92-99-9

Basic information

• Product Name: N,N,2-trimethylquinolin-6-amine
• Synonyms: N,N,2-trimethylquinolin-6-amine;N,N,2-Trimethyl-6-quinolinamine;6-Dimethylamino-2-methylquinoline
• CAS NO: 92-99-9
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25296
• EINECS: 202-207-3
• Product Categories: Quinoline series
• Mol File: 92-99-9.mol
• Article Data: 19

Chemical Properties

• Melting Point: 101°C
• Boiling Point: 310.75°C (rough estimate)
• Flash Point: 433.5°C
• Appearance: /
• Density: 1.0859 (rough estimate)
• Vapor Pressure: 3.8E-25mmHg at 25°C
• Refractive Index: 1.6648 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 6.58±0.43(Predicted)
• CAS DataBase Reference: N,N,2-trimethylquinolin-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2-trimethylquinolin-6-amine(92-99-9)
• EPA Substance Registry System: N,N,2-trimethylquinolin-6-amine(92-99-9)

Safety Data

• Hazardous Substances Data: 92-99-9(Hazardous Substances Data)

Usage

General Description

N,N,2-trimethylquinolin-6-amine, also known as TMQA, is a chemical compound that belongs to the quinoline family. It is a derivative of quinoline with two methyl groups attached to the nitrogen atom, and an amine group attached to the sixth carbon atom. TMQA is often used as a building block in the synthesis of various organic compounds and pharmaceuticals. It has also been studied for its potential applications in the fields of medicine and materials science. TMQA exhibits interesting properties due to its unique structure, making it a valuable compound for research and industrial purposes.

InChI:InChI=1/C22H25BrCl2N6O/c23-17-5-7-21(29-12-17)31(14-16-4-6-19(24)20(25)11-16)10-2-9-28-22(32)27-8-1-3-18-13-26-15-30-18/h4-7,11-13,15H,1-3,8-10,14H2,(H,26,30)(H2,27,28,32)

Synthetic route

4-amino-N,N-dimethylaniline (99-98-9) + ethyl vinyl ether (109-92-2) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With iodine In benzene at 80℃; for 2h; Green chemistry;	83%

trans-Crotonaldehyde (123-73-9) + 4-amino-N,N-dimethylaniline (99-98-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride In water at 20℃; for 1h;	70%
With hydrogenchloride In water; toluene Inert atmosphere; Reflux;	62%
In toluene at 20℃;
In toluene at 20℃;

4-amino-N,N-dimethylaniline (99-98-9) + crotonaldehyde (123-73-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride In water	70%
With hydrogenchloride In water; toluene at 20℃;	70%
With hydrogenchloride In toluene Reflux;	65%

2-hydroxy-3-butene (598-32-3) + 4-amino-N,N-dimethylaniline (99-98-9) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Stage #1: 4-amino-N,N-dimethylaniline With acetic anhydride In tetrahydrofuran Inert atmosphere; Stage #2: 2-hydroxy-3-butene With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In tetrahydrofuran at 120℃; Inert atmosphere; Sealed tube;	65%

2-methylquinolin-6-amine (65079-19-8) + methyl iodide (74-88-4) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Stage #1: 2-methylquinolin-6-amine With sodium hydride In N,N-dimethyl-formamide at 40℃; for 3h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 40℃;	39%

C15H19N3O2 (78827-70-0) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 7-Dimethylamino-2-methyl-benzo[d][1,3]diazepine-3-carboxylic acid ethyl ester (78827-75-5)

Conditions	Yield
In benzene Irradiation;	A 32% B 26%

4-amino-N,N-dimethylaniline (99-98-9) + paracetaldehyde (123-63-7) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
With hydrogenchloride

2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; (84689-24-7) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature 2: 32 percent / benzene / Irradiation View Scheme

N,N-Dimethyl-4-nitroaniline (100-23-2) → 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium 10% on activated carbon; hydrogen / methanol / 0.33 h / 25 °C / 750.08 - 2250.23 Torr / Inert atmosphere 2.1: acetic anhydride / tetrahydrofuran / Inert atmosphere 2.2: 120 °C / Inert atmosphere; Sealed tube View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl iodide (74-88-4) → 6-(dimethylamino)-1,2-dimethylquinolin-1-ium iodide

Conditions	Yield
Sealed tube;	100%
In ethanol at 79℃; for 12h; Sealed tube;	25.06%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; (84689-24-7)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	88%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 2-phenyl-1,2,3,4-tetrahydroisoquinoline (3340-78-1) → N,N-dimethyl-2-((2-phenyl-1,2,3,4-tetrahydroisoquinoline-1-yl)methyl)quinoline-6-amine

Conditions	Yield
With C52H49B9CuN2P2; oxygen; m-Toluic acid In methanol; acetonitrile for 35h; Photolysis;	77%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → 6-(dimethylamino)quinoline-2-carboxaldehyde (1267631-83-3)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane; water at 80℃; for 4h;	58%
With selenium(IV) oxide	40%
With selenium(IV) oxide In 1,4-dioxane; water at 80℃; for 4h;	38%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → C14H20N2*I(1-)

Conditions	Yield
In ethanol at 60℃; for 12h;	43.72%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 6-(dimethylamino)-2-methylquinoline-5-carbaldehyde

Conditions	Yield
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In chloroform at 0℃; for 1h; Vilsmeier-Haack Formylation; Inert atmosphere; Stage #2: 6-(N,N-dimethylamino)-2-methylquinoline In chloroform for 16h; Vilsmeier-Haack Formylation; Reflux; Inert atmosphere;	38.6%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl p-toluene sulfonate (80-48-8) → 6-dimethylamino-1,2-dimethylquinolinium tosylate (902158-30-9)

Conditions	Yield
In chloroform for 14h; Solvent; Reflux;	34%
In chloroform for 12h; Heating / reflux;

1,4-butane sultone (1633-83-6) + 6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → C16H22N2O3S

Conditions	Yield
In 1,2-dichloro-benzene at 120℃; for 12h;	30.44%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde (83-18-1) → N,N-Dimethyl-2-((E)-2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)quinolin-6-amine

Conditions	Yield
Stage #1: 6-(N,N-dimethylamino)-2-methylquinoline; 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carbaldehyde With zinc(II) chloride In N,N-dimethyl-formamide at 160℃; Stage #2: With sodium hydroxide; water In N,N-dimethyl-formamide	2.1%

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-iodo-butane (542-69-8) → 1-butyl-6-dimethylamino-2-methyl-quinolinium; iodide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-Bromoheptane (629-04-9) → 6-dimethylamino-1-heptyl-2-methyl-quinolinium; bromide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 1-Iodoheptane (4282-40-0) → 6-dimethylamino-1-heptyl-2-methyl-quinolinium; iodide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 3-(4-dimethylamino-phenyl)-propenal (20432-35-3, 6203-18-5) → 6-dimethylamino-2-[4t-(4-dimethylamino-phenyl)-buta-1,3-dien-t-yl]-quinoline

Conditions	Yield
With hydrogenchloride

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → 1-ethyl-6-dimethylamino-2-methyl-quinolinium; iodide + ethyl-dimethyl-(2-methyl-[6]quinolyl)-ammonium; iodide

Conditions	Yield
at 140 - 150℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + allyl bromide (106-95-6) → 1-allyl-6-dimethylamino-2-methyl-quinolinium; bromide

Conditions	Yield
With ethanol

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + 4-dimethylamino-benzaldehyde (100-10-7) → [2-(4-dimethylamino-trans-styryl)-[6]quinolyl]-dimethyl-amine (36429-38-6)

Conditions	Yield
With hydrogenchloride at 120℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + methyl iodide (74-88-4) → trimethyl-<2-methyl-quinolyl-(6)>-ammonium iodide + 6-dimethylamino-quinaldine iodomethylate

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) + ethyl iodide (75-03-6) → ethyl-dimethyl-(2-methyl-[6]quinolyl)-ammonium; iodide + 1-ethyl-6-dimethylamino-2-methyl-quinolinium

Conditions	Yield
at 140 - 150℃;

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → 7-Dimethylamino-2-methyl-benzo[d][1,3]diazepine-3-carboxylic acid ethyl ester (78827-75-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / CH2Cl2 / 1 h / Ambient temperature 2: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature 3: 26 percent / benzene / Irradiation View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → C15H19N3O2 (78827-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / CH2Cl2 / 1 h / Ambient temperature 2: 20 percent / potassium carbonate / ethanol / 8 h / Ambient temperature View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → (6-(dimethylamino)quinolin-2-yl)methanol (1267895-81-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: selenium(IV) oxide / water; 1,4-dioxane / 4 h / 80 °C 2: sodium tetrahydroborate / ethanol / 1 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: selenium(IV) oxide / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: sodium tetrahydroborate; ethanol / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

6-(N,N-dimethylamino)-2-methylquinoline (92-99-9) → (6-(dimethylamino)quinolin-2-yl)methyl acetate (1221541-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: selenium(IV) oxide / water; 1,4-dioxane / 4 h / 80 °C 2: sodium tetrahydroborate / ethanol / 1 h / 20 °C 3: triethylamine; dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere; Darkness View Scheme

Upstream product

• 99-98-9 4-amino-N,N-dimethylaniline 
• 123-73-9 crotonaldehyde 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 598-32-3 2-hydroxy-3-butene 
• 109-92-2 ethyl vinyl ether 
• 123-73-9 trans-Crotonaldehyde 
• 65079-19-8 2-methylquinolin-6-amine 
• 74-88-4 methyl iodide 
• 84689-24-7 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; 
• 78827-70-0 C₁₅H₁₉N₃O₂ 
• 123-63-7 paracetaldehyde 

Downstream Products

• 84689-24-7 2,4,6-Trimethyl-benzenesulfonate1-amino-6-dimethylamino-2-methyl-quinolinium; 
• 35648-29-4 (E)-2-(2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl)-6-(dimethylamino)-1-methylquinolin-1-ium iodide 
• 3546-41-6 pyrvinium pamoate 
• 61791-77-3 (E)-2-[2-(2,5-dimethyl-1-phenyl-1H-pyrrol-3-yl)vinyl]-1-methyl-6-(dimethylamino)quinolinium methyl sulphate salt 
• 902158-30-9 6-dimethylamino-1,2-dimethylquinolinium tosylate 

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