| Identification | More | [Name]
2-PYRIDYLTHIOUREA | [CAS]
14294-11-2 | [Synonyms]
1-(2-PYRIDYL)-2-THIOUREA
1-PYRIDIN-2-YLTHIOUREA
2-PYRIDYLTHIOUREA
AKOS BBS-00007311
N-PYRIDIN-2-YLTHIOUREA | [EINECS(EC#)]
673-673-7 | [Molecular Formula]
C6H7N3S | [MDL Number]
MFCD00041227 | [Molecular Weight]
153.2 | [MOL File]
14294-11-2.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
2811 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [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 |
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