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500-22-1 Usage

Chemical Properties

clear yellow to light brown liquid

Uses

3-Pyridinecarboxaldehyde is a substituted pyridine with niacin activity. 3-Pyridinecarboxaldehyde is a component of tobacco smoke.

Definition

ChEBI: A pyridinecarbaldehyde that is pyridine substituted by a formyl group at position 3.

Synthesis Reference(s)

Synthetic Communications, 21, p. 1777, 1991 DOI: 10.1080/00397919108021576Tetrahedron, 32, p. 2549, 1976 DOI: 10.1016/0040-4020(76)88025-8Tetrahedron Letters, 35, p. 8019, 1994 DOI: 10.1016/0040-4039(94)80038-3

Purification Methods

Purified as for pyridine-2-aldehyde. [Beilstein 21 I 288, 21 III/IV 3517, 21/7 V 334.]

Check Digit Verification of cas no

The CAS Registry Mumber 500-22-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 0 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 500-22:
(5*5)+(4*0)+(3*0)+(2*2)+(1*2)=31
31 % 10 = 1
So 500-22-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NO/c8-5-6-2-1-3-7-4-6/h1-5H

500-22-1 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (N0090)  3-Pyridinecarboxaldehyde  >98.0%(GC)

  • 500-22-1

  • 25mL

  • 360.00CNY

  • Detail
  • TCI America

  • (N0090)  3-Pyridinecarboxaldehyde  >98.0%(GC)

  • 500-22-1

  • 100mL

  • 990.00CNY

  • Detail
  • TCI America

  • (N0090)  3-Pyridinecarboxaldehyde  >98.0%(GC)

  • 500-22-1

  • 500mL

  • 3,220.00CNY

  • Detail
  • Aldrich

  • (P62208)  3-Pyridinecarboxaldehyde  98%

  • 500-22-1

  • P62208-25G

  • 369.72CNY

  • Detail
  • Aldrich

  • (P62208)  3-Pyridinecarboxaldehyde  98%

  • 500-22-1

  • P62208-100G

  • 1,097.46CNY

  • Detail

500-22-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name pyridine-3-carbaldehyde

1.2 Other means of identification

Product number -
Other names Nicotinaldehyde

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:500-22-1 SDS

500-22-1Synthetic route

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 10% Ru/C; oxygen In toluene at 90℃; under 760.051 Torr; for 24h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 0.25h; Ambient temperature;99%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h;99%
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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;96%
Stage #1: pyridine-3-carbonitrile With diisobutylaluminium hydride In toluene at 20℃; for 0.222222h; Flow reactor;
Stage #2: With water; sodium L-tartrate In toluene at 0℃; chemoselective reaction;
52%
N,N-diethylnicotinamide
59-26-7

N,N-diethylnicotinamide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h;99%
With diethyl ether; diisobutylaluminium hydride
nicotinaldehyde oxime
51892-16-1

nicotinaldehyde oxime

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With titanium tetrachloride; sodium iodide In acetonitrile for 0.0833333h; Ambient temperature; other oximes, var. time;97%
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;97%
Multi-step reaction with 2 steps
1: diethyl ether; lithium alanate
2: lead (IV)-acetate; benzene
View Scheme
N-methyl-N-(3-pyridylmethyl)amine
20173-04-0

N-methyl-N-(3-pyridylmethyl)amine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform for 12h; Reflux;95%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In chloroform for 24h; Reflux;93%
pyridine-3-carboxaldehyde semicarbazone

pyridine-3-carboxaldehyde semicarbazone

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water; silica gel In dichloromethane at 20℃; for 1.8h;91%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 90.1%
B 3.4%
With sodium hypochlorite; C13H26N2OPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 87.7%
B 3.5%
With sodium hypochlorite; C16H28N2O5Pol; sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 15 - 20℃; for 4.5h; Product distribution / selectivity;A 85.3%
B 5.3%
3-pyridinecarbonyl chloride
10400-19-8

3-pyridinecarbonyl chloride

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature;90%
With diethylene glycol dimethyl ether; lithium tri-t-butoxyaluminum hydride at -78℃;
With piperidine; diethyldihydroaluminate 1.) THF, RT, 30 min, 2.) THF, toluene, RT, 1 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: benzene; pyridine
2: lithium alanate; tetrahydrofuran / 0 °C
View Scheme
3-(pyridin-3-yl)acrylic acid
1126-74-5

3-(pyridin-3-yl)acrylic acid

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With aluminum oxide; potassium permanganate In dichloromethane at 20℃;90%
3-Bromopyridine
626-55-1

3-Bromopyridine

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

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

N,N-dimethyl-formamide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
Stage #1: 3-Bromopyridine; n-butyllithium In toluene at -50℃;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - -15℃;
90%
3-pyridinealdoxime
1193-92-6

3-pyridinealdoxime

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 2,6-dicarboxypyridinium fluorochromate for 0.333333h;90%
With dihydrogen peroxide; phosphotungstic acid In various solvent(s) at 20℃; for 5h; Product distribution; Further Variations:; Catalysts;76%
With oxygen; benzaldehyde In benzonitrile; toluene at 60℃; for 2.58333h; Green chemistry;
3-Bromopyridine
626-55-1

3-Bromopyridine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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;90%
3-iodopyridine
1120-90-7

3-iodopyridine

carbon dioxide
124-38-9

carbon dioxide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; under 7500.75 Torr; for 20h; Autoclave; Green chemistry;89%
With rhodium(III) iodide; hydrogen; acetic anhydride; triethylamine; triphenylphosphine In N,N-dimethyl acetamide at 100℃; for 24h; Autoclave;60%
3-Methylpyridine
108-99-6

3-Methylpyridine

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

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

C

nicotinic acid
59-67-6

nicotinic 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; Product distribution;A 5%
B 18%
C 60%
D 88%
at 140℃; for 14h; Further byproducts given;A 5%
B 18%
C 60%
D 88%
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

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

C

nicotinic acid
59-67-6

nicotinic 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 3-Methylpyridine at 140℃; for 14h; Further byproducts given;A 5%
B 18%
C 60%
D 88%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Green chemistry;88%
Multi-step reaction with 2 steps
1: 85 percent / CH2Cl2 / 12 h
2: 15 percent / NaOMe / methanol / 35 deg C -> 20 deg C, 2 h
View Scheme
nicotinamide
98-92-0

nicotinamide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.166667h;86%
With lithium-tris(diethylamino)hydridoaluminate In tetrahydrofuran for 12h; Ambient temperature;53%
3-Methylpyridine
108-99-6

3-Methylpyridine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; nitric acid; acetic acid at 40℃; under 1520.1 Torr; for 5h; Temperature; Pressure; Reagent/catalyst; Autoclave; Sealed tube;85%
With tert.-butylhydroperoxide at 120℃; for 5h; Sealed tube; Green chemistry;80%
With oxygen; V-Mo oxide at 370 - 430℃; Mechanism;
With selenium(IV) oxide
With oxygen In water at 290℃; under 760.051 Torr; Reagent/catalyst;
N-methoxy-N-methylpyridine-3-carboxamide
95091-91-1

N-methoxy-N-methylpyridine-3-carboxamide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.25h;85%
With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃; Inert atmosphere; chemoselective reaction;> 99 %Chromat.
3-picolyl bromide
69966-55-8

3-picolyl bromide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With oxygen; kieselguhr; copper(l) chloride In hexane for 2.5h; Oxidation; Heating;84%
2-nitropropane
79-46-9

2-nitropropane

3-(bromomethyl)pyridine hydrobromide

3-(bromomethyl)pyridine hydrobromide

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

α-(1-methyl-1-nitroethyl)-3-pyridinemethanol
36757-33-2

α-(1-methyl-1-nitroethyl)-3-pyridinemethanol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran Hass-Bender/Henry reaction;A n/a
B 84%
C13H13N3O3S
6281-93-2

C13H13N3O3S

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With sodium carbonate In ethylene glycol for 0.025h; McFadyen-Stevens reaction; microwave irradiation;82%
3-iodopyridine
1120-90-7

3-iodopyridine

carbon monoxide
201230-82-2

carbon monoxide

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With sodium formate In N,N-dimethyl-formamide at 110℃; under 760.051 Torr; for 8h;80%
With sodium formate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 10h;79%
With palladium(II) acetylacetonate; N,N,N,N,-tetramethylethylenediamine; hydrogen; bis-diphenylphosphinomethane In toluene at 100℃; under 7500.75 Torr; for 10h; Autoclave;78%
3-Bromopyridine
626-55-1

3-Bromopyridine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With carbon monoxide; triethylamine In benzene80%
3-<(methylsulfinyl)(methylsulfanyl)methyl>pyridine

3-<(methylsulfinyl)(methylsulfanyl)methyl>pyridine

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With tetrafluoroboric acid In tetrahydrofuran; water for 192h; Ambient temperature;78%
3-iodopyridine
1120-90-7

3-iodopyridine

9-methyl-9H-fluorene-9-carbonyl chloride
82102-37-2

9-methyl-9H-fluorene-9-carbonyl chloride

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; potassium formate; tetra-(n-butyl)ammonium iodide; tricyclohexylphosphine tetrafluoroborate; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; for 18h; Sealed tube; Glovebox; Inert atmosphere;78%
nicotinic anhydride
16837-38-0

nicotinic anhydride

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With P(p-CH3OC6H4)3; methylphenylsilane; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 20h; Schlenk technique; Inert atmosphere;75%
3-iodopyridine
1120-90-7

3-iodopyridine

formic acid
64-18-6

formic acid

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube;71%
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube;70%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

benzoic acid hydrazide
613-94-5

benzoic acid hydrazide

(E)-N'-(pyridin-3-ylmethylene)benzohydrazide
1215-53-8

(E)-N'-(pyridin-3-ylmethylene)benzohydrazide

Conditions
ConditionsYield
at 205℃; under 4350.44 Torr; for 0.0666667h; Microwave irradiation; neat (no solvent);100%
In ethanol for 3h; Heating;89%
With hydrogenchloride In ethanol at 20℃; for 0.5h; Condensation;84%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

nicotinaldehyde oxime
51892-16-1

nicotinaldehyde oxime

Conditions
ConditionsYield
With pyridine; hydroxylamine hydrochloride In ethanol100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water for 0.5h; Reflux;58%
With hydroxylamine hydrochloride; sodium hydroxide In water at 20℃; for 0.5h;47%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

2-Pyridin-3-yl-1,4-dihydro-2H-benzo[d][1,3]oxazine
134778-04-4

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

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-hydrazino-5H-[1,2,4]triazino[5,6-b]indole
31523-22-5

3-hydrazino-5H-[1,2,4]triazino[5,6-b]indole

3-(Pyridine-3-aldehyde)hydrazono-1,2,4-triazino<5,6-b>indole
73718-28-2

3-(Pyridine-3-aldehyde)hydrazono-1,2,4-triazino<5,6-b>indole

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 1h; Heating;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2-Hydroxybenzylamine
932-30-9

2-Hydroxybenzylamine

2-Pyridin-3-yl-3,4-dihydro-2H-benzo[e][1,3]oxazine
134778-03-3

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

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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

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

3-((4S,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
134778-06-6, 134778-07-7, 134876-47-4, 134876-48-5

3-((4S,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature; Further byproducts given;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Norpseudoephedrine
37577-07-4

Norpseudoephedrine

3-((4R,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine
134778-06-6, 134778-07-7, 134876-47-4, 134876-48-5

3-((4R,5R)-4-Methyl-5-phenyl-oxazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature; Further byproducts given;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

potassium cyanide
151-50-8

potassium cyanide

2-hydroxy-2-(pyridin-3-yl)acetonitrile
17604-74-9

2-hydroxy-2-(pyridin-3-yl)acetonitrile

Conditions
ConditionsYield
With water; acetic acid at 5 - 10℃; for 2h;100%
With hydrogenchloride
With acetic acid In water for 18h; Ambient temperature;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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

2-Amino-2-methyl-1-propanol

3-(4,4-Dimethyl-oxazolidin-2-yl)-pyridine
134778-05-5

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

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

sulfanilamide
63-74-1

sulfanilamide

N4-(3-pyridylidene) sulfanilamide
74028-05-0

N4-(3-pyridylidene) sulfanilamide

Conditions
ConditionsYield
at 150 - 155℃; for 0.0833333h;100%
In ethanol for 3h; Heating;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 2-[hydroxy(pyridin-3-yl)methyl]propenoate
87102-11-2

methyl 2-[hydroxy(pyridin-3-yl)methyl]propenoate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane; water at 20℃; for 8h; Baylis-Hillman reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.75h; Baylis-Hillman reaction; neat (no solvent);100%
With uracil-Cu2+ nanoparticles immobilized on alpha-zirconium hydrogen phosphate In N,N-dimethyl-formamide at 20℃; for 8.5h; Morita-Baylis-Hillman Alkylation;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2,3-dimethylquinolizinium perchlorate

2,3-dimethylquinolizinium perchlorate

3-Methyl-2-((E)-2-pyridin-3-yl-vinyl)-quinolizinylium; perchlorate

3-Methyl-2-((E)-2-pyridin-3-yl-vinyl)-quinolizinylium; perchlorate

Conditions
ConditionsYield
With piperidine In acetonitrile for 4h; Heating;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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

propan-1-ol-3-amine

2-Pyridin-3-yl-[1,3]oxazinane
134778-02-2

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

Conditions
ConditionsYield
In ethanol for 2h; Ambient temperature;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

p-aminoethylbenzoate
94-09-7

p-aminoethylbenzoate

ethyl p-(3-pyridylmethyleneamino)benzoate
25927-67-7

ethyl p-(3-pyridylmethyleneamino)benzoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 12h; Reflux;100%
toluene-4-sulfonic acid In toluene for 12h; Reflux;100%
In benzene for 6h; Heating;98.5%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

acrylonitrile
107-13-1

acrylonitrile

3-hydroxy-2-methylene-3-(3-pyridyl)propanenitrile

3-hydroxy-2-methylene-3-(3-pyridyl)propanenitrile

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 0℃; for 0.833333h; Morita-Baylis-Hillman reaction;100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat (no solvent) at 0℃; for 0.833333h; Catalytic behavior; Solvent; Temperature; Time; Morita-Baylis-Hillman Alkylation;100%
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃; for 0.2h; Baylis-Hillman reaction; neat (no solvent);99%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

phenethyl azide
6926-44-9

phenethyl azide

phenethyl-pyridin-3-ylmethylene-amine

phenethyl-pyridin-3-ylmethylene-amine

Conditions
ConditionsYield
With triphenylphosphine-bound polystyrene In tetrahydrofuran at 20℃; for 24h; Staudinger/Aza-Wittig reaction;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

N-(4-methoxyphenyl)-N-[(E)-1-(3-pyridyl)methylidene]amine

N-(4-methoxyphenyl)-N-[(E)-1-(3-pyridyl)methylidene]amine

Conditions
ConditionsYield
With triphenylphosphine-bound polystyrene In tetrahydrofuran at 20℃; for 24h; Staudinger/Aza-Wittig reaction;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

p-toluidine
106-49-0

p-toluidine

3-<(4-methylphenyl)iminomethyl>pyridine
110684-48-5

3-<(4-methylphenyl)iminomethyl>pyridine

Conditions
ConditionsYield
at 120 - 130℃; for 2.5h;100%
In ethanol Heating;
With sulfonic acid supported on hydroxyapatite-γ-Fe2O3 In ethanol
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-pyridinealdoxime
1193-92-6

3-pyridinealdoxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol for 0.416667h; Heating;100%
With hydroxylamine hydrochloride100%
With hydroxylamine hydrochloride; triethylamine In methanol at 80℃; Inert atmosphere;92%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

ethylenediamine
107-15-3

ethylenediamine

N,N’-bis[1-pyridin-3-ylmeth-(E)-ylidene]ethane-1,2-diamine

N,N’-bis[1-pyridin-3-ylmeth-(E)-ylidene]ethane-1,2-diamine

Conditions
ConditionsYield
In ethanol Heating;100%
With iron(III) chloride In methanol at 20℃; for 0.5h;90%
In methanol for 3h; Heating;85%
In methanol at 80℃; for 0.5h;47%
In methanol for 0.166667h;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-<(4-methoxyphenyl)iminomethyl>pyridine
41855-73-6

3-<(4-methoxyphenyl)iminomethyl>pyridine

Conditions
ConditionsYield
In ethanol for 1h; Sonication;100%
With acetic acid In ethanol at 85℃; for 12h;50.3%
In tetrahydrofuran for 0.5h; Heating;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

1,4-diaminobutane
110-60-1

1,4-diaminobutane

N,N-bis-(pyridin-3-ylmethylene)butane-1,4-diamine

N,N-bis-(pyridin-3-ylmethylene)butane-1,4-diamine

Conditions
ConditionsYield
In ethanol Heating;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

C14H14N2O

C14H14N2O

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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

(R)-1-phenyl-ethyl-amine

((R)-1-Phenyl-ethyl)-[1-pyridin-3-yl-meth-(E)-ylidene]-amine
1000387-97-2

((R)-1-Phenyl-ethyl)-[1-pyridin-3-yl-meth-(E)-ylidene]-amine

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
In dichloromethane at 20℃; for 48h;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

C14H14N2O

C14H14N2O

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

(R)-2-methoxy-1-phenylethylamine
64715-85-1, 91298-74-7, 127180-88-5

(R)-2-methoxy-1-phenylethylamine

C15H16N2O

C15H16N2O

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 12h;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

4-[bromo-(piperidin-4-ylidene)methyl]-N,N-diethylbenzamide
725229-81-2

4-[bromo-(piperidin-4-ylidene)methyl]-N,N-diethylbenzamide

4-[bromo[1-(3-pyridinylmethyl)-4-piperidinylidene]methyl]-N,N-diethyl-benzamide
725242-76-2

4-[bromo[1-(3-pyridinylmethyl)-4-piperidinylidene]methyl]-N,N-diethyl-benzamide

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 18h;100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-(cyclopentyloxy)-4-methoxybenzenamine
154464-26-3

3-(cyclopentyloxy)-4-methoxybenzenamine

3-Cyclopentyl-4-methoxy-N-(pyridin-3-ylmethyl)aniline

3-Cyclopentyl-4-methoxy-N-(pyridin-3-ylmethyl)aniline

Conditions
ConditionsYield
Stage #1: 3-pyridinecarboxaldehyde; 3-(cyclopentyloxy)-4-methoxybenzenamine With toluene-4-sulfonic acid In methanol for 4h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 20h;
100%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

4-(2,4-difluorophenoxy)aniline
286932-63-6

4-(2,4-difluorophenoxy)aniline

N-(4-(2,4-difluorophenoxy)phenyl)pyrid-3-ylmethyleneamine
353235-61-7

N-(4-(2,4-difluorophenoxy)phenyl)pyrid-3-ylmethyleneamine

Conditions
ConditionsYield
In methanol at 55℃; for 3h;100%

500-22-1Relevant articles and documents

-

Suvorov et al.

, (1969)

-

Selective photocatalytic oxidation of 3-pyridinemethanol on platinized acid/base modified TiO2

?etinkaya, S?d?ka,Augugliaro, Vincenzo,Garlisi, Corrado,Lewin, Erik,Palmisano, Giovanni,Sá, Jacinto,Yurdakal, Sedat

, p. 4549 - 4559 (2021)

TiO2catalysts, modified with acidic or alkaline solutions and then platinized, were used for the partial photocatalytic oxidation of 3-pyridinemethanol to 3-pyridinemethanal and vitamin B3under environmentally friendly conditions. The reaction took place in water under UVA light and air oxygen. Catalysts were characterized by TEM, photoluminescence, DRIFT-IR, Raman, DRS, XPS, and photocurrent measurements. The photocatalytic activity results show that Pt loading of untreated samples leads to a significant activity improvement (hence product yield) as much as acid and alkaline treatments do. Moreover, the alkaline treated TiO2samples exhibit a further increase in activity after loading with Pt. Pt acts as an electron scavenger promoting electron transfer from the TiO2conduction band, consequently boosting the photogenerated pair numbers available for the reactive process. Photocurrent measurements show that the TiO2photocatalysts' active sites increase significantly after platinization and alkaline/acid treatment. The treated and/or Pt loaded catalysts showed good thermal stability (at least up to 400 °C).

Mild reductive deoximation with TiCl4/NaI reagent system

Balicki,Kaczmarek

, p. 1777 - 1782 (1991)

The application of the TiCl4/NaI reagent system in the reductive cleavage of oximes under mild conditions is reported.

-

Schoenberg,A.,Heck,R.F.

, p. 7761 - 7764 (1974)

-

Micellar effects on kinetics and mechanism of Vilsmeier–Haack formylation and acetylation with Pyridines

Alyami, Bandar A.,Iqubal, S. M. Shakeel,Khan, Aejaz Abdullatif,Mohammed, Tasneem

, (2022/01/19)

An efficient preparation of Vilsmeier–Haack formylated and acetylated derivatives with pyridine and substituted pyridines has been developed by employing micelles as catalyst. Their kinetic study reveals a phenomenal rate enhancement in anionic SDS, cationic CTAB, and nonionic TX-100 micellar media. The Vilsmeier–Haack reaction follows second order kinetics. Piszkiewicz’s co-operativity model was used to interpret the results in micellar media. The observed activation parameters ΔH and ΔS values were calculated from Eyring’s plots. The main features of this study were easy process, mild reaction conditions and readily available reagents. Graphical abstract: [Figure not available: see fulltext.].

Photoredox-Catalyzed Simultaneous Olefin Hydrogenation and Alcohol Oxidation over Crystalline Porous Polymeric Carbon Nitride

Qiu, Chuntian,Sun, Yangyang,Xu, Yangsen,Zhang, Bing,Zhang, Xu,Yu, Lei,Su, Chenliang

, p. 3344 - 3350 (2021/07/26)

Booming of photocatalytic water splitting technology (PWST) opens a new avenue for the sustainable synthesis of high-value-added hydrogenated and oxidized fine chemicals, in which the design of efficient semiconductors for the in-situ and synergistic utilization of photogenerated redox centers are key roles. Herein, a porous polymeric carbon nitride (PPCN) with a crystalline backbone was constructed for visible light-induced photocatalytic hydrogen generation by photoexcited electrons, followed by in-situ utilization for olefin hydrogenation. Simultaneously, various alcohols were selectively transformed to valuable aldehydes or ketones by photoexcited holes. The porosity of PPCN provided it with a large surface area and a short transfer path for photogenerated carriers from the bulk to the surface, and the crystalline structure facilitated photogenerated charge transfer and separation, thus enhancing the overall photocatalytic performance. High reactivity and selectivity, good functionality tolerance, and broad reaction scope were achieved by this concerted photocatalysis system. The results contribute to the development of highly efficient semiconductor photocatalysts and synergistic redox reaction systems based on PWST for high-value-added fine chemical production.

Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source

Dogga, Bhushanarao,Joseph, Jayan T.,Kumar, C. S. Ananda

supporting information, p. 309 - 313 (2020/12/23)

An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.

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