15937-07-2

Basic information

• Product Name: 5,6-DiMethoxyindoline
• Synonyms: 5,6-DiMethoxyindoline;1H-INDOLE, 2,3-DIHYDRO-5,6-DIMETHOXY;6-broMo-7-MethyliMidazo[1,2-b]pyridazine;2,3-dihydro-5,6-diMethoxy-1H-Indole;5,6-diMethoxy-2,3-dihydro-1H-indole
• CAS NO: 15937-07-2
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.21572
• Mol File: 15937-07-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 105℃ (benzene )
• Boiling Point: 301.244°C at 760 mmHg
• Flash Point: 116.88°C
• Appearance: /
• Density: 1.102g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: 2-8°C
• PKA: 5.72±0.20(Predicted)
• CAS DataBase Reference: 5,6-DiMethoxyindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DiMethoxyindoline(15937-07-2)
• EPA Substance Registry System: 5,6-DiMethoxyindoline(15937-07-2)

Safety Data

• Hazardous Substances Data: 15937-07-2(Hazardous Substances Data)

Usage

Uses

5,6-Dimethoxyindoline is used in preparation of Biphenyl derivatives for treating obstructive airways disease.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 21, p. 548, 1978 DOI: 10.1021/jm00204a009

InChI:InChI=1/C10H13NO2/c1-12-9-5-7-3-4-11-8(7)6-10(9)13-2/h5-6,11H,3-4H2,1-2H3

Synthetic route

5,6-dimethoxyindole (14430-23-0) → 5,6-dimethoxyindoline (15937-07-2)

Conditions	Yield
With sodium cyanoborohydride; acetic acid for 0.5h; Ambient temperature;	92%
With sodium cyanoborohydride; acetic acid for 1.25h; Ambient temperature;	80%
With sodium cyanoborohydride; acetic acid at 20℃; for 1h;	56%
With sodium cyanoborohydride; acetic acid at 20℃; for 1h;

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → 5,6-dimethoxyindoline (15937-07-2)

Conditions	Yield
With naphthalene-1,4-dicarbonitrile; oxygen In methanol Irradiation; or with 9,10-dihydroanthracene, MeCN;	80%

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine (63375-81-5) → 5,6-dimethoxyindoline (15937-07-2)

Conditions	Yield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 70℃; for 45h; Inert atmosphere;	36%

2,2,2-trifluoro-N-<2-(2-iodo-4,5-dimethoxyphenyl)ethyl>acetamide (154138-43-9) → 5,6-dimethoxyindoline (15937-07-2)

Conditions	Yield
With potassium carbonate In methanol at 25 - 26℃; Inert atmosphere; Reflux;

5,6-dimethoxyindoline (15937-07-2) → 5,6-dimethoxyindole (14430-23-0)

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; Reagent/catalyst; Solvent; Sealed tube;	82%

5,6-dimethoxyindoline (15937-07-2) + 2-(4-bromobutyl)isoindoline-1,3-dione (5394-18-3) → C22H24N2O4 (1313202-17-3)

Conditions	Yield
With potassium carbonate; sodium iodide at 60℃; for 2h;	74%

5,6-dimethoxyindoline (15937-07-2) + 4-Fluoronitrobenzene (350-46-9) → 5,6-dimethoxy-1-(4-nitrophenyl)-indoline (441349-89-9)

Conditions	Yield
With sodium bicarbonate In dimethyl sulfoxide	65.6%

5,6-dimethoxyindoline (15937-07-2) → 5,6-dihydroxyindoline hydrobromide

Conditions	Yield
With hydrogen bromide at 140℃; for 3h;	62%

2-chloro-5-nitropyridine (4548-45-2) + 5,6-dimethoxyindoline (15937-07-2) → 5,6-Dimethoxy-1-(5-nitro-(2-pyridyl))-indoline (441349-90-2)

Conditions	Yield
With sodium bicarbonate In dimethyl sulfoxide	23.1%

5,6-dimethoxyindoline (15937-07-2) + 2,4-Diamino-5-methyl-pyrido[2,3-d]pyrimidine-6-carbaldehyde; compound with acetic acid → 6-(5,6-Dimethoxy-2,3-dihydro-indol-1-ylmethyl)-5-methyl-pyrido[2,3-d]pyrimidine-2,4-diamine

Conditions	Yield
With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride 1.) MeOH, 6 h, 2.) MeOH, 22 h; Yield given. Multistep reaction;

5,6-dimethoxyindoline (15937-07-2) → 4-(5,6-dimethoxyindolin-1-yl)butan-1-amine (1285549-15-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; sodium iodide / 2 h / 60 °C 2: hydrazine hydrate / methanol / 3 h / Reflux View Scheme

5,6-dimethoxyindoline (15937-07-2) → 5-bromo-N-(4-(5,6-dimethoxyindolin-1-yl)butyl)-2,3-dimethoxybenzamide (1285548-89-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; sodium iodide / 2 h / 60 °C 2: hydrazine hydrate / methanol / 3 h / Reflux 3: triethylamine / dichloromethane / 20 °C View Scheme

5,6-dimethoxyindoline (15937-07-2) → 1-(2-(5,6-dimethoxyindolin-1-yl)ethyl)-1H-pyrazol-4-amine (1394162-05-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 1 h / 20 °C 2: hydrogen / platinum(IV) oxide / methanol / 1 h / 20 °C View Scheme

5,6-dimethoxyindoline (15937-07-2) → 1-[2-(5,6-dimethoxy-indol-1-yl)-ethyl]-1H-pyrazol-4-ylamine (1394162-06-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tris(acetoxy)borohydride / dichloromethane / 1 h / 20 °C 2: hydrogen / platinum(IV) oxide / methanol / 1 h / 20 °C 3: manganese(IV) oxide / acetone / 20 °C View Scheme

5,6-dimethoxyindoline (15937-07-2) + 2-(4-nitro-1H-pyrazol-1-yl)acetaldehyde (1015939-59-9) → 5,6-dimethoxy-1-(2-(4-nitro-1H-pyrazol-1-yl)ethyl)indoline (1394162-04-9)

Conditions	Yield
Stage #1: 5,6-dimethoxyindoline; 2-(4-nitro-1H-pyrazol-1-yl)acetaldehyde With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h; Stage #2: With water In dichloromethane

5,6-dimethoxyindoline (15937-07-2) → C16H14N2O3*BrH

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetonitrile / 20 °C 2.1: boron tribromide / dichloromethane / 3 h / -78 - 25 °C / Inert atmosphere 2.2: 0.5 h / 0 °C 3.1: hydrogen bromide / water / 2.5 h / 0 - 25 °C View Scheme

5,6-dimethoxyindoline (15937-07-2) → C16H14N2O3*ClH

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetonitrile / 20 °C 2.1: boron tribromide / dichloromethane / 3 h / -78 - 25 °C / Inert atmosphere 2.2: 0.5 h / 0 °C 3.1: hydrogenchloride / methanol / 2.5 h / 0 - 25 °C View Scheme

5,6-dimethoxyindoline (15937-07-2) → 5-(5,6-dimethoxyindolin-1-yl)-6-methoxy-1H-indole

Conditions	Yield
In acetonitrile at 20℃;	11.5 g

5,6-dimethoxyindoline (15937-07-2) → 1-(6-hydroxy-1H-indol-5-yl)indoline-5,6-diol

Conditions	Yield
Multi-step reaction with 2 steps 1.1: acetonitrile / 20 °C 2.1: boron tribromide / dichloromethane / 3 h / -78 - 25 °C / Inert atmosphere 2.2: 0.5 h / 0 °C View Scheme

Upstream product

• 154138-43-9 2,2,2-trifluoro-N-<2-(2-iodo-4,5-dimethoxyphenyl)ethyl>acetamide 
• 63375-81-5 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine 
• 14430-23-0 5,6-dimethoxyindole 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 

Downstream Products

• 441349-89-9 5,6-dimethoxy-1-(4-nitrophenyl)-indoline 
• 1285548-89-1 5-bromo-N-(4-(5,6-dimethoxyindolin-1-yl)butyl)-2,3-dimethoxybenzamide 
• 14430-23-0 5,6-dimethoxyindole 
• 138937-28-7 5,6-dihydroxyindoline hydrobromide 

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