36946-70-0

Basic information

• Product Name: 2-Aminoindole hydrochloride
• Synonyms: 1H-INDOL-2-AMINE HCL;2-AMINOINDOLE, HYDROCHLORIDE;1H-indol-2-aMine hydrochloride;2-AMinoindoleHCL
• CAS NO: 36946-70-0
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 168.62
• Product Categories: Nitrogen cyclic compounds;Indole Derivatives;Heterocycle-Indole series
• Mol File: 36946-70-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 215-220°C dec.
• Boiling Point: 372.4°C at 760 mmHg
• Flash Point: 179°C
• Appearance: /
• Density: 1.268±0.06 g/cm3(Predicted)
• Vapor Pressure: 6.6E-06mmHg at 25°C
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 18.89±0.30(Predicted)
• CAS DataBase Reference: 2-Aminoindole hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminoindole hydrochloride(36946-70-0)
• EPA Substance Registry System: 2-Aminoindole hydrochloride(36946-70-0)

Safety Data

• Hazardous Substances Data: 36946-70-0(Hazardous Substances Data)

Usage

Chemical Properties

Pale Brown Solid

InChI:InChI=1/C8H8N2.ClH/c9-8-5-6-3-1-2-4-7(6)10-8;/h1-5,10H,9H2;1H

Synthetic route

(1H-indol-1-yl)(pyridin-2-yl)methanone (1131148-08-7) → indoleamine (36946-70-0)

Conditions	Yield
Stage #1: (1H-indol-1-yl)(pyridin-2-yl)methanone With tert.-butylnitrite; copper diacetate In 1,4-dioxane at 70℃; for 16h; Stage #2: With hydrazine hydrate; FeCl3/C In 1,4-dioxane; ethanol at 70℃;	93%

2-nitroindole (193686-70-3) → indoleamine (36946-70-0)

Conditions	Yield
With sodium tetrahydroborate In water at 60℃; for 0.25h; Sonication;	88%

2-nitro-benzeneacetonitrile (610-66-2) → indoleamine (36946-70-0)

Conditions	Yield
With hydrogenchloride In ethanol at 30℃; for 3h;	52%

2-methyl-2-pyrrolidin-1-yl-propan-1-ol (101258-96-2) + 5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester (27667-51-2) + Toluene-2-sulfonyl chloride (133-59-5) → indoleamine (36946-70-0) + 2-Methyl-5-(2-methyl-2-pyrrolidin-1-yl-propoxy)-1H-indole-3-carboxylic acid benzyl ester (459449-48-0)

Conditions	Yield
With potassium carbonate; triethylamine; trifluoroacetic acid In acetonitrile	A n/a B 5%

2-aminophenylacetonitrile (2973-50-4) + sodium ethanolate (141-52-6) + hydrogen → indoleamine (36946-70-0)

(2-formylamino-phenyl)-acetonitrile (861571-31-5) + potassium carbonate → indoleamine (36946-70-0)

indoleamine (36946-70-0) + 1-Phenyl-4,4,4-trifluorobutane-1,3-dione (326-06-7) → 2-phenyl-4-(trifluoromethyl)-9H-pyrido[2,3-b]indole (869465-09-8)

Conditions	Yield
With acetic acid for 1h; Heating;	89%
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	89%

indoleamine (36946-70-0) + sodium 5,5,6,6,6-pentafluoro-2,4-hexanedione (356-40-1) → 2-methyl 4-(perfluoroethyl)-9H-pyrido[2,3-b]indole (1190370-62-7)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	87%

indoleamine (36946-70-0) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → 2,4-bis(trifluoromethyl)-9H-pyrido[2,3-b]indole (869465-16-7)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	86%

indoleamine (36946-70-0) + 1-Chlor-1,1-difluor-3-benzoyl-aceton (2062-21-7) → 4-(chlorodifluoromethyl)-2-phenyl-9H-pyrido[2,3-b]indole (869465-10-1)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	85%

indoleamine (36946-70-0) + 1,1,1-Trifluoro-2,4-pentanedione (367-57-7) → 2-methyl-4-(trifluoromethyl)-9H-pyrido[2,3-b]indole (1018966-60-3)

Conditions	Yield
With acetic acid for 1h; Heating;	84%
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	84%

indoleamine (36946-70-0) + 1,1-difluoro-1-phenyl-1,3-butanedione (41739-23-5) → 4-(difluoromethyl)-2-methyl-9H-pyrido[2,3-b]indole (1018966-65-8)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	81%

indoleamine (36946-70-0) + α-(2,2,2-trifluoroacetyl)-δ-valerolactone → 3-(3-hydroxypropyl)-4-(trifluoromethyl)-1,9-dihydro-2H-pyrido[2,3-b]indol-2-one (1190370-42-3)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	74%

indoleamine (36946-70-0) + 3-[(2-chlorophenyl)hydrazono]pentane-2,4-dione (24756-05-6) → 3-(2-chlorophenyldiazenyl)-2,4-dimethyl-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	68%

indoleamine (36946-70-0) + perfluorobenzaldehyde (653-37-2) → 1,2,3,4-tetrafluoro-6H-indolo[2,3-b]quinoline (1190370-41-2) + C15H10F5N3

Conditions	Yield
With acetic acid In N,N-dimethyl-formamide Inert atmosphere; Reflux; regiospecific reaction;	A 67% B n/a

indoleamine (36946-70-0) + 2-(2,2,2-trifluoroacetyl)-3,4-dihydro-2H-naphthalen-1-one (318-46-7) → 7-(trifluoromethyl)-6,12-dihydro-5H-12,13-diazaindeno[1,2-b]phenanthrene (869465-12-3)

Conditions	Yield
With acetic acid for 2h; Inert atmosphere; Reflux; regiospecific reaction;	64%

indoleamine (36946-70-0) + S-ketoprofen (22161-81-5) → 2-(3-benzoylphenyl)-N-(1H-indol-2-yl)propanamide (1239447-49-4)

Conditions	Yield
Stage #1: S-ketoprofen With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: indoleamine In N,N-dimethyl-formamide at 20℃; for 2h;	62%

indoleamine (36946-70-0) + benzaldehyde (100-52-7) → 2,4-diphenyl-5H-pyrimido[5,4-b]indole (56807-26-2)

Conditions	Yield
With ammonium iodide; oxygen; sodium hydrogencarbonate; dimethyl sulfoxide In chlorobenzene at 140℃; for 16h; Molecular sieve; Inert atmosphere;	57%

indoleamine (36946-70-0) + 3-(2-(4-bromophenyl)hydrazineylidene) pentane-2,4-dione (24756-09-0) → 3-(4-bromophenyldiazenyl)-2,4-dimethyl-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	51%

indoleamine (36946-70-0) + pentane-2,3,4-trione 3-[(3-nitro-phenyl)-hydrazone] (3490-72-0) → 2,4-dimethyl-3-(3-nitrophenyldiazenyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	50%

3-[(2-bromo-phenyl)-hydrazono]-pentane-2,4-dione + indoleamine (36946-70-0) → 3-(2-bromophenyldiazenyl)-2,4-dimethyl-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	49%

indoleamine (36946-70-0) + 4-ethyl 4-(2-(2,4-dioxopentan-3-ylidene)hydrazineyl)benzoate (41095-26-5) → ethyl 4-(2,4-dimethyl-9H-pyrido[2,3-b]indol-3-yldiazenyl)benzoate

Conditions	Yield
With pyridine at 20℃; for 72h;	48%

3-[(2-iodo-phenyl)-hydrazono]-pentane-2,4-dione + indoleamine (36946-70-0) → 3-(2-iodophenyldiazenyl)-2,4-dimethyl-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	45%

indoleamine (36946-70-0) + benzoyl chloride (98-88-4) → 2-(benzoylamino)indole (92264-37-4) + 1-benzoyl-2-benzamidoindole

Conditions	Yield
With pyridine; dmap for 1h; Ambient temperature;	A 35% B 14%

indoleamine (36946-70-0) + C12H12O3 (1612153-85-1) → C20H16N2O (1612154-11-6)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 120℃; Michael Addition; Microwave irradiation;	34%

indoleamine (36946-70-0) + 1-(3-hydroperoxyprop-1-ynyl)-4-methoxybenzene (1416983-93-1) → 2-(4-methoxyphenyl)-9H-pyrido[2,3-b]indole (1175675-37-2) + C18H14N2O (1612154-12-7)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 120℃; Michael Addition; Microwave irradiation;	A 30% B 28%

indoleamine (36946-70-0) + ethyl 3-(ethoxymethylene)-2,4-dioxovalerate (57397-70-3) → ethyl 3-acetyl-9H-pyrimido<2,3-b>indole-4-carboxylate (77740-29-5)

Conditions	Yield
In ethanol for 2h;	28%

indoleamine (36946-70-0) + C9H7BrO2 (1416984-00-3) → C17H11BrN2 (1612154-09-2) + C17H11BrN2 (1612154-13-8)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 120℃; Michael Addition; Microwave irradiation;	A 26% B 23%

indoleamine (36946-70-0) + diethyl(ethoxymethylene)oxalacetate (52942-64-0) → diethyl 9H-pyrimido<2,3-b>indole-3,4-dicarboxylate (77740-30-8)

Conditions	Yield
In ethanol for 2h;	25%

indoleamine (36946-70-0) + C16H14O3 (1612153-84-0) → C24H18N2O (1612154-10-5) + C24H18N2O (1612154-14-9)

Conditions	Yield
With (triphenylphosphine)gold(I) chloride; water; silver trifluoromethanesulfonate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 120℃; Michael Addition; Microwave irradiation;	A 24% B 25%

indoleamine (36946-70-0) + 3-[(2-methylphenyl)hydrazono]pentane-2,4-dione (24756-03-4) → 2,4-dimethyl-3-(2-methylphenyldiazenyl)-9H-pyrido[2,3-b]indole

Conditions	Yield
With pyridine at 20℃; for 72h;	19%

indoleamine (36946-70-0) + (5α,17α)-17-hydroxy-2-(hydroxymethylene)pregn-20-yn-3-one (78094-38-9, 138231-82-0) → C30H34N2O (138091-32-4)

Conditions	Yield
In ethanol Heating;	18%

indoleamine (36946-70-0) + (5α,17α)-17-hydroxy-2-(hydroxymethylene)pregn-20-yn-3-one (78094-38-9, 138231-82-0) → C30H34N2O (138091-31-3)

Conditions	Yield
In ethanol Heating;	18%

Upstream product

• 610-66-2 2-nitro-benzeneacetonitrile 
• 2973-50-4 2-aminophenylacetonitrile 
• 141-52-6 sodium ethanolate 
• 861571-31-5 (2-formylamino-phenyl)-acetonitrile 
• 101258-96-2 2-methyl-2-pyrrolidin-1-yl-propan-1-ol 
• 27667-51-2 5-Hydroxy-2-methyl-1H-indole-3-carboxylic acid benzyl ester 
• 133-59-5 Toluene-2-sulfonyl chloride 
• 1131148-08-7 (1H-indol-1-yl)(pyridin-2-yl)methanone 
• 193686-70-3 2-nitroindole 

Downstream Products

• 271-26-1 3H-indole 
• 68006-83-7 3-Methyl-2-Amino-alpha-carboline 
• 79801-90-4 2-amino-3-propyl-9H-pyrido<2,3-b>indole 
• 79801-91-5 2-amino-3-butyl-9H-pyrido<2,3-b>indole 
• 79801-92-6 2-amino-3-amyl-9H-pyrido<2,3-b>indole 
• 79801-93-7 2-amino-3-benzyl-9H-pyrido<2,3-b>indole 
• 869465-09-8 2-phenyl-4-(trifluoromethyl)-9H-pyrido[2,3-b]indole 
• 1190370-41-2 1,2,3,4-tetrafluoro-6H-indolo[2,3-b]quinoline 
• 869465-10-1 4-(chlorodifluoromethyl)-2-phenyl-9H-pyrido[2,3-b]indole 
• 1175675-37-2 2-(4-methoxyphenyl)-9H-pyrido[2,3-b]indole 
• 1612154-12-7 C₁₈H₁₄N₂O 
• 1612154-10-5 C₂₄H₁₈N₂O 
• 1612154-14-9 C₂₄H₁₈N₂O 
• 1612154-11-6 C₂₀H₁₆N₂O 

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