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872-85-5

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872-85-5 Usage

Flavor Type

Flavor Type: fruity

Chemical Properties

Different sources of media describe the Chemical Properties of 872-85-5 differently. You can refer to the following data:
1. 4-Pyridinecarboxaldehyde(4PCA) is a slightly yellow oily liquid. Its relative density is 1.122, and its refractive index is 1.5352 (25°C). Flash point is 54 ° C. 4-Pyridinecarboxaldehyde is soluble in water and ether.4-Pyridinecarboxaldehyde, also commonly called pyridine-2-carboxaldehyde, is an organic compound with the formula NC5H4CHO. 4-Pyridinecarboxaldehyde is a colorless oily liquid with a distinctive odor. Older samples are often brown-colored owing to impurities.
2. clear yellow-brown liquid. soluble in water and ether.

Uses

Different sources of media describe the Uses of 872-85-5 differently. You can refer to the following data:
1. 4-Pyridinecarboxaldehyde is an heterocyclic building block used for the synthesis of various pharmaceutical compounds, such as new 1,4-dihydropyridin-4-yl-phenoxyacetohydrazones, having anticonvulsant and anti-inflammatory properties.4-Pyridinecarboxaldehyde and some of its derivatives have also been reported as useful transamination reagents to introduce ketone or aldehyde groups onto the N-termini of antibodies for subsequent site-specifically conjugate aminooxy-functionalized molecules (including fluorescent dyes, polyethylene glycol, or porphyrins) to these entities. 4-Pyridinecarboxaldehyde can be used for the synthesis of: β-Unsaturated amides by coupling with N,N-disubstituted formamides; meso-Substituted A3-corroles; N-(4-pyridylmethyl)-L-valine as a ligand to construct zinc metal–organic frameworks (Zn-MOFs); 4′-Pyridyl terpyridines, with potential application as anticancer and antimicrobial agents; 4-pyridinecarboxaldehyde thiosemicarbazone, as a corrosion inhibitor for mild steel.
2. 4-Pyridinecarboxaldehyde, is an heterocyclic building block used for the synthesis of various pharmaceutical compounds, such as new 1,4-dihydropyridin-4-yl-phenoxyacetohydrazones, having anticonvulsant and anti-inflammatory properties.
3. 4-Pyridinecarboxaldehyde can be used for the synthesis of:?,β-Unsaturated amides by coupling with N,N-disubstituted formamides.meso-Substituted A3-corroles.N-(4-pyridylmethyl)-L-valine as a ligand to construct zinc metal–organic frameworks (Zn-MOFs).4′-Pyridyl terpyridines, with potential application as anticancer and antimicrobial agents.4-pyridinecarboxaldehyde thiosemicarbazone, as a corrosion inhibitor for mild steel.

Preparation

4-Pyridinecarbaldehyde is synthesized by oxidation of 4-picoline. The mixed gas of 4-picoline and air is passed through the vanadium-molybdenum catalyst layer heated to 400°C, and oxidized to generate 4-pyridinecarbaldehyde.

Synthesis Reference(s)

Synthetic Communications, 20, p. 3385, 1990 DOI: 10.1080/00397919008051576

Purification Methods

Purified as for pyridine-2-aldehyde. [Beilstein 21 III/IV 2529, 21/7 V 351.]

Check Digit Verification of cas no

The CAS Registry Mumber 872-85-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 2 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 872-85:
(5*8)+(4*7)+(3*2)+(2*8)+(1*5)=95
95 % 10 = 5
So 872-85-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO/c8-5-6-1-3-7-4-2-6/h1-5H

872-85-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (I0143)  4-Pyridinecarboxaldehyde  >96.0%(GC)

  • 872-85-5

  • 25mL

  • 360.00CNY

  • Detail
  • TCI America

  • (I0143)  4-Pyridinecarboxaldehyde  >96.0%(GC)

  • 872-85-5

  • 500mL

  • 3,200.00CNY

  • Detail
  • Alfa Aesar

  • (A10656)  Pyridine-4-carboxaldehyde, 97%   

  • 872-85-5

  • 25g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (A10656)  Pyridine-4-carboxaldehyde, 97%   

  • 872-85-5

  • 100g

  • 713.0CNY

  • Detail
  • Alfa Aesar

  • (A10656)  Pyridine-4-carboxaldehyde, 97%   

  • 872-85-5

  • 500g

  • 2710.0CNY

  • Detail
  • Aldrich

  • (P62402)  4-Pyridinecarboxaldehyde  97%

  • 872-85-5

  • P62402-25G

  • 258.57CNY

  • Detail
  • Aldrich

  • (P62402)  4-Pyridinecarboxaldehyde  97%

  • 872-85-5

  • P62402-100G

  • 855.27CNY

  • Detail
  • Aldrich

  • (P62402)  4-Pyridinecarboxaldehyde  97%

  • 872-85-5

  • P62402-500G

  • 4,024.80CNY

  • Detail

872-85-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Pyridinecarboxaldehyde

1.2 Other means of identification

Product number -
Other names pyridine-4-carbaldehyde

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:872-85-5 SDS

872-85-5Synthetic route

pyridine-4-carbonitrile
100-48-1

pyridine-4-carbonitrile

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; High pressure; Green chemistry;99.9%
With C13H26B(1-)*K(1+) In tetrahydrofuran for 24h; Ambient temperature;65%
With sulfuric acid; hydrogen In water at 50℃; for 3h;59%
picoline
108-89-4

picoline

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With copper(II) choride dihydrate; acetic acid In N,N-dimethyl-formamide at 130℃; for 6h; Reagent/catalyst;99%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;87%
With copper(II) choride dihydrate; oxygen In N,N-dimethyl-formamide at 130℃; under 760.051 Torr; for 12h; Sealed tube;45%
pyridine-4-methanol
586-95-8

pyridine-4-methanol

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With 1H-imidazole; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 0.166667h;99%
With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen; cyclohexene at 60℃; under 760.051 Torr; for 1.5h;99%
With 4-hydroxy-TEMPO benzoate; sodium acetate; tetra-N-butylammonium tribromide In dichloromethane at 20℃; for 1.5h;94%
1-phenyl-2-(pyridin-4-ylmethylene)hydrazine
7757-39-3

1-phenyl-2-(pyridin-4-ylmethylene)hydrazine

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With CuCl*Kieselghur; oxygen In dichloromethane at 20℃; for 0.5h;95%
With tetrachlorosilane; silica gel In hexane; water for 0.17h; Heating;89%
With sulfuric acid; silica gel In hexane for 0.666667h;
pyridine-4-aldoxime
696-54-8

pyridine-4-aldoxime

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With silica chromate; silica gel for 0.0833333h; microwave irradiation;92%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 2.5h;90%
With dicyclohexyl-carbodiimide; pyridinium chlorochromate In chloroform; ethyl acetate at 30℃; for 0.5h;85%
4-vinylpyridine
100-43-6

4-vinylpyridine

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With ozone In methanol91.5%
With cadmium sulphide In neat (no solvent) at 20℃; for 12h; Irradiation;64%
With air; Ag/AgBr/TiO2 nanotubes In acetonitrile at 20℃; for 48h; Irradiation;54%
4-allylpyridine
80880-49-5

4-allylpyridine

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With dimethyl(ethoxy)silane; iron(II) diacetylacetonate In water; glycerol at 80℃; for 24h;90%
pyridine-4-carboxaldehyde semicarbazone

pyridine-4-carboxaldehyde semicarbazone

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 2.2h;89%
pyridine-4-acetic acid
28356-58-3

pyridine-4-acetic acid

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;87%
picoline
108-89-4

picoline

A

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

B

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With water; oxygen; CrV0.95P0.05O4 at 324.84℃;A 8.9%
B 84.3%
With tert.-butylhydroperoxide; selenium(IV) oxide In 1,4-dioxane for 24h;A 34%
B 11%
With selenium(IV) oxide In 1,4-dioxane for 24h;A 2%
B 19%
4-trimethylsilylpryridine
18301-46-7

4-trimethylsilylpryridine

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With triethylammoniumperfluorocyclobutane tetrafluoroborate at 50℃; for 1h;78%
isonicotinic acid ethylester
1570-45-2

isonicotinic acid ethylester

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;76%
Multi-step reaction with 2 steps
1: diethyl ether; lithium alanate
2: lead (IV)-acetate; benzene
View Scheme
isoniazid
54-85-3

isoniazid

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With ammonia; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform at 20℃; for 1h;75%
With ammonium hydroxide; potassium hexacyanoferrate(III) In water at 0℃;71.3%
4-bromopyridin
1120-87-2

4-bromopyridin

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate In acetonitrile at 60℃; for 16h; Schlenk technique; Inert atmosphere;74%
4-iodopyridine
15854-87-2

4-iodopyridine

carbon monoxide
201230-82-2

carbon monoxide

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 90℃; under 7500.75 Torr; for 12h; Autoclave;73%
4-(aminomethyl)pyridine
3731-53-1

4-(aminomethyl)pyridine

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With palladium on activated charcoal In various solvent(s) at 170℃; for 3h; Irradiation; microwave;66%
formic acid
64-18-6

formic acid

4-iodopyridine
15854-87-2

4-iodopyridine

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;63%
4-iodopyridine
15854-87-2

4-iodopyridine

carbon dioxide
124-38-9

carbon dioxide

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;61%
picoline
108-89-4

picoline

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
at 140℃; for 14h; Further byproducts given;A 31%
B 13%
C 10%
D 55%
picoline
108-89-4

picoline

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

formaldehyd
50-00-0

formaldehyd

E

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
at 140℃; for 14h; Product distribution;A 31%
B 13%
C 10%
D n/a
E 55%
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
2196-95-4, 17213-48-8

2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

D

2,2'-diphenyl-1H,1'H-3,3'-biindole
2415-33-0

2,2'-diphenyl-1H,1'H-3,3'-biindole

Conditions
ConditionsYield
With picoline at 140℃; for 14h; Further byproducts given;A 31%
B 13%
C 10%
D 55%
ethanol
64-17-5

ethanol

N-<(α-acetoxy)-4-pyridylmethyl>-3,5-dimethylbenzamide
79988-86-6

N-<(α-acetoxy)-4-pyridylmethyl>-3,5-dimethylbenzamide

A

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

B

3,5-dimethylbenzamide
5692-35-3

3,5-dimethylbenzamide

C

N-<(α-ethoxy)-4-pyridylmethyl>-3,5-dimethylbenzamide
79988-87-7

N-<(α-ethoxy)-4-pyridylmethyl>-3,5-dimethylbenzamide

Conditions
ConditionsYield
Product distribution; chromatography on a silica gel;A n/a
B 50%
C 26%
picoline
108-89-4

picoline

A

pyridine
110-86-1

pyridine

B

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

C

pyridine-4-methanol
586-95-8

pyridine-4-methanol

D

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With oxygen; CrV0.95P0.05O4 at 325℃; Product distribution; Further Variations:; Temperatures; Reagents; atmospheric pressure;A n/a
B 38.5%
C n/a
D 42.1%
C12H20N2O

C12H20N2O

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With methanesulfonic acid In [D3]acetonitrile at 20℃; for 24h; Molecular sieve;42%
N-methoxy-4-methylpyridin-1-ium tetrafluoroborate

N-methoxy-4-methylpyridin-1-ium tetrafluoroborate

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With cesium fluoride In ethyl acetate at 25℃; for 15h;41%
C12H20N2O

C12H20N2O

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With methanesulfonic acid In [D3]acetonitrile at 20℃; for 24h; Molecular sieve;22%
3-[2-(6-methoxycarbonylhexyl)-3-oxocyclopentyl]-5-(4-pyridyl)-4,5-dihydroisoxazole

3-[2-(6-methoxycarbonylhexyl)-3-oxocyclopentyl]-5-(4-pyridyl)-4,5-dihydroisoxazole

A

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

B

methyl 7-(2-acetyl-5-oxocyclopentyl)heptanoate

methyl 7-(2-acetyl-5-oxocyclopentyl)heptanoate

Conditions
ConditionsYield
With molybdenum hexacarbonyl In acetonitrile for 48h; Heating;A n/a
B 20%
isonicotinamide
1453-82-3

isonicotinamide

A

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

B

pyridine-4-methanol
586-95-8

pyridine-4-methanol

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran for 1.66667h; Ambient temperature;A 8%
B 19%
C14H25N3O2

C14H25N3O2

C19H26N2O2

C19H26N2O2

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With methanesulfonic acid In [D3]acetonitrile at 20℃; for 24h; Molecular sieve;18%
C14H25N3O2

C14H25N3O2

C15H26N2O2

C15H26N2O2

pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Conditions
ConditionsYield
With methanesulfonic acid In [D3]acetonitrile at 20℃; for 24h; Molecular sieve;13%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2,2-diethoxy-ethanamine
645-36-3

2,2-diethoxy-ethanamine

(2,2-diethoxyethyl)pyridin-4-ylmethyleneamine
93138-82-0

(2,2-diethoxyethyl)pyridin-4-ylmethyleneamine

Conditions
ConditionsYield
With magnesium sulfate100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

2-Pyridin-4-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine
134778-10-2

2-Pyridin-4-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

4-carbethoxypiperidine
1126-09-6

4-carbethoxypiperidine

1-Pyridin-4-ylmethyl-piperidine-4-carboxylic acid ethyl ester
138030-54-3

1-Pyridin-4-ylmethyl-piperidine-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane molecular sieve;100%
Stage #1: pyridine-4-carbaldehyde; 4-carbethoxypiperidine In dichloromethane at 20℃; for 1h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 5h;
99%
Stage #1: pyridine-4-carbaldehyde; 4-carbethoxypiperidine In dichloromethane for 0.166667h;
Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 23℃; for 16h;
91%
With borane pyridine In ethanol27%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

N,N'-diacetylpiperazin-2,5-dione
3027-05-2

N,N'-diacetylpiperazin-2,5-dione

1-acetyl-3-<(4-pyridyl)methylene>piperazine-2,5-dione
133318-03-3

1-acetyl-3-<(4-pyridyl)methylene>piperazine-2,5-dione

Conditions
ConditionsYield
With potassium fluoride on basic alumina Irradiation;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2-Hydroxybenzylamine
932-30-9

2-Hydroxybenzylamine

2-Pyridin-4-yl-3,4-dihydro-2H-benzo[e][1,3]oxazine
134778-09-9

2-Pyridin-4-yl-3,4-dihydro-2H-benzo[e][1,3]oxazine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

u-2-amino-1-phenylpropan-1-ol
14838-15-4

u-2-amino-1-phenylpropan-1-ol

4-((4S,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
134778-12-4, 134778-13-5, 134876-49-6, 134876-50-9, 142927-67-1, 142927-68-2

4-((4S,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature; Further byproducts given;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

Norpseudoephedrine
37577-07-4

Norpseudoephedrine

4-((4R,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
134778-12-4, 134778-13-5, 134876-49-6, 134876-50-9, 142927-67-1, 142927-68-2

4-((4R,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature; Further byproducts given;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2-Amino-2-methyl-1-propanol
124-68-5

2-Amino-2-methyl-1-propanol

4-(4,4-Dimethyl-oxazolidin-2-yl)-pyridine
134778-11-3

4-(4,4-Dimethyl-oxazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

2-[hydroxy(pyridin-4-yl)methyl]acrylic acid methyl ester
118488-73-6

2-[hydroxy(pyridin-4-yl)methyl]acrylic acid methyl ester

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.5h; Baylis-Hillman reaction; neat (no solvent);100%
With 1,4-diaza-bicyclo[2.2.2]octane at 80℃; for 0.0833333h; Baylis-Hillman reaction; Microwave irradiation; neat (no solvent);99%
With N-(nBu)-N'-[3-(quinuclidin-3-ylamino)(CH2)3]imidazolium BF4 In methanol at 20℃; for 0.5h; Baylis-Hillman reaction;98%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

aniline
62-53-3

aniline

N-(pyridin-4-ylmethylene)aniline
27768-46-3

N-(pyridin-4-ylmethylene)aniline

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;100%
In ethanol at 20℃;100%
With TiO2 nanotubes at 20℃; for 0.0833333h; Neat (no solvent); Sunlight;98%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2,3-dimethylquinolizinium perchlorate

2,3-dimethylquinolizinium perchlorate

3-methyl-2-<2-(4-pyridyl)vinyl>quinolizinium perchlorate

3-methyl-2-<2-(4-pyridyl)vinyl>quinolizinium perchlorate

Conditions
ConditionsYield
With piperidine In acetonitrile for 1.5h; Heating;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

2-Pyridin-4-yl-[1,3]oxazinane
134778-08-8

2-Pyridin-4-yl-[1,3]oxazinane

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

pyridine-4-methanol
586-95-8

pyridine-4-methanol

Conditions
ConditionsYield
With magnesium(II) perchlorate; polymer-bound NADH (2a) In acetonitrile; benzene at 80℃; for 120h; Further byproducts given;100%
With sodium tetrahydroborate; lithium perchlorate In acetonitrile for 0.25h;98%
With methanol; sodium tetrahydroborate for 0.5h; Product distribution / selectivity; Cooling with ice;98%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

pyridine-4-aldoxime
696-54-8

pyridine-4-aldoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride100%
Stage #1: pyridine-4-carbaldehyde With hydroxylamine hydrochloride In ethanol; water at 20℃; for 0.0166667h; Sealed tube;
Stage #2: In ethanol; water at 120℃; for 1h; Sealed tube; Microwave irradiation;
98%
With hydroxylamine hydrochloride In methanol Reflux;94%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

pyridine-4-carboxylic acid
55-22-1

pyridine-4-carboxylic acid

Conditions
ConditionsYield
With formic acid; dihydrogen peroxide at 0 - 4℃; for 12h; other aromatic aldehydes;100%
With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In water; acetonitrile at 10℃; for 1h;100%
With formic acid; dihydrogen peroxide at 0 - 4℃; for 12h;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

2-(2,6-dichlorophenyl)ethylamine
14573-23-0

2-(2,6-dichlorophenyl)ethylamine

(2,6-dichlorophenethyl)(4-pyridin-yl-methylene)amine
163129-82-6

(2,6-dichlorophenethyl)(4-pyridin-yl-methylene)amine

Conditions
ConditionsYield
With 4 A molecular sieve In toluene for 17h; Ambient temperature;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

propylamine
107-10-8

propylamine

N-(pyridin-4-ylmethylene)propan-1-amine

N-(pyridin-4-ylmethylene)propan-1-amine

Conditions
ConditionsYield
In toluene for 1h; Ambient temperature;100%
In methanol for 4h; Inert atmosphere;
In dichloromethane at 20℃; for 24h;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

4-amino-1-benzylpiperidine
50541-93-0

4-amino-1-benzylpiperidine

pyridine-4-carboxaldehyde (1-benzylpiperidin-4-yl)imine
165807-04-5

pyridine-4-carboxaldehyde (1-benzylpiperidin-4-yl)imine

Conditions
ConditionsYield
In ethanol for 1h; Heating / reflux;100%
In ethanol for 1h; Heating / reflux;100%
In ethanol for 1h; Heating / reflux;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

4-methylsulfanylaniline
104-96-1

4-methylsulfanylaniline

pyridine-4-carboxaldehyde (4-methylthiophenyl)imine
165806-92-8

pyridine-4-carboxaldehyde (4-methylthiophenyl)imine

Conditions
ConditionsYield
With magnesium sulfate100%
With magnesium sulfate In toluene for 18h;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

4-methoxy-aniline
104-94-9

4-methoxy-aniline

(E)-4-methoxy-N-(pyridin-4-ylmethylene)phenylamine
129985-68-8

(E)-4-methoxy-N-(pyridin-4-ylmethylene)phenylamine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
In ethanol for 2h; Condensation; Heating;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

ethyl 3-(pyridin-4-yl)prop-2-enoate
24489-96-1

ethyl 3-(pyridin-4-yl)prop-2-enoate

Conditions
ConditionsYield
With potassium carbonate In ethanol at 70℃; for 2.5h; Condensation;100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Wittig-Horner Reaction; Inert atmosphere;
Stage #2: pyridine-4-carbaldehyde In tetrahydrofuran for 0.5h; Wittig-Horner Reaction; Inert atmosphere;
91%
With sodium hydride In tetrahydrofuran at 20℃; Wittig Olefination;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

p-toluidine
106-49-0

p-toluidine

4-methyl-N-pyridin-4-ylmethylene-aniline
26825-35-4

4-methyl-N-pyridin-4-ylmethylene-aniline

Conditions
ConditionsYield
at 120 - 130℃; for 2.5h;100%
In ethanol Heating;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

3-monochloro-1,2-propanediol
96-24-2

3-monochloro-1,2-propanediol

4-[4-(chloromethyl)-[1,3]dioxolan-2-yl]-pyridine

4-[4-(chloromethyl)-[1,3]dioxolan-2-yl]-pyridine

Conditions
ConditionsYield
Stage #1: pyridine-4-carbaldehyde; 3-monochloro-1,2-propanediol With toluene-4-sulfonic acid In benzene Heating; Dean-Stark apparatus;
Stage #2: With sodium carbonate at 100℃; for 3h;
100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone
627546-31-0

1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone

3-(4-pyridyl)-1-pyrrol-1-yl-2-propen-1-one

3-(4-pyridyl)-1-pyrrol-1-yl-2-propen-1-one

Conditions
ConditionsYield
In toluene at 100℃; for 48h; Wittig olefination;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

(R)-1-phenyl-ethyl-amine
3886-69-9

(R)-1-phenyl-ethyl-amine

((R)-1-Phenyl-ethyl)-[1-pyridin-4-yl-meth-(E)-ylidene]-amine
1000387-94-9

((R)-1-Phenyl-ethyl)-[1-pyridin-4-yl-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
With boron trifluoride diethyl etherate at 20℃; for 0.0166667h;
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

N-trityl-4(5)-iodoimidazole
96797-15-8

N-trityl-4(5)-iodoimidazole

pyridin-4-yl-(1-trityl-1H-imidazol-4-yl)methanol
224168-75-6

pyridin-4-yl-(1-trityl-1H-imidazol-4-yl)methanol

Conditions
ConditionsYield
Stage #1: ethylmagnesium bromide; N-trityl-4(5)-iodoimidazole In dichloromethane
Stage #2: pyridine-4-carbaldehyde In dichloromethane
100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

acrylonitrile
107-13-1

acrylonitrile

3-hydroxy-2-methylene-3-(4-pyridinyl)propanenitrile

3-hydroxy-2-methylene-3-(4-pyridinyl)propanenitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 0℃; for 0.166667h; Morita-Baylis-Hillman reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 0℃; for 0.166667h; Catalytic behavior; Solvent; Temperature; Time; Morita-Baylis-Hillman Alkylation;100%
With 1,4-diaza-bicyclo[2.2.2]octane; 1-methyl-3-butyl-1,2,3-triazolium hexafluorophosphate at 20℃; Baylis-Hillman reaction; Inert atmosphere; Ionic liquid;99%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

aniline
62-53-3

aniline

N-((pyridin-4-yl)methyl)benzenamine
3034-32-0

N-((pyridin-4-yl)methyl)benzenamine

Conditions
ConditionsYield
With phosphotungstic acid; sodium tetrahydroborate In methanol100%
With N-1-phenyl-benzotriazole-N-3-borane In 1,2-dichloro-ethane at 20℃; for 2h;99%
With Au0998Ag0002; hydrogen In ethanol at 90℃; under 6080.41 Torr; for 24h; chemoselective reaction;94%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

C14H14N2O

C14H14N2O

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
pyridine-4-carbaldehyde
872-85-5

pyridine-4-carbaldehyde

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

C14H14N2O
1000387-95-0

C14H14N2O

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%

872-85-5Relevant articles and documents

TEMPO mediated electrocatalytic oxidation of pyridyl carbinol using palladium nanoparticles dispersed on biomass derived porous nanoparticles

B, Akshaya K.,Bhat, Vinay S.,Hegde, Gurumurthy,Mathew, Agnus T.,S, Supriya,T, Maiyalagan,Varghese, Anitha

, (2020)

Remarkable electrocatalytic property of Pd nanostructures dispersed on CNSareca coated CFP electrode towards TEMPO mediated electrooxidation of pyridyl carbinol was reported for the first time. Carbon nanospheres (CNSs) derived from Areca catechu decorated with Pd nanoparticles were coated on carbon fiber paper (CFP) and was employed for electrooxidation of pyridyl carbinol in aqueous acidic medium. An environmentally benign and economic strategy was utilized for the preparation of CNSs obtained from Areca catechu. The physical characterizations, electronic state and chemical composition of the modified electrode were studied using Fourier transform infrared (FTIR) spectroscopy, X-ray diffraction (XRD) spectroscopy and X-ray photoelectron spectroscopy (XPS). Scanning electron microscopy (SEM), Transmission electron microscopy (TEM) and high resolution transmission electron microscopy (HRTEM) techniques were used for analyzing the morphology of modified electrode. The electrochemical characterizations of the modified electrodes were performed by Cyclic voltammetry (CV) and Electrochemical impedance spectroscopy (EIS). Pd decorated CNSareca dispersed on CFP electrode has exhibited strong electrocatalytic activity towards TEMPO mediated oxidation of pyridyl carbinol.

Zn-doped W/aluminium oxide catalyst: Efficient strategy towards sustainable oxidation of alcohols

An, Yu,Cai, Menglu,Chen, Yingqi,Dai, Liyan,Fang, Yangyang,Li, Jun,Wang, Xiaozhong,Zhang, Ming

, (2020)

Bifunctional catalysts have been considered to have vital importance in catalytic chemical process, but there is still some developing room for convenient materials with dual active sites. These catalysts have a notorious reputation for inhibiting mutual neutralization and controlling the distribution of active sites in order to perform their functions. We tailor a series of W-Zn-Al2O3 catalysts by modulating the doping density of metal species, which can boost the catalytic process of alcohols into corresponding carbonyl compounds in an additive-free-condition. Test results indicate that the proper content of zinc element can promote the overall activities, and subsequent adjustment of doping zinc can dramatically increase the electronic interaction and change the distribution of chemical active sites. Also, a plausible reaction mechanism was proposed to better understand the acid-base bifunctional catalytic process. Theoretical results confirm this system can provide certain references for similar reactants. Present reaction system is a green procedure and features a broad substrate scope, which reveals a sustainable method to process oxidative dehydrogenation reaction.

Iodine-imine Synergistic Promoted Povarov-Type Multicomponent Reaction for the Synthesis of 2,2′-Biquinolines and Their Application to a Copper/Ligand Catalytic System

Hu, Qi-Qi,Gao, Yan-Ting,Sun, Jia-Chen,Gao, Jing-Jing,Mu, Hong-Xiao,Li, Yi-Ming,Zheng, Ya-Nan,Yang, Kai-Rui,Zhu, Yan-Ping

supporting information, p. 9000 - 9005 (2021/11/24)

An efficient iodine-imine synergistic promoted Povarov-type multicomponent reaction was reported for the synthesis of a practical 2,2′-biquinoline scaffold. The tandem annulation has reconciled iodination, Kornblum oxidation, and Povarov aromatization, where the methyl group of the methyl azaarenes represents uniquely reactive input in the Povarov reaction. This method has broad substrate scope and mild conditions. Furthermore, these 2,2′-biquinoline derivatives had been directly used as bidentate ligands in metal-catalyzed reactions.

Pyridinium Chlorochromate Supported on Montmorillonite–KSF as a Versatile Oxidant under Ball Milling Conditions

Hosseinzadeh, Rahman,Narimani, Erfan,Mavvaji, Mohammad

, p. 461 - 471 (2021/08/09)

-

Combining photo-redox and enzyme catalysis for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives in one pot

Yu, Yuan,Lu, Wei-Fan,Yang, Zeng-Jie,Wang, Na,Yu, Xiao-Qi

supporting information, (2020/12/25)

A novel strategy combining visible-light and enzyme catalysis in one pot for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives from alcohols is described for the first time. Fourteen 4H-pyrimido[2,1-b] benzothiazole derivatives were prepared with yields of up to 98% under mild reaction conditions by a simple operation. The photoorgano catalyst rose Bengal (rB) was employed to oxyfunctionalise alcohols to aldehydes. Compared with aldehydes, alcohols with more stable properties and lower cost, thus we used photocatalysis to oxidize alcohols into aldehydes. Next, the enzyme was used to further catalyze the reaction of Biginelli to produce the target product of 4H-pyrimidine [2,1-b] benzothiazole. Experimental results show that this method provides a more efficient and eco-friendly strategy for the synthesis of 4H-pyrimido[2,1-b] benzothiazole derivatives.

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