3-Pyridinecarboxaldehyde, 2-amino-
2-AMINONICOTINALDEHYDE · 2-AMINO-PYRIDINE-3-CARBALDEHYDE · 3-PYRIDINECARBOXALDEHYDE, 2-AMINO- · 3-formylpyridin-2-amine · 2-AMINO-3-FORMYLPYRIDINE · 2-aminonicotinaldehyde 1 · 2-Aminonicotinaldehyde 99% · 2-Aminonicotinaldehyde >2-Aminopyridine-3-carboxaL
Identifiers & Physical Properties
| CAS No. | 7521-41-7 |
|---|---|
| Molecular formula | C6H6N2O |
| Average molar mass | 122.12 g/mol |
| Monoisotopic mass | 122.04801282 g/mol |
| SMILES | Nc1ncccc1C=O |
| InChIKey | NXMFJCRMSDRXLD-UHFFFAOYSA-N |
| PubChem CID | 737633 |
| EC No. | 626-730-5 |
| DTXSID | DTXSID20226184 |
Chemical & Physical Properties
| XLogP | 0.5 |
|---|---|
| Topological polar surface area | 56 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 9 |
| Formal charge | 0 |
| Complexity | 105 |
| 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 conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Solubility | Soluble in Ether, Ethyl acetate, Chloroform (Slightly), Methanol (Slightly)insoluble |
| pKa (acidity coefficient) | 4.99±0.36(Predicted) |
| Physical state | Powder, Crystals and/or Chunks |
| Color | Yellow to light brown |
| Sensitivity | 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) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P280a-P304+P340-P405-P501a-P261-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi,Xn |
| Risk statements (R) | 36/37/38-20/21/22 |
| Safety statements (S) | 26-36-36/37/39 |
| Water hazard class (WGK) | 3 |
| Hazard class | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Packing group | II |
| Customs code | 29339900 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (98%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (98%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| Customs code | 29339900 |
| Risk statements (R) | 36/37/38-20/21/22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi,Xn |
| Safety statements (S) | 26-36-36/37/39 |
| Hazard class | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Storage class | 11 - Combustible Solids |
| Packing group | II |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P280a-P304+P340-P405-P501a-P261-P305+P351+P338 |
Applications & Uses
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 & Synthesis
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.