4-AMIDINOPYRIDINIUM CHLORIDE

4-AMIDINOPYRIDINIUM CHLORIDE Property

Melting point:

263 °C

storage temp. 

Inert atmosphere,Room Temperature

Appearance

White to off-white Solid

InChI

InChI=1S/C6H7N3.ClH/c7-6(8)5-1-3-9-4-2-5;/h1-4H,(H3,7,8);1H

InChIKey

IONKMFGAXKCLMI-UHFFFAOYSA-N

SMILES

C(C1=CC=NC=C1)(N)=N.Cl

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

HazardClass 

IRRITANT

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P233Keep container tightly closed.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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.

P304IF INHALED:

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).

P322Specific measures (see …on this label).

P330Rinse mouth.

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

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

P340Remove victim to fresh air and keep at rest in a position comfortable for breathing.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P403Store in a well-ventilated place.

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

P405Store locked up.

P501Dispose of contents/container to..…

4-AMIDINOPYRIDINIUM CHLORIDE Chemical Properties,Usage,Production

Chemical Properties

White to light brown solid

Synthesis

The general procedure for the synthesis of 4-formamidopyridine hydrochloride from 4-cyanopyridine was as follows: 4-cyanopyridine (20.0 g, 0.2 mol) was dissolved in anhydrous methanol (200 mL), followed by a one-time addition of powdered sodium methanol (1.1 g, 20 mmol). The reaction mixture was stirred at room temperature overnight. Next, ammonium chloride (16.5 g, 0.31 mol) was added and the reaction mixture was heated to reflux for 4 hours, after which it was cooled to room temperature. After the solvent was removed by evaporation, anhydrous ethanol (300 mL) was added. The mixture was heated to reflux and maintained for 15 min before the solid was removed by filtration. The filtrate was cooled to room temperature and allowed to stand overnight. The filtrate was filtered again to remove inorganic salts and the reaction mixture was subsequently concentrated to about one-third of the original volume to give 24.0 g (76% yield) of 4-formamidinopyridine hydrochloride by final filtration.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 15, p. 3487 - 3490
[2] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 11, p. 3347 - 3356
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 12, p. 2990 - 2993
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1230 - 1241
[5] Patent: US5294612, 1994, A