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1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE, also known as 2-Acetyl-6-methylpyridine, is an organic compound with a molecular structure that features a pyridine ring with a methyl group at the 6th position and an acetyl group at the 1st position. It is characterized by its distinct chemical properties and versatile applications in various industries.

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  • 6940-57-4 Structure
  • Basic information

    1. Product Name: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE
    2. Synonyms: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE;2-ACETYL-6-METHYLPYRIDINE;1-(6-Methyl-2-pyridinyl)ethanone;6-Acetyl-2-methylpyridine;1-(6-Methylpyridin-2-yl)ethan-1-one;2-ACETYL-6-METHYLPYRIDINE 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE;Ethanone, 1-(6-methyl-2-pyridinyl)-;6-methyl-2-acetylpyridine
    3. CAS NO:6940-57-4
    4. Molecular Formula: C8H9NO
    5. Molecular Weight: 135.16
    6. EINECS: N/A
    7. Product Categories: Pyridine series;Building Blocks;Pyridine;Pyridines
    8. Mol File: 6940-57-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 209℃
    3. Flash Point: 84°(183°F)
    4. Appearance: Pale yellow/Solid
    5. Density: 1.036 g/cm3
    6. Vapor Pressure: 0.208mmHg at 25°C
    7. Refractive Index: 1.5150
    8. Storage Temp.: Inert atmosphere,Room Temperature
    9. Solubility: N/A
    10. PKA: 3.24±0.10(Predicted)
    11. CAS DataBase Reference: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(6940-57-4)
    13. EPA Substance Registry System: 1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE(6940-57-4)
  • Safety Data

    1. Hazard Codes: Xi,Xn
    2. Statements: 36/37/38-22
    3. Safety Statements: 26-36
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6940-57-4(Hazardous Substances Data)

6940-57-4 Usage

Uses

Used in Flavor Industry:
1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE is used as a flavor constituent for its unique aromatic properties, specifically in the production of rum. It imparts a distinct flavor profile to the beverage, enhancing its overall taste and quality.
Used in Synthetic and Industrial Applications:
1-(6-METHYL-PYRIDIN-2-YL)-ETHANONE serves as a valuable synthetic and industrial reagent due to its chemical reactivity and stability. It is utilized in the synthesis of various compounds and as an intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatility as a reagent makes it an essential component in the development of new and innovative products across different industries.

Check Digit Verification of cas no

The CAS Registry Mumber 6940-57-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,9,4 and 0 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6940-57:
(6*6)+(5*9)+(4*4)+(3*0)+(2*5)+(1*7)=114
114 % 10 = 4
So 6940-57-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO/c1-6-4-3-5-8(9-6)7(2)10/h3-5H,1-2H3

6940-57-4 Well-known Company Product Price

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  • Alfa Aesar

  • (H65997)  2-Acetyl-6-methylpyridine, 98%   

  • 6940-57-4

  • 250mg

  • 155.0CNY

  • Detail
  • Alfa Aesar

  • (H65997)  2-Acetyl-6-methylpyridine, 98%   

  • 6940-57-4

  • 1g

  • 494.0CNY

  • Detail
  • Alfa Aesar

  • (H65997)  2-Acetyl-6-methylpyridine, 98%   

  • 6940-57-4

  • 5g

  • 2058.0CNY

  • Detail

6940-57-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-(6-methylpyridin-2-yl)ethanone

1.2 Other means of identification

Product number -
Other names Ketone,methyl 6-methyl-2-pyridyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6940-57-4 SDS

6940-57-4Synthetic route

N-methoxy-N,6-dimethylpyridine-2-carboxamide
476471-33-7

N-methoxy-N,6-dimethylpyridine-2-carboxamide

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 20℃; for 2h; Inert atmosphere;100%
(+/-)-1-[2-(6-methylpyridyl)]ethanol
71777-66-7

(+/-)-1-[2-(6-methylpyridyl)]ethanol

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
Stage #1: (+/-)-1-[2-(6-methylpyridyl)]ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333h;
Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2h;
92%
oxalyl dichloride
79-37-8

oxalyl dichloride

(+/-)-1-[2-(6-methylpyridyl)]ethanol
71777-66-7

(+/-)-1-[2-(6-methylpyridyl)]ethanol

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide92%
2-bromo-6-methylpyridine
5315-25-3

2-bromo-6-methylpyridine

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane88%
With n-butyllithium In diethyl ether; hexane24%
With n-butyllithium 1.) diethyl ether, hexane, THF, -78 deg C, 2.) diethyl ether, hexane, THF, 5-30 min; Multistep reaction;
N-methoxy-N,6-dimethylpyridine-2-carboxamide
476471-33-7

N-methoxy-N,6-dimethylpyridine-2-carboxamide

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
In tetrahydrofuran at -30 - 20℃; for 2h; Inert atmosphere;100%
(+/-)-1-[2-(6-methylpyridyl)]ethanol
71777-66-7

(+/-)-1-[2-(6-methylpyridyl)]ethanol

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
Stage #1: (+/-)-1-[2-(6-methylpyridyl)]ethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -75℃; for 1.33333h;
Stage #2: With triethylamine In dichloromethane at -75 - 20℃; for 2h;
92%
oxalyl dichloride
79-37-8

oxalyl dichloride

(+/-)-1-[2-(6-methylpyridyl)]ethanol
71777-66-7

(+/-)-1-[2-(6-methylpyridyl)]ethanol

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide92%
2-bromo-6-methylpyridine
5315-25-3

2-bromo-6-methylpyridine

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; diethyl ether; hexane88%
With n-butyllithium In diethyl ether; hexane24%
With n-butyllithium 1.) diethyl ether, hexane, THF, -78 deg C, 2.) diethyl ether, hexane, THF, 5-30 min; Multistep reaction;
2-Cyano-6-methylpyridine
1620-75-3

2-Cyano-6-methylpyridine

methylmagnesium bromide
75-16-1

methylmagnesium bromide

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
Stage #1: 2-Cyano-6-methylpyridine; methylmagnesium bromide In tetrahydrofuran; diethyl ether at -20 - -10℃;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at -40℃; for 0.0833333h;
83%
In tetrahydrofuran at -20℃; for 5h;72%
2-Cyano-6-methylpyridine
1620-75-3

2-Cyano-6-methylpyridine

methyllithium
917-54-4

methyllithium

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
In diethyl ether at -78℃; for 6h; Inert atmosphere;78%
6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With sodium ethanolate In ethyl acetate Acidic conditions;68%
2-methyl-6-vinylpyridine
1122-70-9

2-methyl-6-vinylpyridine

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With sodium hydroxide; chlorine
β-oxo-β-<6-methyl-pyridyl-(2)>-propionic acid ethyl ester

β-oxo-β-<6-methyl-pyridyl-(2)>-propionic acid ethyl ester

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
With hydrogenchloride
hydrogenchloride
7647-01-0

hydrogenchloride

3-(6-methyl-[2]pyridyl)-3-oxo-propionic acid ethyl ester; potassium-compound

3-(6-methyl-[2]pyridyl)-3-oxo-propionic acid ethyl ester; potassium-compound

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

6-methyl-2-pyridinecarboxylic acid
934-60-1

6-methyl-2-pyridinecarboxylic acid

2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Acidic conditions
2: sodium ethanolate / ethyl acetate / Acidic conditions
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 3 h / 20 °C
2: tetrahydrofuran / 2 h / -30 - 20 °C / Inert atmosphere
View Scheme
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-bromo-1-(6-methyl-pyridin-2-yl)-ethanone hydrobromide
147097-80-1

2-bromo-1-(6-methyl-pyridin-2-yl)-ethanone hydrobromide

Conditions
ConditionsYield
With hydrogen bromide; bromine; acetic acid In dichloromethane at 20℃; for 3h; Cooling with ice;95%
With hydrogen bromide; bromine; acetic acid for 1h;
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

1-(6-methyl-1-oxido-2-pyridinyl)ethanone
1563017-55-9

1-(6-methyl-1-oxido-2-pyridinyl)ethanone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;94%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

ethylene glycol
107-21-1

ethylene glycol

2-methyl-6-(2-methyl-1,3-dioxolan-2-yl)pyridine
1425936-72-6

2-methyl-6-(2-methyl-1,3-dioxolan-2-yl)pyridine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 8h; Dean-Stark; Reflux;93%
With toluene-4-sulfonic acid In toluene at 20℃; for 24h; Reflux;22 g
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

4-fluorophenylhydrazine
371-14-2

4-fluorophenylhydrazine

C14H14FN3
1429087-95-5

C14H14FN3

Conditions
ConditionsYield
In ethanol for 0.5h; Reflux;92.5%
In ethanol for 0.5h; Reflux;16.5 g
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-aminobenzaldehyde
529-23-7

2-aminobenzaldehyde

2-(6-methylpyridin-2-yl)quinoline
56100-29-9

2-(6-methylpyridin-2-yl)quinoline

Conditions
ConditionsYield
With potassium hydroxide In ethanol Reflux;92%
With potassium hydroxide In ethanol at 85℃; for 3h; Inert atmosphere;57%
With potassium hydroxide In ethanol at 85℃; for 3h;57%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

C8H11NO

C8H11NO

Conditions
ConditionsYield
Stage #1: 2-acetyl-6-methylpyridine With trimethylaluminum; (R)-2,2’-diphenyl-(4-biphenanthrol); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 20℃; for 2h; Glovebox; Inert atmosphere;
Stage #2: With methanol for 0.5h; enantioselective reaction;
92%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

N-(1-(6-methylpyridin-2-yl)ethylidene)-11-phenylethanamine

N-(1-(6-methylpyridin-2-yl)ethylidene)-11-phenylethanamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 48h; Reflux; Inert atmosphere;90%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E)-3-(dimethylamino)-1-(6-methylpyridin-2-yl)prop-2-en-1-one
854923-64-1

(E)-3-(dimethylamino)-1-(6-methylpyridin-2-yl)prop-2-en-1-one

Conditions
ConditionsYield
at 110℃; for 7h;89%
at 105℃; for 7h; Inert atmosphere;80%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

ethylene glycol
107-21-1

ethylene glycol

2‐bromo‐6‐(2‐methyl‐1,3‐dioxolan‐2‐yl)pyridine
49669-14-9

2‐bromo‐6‐(2‐methyl‐1,3‐dioxolan‐2‐yl)pyridine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene88%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

N-(2-bromophenyl)hydrazinecarbothioamide
25688-12-4

N-(2-bromophenyl)hydrazinecarbothioamide

(E)-N-(2-bromophenyl)-2-(1-(6-methylpyridin-2-yl)ethylidene)hydrazine-1-carbothioamide

(E)-N-(2-bromophenyl)-2-(1-(6-methylpyridin-2-yl)ethylidene)hydrazine-1-carbothioamide

Conditions
ConditionsYield
With acetic acid In methanol for 2h; Reflux;85%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

hydrazinecarbodithioic acid methyl ester
5397-03-5

hydrazinecarbodithioic acid methyl ester

3-<1-(6-Methyl-2-pyridyl)ethylidene>hydrazinecarbothioate
26155-39-5

3-<1-(6-Methyl-2-pyridyl)ethylidene>hydrazinecarbothioate

Conditions
ConditionsYield
In ethanol at 60℃; for 3h;84%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

N-methyl-hydrazinecarbodithioic acid methyl ester
20184-94-5

N-methyl-hydrazinecarbodithioic acid methyl ester

methyl 3-<1-(6-methyl-2-pyridyl)ethylidene>methylhydrazinecarbodithioate
74752-60-6

methyl 3-<1-(6-methyl-2-pyridyl)ethylidene>methylhydrazinecarbodithioate

Conditions
ConditionsYield
With acetic acid In ethanol for 20h; Heating;79%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

6-chloroquinoline
612-57-7

6-chloroquinoline

1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone
476472-48-7

1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone

Conditions
ConditionsYield
Stage #1: 2-acetyl-6-methylpyridine; 6-chloroquinoline With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 80℃; for 18h;
Stage #2: With acetic acid In tetrahydrofuran at 20℃;
78%
With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 80℃; Inert atmosphere;75%
With potassium tert-butylate; palladium diacetate; DavePhos In tetrahydrofuran at 75℃; for 14h;75%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

6-chloroquinoline
612-57-7

6-chloroquinoline

DavePhos
213697-53-1

DavePhos

1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone
476472-48-7

1-(6-methylpyridin-2-yl)-2-(quinolin-6-yl)ethanone

Conditions
ConditionsYield
With potassium tert-butylate; acetic acid; palladium diacetate In tetrahydrofuran78%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

3-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde

(Z)-1-(6-methylpyridin-2-yl)-3-[1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-4-yl]prop-2-en-1-one

(Z)-1-(6-methylpyridin-2-yl)-3-[1-phenyl-3-(3,4,5-trimethoxyphenyl)-1H-pyrazol-4-yl]prop-2-en-1-one

Conditions
ConditionsYield
With sodium hydroxide In methanol Claisen-Schmidt Condensation; Reflux;78%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-(2-aminophenyl)-1H-indole
32566-01-1

2-(2-aminophenyl)-1H-indole

[2-(1H-indol-2-yl)phenyl]-[1-(6-methyl-pyridin-2-yl)ethylidene]amine
1331843-80-1

[2-(1H-indol-2-yl)phenyl]-[1-(6-methyl-pyridin-2-yl)ethylidene]amine

Conditions
ConditionsYield
With acetic acid In ethanol for 3h; Reflux;75%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-methylthioaniline

2-methylthioaniline

N-[1-(6-methylpyridin-2-yl)ethylidene]-2-(methylthio)aniline

N-[1-(6-methylpyridin-2-yl)ethylidene]-2-(methylthio)aniline

Conditions
ConditionsYield
With acetic acid; aniline; zinc(II) chloride for 2h; Reflux;75%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

6-methylpicolinic acid methyl ester
13602-11-4

6-methylpicolinic acid methyl ester

1,3-bis-(6-methyl-pyridin-2-yl)-propane-1,3-dione
93733-12-1

1,3-bis-(6-methyl-pyridin-2-yl)-propane-1,3-dione

Conditions
ConditionsYield
With sodium ethanolate In toluene75%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-bromo-1-(6-methylpyridin-2-yl)ethan-1-one
88625-09-6

2-bromo-1-(6-methylpyridin-2-yl)ethan-1-one

Conditions
ConditionsYield
With hydrogen bromide; bromine; acetic acid at 0 - 20℃; for 1h;75%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

2-amino-5-bromobenzophenone
39859-36-4

2-amino-5-bromobenzophenone

4-phenyl-6-bromo-2-(2'-(6'-methyl)pyridinyl)quinoline

4-phenyl-6-bromo-2-(2'-(6'-methyl)pyridinyl)quinoline

Conditions
ConditionsYield
With phosphorus pentaoxide In various solvent(s) at 135℃; Friedlander reaction;71%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

1,3-bis(4-methylphenyl)prop-2-yn-1-one
97691-66-2

1,3-bis(4-methylphenyl)prop-2-yn-1-one

(4′-methyl-3,5-bis(6-methylpyridin-2-yl)-[1,1′-biphenyl]-2-yl)(p-tolyl)methanone

(4′-methyl-3,5-bis(6-methylpyridin-2-yl)-[1,1′-biphenyl]-2-yl)(p-tolyl)methanone

Conditions
ConditionsYield
With [2,2]bipyridinyl; cobalt(II) bromide; zinc In 1,4-dioxane at 140℃; Sealed tube; Inert atmosphere; regioselective reaction;71%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

[(2-methylpropane-1,3-diyl)bis(oxy)]diammonium dibromide

[(2-methylpropane-1,3-diyl)bis(oxy)]diammonium dibromide

1-(6-methylpyridin-2-yl)ethanone O,O'-(2-methylpropane-1,3-diyl)oxime
1034419-32-3

1-(6-methylpyridin-2-yl)ethanone O,O'-(2-methylpropane-1,3-diyl)oxime

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol for 4h; Product distribution / selectivity; Heating; Reflux;70%
2-acetyl-6-methylpyridine
6940-57-4

2-acetyl-6-methylpyridine

anthranilic acid nitrile
1885-29-6

anthranilic acid nitrile

2-[[1-(6-methylpyridin-2-yl)ethylidene]amino]benzonitrile

2-[[1-(6-methylpyridin-2-yl)ethylidene]amino]benzonitrile

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating / reflux;67.6%

6940-57-4Relevant articles and documents

ADENOSINE RECEPTOR BINDING COMPOUNDS

-

Paragraph 00261, (2020/02/06)

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

FUSED RING HETEROARYL COMPOUNDS AS ALK4/5 INHIBITORS

-

Paragraph 0149; 0150, (2020/08/05)

The invention provides novel substituted heterocyclic compounds represented by Formula I, or a pharmaceutically acceptable salt, solvate, polymorph, ester, tautomer or prodrug thereof, and a composition comprising these compounds. The compounds provided can be used as inhibitors of ALK5 and/or ALK4 and are useful in the treatment of pulmonary fibrosis, NASH, obesity, diabetes, cancers and other inflammation.

NOVEL MORPHOLINE DERIVATIVE OR SALT THEREOF

-

Paragraph 0943; 1201-1205, (2016/07/05)

There is provided a morpholine derivative represented by General Formula [1A] or a salt thereof. (In the formula, a ring A represents a ring represented by General Formula [I]; * represents a bonding position; Z2 represents CH or the like; Z1 represents CR6 or the like; R6 represents a hydrogen atom or the like; X1 represents CHR7 or the like; R7 represents a hydrogen atom or the like; X2 represents CH2 or the like; R1 and R2 are the same as or different from each other, and each of R1 and R2 represents a hydrogen atom or the like; R3, R4, and R5 are the same as or different from each other, and each of R3, R4, and R5 represents a hydrogen atom, NRaRb, or the like; and each of Ra and Rb represents a hydrogen atom, a C1-8 alkyl group which may have a substituent, or the like.)

A two-in-one pincer ligand and its diiron(II) complex showing spin state switching in solution through reversible ligand exchange

Samanta, Subhas,Demesko, Serhiy,Dechert, Sebastian,Meyer, Franc

supporting information, p. 583 - 587 (2015/03/04)

A novel pyrazolate-bridged ligand providing two {PNN} pincer-type compartments has been synthesized. Its diiron(II) complex LFe2(OTf)3(CH3CN) (1; Tf=triflate) features, in solid state, two bridging triflate ligands, with a terminal triflate and a MeCN ligand completing the octahedral coordination spheres of the two high-spin metalions. In MeCN solution, 1 is shown to undergo a sequential, reversible, and complete spin transition to the low-spin state upon cooling. Detailed UV/Vis and 19F NMR spectroscopic studies as well as magnetic measurements have unraveled that spin state switching correlates with a rapid multistep triflate/MeCN ligand exchange equilibrium. The spin transition temperature can be continuously tuned by varying the triflate concentration in solution.

Effects of structural modifications on the metal binding, anti-amyloid activity, and cholinesterase inhibitory activity of chalcones

Fosso, Marina Y.,LeVine, Harry,Green, Keith D.,Tsodikov, Oleg V.,Garneau-Tsodikova, Sylvie

supporting information, p. 9418 - 9426 (2015/09/15)

As the number of individuals affected with Alzheimer's disease (AD) increases and the availability of drugs for AD treatment remains limited, the need to develop effective therapeutics for AD becomes more and more pressing. Strategies currently pursued include inhibiting acetylcholinesterase (AChE) and targeting amyloid-β (Aβ) peptides and metal-Aβ complexes. This work presents the design, synthesis, and biochemical evaluation of a series of chalcones, and assesses the relationship between their structures and their ability to bind metal ions and/or Aβ species, and inhibit AChE/BChE activity. Several chalcones were found to exhibit potent disaggregation of pre-formed N-biotinyl Aβ1-42 (bioAβ42) aggregates in vitro in the absence and presence of Cu2+/Zn2+, while others were effective at inhibiting the action of AChE.

Zinc complexes bearing N,N′-bidentate entiopure ligands: Synthesis, structure and catalytic activity toward ring opening polymerisation of rac-lactide

Nayab, Saira,Lee, Hyosun,Jeong, Jong Hwa

experimental part, p. 55 - 62 (2012/09/22)

Dichloro zinc complexes with (S)-1-phenyl-N-[(S)-1-(pyridin-2-yl)ethyl] ethanamine (PMMA) and (S)-1-(6-methylpyridin-2-yl)-N-[(S)-1-phenylethyl] ethanamine (MPMMA) were prepared and characterised by X-ray diffraction. The catalytic activity of the dimethyl complexes, generated in situ, was high in the ring opening polymerization of rac-lactide. Specifically, the dimethyl derivative of (PMMA)ZnCl2 yielded a highly stereocontrolled polylactide with Pr = 0.84.

PYRAZOLE DERIVATIVE

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Page/Page column 35-36, (2008/06/13)

Not available

Novel fused heteroaromatic compounds as transforming growth factor (TGF) inhibitors

-

, (2008/06/13)

Novel fused heteroaromatic compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor (“TGF”)-β signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer and fibrotic diseases.

NOVEL TRIAZOLE AND OXAZOLE COMPOUNDS AS TRANSFORMING GROWTH FACTOR (TGF) INHIBITOR

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Page 54, (2008/06/13)

Novel oxazole and thiazole compounds, including derivatives thereof, to intermediates for their preparation, to pharmaceutical compositions containing them and to their medicinal use are described. The compounds of the present invention are potent inhibitors of transforming growth factor ("TGF")-β signaling pathway. They are useful in the treatment of various TGF-related disease states including, for example, cancer and fibrotic diseases.

Lanthanide complexes of a new sterically hindered potentially hexadentate podand ligand based on a tris(pyrazolyl)borate core; crystal structures, solution structures and luminescence properties

Reeves, Zoe R.,Mann, Karen L. V.,Jeffery, John C.,McCleverty, Jon A.,Ward, Michael D.,Barigelletti, Francesco,Armaroli, Nicola

, p. 349 - 355 (2007/10/03)

The new podand ligand hydrotris[3-(6-methyl)pyridin-2-ylpyrazol-1-yl]borate [L1]- was prepared which contains three bidentate pyrazolyl/pyridine arms attached to a {BH}- head-group. This ligand differs from an earlier ligand hydrotris[3-(2-pyridyl)pyrazol-1-yl]borate [L2]- by the presence of methyl groups attached to the C6 positions of the pyridyl rings, which would interfere with each other sterically if the ligand co-ordinated in a fully hexadentate manner. Instead, crystallographic analysis of the complexes [M(L1)(NO3)2(H2O)] (M = Eu, Tb or Gd) showed that partial dissociation of the podand occurs to relieve this potential steric problem: either one or two of the pyridyl groups are not co-ordinated, such that [L1]- is penta- or tetra-dentate, but instead are involved in intramolecular N...H-O hydrogen-bonding interactions with the co-ordinated water molecule. The presence of both structural forms in single crystals of the gadolinium and europium complexes shows that interconversion between them in solution must be facile. Variable-temperature 1H NMR spectra of the diamagnetic lanthanum(III) analogue shows that, whereas all three ligand arms are equivalent on the NMR timescale at high temperatures, at -80°C there is mirror symmetry in the complex such that two arms are equivalent and the third is different from the other two; this is consistent with the crystalline form in which [L1]- is tetradentate with two pendant pyridyl arms, which has pseudo-mirror symmetry. Luminescence studies showed that whereas the ligand-based luminescence is retained in the gadolinium(III) complex, in the europium(III) and terbium(III) complexes the ligand-centred emission is quenched by ligand-to-metal energy transfer, resulting in the usual metal-centred emission spectra. The intensity of the emission from the europium(III) and terbium(III) complexes of [L1]- is substantially reduced compared to the emission from the analogous complexes [M(L2)(NO3)2] (M = Eu or Tb) which we ascribe to the sterically induced poorer co-ordination of the podand ligand, resulting in (i) less efficient ligand-to-metal energy transfer, and (ii) co-ordination of labile solvent molecules (H2O) to the metal centres.

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