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52606-01-6

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52606-01-6 Usage

Description

2,6-DIMETHOXYISONICOTINALDEHYDE is a chemical compound with the molecular formula C11H13NO4. It is an aldehyde derivative of isonicotinic acid, featuring two methoxy groups on the 2 and 6 positions of the aromatic ring. 2,6-DIMETHOXYISONICOTINALDEHYDE is recognized for its potential as a building block in organic synthesis, particularly in the development of new drug candidates. Its antioxidant and anti-inflammatory properties have also attracted research interest for potential therapeutic applications.

Uses

Used in Pharmaceutical and Agrochemical Industries:
2,6-DIMETHOXYISONICOTINALDEHYDE is used as a key intermediate in the synthesis of various pharmaceutical and agrochemical products. Its unique structure and functional groups make it a valuable component in the development of new compounds with therapeutic or pesticidal properties.
Used in Organic Synthesis:
2,6-DIMETHOXYISONICOTINALDEHYDE is utilized as a building block in organic synthesis, enabling the creation of a wide range of chemical entities. Its versatility in forming different types of chemical bonds and its compatibility with various synthetic routes contribute to its importance in the field of organic chemistry.
Used in Antioxidant and Anti-Inflammatory Research:
Due to its antioxidant and anti-inflammatory properties, 2,6-DIMETHOXYISONICOTINALDEHYDE is used in research for potential therapeutic applications. Its ability to combat oxidative stress and reduce inflammation may offer new avenues for the treatment of various diseases and conditions.
Used in Drug Development:
2,6-DIMETHOXYISONICOTINALDEHYDE is employed as a starting material in the development of new drug candidates. Its unique chemical properties and potential for modification make it an attractive option for the design of novel therapeutic agents with improved efficacy and selectivity.

Check Digit Verification of cas no

The CAS Registry Mumber 52606-01-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,6,0 and 6 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 52606-01:
(7*5)+(6*2)+(5*6)+(4*0)+(3*6)+(2*0)+(1*1)=96
96 % 10 = 6
So 52606-01-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO3/c1-11-7-3-6(5-10)4-8(9-7)12-2/h3-5H,1-2H3

52606-01-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6-dimethoxypyridine-4-carbaldehyde

1.2 Other means of identification

Product number -
Other names 2,6-Dimethoxyisonicotinaldehyde

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:52606-01-6 SDS

52606-01-6Synthetic route

(2,6-dimethoxypyridine-4-yl)-methanol
52606-06-1

(2,6-dimethoxypyridine-4-yl)-methanol

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

Conditions
ConditionsYield
With manganese(IV) oxide In chloroform at 20℃; for 12h;68%
With manganese(IV) oxide In methanol at 20℃; for 72h;28.8%
citrazinic acid
99-11-6

citrazinic acid

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

2,6-dichloropyridine-4-carboxylic acid
5398-44-7

2,6-dichloropyridine-4-carboxylic acid

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / 1 h / Reflux
2: N,N-dimethyl-formamide / 12 h / Reflux
3: sodium tetrahydroborate / 1,4-dioxane / 1 h / Reflux
4: manganese(IV) oxide / chloroform / 12 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: diethylene glycol dimethyl ether / 24 h / Reflux; Dean-Stark
2: lithium aluminium tetrahydride / tetrahydrofuran / 25 h / 0 - 20 °C
3: manganese(IV) oxide / methanol / 72 h / 20 °C
View Scheme
methyl 2,6-dichloroisonicotinate
42521-09-5

methyl 2,6-dichloroisonicotinate

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 12 h / Reflux
2: sodium tetrahydroborate / 1,4-dioxane / 1 h / Reflux
3: manganese(IV) oxide / chloroform / 12 h / 20 °C
View Scheme
2,6-dimethoxypyridine-4-carboxylic acid
6274-82-4

2,6-dimethoxypyridine-4-carboxylic acid

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 25 h / 0 - 20 °C
2: manganese(IV) oxide / methanol / 72 h / 20 °C
View Scheme
citrazinic acid
99-11-6

citrazinic acid

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trichlorophosphate; tetramethlyammonium chloride / 24 h / 140 °C
2: diethylene glycol dimethyl ether / 24 h / Reflux; Dean-Stark
3: lithium aluminium tetrahydride / tetrahydrofuran / 25 h / 0 - 20 °C
4: manganese(IV) oxide / methanol / 72 h / 20 °C
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

C11H9BrClNOZn

C11H9BrClNOZn

C19H19BrN2O4

C19H19BrN2O4

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;93%
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

(E)-methyl 3-(2,6-dimethoxypyridin-4-yl)acrylate
1000895-93-1

(E)-methyl 3-(2,6-dimethoxypyridin-4-yl)acrylate

Conditions
ConditionsYield
In dichloromethane at 18 - 25℃;60%
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

C37H38BF2I2N5O3

C37H38BF2I2N5O3

C53H52BF2I2N7O7

C53H52BF2I2N7O7

Conditions
ConditionsYield
With piperidine; acetic acid In benzene Reflux; Dean-Stark;58%
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

((4-methoxyphenyl)methyl)triphenylphosphonium bromide
1530-38-7

((4-methoxyphenyl)methyl)triphenylphosphonium bromide

A

(E)-2,6-dimethoxy-4-(4-methoxystyryl)-pyridine

(E)-2,6-dimethoxy-4-(4-methoxystyryl)-pyridine

B

(Z)-2,6-dimethoxy-4-(4-methoxystyryl)-pyridine

(Z)-2,6-dimethoxy-4-(4-methoxystyryl)-pyridine

Conditions
ConditionsYield
Stage #1: ((4-methoxyphenyl)methyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 1h;
Stage #2: 2,6-dimethoxy-4-pyridinecarboxaldehyde In tetrahydrofuran at 20℃; for 24h; Wittig Olefination;
A 12.2%
B 29.2%
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

(2-naphthalenylmethyl)triphenylphosphonium bromide
35160-95-3

(2-naphthalenylmethyl)triphenylphosphonium bromide

A

(E)-2,6-dimethoxy-4-(2-naphth-2-ylvinyl)-pyridine

(E)-2,6-dimethoxy-4-(2-naphth-2-ylvinyl)-pyridine

B

(Z)-2,6-dimethoxy-4-(2-naphth-2-ylvinyl)-pyridine

(Z)-2,6-dimethoxy-4-(2-naphth-2-ylvinyl)-pyridine

Conditions
ConditionsYield
Stage #1: (2-naphthalenylmethyl)triphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at -40℃; for 1h;
Stage #2: 2,6-dimethoxy-4-pyridinecarboxaldehyde In tetrahydrofuran at 20℃; for 24h; Wittig Olefination;
A 13.3%
B 7.5%
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide
61240-20-8

triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide

A

(E)-2,6-dimethoxy-4-(3,4,5-trimethoxystyryl)-pyridine

(E)-2,6-dimethoxy-4-(3,4,5-trimethoxystyryl)-pyridine

B

(Z)-2,6-dimethoxy-4-(3,4,5-trimethoxystyryl)-pyridine

(Z)-2,6-dimethoxy-4-(3,4,5-trimethoxystyryl)-pyridine

Conditions
ConditionsYield
Stage #1: triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide With n-butyllithium In tetrahydrofuran at -40℃; for 1h;
Stage #2: 2,6-dimethoxy-4-pyridinecarboxaldehyde In tetrahydrofuran at 20℃; for 24h; Wittig Olefination;
A 1.9%
B 2.9%
3-Morpholin-4-yl-propionitrile
4542-47-6

3-Morpholin-4-yl-propionitrile

2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

2-(2,6-dimethoxy-pyridin-4-ylmethyl)-3-morpholin-4-yl-acrylonitrile
65873-52-1

2-(2,6-dimethoxy-pyridin-4-ylmethyl)-3-morpholin-4-yl-acrylonitrile

Conditions
ConditionsYield
(i) NaOMe, DMSO, (ii) /BRN= 1448374/; Multistep reaction;
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

4-aminobenzamidine ditoluenesulphonate

4-aminobenzamidine ditoluenesulphonate

Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

(RS)-N-benzyl-2-(4-carbamimidoylphenylamino)-2-(2,6-dimethoxypyridin-4-yl)acetamide

(RS)-N-benzyl-2-(4-carbamimidoylphenylamino)-2-(2,6-dimethoxypyridin-4-yl)acetamide

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether; water2.02 g (28%)
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide
54016-70-5

3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide

1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
106331-50-4

1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

1-(2,6-dimethoxypyrid-4-yl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione
106331-64-0

1-(2,6-dimethoxypyrid-4-yl)-4-(3,4,5-trimethoxyphenyl)-1,4-butanedione

Conditions
ConditionsYield
With triethylamine In ethanol
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

N'-[5-[2-(2,6-dimethoxypyridin-4-yl)ethyl]-1H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine

N'-[5-[2-(2,6-dimethoxypyridin-4-yl)ethyl]-1H-pyrazol-3-yl]-N-[(3-methyl-1,2-oxazol-5-yl)methyl]pyrimidine-2,4-diamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: dichloromethane / 18 - 25 °C
2.1: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 18 - 25 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C
3.2: -78 - 25 °C
4.1: hydrazine hydrochloride / ethanol / 18 h / Heating / reflux
5.1: ethanol / 45 h / 18 - 80 °C
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

methyl 3-(2,6-dimethoxypyridin-4-yl)propanoate
1000895-92-0

methyl 3-(2,6-dimethoxypyridin-4-yl)propanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 18 - 25 °C
2: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 18 - 25 °C
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

5-(2-(2,6-dimethoxypyridin-4-yl)ethyl)-1H-pyrazol-3-amine
1000895-91-9

5-(2-(2,6-dimethoxypyridin-4-yl)ethyl)-1H-pyrazol-3-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dichloromethane / 18 - 25 °C
2.1: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 18 - 25 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C
3.2: -78 - 25 °C
4.1: hydrazine hydrochloride / ethanol / 18 h / Heating / reflux
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

C12H14N2O3

C12H14N2O3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: dichloromethane / 18 - 25 °C
2.1: hydrogen / palladium 10% on activated carbon / ethanol / 18 h / 18 - 25 °C
3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C
3.2: -78 - 25 °C
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

2-methoxy-6-bromoquinoline
99455-05-7

2-methoxy-6-bromoquinoline

C18H17BrN2O4

C18H17BrN2O4

Conditions
ConditionsYield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -75℃; for 4h;
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

6-bromo-3-((2,6-dimethoxypyridin-4-yl)methyl)-2-methoxyquinoline

6-bromo-3-((2,6-dimethoxypyridin-4-yl)methyl)-2-methoxyquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 4 h / -75 °C
2: triethylsilane; trifluoroacetic acid / dichloromethane
View Scheme
2,6-dimethoxy-4-pyridinecarboxaldehyde
52606-01-6

2,6-dimethoxy-4-pyridinecarboxaldehyde

1-(6-bromo-2-methoxyquinolin-3-yl)-1-(2,6-dimethoxypyridin-4-yl)-4-(dimethylamino)-2-(2-ethoxy-6-isopropoxypyridin-4-yl)butan-2-ol

1-(6-bromo-2-methoxyquinolin-3-yl)-1-(2,6-dimethoxypyridin-4-yl)-4-(dimethylamino)-2-(2-ethoxy-6-isopropoxypyridin-4-yl)butan-2-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 2,2,6,6-tetramethylpiperidinyl-lithium / tetrahydrofuran / 4 h / -75 °C
2.1: triethylsilane; trifluoroacetic acid / dichloromethane
3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; cyclohexane / 1.5 h / -78 - -70 °C / Inert atmosphere
3.2: 5 h / -78 - -70 °C / Inert atmosphere
View Scheme

52606-01-6Relevant articles and documents

Potent colchicine-site ligands with improved intrinsic solubility by replacement of the 3,4,5-trimethoxyphenyl ring with a 2-methylsulfanyl-6-methoxypyridine ring

Aramburu, Laura,Gajate, Consuelo,Medarde, Manuel,Mollinedo, Faustino,álvarez, Raquel,Peláez, Rafael,Vicente-Blázquez, Alba

, (2020/03/27)

Colchicine site antimitotic agents typically suffer from low aqueous solubilities and are formulated as phosphate prodrugs of phenolic groups. These hydroxyl groups are the aim of metabolic transformations leading to resistance. There is an urgent need for more intrinsically soluble analogues lacking these hydroxyl groups. The 3,4,5-trimethoxyphenyl ring of combretastatin A-4 is a liability in terms of solubility but it is considered essential for high cytotoxic and tubulin polymerization inhibitory (TPI) activity. We have synthesized 36 new analogues of combretastatin A-4 replacing the trimethoxyphenyl moiety with more polar pyridine based moieties, measured their aqueous solubility, and studied their anti-proliferative effects against 3 human cancer cell lines. We show here that pyridine rings can be successful replacements for the trimethoxyphenyl ring, resulting in potent and more soluble analogues. The more straightforward replacement, a 2,6-dimethoxypyridine ring led to inactive analogues, but a 2-methoxy-6-methylsulfanylpyridine moiety led to active analogues when combined with different B rings. This replacement led to potent cytotoxic activity against sensitive human cancer cell lines due to tubulin inhibition, as shown by cell cycle analysis, confocal microscopy, and tubulin polymerization inhibitory activity studies. Cell cycle analysis also showed apoptotic responses following treatment. Docking studies suggested binding at the colchicine site of tubulin and provided a good agreement with the observed SAR. A 2-methoxy-6-methylsulfanylpyridine moiety is a good trimethoxyphenyl ring replacement for the development of new colchicine site ligands.

New 2,5-diaryl tetryhydrofurans and analogs thereof as paf antagonists

-

, (2008/06/13)

Compounds of formula: are disclosed wherein R and R1 are (a) hydrogen;(b) haloloweralkyl;(c) halo;(d) CONR2R3 wherein R2 and R3 independently represent hydrogen, C1-8 alkyl, or C3-8 cycloalkyl;(e) loweralkenyl;(f)-COR2;(g)-CH?OR2;(h) loweralkynyl;(i)-CH?NR2R3;(j)-CH?SR2;(k) =O; or(l)-OR2;(m)-R2; Ar and Ar1 are (a) phenyl or substituted phenyl of formula where R?-R? independently represent H; R2; YO-wherein Y is loweralkenyl, loweralkynyl,-CH? ,-CH?C(O) OR2,-CH?OR2,-CH?C3-8cycloalkyl,-CH? Ar2 wherein Ar2 is phenyl or substituted phenyl,-CH?-CH(OH)-CH? OH; R2S-(O)n wherein R2 can only be C3-8 cycloalkyl and n is 0 to 2; CF?SO, CF?SO?;-CONR2R3;-NR2COR3;-OCONH?-CR2R3R? wherein R? is the same as or different from R2;-CH?OR2;-CH?CO?R2;-CH?OCOR3;-CH?O-CO-OR2;-NHCH?COOR2; halo; or N?R2R3R?X? wherein X? is an anion;(b) monoheteroaryl, di-or polyheteroaryl or fused heteroaryl containing 1 to 3 of any one or more of the heteroatoms N, S or O;(c) heteroarylalkyl;(d) heterocycloalkyl; or(e) heterocycloalkenyl. These compounds are found to have potent and specific PAF (Platelet Activating Factor) antagonistic activities.

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