2-Amino-3-pyridinecarboxaldehyde 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

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Amino-3-pyridinecarboxaldehyde 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.

Synthesis

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(7521-41-7)Related Product Information

• 4-Dimethylaminobenzaldehyde
• 2-Aminopyridine
• Molasses
• Glycine
• 2-Pyridinecarboxaldehyde
• 4-Pyridinecarboxaldehyde
• 2-Amino-3-picoline
• 4-Dimethylaminopyridine
• 4-Aminobenzaldehyde
• Betaine
• 3-Aminopyridine
• 3-Pyridinecarboxaldehyde
• ALTRENOGEST
• Nalidixic acid
• 2-Aminonicotinic acid
• Niflumic acid
• Amfonelic acid
• 2-ANILINONICOTINIC ACID