4-[2-(Methyl-2-pyridinylamino)ethoxy]benzaldehyde supplier

Name
4-[2-[METHYL(PYRIDINE-2-YL)AMINO]ETHOXY]-BENZALDEHYDE
EINECS
CAS No. 122321-03-3
Article Data21
CAS DataBase
Density 1.18 g/cm³
Solubility
Melting Point
Formula C₁₅H₁₆N₂O₂
Boiling Point 440.906 °C at 760 mmHg
Molecular Weight 256.304
Flash Point 220.452 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 4-[2-(N-Methyl-N-(2-pyridyl)amino]ethoxy]benzaldehyde;4-[2-[(Methyl)(pyridin-2-yl)amino]ethoxy]benzaldehyde;
PSA 42.43000
LogP 2.40930

Synthetic route

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

: 459-57-4
4-fluorobenzaldehyde

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
With potassium hexamethylsilazane at 60℃; for 1h; Temperature; Williamson Ether Synthesis;	92.3%
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In water; toluene at 85℃; for 0.333333h; Sealed vessel; Microwave irradiation;	90%
Stage #1: 2-(N-methyl-N-(pyridin-2-yl)amino)ethanol With sodium hydride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 4-fluorobenzaldehyde In N,N-dimethyl-formamide at 24 - 50℃; for 24h; Inert atmosphere;	50%

: 196810-03-4
{4-[2-(methylpyridin-2-ylamino)ethoxy]pheny}methanol

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
With polymer-supported chromic acid In tetrahydrofuran for 48h; Heating;	86%
With PS-CrO3 In tetrahydrofuran

: 1014990-30-7
4-(2-[methyl(pyridine-2-yl)amino]ethoxy)benzonitrile

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Stage #1: 4-(2-[methyl(pyridine-2-yl)amino]ethoxy)benzonitrile With formic acid; water; Raney nickel at 30 - 105℃; for 4h; Stage #2: With ammonia; water In water at 5 - 10℃; pH=4.7 - 5;	82%

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

: 123-08-0
4-hydroxy-benzaldehyde

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 80℃; for 0.666667h; Microwave irradiation;	41%

: 372-48-5
2-fluoropyridine

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 24 h / 120 °C 2: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 120 °C 2: PS-CrO3 / tetrahydrofuran View Scheme

: 623-05-2
(4-hydroxyphenyl)methanol

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 96 percent / K2CO3 / dimethylformamide / 2 h / 90 °C 2.1: 100 percent / Amberlyst H-15 / tetrahydrofuran / 48 h / 20 °C 3.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 3.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 3.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 4.1: 82 percent / 24 h / 120 °C 5.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 90 °C 2.1: H-15 / tetrahydrofuran 3.1: borane-THF / 65 °C 3.3: SCX-2 4.1: 120 °C 5.1: PS-CrO3 / tetrahydrofuran View Scheme

Yield

Multi-step reaction with 5 steps
1.1: 96 percent / K2CO3 / dimethylformamide / 2 h / 90 °C
2.1: 100 percent / Amberlyst H-15 / tetrahydrofuran / 48 h / 20 °C
3.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C
3.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C
3.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C
4.1: 82 percent / 24 h / 120 °C
5.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating
View Scheme

Multi-step reaction with 5 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 90 °C
2.1: H-15 / tetrahydrofuran
3.1: borane-THF / 65 °C
3.3: SCX-2
4.1: 120 °C
5.1: PS-CrO3 / tetrahydrofuran
View Scheme

: 103258-64-6
ethyl 2-(4-hydroxymethylphenoxy)acetate

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 100 percent / Amberlyst H-15 / tetrahydrofuran / 48 h / 20 °C 2.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 2.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 2.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 3.1: 82 percent / 24 h / 120 °C 4.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: H-15 / tetrahydrofuran 2.1: borane-THF / 65 °C 2.3: SCX-2 3.1: 120 °C 4.1: PS-CrO3 / tetrahydrofuran View Scheme

: 142558-11-0
4-[2-(methylamino)ethoxypheny]methanol

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / 24 h / 120 °C 2: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 120 °C 2: PS-CrO3 / tetrahydrofuran View Scheme

: 666846-74-8
2-[4-(hydroxymethyl)phenoxy]-N-methylacetamide

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: BH3*THF / tetrahydrofuran / 24 h / 65 °C 1.2: aq. HCl / tetrahydrofuran / 1 h / 20 °C 1.3: 84 percent / Et2NH / tetrahydrofuran / 16 h / 20 °C 2.1: 82 percent / 24 h / 120 °C 3.1: 86 percent / polymer-supported chromic acid / tetrahydrofuran / 48 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: borane-THF / 65 °C 1.3: SCX-2 2.1: 120 °C 3.1: PS-CrO3 / tetrahydrofuran View Scheme

: 109-09-1
2-chloropyridine

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / 15 h / 120 °C 2: 1.) NaH / 1.) DMF, RT, 2.) DMF, RT, 18 h View Scheme
Multi-step reaction with 2 steps 1: 145 - 155 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 10 h / 25 - 35 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 13 h / 120 °C / Neat (no solvent) 2: sodium hydride / N,N-dimethyl-formamide / 80 °C View Scheme

: 459-57-4
4-fluorobenzaldehyde

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

Conditions

Conditions	Yield
Stage #1: 2-(N-methyl-N-(pyridin-2-yl)amino)ethanol With potassium hydroxide In DMF (N,N-dimethyl-formamide) at 20℃; for 2h; Stage #2: 4-fluorobenzaldehyde In DMF (N,N-dimethyl-formamide) at 20 - 40℃; for 24h;

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

: 459-57-4
4-fluorobenzaldehyde

A 4-[2-(N-Methyl-N-[2-(4,5-dimethyloxazolyl)]amino) ethoxy]benzaldehyde: 4-[2-(N-Methyl-N-[2-(4,5-dimethyloxazolyl)]amino) ethoxy]benzaldehyde

B: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

...Expand

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

: 459-57-4
4-fluorobenzaldehyde

A 4-[2-(N-Methyl-N-2-(4,5-dimethyloxazolyl)]amino) ethoxy]benzaldehyde: 4-[2-(N-Methyl-N-2-(4,5-dimethyloxazolyl)]amino) ethoxy]benzaldehyde

B: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

...Expand

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

: 459-57-4
4-fluorobenzaldehyde

A 4-[2-(N-Methyl-N-[2-(4,5-dimethyloxazolyl)]amino)ethoxy]benzaldehyde: 4-[2-(N-Methyl-N-[2-(4,5-dimethyloxazolyl)]amino)ethoxy]benzaldehyde

B: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

...Expand

: 2295-31-0
2,4-thiazolidinedion

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 160596-25-8
(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione

Conditions

Conditions	Yield
With piperazinomethyl polystyrene In toluene at 88℃; for 24h;	99%
With piperdinium acetate In toluene for 2h; Heating;	95%
With piperidine; silica gel; acetic acid In toluene at 130℃; for 0.333333h; Knoevenagel condensation; Microwave irradiation; Sealed vessel;	93%

: 2295-31-0
2,4-thiazolidinedion

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 122320-74-5
5-{4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzylidene}thiazolin-2,4-dione

Conditions

Conditions	Yield
With pyrrolidine; acetic acid In toluene for 3h; Heating; Reflux;	95%
In toluene for 5h; Reflux;	95.3%
piperdinium acetate In toluene for 5h; Heating / reflux;

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 196810-03-4
{4-[2-(methylpyridin-2-ylamino)ethoxy]pheny}methanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 0.5h;	94%

: 790-04-5
3-phenyl-2-(phenylimino)-1,3-thiazolidin-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-phenyl-2-(phenylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 1h; Reflux;	89.2%

: 3-isopropyl-2-hydroxyimino-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-isopropyl-2-(hydroxylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 3.5h; Reflux;	87.5%

: 2295-31-0
2,4-thiazolidinedion

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-{-4-[2-(N-methyl-N-(2-pyridyl)-amino)-ethoxy]-benzylidene}-2,4-thiazolidinedione

Conditions

Conditions	Yield
With piperidine; acetic acid In toluene at 130 - 140℃; for 1h; Product distribution / selectivity; Heating / reflux;	87%

: 3-(3-trifluoromethylphenyl)-2-(3-trifluoromethylphenylimino)-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-(3-trifluoro methylphenyl)-2-(3-trifluoromethylphenylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 9h; Reflux;	69.2%

: 2295-31-0
2,4-thiazolidinedion

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 122320-73-4
rosiglitazone

Conditions

Conditions	Yield
Stage #1: thiazoline-2,4-dione; 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde With pyrrolidine; acetic acid In toluene at 110℃; for 2h; Stage #2: With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silica gel In toluene for 13h; Product distribution / selectivity; Heating / reflux;	58%

: 38825-42-2
3-(4-methylphenyl)-2-(4-methylphenylimino)-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-(4-methylphenyl)-2-(4-methylphenylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 9h; Reflux;	52.7%

: 3-(3-chloro-2-methylphenyl)-2-(3-chloro-2-methylphenylimino)-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-(3-chloro-2-methylphenyl)-2-(3-chloro-2-methyl phenylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 1h; Reflux;	35.5%

: 537660-16-5
3-n-butyl-2-(n-butylimino)-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-n-butyl-1,3-thiazolidine-2,4-dione

Conditions

Conditions	Yield
With pyridine In ethanol for 9h; Reflux;	32.3%

: 39139-62-3
3-(4-methoxyphenyl)-2-(4-methoxyphenylimino)-1,3-thiazolidine-4-one

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 5-[[4-[2-[N-methyl-N-(2-pyridyl)]amino]ethoxy]phenylmethylene]-3-(4-methoxyphenyl)-2-(4-methoxyphenylimino)-1,3-thiazolidine-4-one

Conditions

Conditions	Yield
With pyridine In ethanol for 9h; Reflux;	30.3%

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 189640-64-0
2-[N-[2-(4-chloromethylphenoxy)ethyl]-N-methylamino]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 2: thionyl chloride / toluene / 0.5 h / 20 °C View Scheme

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 1027314-55-1
4-{(E)-4-[2-(Methyl-pyridin-2-yl-amino)-ethoxy]-benzyloxyimino}-4-phenyl-butyric acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 94 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 2: thionyl chloride / toluene / 0.5 h / 20 °C 3: sodium hydride / dimethylformamide / 2 h / 0 °C View Scheme

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: (E)-4-{4-[2-(methyl-2-pyridylamino)ethoxy]benzyloxyimino}-4-phenylbutyric acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / 20 °C 2: thionyl chloride / toluene / 0.5 h / 20 °C 3: sodium hydride / dimethylformamide / 2 h / 0 °C 4: 1 M aq. NaOH / tetrahydrofuran; methanol / 2 h / 20 °C View Scheme

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: (+)-Rosiglitazone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / piperidine, acetic acid / toluene / 1.) reflux, 4 h, 2.) room temperature, overnight 2: Rhodotorula rubra CBS 6469, pH 3 / dioxane / 4 h View Scheme

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: (-)-Rosiglitazone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / piperidine, acetic acid / toluene / 1.) reflux, 4 h, 2.) room temperature, overnight 2: Mg, I2 / methanol View Scheme

: 122321-03-3
4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

: 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzaldehyde sodium metabisulphite complex

Conditions

Conditions	Yield
With sodium disulfite In industrial spirit; water at 10 - 20℃; for 1.25 - 2.33333h; Product distribution / selectivity;
With sodium disulfite In methanol; water at 10 - 20℃; for 2.25 - 2.33333h; Product distribution / selectivity;

4-[2-(Methyl-2-pyridinylamino)ethoxy]benzaldehyde Specification

The 4-[2-(Methyl-2-pyridinylamino)ethoxy]benzaldehyde, with the CAS registry number 122321-03-3, is also known as Benzaldehyde, 4-[2-(methyl-2-pyridinylamino)ethoxy]-. This chemical's molecular formula is C₁₅H₁₆N₂O₂ and molecular weight is 256.30. Its systematic name is called 4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde.

Physical properties of 4-[2-(Methyl-2-pyridinylamino)ethoxy]benzaldehyde: (1)ACD/LogP: 2.93; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 8; (5)ACD/BCF (pH 7.4): 60; (6)ACD/KOC (pH 5.5): 80; (7)ACD/KOC (pH 7.4): 636; (8)#H bond acceptors: 4; (9)#H bond donors: 0; (10)#Freely Rotating Bonds: 6; (11)Index of Refraction: 1.62; (12)Molar Refractivity: 76.293 cm³; (13)Molar Volume: 217.214 cm³; (14)Surface Tension: 50.938 dyne/cm; (15)Density: 1.18 g/cm³; (16)Flash Point: 220.452 °C; (17)Enthalpy of Vaporization: 69.811 kJ/mol; (18)Boiling Point: 440.906 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
SMILES: O=Cc2ccc(OCCN(c1ncccc1)C)cc2
InChI: InChI=1/C15H16N2O2/c1-17(15-4-2-3-9-16-15)10-11-19-14-7-5-13(12-18)6-8-14/h2-9,12H,10-11H2,1H3
InChIKey: FRMKJZNBTRONBV-UHFFFAOYAO

Product Name

4-[2-[METHYL(PYRIDINE-2-YL)AMINO]ETHOXY]-BENZALDEHYDE

Synthetic route

4-[2-(Methyl-2-pyridinylamino)ethoxy]benzaldehyde Specification

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