2-Amino-3-pyridinecarboxaldehyde

2-Amino-3-pyridinecarboxaldehyde Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-Amino-3-pyridinecarboxaldehyde Chemical Properties,Usage,Production

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.