Furo[2,3-c]pyridine-5-carboxylic acid (9CI)

Furo[2,3-c]pyridine-5-carboxylic acid (9CI) Property

Boiling point:

366.8±22.0 °C(Predicted)

Density 

1.455

storage temp. 

2-8°C

pka

1.06±0.30(Predicted)

Appearance

White to light yellow Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

warning

Hazard statements

H302Harmful if swallowed

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.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

Furo[2,3-c]pyridine-5-carboxylic acid (9CI) Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of furo[2,3-c]pyridine-5-carboxylic acid from furo[2,3-c]pyridine-5-carboxaldehyde was as follows: furo[2,3-c]pyridine-5-carboxaldehyde (850 mg, 5.8 mmol) was dissolved in 10 mL of dimethyl sulfoxide (DMSO). To this solution was added a 3 mL aqueous solution of potassium dihydrogen phosphate (KH2PO4, 221 mg, 1.6 mmol) followed by a 7 mL aqueous solution of sodium chlorite (NaClO2, 920 mg, 8.2 mmol). The reaction mixture was stirred for 3 h at room temperature. After completion of the reaction, the reaction mixture was diluted with 25 mL of water, the pH was adjusted to 10 with 2 N sodium hydroxide (NaOH) solution, and then extracted with ether (3 x 20 mL). The combined ether layers were discarded. The aqueous layer was adjusted to pH 3.5 with 10% aqueous hydrochloric acid (HCl) solution and then extracted with 10% methanol/dichloromethane (MeOH/CH2Cl2, 13 × 10 mL). The combined organic layers were dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated in vacuum to give a light-colored oil. Residual DMSO was removed at room temperature under a stream of nitrogen (N2) to give a white paste. The paste was dissolved in methanol (MeOH) and concentrated to dryness. The white solid was washed with ether and dried to give the crude furano[2,3-c]pyridine-5-carboxylic acid (94% yield). The compound with molecular formula C8H5NO3 was obtained by mass spectrometry (ESI) analysis with a mass-to-charge ratio (m/z) of 162.8 (M-H)-.

References

[1] Patent: US2003/153595, 2003, A1
[2] Patent: US2003/45540, 2003, A1
[3] Patent: WO2004/52894, 2004, A1. Location in patent: Page 36
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4425 - 4436