2-PYRIDYLTHIOUREA

2-PYRIDYLTHIOUREA Property

Melting point:

148-150°C

Boiling point:

298.7±32.0 °C(Predicted)

Density 

1.382±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

12.00±0.70(Predicted)

color 

White to Light yellow

BRN 

117849

InChI

InChI=1S/C6H7N3S/c7-6(10)9-5-3-1-2-4-8-5/h1-4H,(H3,7,8,9,10)

InChIKey

SLUHLANJIVXTRQ-UHFFFAOYSA-N

SMILES

N(C1=NC=CC=C1)C(N)=S

CAS DataBase Reference

14294-11-2(CAS DataBase Reference)

Safety

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RIDADR 

2811

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

2-PYRIDYLTHIOUREA Chemical Properties,Usage,Production

Uses

2-Pyridylthiourea is an intermediate used to prepare disubstituted thiazoles as potential antibacterial and antiinflammatory agents via condensation of phenacyl bromide with thioureas and thiosemicarbazones. It is also used in the synthesis of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors.

Synthesis

The general procedure for the synthesis of 1-(2-pyridyl)thiourea from 1-benzoyl-3-(2-pyridyl)-2-thiourea was as follows: N-(pyridin-2-ylthiocarbonyl)benzamide (2.3 g, 8.95 mmol) was suspended in a 10% aqueous NaOH solution (10.4 mL, 26 mmol) and stirred for 10 min at room temperature, then heated to reflux to continue the reaction for 10 minutes. Upon completion of the reaction, the mixture was cooled to 0 °C, diluted with 100 mL of water and subsequently extracted with ethyl acetate (3 × 150 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated to give the crude product 1-(2-pyridyl)thiourea (1.2 g). Mass spectrometry (electrospray ionization) m/z (M+H) confirmed the product.

References

[1] Synthesis, 1988, # 6, p. 456 - 459
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 14, p. 3706 - 3712
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 2, p. 634 - 639
[4] Journal of the Chemical Society, 1955, p. 803
[5] Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 1.2, p. 177 - 182