2-Amino-3-pyridinecarboxaldehyde CAS 7521-41-7
Introduction：Basic information about 2-Amino-3-pyridinecarboxaldehyde CAS 7521-41-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Amino-3-pyridinecarboxaldehyde Basic information
| Product Name: | 2-Amino-3-pyridinecarboxaldehyde |
| Synonyms: | 2-Aminopyridine-3-carboxaldehyde,98%;2-Amino-3-pyridinecarboxaldehyde 97%;2-AMINO-3-FORMYLPYRIDINE;2-AMINO-3-PYRIDINECARBOXALDEHYDE;2-AMINONICOTINALDEHYDE;2-AMINO-PYRIDIN-3-CARBALDEHYDE;2-AMINO-PYRIDINE-3-CARBALDEHYDE;2-AMINOPYRIDINE-3-CARBOXALDEHYDE |
| CAS: | 7521-41-7 |
| MF: | C6H6N2O |
| MW: | 122.12 |
| EINECS: | 626-730-5 |
| Product Categories: | Aldehydes;Building Blocks;FINE Chemical & INTERMEDIATES;Pyridine;C6;Heterocyclic Building Blocks;pharmacetical;Pyridine series;Pyridines;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Heterocycle-Pyridine series;Pyrimidines |
| Mol File: | 7521-41-7.mol |
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) |
| Fp | >300℃ |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Soluble in Ether, Ethyl acetate, Chloroform (Slightly), Methanol (Slightly) |
| form | Powder, Crystals and/or Chunks |
| pka | 4.99±0.36(Predicted) |
| 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 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| 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 | 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 Preparation Products And Raw materials
| Raw materials | 1H-Isoindole-1,3(2H)-dione, 2-[3-(dibromomethyl)-2-pyridinyl]--->Pyrido[2,3-d]pyrimidine, 2-(3-pyridinyl)--->(2-Aminopyridin-3-yl)methanol-->N-(3-FORMYL-2-PYRIDINYL)-2,2-DIMETHYLPROPANAMIDE |
| Preparation Products | 2-(piperidin-4-yl)-1,8-naphthyridine-->[1,8]NAPHTHYRIDINE-2-CARBALDEHYDE-->(E)-Methyl 3-(2-aminopyridin-3-yl)acrylate-->3-(1,8-NAPHTHYRIDIN-2-YL)PROPAN-1-OL-->2-(chloromethyl)-1,8-naphthyridine-->3-(1H-Benzoimidazol-2-yl)-pyridin-2-ylamine-->3-Nitro-1,8-naphthyridin-2-ol-->ethyl 2-(1,8-naphthyridin-2-yl)acetate-->2-AMINO-5-IODO-PYRIDINE-3-CARBALDEHYDE-->2-OXO-1,2-DIHYDRO-[1,8]NAPHTHYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER-->2-Oxo-1,2-dihydro-1,8-naphthyridine-3-carbonitrile |
