ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Pyridine derivatives 2-Amino-3-pyridinecarboxaldehyde

2-Amino-3-pyridinecarboxaldehyde

Product Name2-Amino-3-pyridinecarboxaldehyde
CAS7521-41-7
MFC6H6N2O
MW122.12
EINECS626-730-5
MOL File7521-41-7.mol

Chemical Properties

Melting point	98-102 °C (lit.)
Boiling point	290.7±25.0 °C(Predicted)
Density	1.264±0.06 g/cm3(Predicted)
Flash point	>300℃
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
solubility	Soluble in Ether, Ethyl acetate, Chloroform (Slightly), Methanol (Slightly)
pka	4.99±0.36(Predicted)
form	Powder, Crystals and/or Chunks
color	Yellow to light brown
Water Solubility	insoluble
Sensitive	Air Sensitive
BRN	109598
InChI	InChI=1S/C6H6N2O/c7-6-5(4-9)2-1-3-8-6/h1-4H,(H2,7,8)
InChIKey	NXMFJCRMSDRXLD-UHFFFAOYSA-N
SMILES	C1(N)=NC=CC=C1C=O
CAS DataBase Reference	7521-41-7(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,Xn
Risk Statements	36/37/38-20/21/22
Safety Statements	26-36-36/37/39
WGK Germany	3
HazardClass	IRRITANT
PackingGroup	II
HS Code	29339900

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

yellow crystals

Uses

2-Aminonicotinaldehyde is commonly employed as a starting material for a wide variety of N-heterocyclic compounds (e.g. β-nicotyrine [N445000]) . 2-Aminonicotinaldehyde is also used as a reagent to synthesize hydrazones (e.g.thionaphthenquinone 3-hydrazone [T367720]), which possess antituburcular properties.

Preparation

Preparative Methods of 2-Amino-3-pyridinecarboxaldehyde: the reagent is best when freshly prepared. A multistep procedure starting from 2-amino-3- picoline has been improved upon by a simple two-step approach. Sulfamation of nicotinamide with ammonium sulfamate (both commercially available) provides 2-(3′-pyridyl)pyrido[2,3-d]pyridimine which may be hydrolyzed in 2 N HCl to provide the reagent (eq 1)^[1]. Substituted derivatives of the reagent may be prepared via a similar intermediate.
2-Amino-3-pyridinecarboxaldehyde synthesis

Synthesis

Pyrido[2,3-d]pyrimidine, 2-(3-pyridinyl)-

7521-27-9

7521-41-7

General procedure for the synthesis of 2-amino-3-pyridinecarboxaldehyde from the compound (CAS: 7521-27-9): first, a 2 mol/L hydrochloric acid solution was prepared. The dried feedstock was transferred to a 50 mL single neck flask and about 30 mL of the above hydrochloric acid solution was added. The mixture was heated to reflux for 4 hours and subsequently cooled to room temperature. The pH of the reaction mixture was adjusted to 7-8 using 10 mol/L sodium hydroxide solution. 5 extractions were carried out with ether and the organic phases were combined and dried over anhydrous potassium carbonate. The solvent was removed by rotary evaporation to give a yellow solid product. Finally, it was purified by column chromatography (unfolding agent ratio VD TM/VEIQH = 30:1) and dried at low temperature to obtain pure 2-amino-3-pyridinecarboxaldehyde in light yellow color in 30% yield.

storage

2-Amino-3-pyridinecarboxaldehyde is somewhat more stable than 2-Aminobenzaldehyde and may be stored for up to several months at 0 °C under an inert atmosphere. Sublimation is a convenient method for the separation of higher oligomers which may accumulate during storage. Use in a fume hood.

References

1. (a) Caluwe, P. T 1980, 36, 2359. (b) Cheng, C.-C.; Yan, S.-J. OR 1982, 28, 37. (c) Thummel, R. P. SL 1992, 1.

2-Amino-3-pyridinecarboxaldehyde

Chemical Properties

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Usage And Synthesis

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