2-chloro-5-{[(2E)-2-(nitroimino)imidazolidin-1-yl]methyl}pyridine

• ChemBase ID: 5609
• Molecular Formular: C9H10ClN5O2
• Molecular Mass: 255.661
• Monoisotopic Mass: 255.05230227
• SMILES: c1cc(Cl)ncc1CN1CCN/C/1=N\[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)/N=C/1\NCCN1Cc1ccc(nc1)Cl
• InChI: InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)
• InChIKey: YWTYJOPNNQFBPC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-5-{[(2E)-2-(nitroimino)imidazolidin-1-yl]methyl}pyridine
• IUPAC Traditional name: C9H10ClN5O2; imidacloprid
• Synonyms: (2E)-1-[(6-chloropyridin-3-yl)methyl]-N-nitroimidazolidin-2-imine; (2E)-1-[(6-Chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine; 1-[(6-Chloro-3-pyridinyl)methyl]-4,5-dihydro-N-nitro-1H-imidazol-2-amine; 1-[(6-Chloro-3-pyridinyl)methyl]-N-nitro-2-imidazolidinimine; Couraze; Premis; Grubex; Imidacloprid

Database IDs

• CAS Number: 138261-41-3; 105827-78-9
• MDL Number: MFCD00468059
• PubChem SID: 99444451; 160969037
• PubChem CID: 86418

CALCULATED PROPERTIES

JChem

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.7601833
• LogD (pH = 7.4): 0.7601846
• Log P: 0.7601846
• Molar Refractivity: 63.549 cm^3
• Polarizability: 23.06492 Å^3
• Polar Surface Area: 86.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.65
• LOG S: -2.87
• Solubility (Water): 3.46e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT

DETAILS

DrugBank - DB07980

Drug information: experimental

Toronto Research Chemicals - I274990

A neonicotinoid; the active ingredient in certain neuro-active insecticides. Reports show that when exposed to neonicotinid pesticides honeybees have probelms returnign home after foraging and bumblebee colonies grow poorly and produce fewer queens.

REFERENCES

• Chauzat, M., et al.: Env. Entomol., 38, 514 (2009)
• Patial, A., et al.: Env. Ecol., 27, 320 (2009)
• Fernandez-Bayo, J., et al.: J. Agric., Food Chem., 57, 5435 (2009)
• Tomizawa, M., et al.: J. Med. Chem., 52, 3735 (2009)
• Chem. and Eng. News 90: 10 (2012)