Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere; | 96% |
Stage #1: indole-3-acetic acid With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane at 20℃; for 12h; Inert atmosphere; Stage #2: With silica gel In methanol at 50℃; for 3h; | 92% |
2-(3-indolyl)oxoacetic acid methyl ester
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 70℃; for 5h; Inert atmosphere; | 80% |
With sodium borohydrid In isopropyl alcohol |
3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With aluminium(III) chloride hexahydrate In methanol at 100℃; for 0.25h; Solvent; Temperature; Microwave irradiation; Sealed tube; chemoselective reaction; | 98% |
With cerium (IV) sulfate tetrahydrate In methanol at 130℃; for 0.333333h; Microwave irradiation; | 90% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran | 96% |
With isopropyl alcohol In hexane at 0 - 20℃; for 0.583333h; Bouveault-Blanc Reduction; Inert atmosphere; | 81% |
With tetrabutylammonium borohydride In dichloromethane for 10h; Heating; | 69% |
Conditions | Yield |
---|---|
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; | 95% |
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; | 81% |
Stage #1: ethyl 3-indoleacetate With polyethylsiloxane; LiTi(OPr-i)4 at 100℃; for 24h; Stage #2: With sodium hydroxide In tetrahydrofuran for 3h; Heating; | 49% |
With lithium aluminium tetrahydride; diethyl ether | |
With samarium diiodide; water; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 99 %Spectr. |
Conditions | Yield |
---|---|
With sulfuric acid In N,N-dimethyl acetamide; water at 100℃; | 92% |
With L-(+)-tartaric acid-urea melt at 70℃; for 1h; Fischer Indole Synthesis; | 90% |
With montmorillonite K-10 In N,N-dimethyl acetamide; water at 80℃; for 2h; | 75% |
1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne
2-bromoaniline
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
Stage #1: 1-triethylsilanyl-4-(triethylsilanyloxy)but-1-yne; 2-bromoaniline With 2 mol% Pd/C; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Larock heteroannulation; Inert atmosphere; Stage #2: With hydrogenchloride In water regioselective reaction; | 87% |
2,3-dihydro-1H-indole-3-ethanol
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen In ethyl acetate at 70℃; under 760.051 Torr; for 46h; Sealed tube; | 85% |
Conditions | Yield |
---|---|
With samarium diiodide; water; triethylamine In tetrahydrofuran at 23℃; for 18h; Inert atmosphere; chemoselective reaction; | 82% |
Multi-step reaction with 2 steps 1: aqueous NaOH 2: lithium alanate; diethyl ether View Scheme |
carbon monoxide
2-[3-(tetrahydro-2H-pyran-2-yloxy)prop-1-yn-1-yl]aniline
A
acetic acid 2-(1H-indol-3-yl)ethyl ester
B
2-(3-indole)-ethanol
C
3-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1H-indole
Conditions | Yield |
---|---|
With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen; 1,2-bis-(diphenylphosphino)ethane In toluene at 100℃; under 18751.9 Torr; for 8h; regioselective reaction; | A n/a B n/a C 78% |
carbon monoxide
(E)-3-(2-aminophenyl)prop-2-en-1-ol
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With carbonylhydridetris(triphenylphosphine)rhodium(I); hydrogen; triphenylphosphine In toluene at 70℃; under 15514.4 Torr; for 70h; | 73% |
Conditions | Yield |
---|---|
With carbonylchloro[4,5-bis(diisopropylphosphinomethyl)acridine]hydridoruthenium(II); water In 1,4-dioxane at 135℃; for 48h; Pressure; Schlenk technique; Inert atmosphere; | 62% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With polymer-supported potassium thiophenolate In tetrahydrofuran; ethylene glycol at 140℃; | 50% |
A
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With ammonia; sodium In tetrahydrofuran at -78 - -50℃; for 4h; | A 22% B 50% |
methanol
2-(Indol-3'-yl)ethyl Trichloroacetate
A
2-(3-indole)-ethanol
B
1,3,4,7-tetrahydro-7,7-dimethoxyoxocino<4,5,6-cd>indol-6-one
Conditions | Yield |
---|---|
With acetonitrile for 0.416667h; Irradiation; | A 48% B 42% |
3-phenylpropanoic acid methyl ester
indole-2,3-dione
lithium diisopropyl amide
A
2-(3-indole)-ethanol
B
β-(phenylmethyl)-1H-indole-ethanol
Conditions | Yield |
---|---|
In tetrahydrofuran; cyclohexane; water; 3-Phenylpropionic acid | A 46.9% B n/a |
Conditions | Yield |
---|---|
With acetic acid In water Reflux; | 46% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With Leptosphaeria maculans In acetonitrile for 24h; Enzymatic reaction; | 32% |
2-(1H-indol-3-yl)-N,N-dimethylacetamide
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With ethanol; sodium In hexane; paraffin oil at 0℃; for 0.0833333h; | 32% |
2-ethoxytetrahydrofuran
phenylhydrazine hydrochloride
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
In ethanol Heating; | 21.5% |
indole
2-acetylaminoethanol
A
2-(3-indole)-ethanol
B
N-Acetyltryptamine
Conditions | Yield |
---|---|
With dichloro(pentamethylcyclopentadienyl) iridium; potassium acetate at 150℃; for 48h; Reagent/catalyst; Inert atmosphere; Sealed tube; | A 10% B 12% C 21% |
carbon monoxide
allyl alcohol
phenylhydrazine
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With hydrogen; toluene-4-sulfonic acid; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); acetylacetonatodicarbonylrhodium(l) In 1,4-dioxane at 60 - 100℃; under 15001.2 Torr; for 43h; | 17% |
2-(1-Triisopropylsilanyl-1H-indol-3-yl)-ethanol
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 0.166667h; Yield given; |
4-(trimethylsilyl)but-3-yn-1-ol
2-iodophenylamine
A
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
Yield given; Multistep reaction; |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With sodium methylate In methanol |
Conditions | Yield |
---|---|
With diethyl ether; benzene und folgenden Erhitzen des Reaktionsgemisches auf ca. 100grad nach Abdestillieren des Aethers.; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: diethyl ether 2: diethyl ether / 12 h / 20 °C 3: 100 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C View Scheme |
indolyl-3-glyoxylyl chloride
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether / 12 h / 20 °C 2: 100 percent / LiAlH4 / tetrahydrofuran / 12 h / 20 °C View Scheme | |
With sodium borohydrid In diethylene glycol dimethyl ether | |
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / 0.5 h / Reflux; Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: NaOMe / methanol View Scheme | |
Multi-step reaction with 2 steps 2: NaOMe / methanol View Scheme |
dichloroacethyl chloride
2-(3-indole)-ethanol
2-(Indol-3'-yl)ethyl Dichloroacetate
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 18h; kept in the dark; | 100% |
2-(3-indole)-ethanol
acetic anhydride
acetic acid 2-(1H-indol-3-yl)ethyl ester
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane for 24h; Ambient temperature; | 100% |
With pyridine at 20℃; for 15h; Inert atmosphere; | 99% |
With pyridine for 1h; Ambient temperature; | 55.3 g |
With pyridine at 20℃; for 15h; Inert atmosphere; |
2-(3-indole)-ethanol
tert-butyldimethylsilyl chloride
3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 16h; Ambient temperature; | 99% |
2-(3-indole)-ethanol
triisopropylsilyl chloride
3-(2-((triisopropylsilyl)oxy)ethyl)-1H-indole
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Substitution; | 99% |
2-(3-indole)-ethanol
2,3-dihydro-1H-indole-3-ethanol
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 3.5h; | 100% |
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 5h; | 38% |
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 3.5h; Inert atmosphere; | 37.4% |
2-(3-indole)-ethanol
3-dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone
Conditions | Yield |
---|---|
Stage #1: 2-(3-indole)-ethanol; 3-dimethylaminomethyl-4-(3-fluorophenyl)-4-hydroxy-cyclohexanone With methanesulfonic acid In dichloromethane at 20℃; for 24h; Stage #2: With sodium hydroxide In water Stage #3: With sodium hydroxide In water | 100% |
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% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 99% |
In N,N-dimethyl-formamide | 99% |
2-(3-indole)-ethanol
4-(Dimethylamino-phenyl-methyl)-cyclohexanone
1,1-[3-(dimethylamino-(phenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydropyrano[3,4-b]indole
Conditions | Yield |
---|---|
Stage #1: 2-(3-indole)-ethanol; 4-(Dimethylamino-phenyl-methyl)-cyclohexanone With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 6h; Stage #2: With sodium hydroxide; water In dichloromethane | 99% |
2-(3-indole)-ethanol
4-[(4-Chloro-phenyl)-dimethylamino-methyl]-cyclohexanone
1,1-[3-(dimethylamino-(4-chlorophenyl)-methyl)-pentamethylene]-1,3,4,9-tetrahydro-pyrano[3,4-b]indole
Conditions | Yield |
---|---|
Stage #1: 2-(3-indole)-ethanol; 4-[(4-Chloro-phenyl)-dimethylamino-methyl]-cyclohexanone With trifluorormethanesulfonic acid In dichloromethane at 20℃; Stage #2: With sodium hydroxide; water In dichloromethane | 99% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 4h; | 99% |
2-(3-indole)-ethanol
tert-butyl (4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)carbamate
Conditions | Yield |
---|---|
With (R)-6,6'-bis(9-phenanthryl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate In toluene at 30℃; for 12h; Molecular sieve; stereoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With (R)-6,6'-bis(9-phenanthryl)-1,1'-spirobiindanyl-7,7'-diyl hydrogen phosphate In toluene at 30℃; for 12h; Molecular sieve; stereoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 30℃; for 3h; Molecular sieve; diastereoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 40℃; for 8h; chemoselective reaction; | 99% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene; copper diacetate; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one; 1-butyl-2,3-methylimidazolium tetrafluoroborate In dimethyl sulfoxide at 45℃; for 1.5h; Solvent; Reagent/catalyst; Inert atmosphere; | 98.5% |
2-(3-indole)-ethanol
2,2-dimethoxy-propane
1,1-dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction; | 98% |
With iron(II) triflate In toluene at 70℃; for 24h; Pictet-Spengler Synthesis; Green chemistry; | 98% |
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; triethyl borane; palladium diacetate In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; diastereoselective reaction; | 98% |
2-(3-indole)-ethanol
methanesulfonic acid
4-morpholino-4-phenylcyclohexanone
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 16h; | 98% |
2-(3-indole)-ethanol
4-methylacetophenone dimethyl acetal
Conditions | Yield |
---|---|
With 2,3,4,5-tetrabromo-6-(((1R,2R)-2-(3-(4-nitro-3-(trifluoromethyl)phenyl)thioureido)-cyclohexyl)carbamoyl)benzoic acid In toluene at -30℃; for 18h; Pictet-Spengler Synthesis; Molecular sieve; Inert atmosphere; enantioselective reaction; | 98% |
Conditions | Yield |
---|---|
With iron(II) triflate; (S)-(+)-N-(3,5-dioxa-4-phosphacyclohepta-[2,1-a;3,4-a′]dinaphthalen-4-yl)dibenz[b,f]azepine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In diethyl ether at 20℃; for 8h; Reagent/catalyst; Time; Temperature; Solvent; enantioselective reaction; | 97% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In tetrahydrofuran at 25℃; for 5h; Molecular sieve; Inert atmosphere; | 97% |
2-(3-indole)-ethanol
[bromo(difluoro)methyl](trimethyl)silane
Conditions | Yield |
---|---|
With potassium hydrogenfluoride In dichloromethane at 20℃; for 2h; | 97% |
With potassium hydrogen difluoride In dichloromethane; water at 20℃; for 10h; Reagent/catalyst; | 93% |
2-(3-indole)-ethanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform at 30℃; for 3h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Molecular sieve; diastereoselective reaction; | 97% |
Product Name: Tryptophol (CAS NO.526-55-6)
Molecular Formula: C10H11NO
Molecular Weight: 161.2g/mol
Mol File: 526-55-6.mol
Einecs: 208-393-2
Melting Point: 56-59 °C(lit.)
Boiling point: 357.8 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 170.2 °C
Density: 1.219 g/cm3
Water Solubility: 10 g/L (20 ºC)
Surface Tension: 57.5 dyne/cm
Enthalpy of Vaporization: 63.65 kJ/mol
Vapour Pressure: 9.66E-06 mmHg at 25°C
XLogP3-AA: 1.8
H-Bond Donor: 2
H-Bond Acceptor: 1
Structure Descriptors of Tryptophol (CAS NO.526-55-6):
IUPAC Name: 2-(1H-indol-3-yl)ethanol
Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCO
InChI: InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2
InChIKey: MBBOMCVGYCRMEA-UHFFFAOYSA-N
Product Categories: Heterocyclic Compounds; Indoles; Simple Indoles
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 351mg/kg (351mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Journal of Toxicology and Environmental Health. Vol. 1, Pg. 515, 1976. |
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00777, |
Safety Information of Tryptophol (CAS NO.526-55-6):
Hazard Codes: Xi
Safety Statements: 24/25
24: Avoid contact with skin
25: Avoid contact with eyes
Tryptophol ,its CAS NO. is 526-55-6,the synonyms is 1H-Indole-3-ethanol ; 2-(3-Indolyl)ethanol ; 3-(2-Hydroxyethyl)indole ; 3-(beta-Hydroxyethyl)indole ; 3-Indolylethanol ; 5-21-03-00061 (Beilstein Handbook Reference) ; BRN 0125553 ; EINECS 208-393-2 ; Ethanol, 2-indol-3-yl- ; Ethanol, 3-indolyl- ; IEA ; Indole ethanol ; NSC 3884 .
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