Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 80℃; for 2h; | 99% |
With 2-iodoxybenzoic acid In acetonitrile at 80℃; for 3h; | 91% |
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide | 87% |
2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.75h; | 80% |
Stage #1: 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Stage #2: With potassium hydrogensulfate; water In tetrahydrofuran | |
With diisobutylaluminium hydride In dichloromethane; toluene at -78℃; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride at -78℃; | 75% |
Multi-step reaction with 2 steps 1: 94.4 percent / 5percent H2SO4 / 1 h / Ambient temperature 2: 75 percent / 25percent DIBAL / CH2Cl2; 1,2-dimethoxy-ethane; toluene / 1 h / -78 °C View Scheme | |
Multi-step reaction with 2 steps 1: 84 percent / DCC, NEt3 / CH2Cl2 / 2 h / Ambient temperature 2: 80 percent / LiAlH4 / tetrahydrofuran / 0.75 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In 1,2-dimethoxyethane; dichloromethane; toluene at -78℃; for 1h; | 75% |
With diisobutylaluminium hydride | |
Multi-step reaction with 2 steps 1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 2 h / 80 °C View Scheme | |
With diisobutylaluminium hydride | |
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide View Scheme |
Conditions | Yield |
---|---|
With sodium hypochlorite In aq. phosphate buffer; water at 37℃; | 72% |
With sodium hypochlorite | 10% |
With peroxomonophosphoric acid In water at 35℃; Rate constant; Kinetics; Thermodynamic data; other reaction temperatures, times and pH, addition of NaClO4; E(excit.), ΔS(excit.); mechanism; oxidation rate vs. pH at different temperatures; | |
With perchloric acid; hexacyanoferrate(III); palladium dichloride In water at 25℃; for 24h; Kinetics; Mechanism; | |
With tryptophan lyase wild type; S-Adenosyl-L-methionine; dithionite(2-) In aq. phosphate buffer for 2h; pH=7.5; Catalytic behavior; Reagent/catalyst; Inert atmosphere; |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In benzene at 0℃; for 1h; | 66% |
With diisobutylaluminium hydride In dichloromethane; toluene at -78 - -50℃; Inert atmosphere; | 33% |
Multi-step reaction with 2 steps 1: Raney nickel; methanol; acetic acid / 40 °C / 80905.8 Torr / Hydrogenation 2: diethyl ether; water; hydrochloric acid View Scheme | |
Stage #1: indole-3-acetonitrile With diisobutylaluminium hydride In toluene at -78℃; for 0.333333h; Inert atmosphere; Stage #2: With hydrogenchloride; water In toluene Inert atmosphere; Cooling with ice; |
S-ethyl 2-(1H-indol-3-yl)ethanethioate
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With triethylsilane; palladium 10% on activated carbon In acetone at 0 - 18℃; | 49% |
Conditions | Yield |
---|---|
With sodium hypochlorite In water; benzene at 43 - 45℃; for 0.583333h; pH 9-10; | 44% |
With Flavin mononucleotide In water Mechanism; Irradiation; var. flavin; | 7.4% |
With flavin adenine dinucleotide In water Irradiation; N2; | 4% |
With sodium hypochlorite; water; benzene at 50℃; |
Conditions | Yield |
---|---|
biochemischen Oxydation in Gegenwart von Aminoxydase-und Katalase-Praeparaten in Phosphatpuffer-Loesung bei pH 7; | |
With Lathyrus cicera copper amine oxidase at 25℃; pH=7.2; Kinetics; Concentration; pH-value; aq. phosphate buffer; | |
With 4-amino-2,3-dimethyl-1-phenylpyrazolin-5-one; N-ethyl-N-(2-hydroxy-3-sulfopropyl)-3-methylaniline sodium salt dihydrate; oxygen In aq. phosphate buffer pH=7.0; Enzymatic reaction; |
Conditions | Yield |
---|---|
With sodium periodate; water |
3-(1,3-diphenyl-imidazolidin-2-ylmethyl)-indole
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride; diethyl ether; water |
(1H-Indol-3-yl)acetaldehyde oxime
A
indole-3-acetaldehyde
B
indole-3-acetic acid
Conditions | Yield |
---|---|
With Tris-HCl buffer; ethylenediaminetetraacetic acid; GLUTATHIONE; NAD at 35℃; for 6h; investigation of enzyme, concentration, pH and buffer; |
Conditions | Yield |
---|---|
In water Irradiation; |
Conditions | Yield |
---|---|
In water for 10h; Mechanism; Irradiation; |
Conditions | Yield |
---|---|
With cetyltrimethylammonim bromide; coenzyme PQQ In water at 30℃; for 24h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In 1,2-dimethoxyethane; toluene at -78℃; Reduction; |
2-imino-3-(indol-3-yl)propanoic acid
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2O 2: H2O / Irradiation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: benzene; ethyl magnesium bromide; diethyl ether / anschl. mit Allylbromid 2: pyridine; diethyl ether; osmium(VIII)-oxide / -30 °C 3: sodium periodate; water View Scheme | |
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 0.17 h / 0 °C 1.2: 2 h / 45 °C 2.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 2.2: 2 h / 20 °C 3.1: hydrogenchloride / water / 3 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1.1: diethyl ether / 6 h / 0 - 20 °C 1.2: 0.5 h / 0 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 70 °C / Inert atmosphere 3.1: dimethyl sulfoxide / 1.5 h View Scheme |
3-allylindole
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine; diethyl ether; osmium(VIII)-oxide / -30 °C 2: sodium periodate; water View Scheme |
Conditions | Yield |
---|---|
With thia-containing Schiff-base iron(III) complex adsorbed on glassy carbon electrode Kinetics; Electrochemical reaction; aq. buffer; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Sclerotinia sclerotiorum indolyl-3-acetaldoxime dehydratase / 1 h / 23 °C / pH 7.5 / aq. buffer; Darkness; Enzymatic reaction 2.1: diisobutylaluminium hydride / toluene / 0.33 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere; Cooling with ice View Scheme |
Conditions | Yield |
---|---|
Stage #1: Trp With C22H20FeN4O4; sodium hydroxide In water at 20℃; for 24h; Inert atmosphere; Stage #2: With hydrogenchloride In water pH=2 - 3; |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride In water for 3h; Reflux; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere 1.2: 2 h / 20 °C 2.1: hydrogenchloride / water / 3 h / Reflux View Scheme |
2,5-dioxopyrrolidin-1-yl (((9H-fluoren-9-yl)methoxy)carbonyl)-L-tryptophanate
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium hydrogen sulfide / ethanol / 8 h / 20 °C 2: pyrrolidine / N,N-dimethyl-formamide / 4 h / 20 °C 3: tryptophan lyase wild type; S-Adenosyl-L-methionine; dithionite(2-) / aq. phosphate buffer / 2 h / pH 7.5 / Inert atmosphere; Enzymatic reaction View Scheme |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyrrolidine / N,N-dimethyl-formamide / 4 h / 20 °C 2: tryptophan lyase wild type; S-Adenosyl-L-methionine; dithionite(2-) / aq. phosphate buffer / 2 h / pH 7.5 / Inert atmosphere; Enzymatic reaction View Scheme |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With tryptophan lyase wild type; S-Adenosyl-L-methionine; dithionite(2-) In aq. phosphate buffer for 2h; pH=7.5; Inert atmosphere; Enzymatic reaction; |
2-(3-indolyl)oxoacetic acid methyl ester
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 70 °C / Inert atmosphere 2: dimethyl sulfoxide / 1.5 h View Scheme |
morpholine
indole-3-acetaldehyde
(E)-3-<2-(morpholin-4-yl)vinyl>-1H-indole
Conditions | Yield |
---|---|
With molecular sieve In diethyl ether for 24h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 30℃; for 2h; | 99% |
indole-3-acetaldehyde
ethyl acetoacetate
1-Methyl-9H-carbazol-2-carbonsaeure-ethylester
Conditions | Yield |
---|---|
With hydrogen bromide In acetonitrile at 80℃; for 2h; Reagent/catalyst; | 93% |
indole-3-acetaldehyde
(S)-tert-butyl 4-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl)amino)butanoate
(S)-tert-butyl-4-((2-(1H-indol-3-yl)ethyl)(((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)amino)-2-((tert-butoxycarbonyl) amino)butanoate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 12h; | 89% |
indole-3-acetaldehyde
phosphonic acid diethyl ester
2-iodo-4-(trifluoromethyl)aniline
Conditions | Yield |
---|---|
With titanium(IV) dioxide In neat (no solvent) at 50℃; for 0.5h; | 84% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; Inert atmosphere; | 82% |
indole-3-acetaldehyde
(1,2,3,4-tetrahydroquinolin-6-yl)carbamic acid tert-butyl ester
C24H29N3O2
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 18h; | 80% |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; Inert atmosphere; | 78% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 25℃; for 0.5h; regioselective reaction; | 77% |
indole-3-acetaldehyde
(4R)-3-((E)-2-BUTENOYL)-4-(PHENYLMETHYL)-2-OXAZOLIDINONE
Conditions | Yield |
---|---|
Stage #1: (4R)-3-((E)-2-BUTENOYL)-4-(PHENYLMETHYL)-2-OXAZOLIDINONE With di-n-butylboryl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78 - 0℃; Inert atmosphere; Stage #3: indole-3-acetaldehyde In dichloromethane at -78 - 0℃; for 2h; Inert atmosphere; | 74% |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane | 70% |
indole-3-acetaldehyde
(E)-N-methoxy-6-(trimethylsilyl)hex-4-enamide
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -20℃; for 0.333333h; Inert atmosphere; | 68% |
indole-3-acetaldehyde
allyl bromide
(R)-2-methylpropane-2-sulfinamide
Conditions | Yield |
---|---|
Stage #1: indole-3-acetaldehyde; (R)-2-methylpropane-2-sulfinamide With titanium(IV) tetraethanolate; indium In tetrahydrofuran at 23℃; for 3h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 60℃; for 20h; Inert atmosphere; | 68% |
indole-3-acetaldehyde
(S)-(1-p-menthen-8-yl)amine
Conditions | Yield |
---|---|
In benzene at 5℃; for 2h; | 67% |
indole-3-acetaldehyde
Methyl (1S,4aS,8aR)-4a,5,6,7,8,8a-hexahydro-1-methyl-1H-pyrano<3,4-c>pyridine-4-carboxylate
2,3-secoajmalicine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere; | 67% |
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere; | 67% |
indole-3-acetaldehyde
(1S,4aS,8aS)-methyl 1-methyl-4a,5,6,7,8,8a-hexahydro-1H-pyrano [3,4-c]pyridine-4-carboxylate
2,3-seco-2,3-dihydroakuammigine
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere; | 66% |
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h; Inert atmosphere; | 33 mg |
indole-3-acetaldehyde
Conditions | Yield |
---|---|
Stage #1: endo-benzyl 7-(benzyloxymethyl)-2-azabicyclo[2.2.2]oct-5-ene-2-carboxylate With trimethylsilyl iodide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: indole-3-acetaldehyde With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane at 20℃; for 3h; | 62% |
Conditions | Yield |
---|---|
Stage #1: 1-chloro-3,7-dimethylocta-2,6-diene With chromium dichloride; lithium iodide In tetrahydrofuran at 22℃; for 0.0833333h; Inert atmosphere; Stage #2: indole-3-acetaldehyde In tetrahydrofuran at 22℃; for 3h; Inert atmosphere; | 62% |
Conditions | Yield |
---|---|
Stage #1: indole-3-acetaldehyde; C16H17N3O With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 18h; Stage #2: With sodium hydrogencarbonate In methanol; water | 52% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In tetrahydrofuran at 20℃; Inert atmosphere; | 48% |
indole-3-acetaldehyde
N-butylamine
N-(2-(1H-indol-3-yl)ethyl)butan-1-amine
Conditions | Yield |
---|---|
Stage #1: indole-3-acetaldehyde; N-butylamine In methanol at 20℃; for 0.166667h; Stage #2: With sodium cyanoborohydride In methanol for 16h; Reflux; | 48% |
The 1H-Indole-3-acetaldehyde, with the CAS registry number 2591-98-2, is also known as 2-(1H-Indol-3-yl)acetaldehyde and Indole3-acetaldehyde. It belongs to the product category of Indole. This chemical's molecular formula is C10H9NO and molecular weight is 159.1846. What's more, its systematic name is 1H-Indol-3-ylacetaldehyde.
Physical properties about this chemical are: (1)ACD/LogP: 1.70; (2)#of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.7; (4)ACD/LogD (pH 7.4): 1.7; (5)ACD/BCF (pH 5.5): 11.6; (6) ACD/BCF (pH 7.4): 11.6; (7)ACD/KOC (pH 5.5): 201.15; (8) ACD/KOC (pH 7.4): 201.15; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 22 Å2; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 48.26 cm3; (15)Molar Volume: 132 cm3; (16)Polarizability: 19.13×10-24cm3; (17)Surface Tension: 53 dyne/cm; (18)Density: 1.205 g/cm3; (19)Flash Point: 174.9 °C; (20)Enthalpy of Vaporization: 59.75 kJ/mol; (21)Boiling Point: 352.7 °C at 760 mmHg; (22)Vapour Pressure: 3.78E-05 mmHg at 25 °C.
Preparation of 1H-Indole-3-acetaldehyde: this chemical can be prepared by Indol-3-yl-acetonitrile.
This reaction needs reagent DIBAH and solvent Benzene at temperature of 0 °C. The reaction time is 1 hour. The yield is 66 %.
Uses of 1H-Indole-3-acetaldehyde: it can react with 2-Amino-benzaldehyde to give 3-(1H-Indol-3-yl)quinoline.
The reaction occurs with reagent NaOH and solvent Ethanol other condition of heating for 20 mins. The yield is 32 %.
You can still convert the following datas into molecular structure:
(1) SMILES: O=CCc2c1ccccc1nc2
(2) InChI: InChI=1/C10H9NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,6-7,11H,5H2
(3) InChIKey: WHOOUMGHGSPMGR-UHFFFAOYAR
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