |
With sodium disulfide |
4,4'-diformylazobenzene
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With aminomethyl polysterene resin formic acid salt; zinc In methanol at 20℃; for 0.333333h; | 95% |
With aminomethylpolystyrene-supported formate; palladium on activated charcoal In methanol at 20℃; for 3.5h; | 93% |
With polystyrene-CH2-NH3(+)HCO2(-); magnesium In methanol at 20℃; for 0.25h; | 92% |
With zinc In methanol at 25℃; for 0.2h; Inert atmosphere; | 90% |
With magnesium In methanol at 25℃; for 0.233333h; Inert atmosphere; | 90% |
4-azidobenzaldehyde
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With formic acid; tris(2,2'-bipyridyl)ruthenium dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Irradiation; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | 90% |
With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 6h; Ambient temperature; | 79% |
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 6 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In water at 60℃; for 2.5h; Green chemistry; | 90% |
With sodium hydroxide In 4-amino-N-hydroxyphthalimide | 62% |
With hydrogenchloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In water at 20℃; for 2h; regiospecific reaction; | 62% |
Conditions | Yield |
---|---|
With hydrogenchloride; iron In methanol; water for 0.5h; Heating; | 90% |
Conditions | Yield |
---|---|
With ammonium hydroxide; (2-methylacetatobenzyl)triphenylphosphonium hexabromodipalladate(II) at 60℃; for 5h; | 90% |
With ammonium hydroxide; trans-bis(triphenylphosphine)palladium dichloride; sodium carbonate In neat (no solvent) at 80℃; for 6h; | 90% |
With ammonium hydroxide; bis[(2-methylacetatobenzyl)tri(p-tolyl)phosphonium] hexabromodipalladate(II) In neat (no solvent) at 60℃; for 5h; | 88% |
4-formylphenylboronic acid,
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 18h; | 83% |
Conditions | Yield |
---|---|
With sodium sulfide; water; sulfur; sodium hydroxide In ethanol; N,N-dimethyl-formamide at 65 - 90℃; for 3.5h; | 80% |
With sodium sulphide nonahydrate; sulfur; sodium hydroxide In ethanol; water at 80℃; for 3h; | 45% |
With sodium sulfide; sodium hydroxide; sulfur | 27% |
Conditions | Yield |
---|---|
With titanium(IV) oxide In isopropyl alcohol; acetonitrile for 20h; Kinetics; UV-irradiation; Inert atmosphere; chemoselective reaction; | A n/a B 80% |
With hydrogen In toluene at 30℃; under 3750.38 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Autoclave; High pressure; | A 26% B 74% |
With 0.2C27H36N2*Pt; hydrogen In tetrahydrofuran at 30℃; under 750.075 Torr; for 3h; Overall yield = 94 %; chemoselective reaction; |
Conditions | Yield |
---|---|
With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; hydrogen; bis-diphenylphosphinomethane In toluene at 100℃; under 7500.75 Torr; for 10h; Autoclave; | 75% |
Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h; Title compound not separated from byproducts; | A 73% B 24% |
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; Title compound not separated from byproducts.; | |
With pyridine; hydrogen In water at 80℃; under 15001.5 Torr; for 4h; chemoselective reaction; |
4-formylphenylboronic acid,
A
4-aminobenzaldehyde
B
4-hydroxy-benzaldehyde
Conditions | Yield |
---|---|
With ammonium hydroxide; potassium nitrate In water at 20℃; for 2h; Electrochemical reaction; chemoselective reaction; | A 70% B n/a |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water for 2h; Reflux; | 64% |
With sodium hydroxide In methanol |
4-nitrobenzyl chloride
A
4-aminobenzaldehyde
B
4-nitrobenzaldehdye
C
4,4'-diformylazobenzene
D
4,4'-diformylazoxybenzene
Conditions | Yield |
---|---|
With cadmium(II) sulphide In water; acetonitrile at 20℃; under 37.5038 Torr; for 24h; Inert atmosphere; Irradiation; | A 9% B 60% C 13% D 7% |
2-(4-formylphenoxy)propanamide
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 8h; Green chemistry; | 56% |
p-(iodophenyl)carboxaldehyde
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube; | 33% |
N-(4-nitrobenzyl)aniline
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With sodium sulfide; ethanol; sulfur man behandelt das Produkt mit Wasser oder mit waessr. Loesungen von Alkalidisulfiten; | |
With sodium sulfide; ethanol; sulfur | |
With sodium sulfide; ethanol; sulfur |
Conditions | Yield |
---|---|
With hydrogenchloride man loest das Produkt in Wasser, fuegt zu der Loesung Natronlauge und schuettelt die Loesung mit Aether aus; |
Conditions | Yield |
---|---|
With diethyl ether Erhitzen des Reaktionsprodukts bis auf 300grad und kurzes Erwaermen des Reaktionsgemisches mit wss. Kalilauge; |
Conditions | Yield |
---|---|
With hydrogenchloride; diethyl ether Erhitzen des Reaktionsprodukts bis auf 300grad und kurzes Erwaermen des Reaktionsgemisches mit wss. Kalilauge; | |
With formaldehyd; 4-hydroxyl-amino-toluene-sulfonic acid-(2) man zersetzt das Reaktionsprodukt durch Kochen mit Ammoniak oder Natronlauge; |
Conditions | Yield |
---|---|
With ammonia; potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
With acetic acid ester; ethanol; nickel |
ethyl 2-cyano-3-(4-(dimethylamino)phenyl)acrylate
A
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; water at 30℃; Rate constant; Thermodynamic data; Kinetics; other temperatures; ΔH(excit.), ΔS(excit.); |
4-nitrobenzaldehdye
A
4-aminobenzaldehyde
B
4-aminobenzenemethanol
C
4-hydroxyamino-benzaldehyde
D
4-(hydroxyamino)benzyl alcohol
Conditions | Yield |
---|---|
In ethanol; water at 25℃; Rate constant; Mechanism; Product distribution; polarographic reduction; potential dependent rate constanzs kf,h, αna; pH = 1.81-11.00; |
4-aminobenzaldehyde
Conditions | Yield |
---|---|
In acetic acid at 19.9℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), ΔG(excit.), var. temp.; |
sulfuric acid
5-(4-amino-phenyl)-5-hydroxy-barbituric acid
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol for 5h; | 99.2% |
With sodium tetrahydroborate; silica gel at 40 - 45℃; for 1.5h; | 94% |
With Zn(BH4)2(bpy) In acetonitrile at 20℃; for 0.133333h; | 94% |
Conditions | Yield |
---|---|
With lemon juice In water at 20℃; for 0.25h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry; | 99% |
Conditions | Yield |
---|---|
With aluminum oxide; hydroxylamine hydrochloride; methanesulfonyl chloride; water at 100℃; for 1.5h; | 97% |
With hydroxylamine hydrochloride; methanesulfonyl chloride In neat (no solvent) at 70℃; for 3h; | 88% |
With tert.-butylhydroperoxide; titanium superoxide; saccharin In 1,4-dioxane; hexane at 90℃; for 1h; Green chemistry; | 38% |
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; pyridine / methanol / 24 h / 20 °C 2: [RuCl2(η2-C6H6){P(NMe2)3}]; water / 7 h / 100 °C / Inert atmosphere; Sealed tube View Scheme |
4-aminobenzaldehyde
4-hydrazinyl-3-(methylsulfanyl)-1-phenyl-pyrazolo[3,4-d]pyrimidine
4-[2-(4-aminobenzylidene)hydrazinyl]-3-(methylsulphanyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine
Conditions | Yield |
---|---|
In ethanol; acetic acid for 4h; Reflux; | 97% |
Conditions | Yield |
---|---|
With titanium(III) chloride; tin(ll) chloride In water at 20℃; for 24h; | 96% |
With titanium(III) chloride; tin(ll) chloride In water at 20℃; for 8h; Barbier reaction; | 95% |
With tin(ll) chloride; cobalt acetylacetonate In water at 20℃; for 6h; Barbier coupling reaction; | 95% |
Conditions | Yield |
---|---|
With titanium(III) chloride; tin(ll) chloride In water at 20℃; for 24h; | 96% |
With titanium(III) chloride; tin(ll) chloride In water at 20℃; for 8h; Barbier reaction; | 95% |
4-aminobenzaldehyde
7-isopropyl-1,4-dimethyl-azulene
4-[(E)-2-(3-guaiazulenyl)diazenyl]benzene-1-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 0.25h; Stage #2: 7-isopropyl-1,4-dimethyl-azulene In ethanol; water at 20℃; for 2h; | 96% |
4-aminobenzaldehyde
1-nitro-4-[(E)-2-nitroeth-1-enyl]benzene
(2E)-1-(4-aminophenyl)-3-(4-nitrophenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 8h; Inert atmosphere; Irradiation; Green chemistry; | 96% |
4-aminobenzaldehyde
4-azidobenzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water cooling with ice; Stage #2: With sodium azide In water at 0 - 20℃; | 95% |
Diazotization.Einw. von Brom auf die Diazoniumloesung und Behandlung des entstandenen Perbromids mit Ammoniak; | |
Stage #1: 4-aminobenzaldehyde With sulfuric acid; sodium nitrite In water; acetic acid at 5℃; Stage #2: With sodium azide In water; acetic acid for 1h; | |
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; methyl nitrite In methanol; water at 20℃; for 2.5h; pH=8; Stage #2: With sodium azide In methanol; water at 60℃; for 2.5h; | |
With hydrogenchloride; sodium azide; water; sodium nitrite at 0℃; for 2h; |
4-aminobenzaldehyde
phenol
(E)-4-[2-(4-hydroxyphenyl)diazenyl]benzaldehyde
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydrogenchloride In water; acetone for 0.0833333h; Cooling with ice; Stage #2: With sodium nitrite In water; acetone at -5 - 0℃; for 0.5h; Stage #3: phenol With sodium hydroxide In water; acetone at 5 - 20℃; for 1.5h; | 95% |
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 6h; Stage #2: phenol With sodium hydroxide In water at 0 - 5℃; for 4h; pH=8; | 84% |
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In water; acetone at -10℃; for 1h; Stage #2: phenol With sodium hydroxide; sodium carbonate In water; acetone at 0℃; for 2h; Further stages.; | 41% |
Stage #1: 4-aminobenzaldehyde With hydrogenchloride; sodium nitrite In acetone at -15℃; for 0.25h; Stage #2: phenol With sodium hydroxide In acetone at -15 - 20℃; for 0.5h; | 35% |
With hydrogenchloride; sodium hydroxide; sodium nitrite 1.) Me2CO, -15 deg C, 2.) Me2CO, -15 deg C; Yield given. Multistep reaction; |
4-aminobenzaldehyde
N-methyl-2-methylpyridinium iodide
C14H15N2(1+)*I(1-)
Conditions | Yield |
---|---|
With piperidine In dichloromethane at 40℃; for 12h; | 95% |
4-aminobenzaldehyde
4-methyl-1,2,3-thiadiazole-5-yl-formyl isocyanate
1-(4-formylphenyl)-3-[(4-methyl-1,2,3-thiadiazol-5-yl)carbonyl]urea
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane at 20℃; for 8h; | 95% |
In 1,2-dichloro-ethane at 20℃; for 8.25h; | 95% |
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With diamine functionalized mesoporous silica (AAPTMS(at)MCM-41) In acetonitrile at 27℃; for 0.15h; | 95% |
Conditions | Yield |
---|---|
In toluene at 70℃; for 6h; Inert atmosphere; Schlenk technique; | 95% |
Conditions | Yield |
---|---|
With inorganic-organic hybrid containing imidazolium chloride-butyl sulfonic acid supported on the rice husk silica nanoparticles In ethanol for 0.333333h; Reflux; Green chemistry; | 95% |
Conditions | Yield |
---|---|
With iodosylbenzene In dichloromethane for 2h; | 94% |
Conditions | Yield |
---|---|
With sulfuric acid; silica gel at 80℃; | 93% |
3-(4-methylphenyl)-2-(phenylimino)-4-thiazolidinone
4-aminobenzaldehyde
5-(4-aminobenzylidene)-3-(4-methylphenyl)-2-(phenylimino)-4-thiazolidinone
Conditions | Yield |
---|---|
With tetrabutylammomium bromide In water at 110℃; for 0.1h; Microwave irradiation; | 92% |
Conditions | Yield |
---|---|
With WOx/ZrO2 In 1,4-dioxane at 100℃; for 5h; | 92% |
With sodium metabisulfite In ethanol; water at 74℃; for 0.021h; Wavelength; Microwave irradiation; Sealed tube; Green chemistry; | 87% |
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde; 2-amino-phenol In ethanol for 3h; Reflux; Stage #2: With lead(IV) tetraacetate In acetic acid at 20℃; for 1h; | 92% |
With zinc(II) acetate dihydrate at 20℃; for 0.05h; neat (no solvent, solid phase); | 89% |
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydrogenchloride In water; acetone for 0.0833333h; Cooling with ice; Stage #2: With sodium nitrite In water; acetone at -5 - 0℃; for 0.5h; Stage #3: 2,7-Dihydroxynaphthalene With sodium hydroxide In water; acetone at 5 - 20℃; for 1.5h; | 92% |
4-aminobenzaldehyde
4-(1H-tetrazol-5-yl)aniline
Conditions | Yield |
---|---|
Stage #1: 4-aminobenzaldehyde With hydroxylamine hydrochloride; nitric acid; dimethyl sulfoxide In water at 40℃; for 0.333333h; Stage #2: With sodium azide In water at 40℃; for 3.5h; | 92% |
Conditions | Yield |
---|---|
With H4[PVMo11O40] suppoted montmorillonite K-10 clay In neat (no solvent) at 100℃; for 1h; Green chemistry; | 92% |
4-aminobenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate In neat (no solvent) at 100℃; for 0.4h; | 91% |
Conditions | Yield |
---|---|
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 10h; Sealed tube; | 91% |
The IUPAC name of 4-Aminobenzaldehyde is 4-aminobenzaldehyde. With the CAS registry number 556-18-3, it is also named as 4-Formylaniline. The product's categories are Fine Chemical & Intermediates; Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde. Besides, it is yellow crystalline powder, which should be stored in sealed and dark place. In addition, its molecular formula is C7H7NO and molecular weight is 121.14.
The other characteristics of this product can be summarized as: (1)EINECS: 209-115-2; (2)ACD/LogP: 0.64; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.636; (5)ACD/LogD (pH 7.4): 0.636; (6)ACD/BCF (pH 5.5): 1.791; (7)ACD/BCF (pH 7.4): 1.792; (8)ACD/KOC (pH 5.5): 52.819; (9)ACD/KOC (pH 7.4): 52.831; (10)#H bond acceptors: 2; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.64; (14)Molar Refractivity: 37.242 cm3; (15)Molar Volume: 103.38 cm3; (16)Surface Tension: 52.418 dyne/cm; (17)Density: 1.172 g/cm3; (18)Flash Point: 121.991 °C; (19)Melting Point: 77-79 °C; (20)Enthalpy of Vaporization: 51.67 kJ/mol; (21)Boiling Point: 278.101 °C at 760 mmHg; (22)Vapour Pressure: 0.004 mmHg at 25 °C.
Preparation of 4-Aminobenzaldehyde: this chemical can be prepared by the oxidation and deoxidation of p-Nitrotoluene. Frist, please add 65% Ethanol and p-Nitrotoluene to the solution of Sodium polysulfide. The reaction will occur at temperature of 80-86 °C for 1.5 hours. Then retrieve Ethanol, and remove p-Amino toluene by steam distillation. Afterwards, please use Benzene to extract the reaction liquid. At last, you will obtain the product after steam distillation, cooling, filtration and drying.
Uses of 4-Aminobenzaldehyde: this chemical can be used as intermediate of pharmaceutical and dye. It is also used in organic synthesis. Additionally, it can react with Carbonyl dichloride to get 4-Formylphenyl isocyanate.
This reaction needs Toluene and Ethyl acηte at room temperature for 0.5 hour. The yield is 72 %.
When you are using this chemical, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
(1)SMILES: c1cc(ccc1C=O)N
(2)InChI: InChI=1/C7H7NO/c8-7-3-1-6(5-9)2-4-7/h1-5H,8H2
(3)InChIKey: VATYWCRQDJIRAI-UHFFFAOYAB
(4)Std. InChI: InChI=1S/C7H7NO/c8-7-3-1-6(5-9)2-4-7/h1-5H,8H2
(5)Std. InChIKey: VATYWCRQDJIRAI-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 912mg/kg (912mg/kg) | BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN | Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 6, Pg. 348, 1947. |
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