4-Hydroxyindole supplier | CasNO.2380-94-1

Name
4-Hydroxyindole
EINECS 219-177-2
CAS No. 2380-94-1
Article Data40
CAS DataBase
Density 1.327 g/cm³
Solubility slightly soluble
Melting Point 97-99 °C(lit.)
Formula C₈H₇NO
Boiling Point 343.2 °C at 760 mmHg
Molecular Weight 133.15
Flash Point 161.4 °C
Transport Information
Appearance off-white cyrstalline solid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,5-Dihydro-indol-4-one;1,5-dihydroindol-4-one;1H-Indol-4-ol;4-Hydroxy Indole (4-Indolol);4-hydroxy-1H-indole;4-Hydroxy Indole;
PSA 36.02000
LogP 1.87350

Synthetic route

: 195992-07-5
3-nitro-2-vinylphenol

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With carbon monoxide; triphenylphosphine; palladium diacetate In acetonitrile under 3040 Torr; Heating;	96%
With carbon monoxide; palladium diacetate; triphenylphosphine In acetonitrile at 90℃; under 3051.25 Torr; for 50h;	96%

: 95969-15-6
(4-Hydroxy-indol-1-yl)-phenyl-methanone

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With potassium hydroxide at 0 - 20℃; for 2h;	96%

: C10H9NO2

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With sodium hydroxide at 0℃; for 1h;	95%

: 20289-26-3
4-benzyloxy-1H-indole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 775.743 Torr; for 12h;	89.4%
With methanol; magnesium hydrosilicate; palladium Hydrogenation;

: 85926-99-4
4-hydroxyindoline

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With palladium on activated charcoal In o-xylene for 2.3h; Heating;	88%

: (E)-6-benzyloxy-2-nitro-β-pyrrolidinostyrene

A: 2380-94-1
1H-indol-4-ol

B: 20289-26-3
4-benzyloxy-1H-indole

Conditions

Conditions	Yield
With hydrogen; 5% rhodium-on-charcoal; nickel(II) nitrate In tetrahydrofuran; water at 20℃; for 32h;	A 6% B 88%
With hydrogen; 5% rhodium-on-charcoal; iron(II) acetate In tetrahydrofuran at 20℃; for 31h;	A 5% B 83%
With hydrogen; 5% rhodium-on-charcoal; tris(acetylacetonato)cobalt In tetrahydrofuran at 20℃; for 38h;	A 3% B 80%

: 112970-68-0
4-acetoxy-N-tosylindole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 12h; Heating;	83%

: 79966-73-7
2-(2-benzyloxy-6-nitrophenyl)acetonitrile

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With hydrogen; acetic acid; 10% palladium on active carbon In ethanol under 2280 Torr; for 2h; Ambient temperature;	81%
With palladium 10% on activated carbon; hydrogen; acetic acid In ethanol	78%

: 13754-86-4
1,5,6,7-tetrahydro-indol-4-one

A: 2380-94-1
1H-indol-4-ol

B: 5192-23-4
4-amino-1H-indole

Conditions

Conditions	Yield
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Reagent/catalyst; Schlenk technique;	A 11% B 80%

: 75201-78-4
ethyl 4-hydroxy-1H-indole-1-carboxylate

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
palladium on activated charcoal	75%

: 81038-33-7
4-hydroxy-1-methoxycarbonylindole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 10h; Heating;	74.9%

: 13754-86-4
1,5,6,7-tetrahydro-indol-4-one

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
palladium on activated charcoal In various solvent(s) Heating;	69%
With diisobutyl ketone; palladium 10% on activated carbon at 190℃; for 48h; Inert atmosphere;	49%
With palladium on activated charcoal; hydrogen In 1,3,5-trimethyl-benzene at 160 - 161℃; for 48h;	67 % Chromat.

: 78283-30-4
2-benzyloxy-6-nitrophenyl acetaldehyde

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With hydrogen; platinum(IV) oxide; palladium on activated charcoal In methanol at 60℃; under 52956.6 Torr; for 15h;	67.7%

: C16H16N4O4

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal under 3102.9 Torr; for 6h;	55%

: 120-72-9
indole

A: 2380-86-1
6-hydroxy-1H-indole

B: 1953-54-4
indol-5-ol

C: 2380-84-9
7-Indolol

D: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With dihydrogen peroxide; edetate disodium; iron(II) sulfate; ascorbic acid phosphate buffer (pH=7.2);	A 10% B 30% C 10% D 50%

...Expand

: 81038-34-8
1-(p-toluenesulphonyl)-4-hydroxyindole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 10h; Heating;	42.1%

: 120-72-9
indole

A: 2380-86-1
6-hydroxy-1H-indole

B: 1953-54-4
indol-5-ol

C: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With hydrogen fluoride; dihydrogen peroxide; antimony pentafluoride at -20℃; for 0.05h;	A 10% B 20% C 5%

...Expand

: 5585-96-6
acetic acid 1H-indol-4-yl ester

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With methanol; ammonia

: 5192-23-4
4-amino-1H-indole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 50 min; Yield given. Multistep reaction;

: 13523-86-9
1-(1H-indol-4-yloxy)-3-(isopropylamino)-2-propanol

A: 2380-94-1
1H-indol-4-ol

B: 2-(1H-Indol-4-yloxy)-3-<(1-isopropyl)-amino>propan-1-ol

Conditions

Conditions	Yield
With hydrogenchloride at 98℃; for 504h;

: 101935-40-4
2-bromo-3-hydroxy-1-nitrobenzene

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / PPh3 / Pd(dba)2 / toluene / 17 h / Heating 2: 96 percent / PPh3, CO / Pd(OAc)2 / acetonitrile / 3040 Torr / Heating View Scheme
Multi-step reaction with 6 steps 1: 44 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / Ambient temperature 2: 93 percent / iron / ethanol; acetic acid / 3.5 h / Heating 3: 60 percent / pyridine / 6 h / Ambient temperature 4: 36 percent / tetrakis(triphenylphosphine)palladium(0) / toluene / Heating 5: 58 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C 6: 83 percent / 20percent aq. NaOH / methanol / 12 h / Heating View Scheme

Yield

Multi-step reaction with 2 steps
1: 30 percent / PPh3 / Pd(dba)2 / toluene / 17 h / Heating
2: 96 percent / PPh3, CO / Pd(OAc)2 / acetonitrile / 3040 Torr / Heating
View Scheme

Multi-step reaction with 6 steps
1: 44 percent / triethylamine, 4-(dimethylamino)pyridine / CH2Cl2 / 10 h / Ambient temperature
2: 93 percent / iron / ethanol; acetic acid / 3.5 h / Heating
3: 60 percent / pyridine / 6 h / Ambient temperature
4: 36 percent / tetrakis(triphenylphosphine)palladium(0) / toluene / Heating
5: 58 percent / bis(acetonitrile)palladium chloride, p-benzoquinone, lithium chloride / dimethylformamide / 28 h / 100 - 110 °C
6: 83 percent / 20percent aq. NaOH / methanol / 12 h / Heating
View Scheme

: 606-20-2
2,6-dinitrotoluene

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / Et4NOTs / dimethylformamide / 0.83 h / Ambient temperature; 3.3 mAcm-2 2: 86 percent / H2 / Raney Ni (W-2) / methanol / 2 h / 55 - 65 °C / 3800 - 6840 Torr 3: 90 percent / aq. 70percent H3PO4 / 24 h / 220 °C 4: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 94 percent / Et4NOTs / dimethylformamide / 0.83 h / Ambient temperature; 3.3 mAcm-2 2: 86 percent / H2 / Raney Ni (W-2) / methanol / 2 h / 55 - 65 °C / 3800 - 6840 Torr 3: 92 percent / aq. 30percent H2SO4 / 24 h / 170 °C 4: 86 percent / aq. 30percent H3PO4 / 24 h / 220 °C 5: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme

: 77759-08-1
2-(2,6-dinitrophenyl)ethanol

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 86 percent / H2 / Raney Ni (W-2) / methanol / 2 h / 55 - 65 °C / 3800 - 6840 Torr 2: 90 percent / aq. 70percent H3PO4 / 24 h / 220 °C 3: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 86 percent / H2 / Raney Ni (W-2) / methanol / 2 h / 55 - 65 °C / 3800 - 6840 Torr 2: 92 percent / aq. 30percent H2SO4 / 24 h / 170 °C 3: 86 percent / aq. 30percent H3PO4 / 24 h / 220 °C 4: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme

: 52537-01-6
4-aminoindoline

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / aq. 30percent H3PO4 / 24 h / 220 °C 2: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme

: 118742-89-5
2-(2,6-diaminophenyl)ethanol

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / aq. 70percent H3PO4 / 24 h / 220 °C 2: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 92 percent / aq. 30percent H2SO4 / 24 h / 170 °C 2: 86 percent / aq. 30percent H3PO4 / 24 h / 220 °C 3: 88 percent / 10percent Pd/C / o-xylene / 2.3 h / Heating View Scheme

: 554-84-7
meta-nitrophenol

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: anhydrous K2CO3 / dimethylformamide 2: 63 percent / tBuOK / dimethylformamide / 0.5 h / -20 - -10 °C 3: 81 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature View Scheme

: 24318-00-1
3-(benzyloxy)nitrobenzol

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / tBuOK / dimethylformamide / 0.5 h / -20 - -10 °C 2: 81 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature View Scheme

: 4769-97-5
4-nitro-1H-indoIe

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 4 h 3: sodium hydroxide / methanol / 10 h / Heating View Scheme
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl-formamide / 4 h 2: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 3: hydrogenchloride; sodium nitrite / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 50 min 4: sodium hydroxide / methanol / 10 h / Heating View Scheme
Multi-step reaction with 4 steps 1: sodium hydride / N,N-dimethyl-formamide; benzene / 17 h 2: titanium(III) chloride / methanol; water / 0.12 h / Ambient temperature 3: hydrogenchloride; sodium nitrite / 1.) water and methanol, 5 deg C, 5 min, 2.) water, 97 deg C, 20 min 4: sodium hydroxide / methanol / 10 h / Heating View Scheme

: 78283-23-5
1-hydroxy-4-nitroindole

: 2380-94-1
1H-indol-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / methanol / 16 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 4: sodium hydroxide / methanol / 10 h / Heating View Scheme
Multi-step reaction with 4 steps 1: triethylamine / methanol / 43 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 4: sodium hydroxide / methanol / 10 h / Heating View Scheme
Multi-step reaction with 4 steps 1: ethyl bromoacetate; triethylamine / methanol / 92.5 h / Ambient temperature 2: sodium hydride / N,N-dimethyl-formamide / 4 h 4: sodium hydroxide / methanol / 10 h / Heating View Scheme

: 2380-94-1
1H-indol-4-ol

: 100-39-0
benzyl bromide

: 20289-26-3
4-benzyloxy-1H-indole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;	100%
With potassium carbonate In acetone for 20h; Ambient temperature;	95%
With potassium carbonate In acetone for 72h; Heating;	94%

: 2380-94-1
1H-indol-4-ol

: 106-89-8
epichlorohydrin

: 35308-87-3
4-(oxiranylmethoxy)-1H-indole

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h;	100%
Stage #1: 1H-indol-4-ol; epichlorohydrin With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h; Stage #2: With ammonium chloride In water	99%
With potassium hydroxide In dimethyl sulfoxide at 45℃; for 4h;	99%

: 2380-94-1
1H-indol-4-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 106792-40-9
4-((tert-butyldimethylsilyl)oxy)-1H-indole

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere;	100%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	91%

: 2380-94-1
1H-indol-4-ol

: 85926-99-4
4-hydroxyindoline

Conditions

Conditions	Yield
Stage #1: 1H-indol-4-ol With sodium cyanoborohydride; acetic acid at 15 - 20℃; for 1.5h; Stage #2: With sodium hydrogencarbonate In water; ethyl acetate	100%
With sodium cyanoborohydride In acetic acid at 15 - 20℃; for 1.5h;	100%
With sodium cyanoborohydride In acetic acid at 15 - 20℃;	99%

: 288-32-4
1H-imidazole

: 2380-94-1
1H-indol-4-ol

: ammonium chloride

: 18162-48-6
tert-butyldimethylsilyl chloride

: 4-t-butyldimethylsilyloxyindole

Conditions

Conditions	Yield
In N-methyl-acetamide	100%

...Expand

: 2380-94-1
1H-indol-4-ol

: 5688-82-4
2-(3,4,5-trimethoxybenzylidene)malononitrile

: 2-amino-4-(3,4,5-trimethoxyphenyl)-4,6-dihydrooxepino[4,3,2-cd]indole-3-carbonitrile

Conditions

Conditions	Yield
With potassium fluoride In ethanol at 60℃; for 6h;	100%

: 2380-94-1
1H-indol-4-ol

: 108-24-7
acetic anhydride

: 5585-96-6
acetic acid 1H-indol-4-yl ester

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 25℃; Inert atmosphere; Large scale;	99.2%
With pyridine at 25 - 32℃;	98%
With pyridine In dichloromethane at 20℃; for 2h;	34 g

: 2380-94-1
1H-indol-4-ol

: 57561-39-4
methyl(2-hydroxyethyl)carbamic acid tert-butyl ester

: 203921-48-6
N-methyl-N-[2-(1H-indol-4-yloxy)-ethyl]-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; for 14h;	99%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 16h; Ambient temperature;	77%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 16h;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 72h;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Schlenk technique;	873.5 mg

: 2380-94-1
1H-indol-4-ol

: 13154-24-0
triisopropylsilyl chloride

: 916574-98-6
4-((triisopropylsilyl)oxy)-1H-indole

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 7h;	99%
With 1H-imidazole In dichloromethane at 20℃;	80%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;

: 2380-94-1
1H-indol-4-ol

: 762-49-2
2-fluoroethyl bromide

: 1240407-42-4
4-(2-fluoroethoxy)indole

Conditions

Conditions	Yield
With potassium carbonate In acetone Reflux;	99%
With potassium carbonate In acetonitrile at 90℃; for 6h;	92%

: 2380-94-1
1H-indol-4-ol

: tert-butyl-(1-allyl-oxoindolin-3-ylidene)carbamate

: C24H25N3O4

Conditions

Conditions	Yield
With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione In toluene at 25℃; for 12h; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: 1673543-00-4
tert-butyl (1-benzyl-5,7-dimethyl-2-oxoindolin-3-ylidene)carbamate

: C30H31N3O4

Conditions

Conditions	Yield
With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione In toluene at 25℃; for 12h; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: 3-trifluoroethylidene oxindole

: tert-butyl (2-((3R,4S)-2-oxo-4-(trifluoromethyl)-2,3,4,7-tetrahydropyrano[2,3-e]indol-3-yl)phenyl)carbamate

Conditions

Conditions	Yield
With C32H28F6N4O3 In dichloromethane at -30℃; for 35h; Solvent; Temperature; Concentration; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: C10H15N3O3

: tert-butyl (S)-(4-(4-hydroxy-1H-indol-5-yl)-1,3-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: tert-butyl (3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)carbamate

: tert-butyl (S)-(4-(4-hydroxy-1H-indol-5-yl)-3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; for 18h; Reagent/catalyst; Solvent; Temperature; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: C15H16ClN3O3

: tert-butyl (S)-(1-(2-chlorophenyl)-4-(4-hydroxy-1H-indol-5-yl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	99%

: 2380-94-1
1H-indol-4-ol

: 96-32-2
bromoacetic acid methyl ester

: 157889-30-0
methyl 2-((1H-indol-4-yl)oxy)acetate

Conditions

Conditions	Yield
With potassium carbonate In acetone	98%
With caesium carbonate In acetonitrile at 20℃; for 0.583333h;	78%
With potassium carbonate In acetone at 20℃;

: 2380-94-1
1H-indol-4-ol

: 612499-61-3
(3-bromopropyl)({ [2-chloro-3-(trifluoromethyl)phenyl]methyl})(2,2-diphenylethyl)amine

: 847990-40-3
(2-chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(1H-indol-4-yloxy)-2-methyl-propyl]-amine

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃;	98%
With potassium carbonate In acetonitrile at 90℃; Product distribution / selectivity;	98%

: 2380-94-1
1H-indol-4-ol

: 104-88-1
4-chlorobenzaldehyde

: 109-77-3
malononitrile

: 2-amino-4-(4-chlorophenyl)-4,6-dihydrooxepino[4,3,2-cd]indole-3-carbonitrile

Conditions

Conditions	Yield
With potassium fluoride In ethanol at 60℃; for 6h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Green chemistry;	98%
Stage #1: 4-chlorobenzaldehyde; malononitrile With guanine-functionalized mesoporous silica In ethanol at 20℃; for 0.333333h; Knoevenagel Condensation; Green chemistry; Stage #2: 1H-indol-4-ol In ethanol at 80℃; for 3.5h; Michael Addition; Green chemistry;	76%

...Expand

: 2380-94-1
1H-indol-4-ol

: 1426931-83-0
tert-butyl (1-benzyl-6-chloro-2-oxoindolin-3-ylidene)carbamate

: C28H26ClN3O4

Conditions

Conditions	Yield
With 3-(3,5-bis-trifluoromethyl-phenylamino)-4-{[(S)-(6-methoxy-quinolin-4-yl)-((R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-amino}-cyclobut-3-ene-1,2-dione In toluene at 25℃; for 12h; Friedel-Crafts Alkylation; enantioselective reaction;	98%

: 2380-94-1
1H-indol-4-ol

: (E) methyl 2-oxo-3-(2,2,2-trifluoroethylidene)indoline-1-carboxylate

: methyl (2-((3R,4S)-2-oxo-4-(trifluoromethyl)-2,3,4,7-tetrahydropyrano[2,3-e]indol-3-yl)phenyl)carbamate

Conditions

Conditions	Yield
With C32H28F6N4O3 In dichloromethane at -30℃; for 72h; Friedel-Crafts Alkylation; enantioselective reaction;	98%

: 2380-94-1
1H-indol-4-ol

: 123-54-6
acetylacetone

: 78-98-8
2-oxopropanal

: 3-acetyl-4-(4-hydroxy-1H-indol-3-yl)hexane-2,5-dione

Conditions

Conditions	Yield
In water at 80℃; for 5h;	98%

...Expand

: 2380-94-1
1H-indol-4-ol

: tert-butyl (3-ethyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)carbamate

: tert-butyl (S)-(3-ethyl-4-(4-hydroxy-1H-indol-5-yl)-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	98%

: 2380-94-1
1H-indol-4-ol

: tert-butyl (3-isopropyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)carbamate

: tert-butyl (S)-(4-(4-hydroxy-1H-indol-5-yl)-3-isopropyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	98%

: 2380-94-1
1H-indol-4-ol

: tert-butyl [5-oxo-1,3-diphenyl-1H-pyrazol-4(5H)-ylidene]carbamate

: tert-butyl (S)-(4-(4-hydroxy-1H-indol-5-yl)-5-oxo-1,3-diphenyl-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	98%

: 2380-94-1
1H-indol-4-ol

: 13081-18-0
ethyl-3,3,3-trifluoropyruvate

: ethyl 3,3,3-trifluoro-2-hydroxy-2-(4-hydroxy-1H-indol-3-yl)propanoate

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 20℃; Friedel-Crafts Acylation;	97%

: 5381-20-4
benzothiophene-3-carboxaldehyde

: 2380-94-1
1H-indol-4-ol

: 109-77-3
malononitrile

: 2-amino-4-(benzo[b]thiophen-3-yl)-4,6-dihydrooxepino[4,3,2-cd]indole-3-carbonitrile

Conditions

Conditions	Yield
With potassium fluoride In ethanol at 60℃; for 6h; Green chemistry;	97%

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: 2380-94-1
1H-indol-4-ol

: 26960-68-9
1-benzyl-5-chloroisatin

A: (S)-1-benzyl-5-chloro-3-hydroxy-3-(4-hydroxy-1H-indol-5-yl)indolin-2-one

B: (+)-(R)-1-benzyl-5-chloro-3-hydroxy-3-(4-hydroxy-1H-indol-5-yl)indolin-2-one

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In diethyl ether at 20 - 25℃; enantioselective reaction;	A n/a B 97%

...Expand

: 2380-94-1
1H-indol-4-ol

: C16H19N3O4

: tert-butyl (S)-(4-(4-hydroxy-1H-indol-5-yl)-1-(4-methoxyphenyl)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)carbamate

Conditions

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)phenyl)amino)-4-(((S)-(6-methoxyquinoline-4-yl))((1S,2S,4S,5R-5-vinylquinuclidine-2-yl)methyl)amino)cyclobutan-3-ene-1,2-dione In 1,2-dichloro-ethane at 0℃; Friedel-Crafts Alkylation; enantioselective reaction;	97%

4-Hydroxyindole Chemical Properties

IUPAC Name: 1H-indol-4-ol
Synonyms of 4-Hydroxyindole (CAS NO.2380-94-1): 4-Indolol
CAS NO: 2380-94-1
Molecular Formula: C₈H₇NO
Molecular Weight: 133.15
Molecular Structure:
EINECS: 219-177-2
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 14.16 Å²
Index of Refraction: 1.739
Molar Refractivity: 40.41 cm³
Molar Volume: 100.3 cm³
Surface Tension: 65.8 dyne/cm
Density: 1.327 g/cm³
Flash Point: 161.4 °C
Enthalpy of Vaporization: 61.03 kJ/mol
Boiling Point: 343.2 °C at 760 mmHg
Vapour Pressure: 3.61E-05 mmHg at 25°C
Melting Point: 97-99 °C(lit.)
Storage temp: 0-6°C
Water Solubility: slightly soluble
Sensitive: Air Sensitive
Appearance: Off-White Cyrstalline Solid
SMILES: c1cc2c(cc[nH]2)c(c1)O
InChI: InChI=1/C8H7NO/c10-8-3-1-2-7-6(8)4-5-9-7/h1-5,9-10H
InChIKey: NLMQHXUGJIAKTH-UHFFFAOYAU
Std. InChI: InChI=1S/C8H7NO/c10-8-3-1-2-7-6(8)4-5-9-7/h1-5,9-10H
Std. InChIKey: NLMQHXUGJIAKTH-UHFFFAOYSA-N
Product Categories of 4-Hydroxyindole (CAS NO.2380-94-1): blocks;IndolesOxindoles;Indoles and derivatives;pharmacetical;Heterocycles series;Pyrroles & Indoles;Indole;Indoles;Indole Derivatives;Simple Indoles;Chiral Compound;Pyrroles & Indoles

4-Hydroxyindole Uses

4-Hydroxyindole (CAS NO.2380-94-1) is used for pharmaceutical intermediates.

4-Hydroxyindole Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant
HazardClass: IRRITANT

4-Hydroxyindole Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store 4-Hydroxyindole (CAS NO.2380-94-1) in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.) Store under nitrogen.

Product Name

4-Hydroxyindole

Synthetic route

4-Hydroxyindole Chemical Properties

4-Hydroxyindole Uses

4-Hydroxyindole Safety Profile

4-Hydroxyindole Specification

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