[(4-tert-butyl-2-chlorophenoxy)(2H3)methoxyphosphoryl](2H3)methylamine

• ChemBase ID: 165044
• Molecular Formular: C12H19ClNO3P
• Molecular Mass: 291.710921
• Monoisotopic Mass: 291.07910778
• SMILES: c1c(cc(c(c1)OP(=O)(NC)OC)Cl)C(C)(C)C
• Canonical SMILES: CNP(=O)(Oc1ccc(cc1Cl)C(C)(C)C)OC
• InChI: InChI=1S/C12H19ClNO3P/c1-12(2,3)9-6-7-11(10(13)8-9)17-18(15,14-4)16-5/h6-8H,1-5H3,(H,14,15)
• InChIKey: BOFHKBLZOYVHSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4-tert-butyl-2-chlorophenoxy)(^2H₃)methoxyphosphoryl](^2H₃)methylamine
• IUPAC Traditional name: [4-tert-butyl-2-chlorophenoxy(^2H₃)methoxyphosphoryl](^2H₃)methylamine
• Synonyms: Methylphosphoramidic Acid 2-Chloro-4-(1,1-dimethylethyl)phenyl Methyl Ester-d6; Methylphosphoramidic Acid 4-tert-Butyl-2-chlorophenyl Methyl Ester-d6; 4-tert-Butyl-2-chlorophenyl N-Methyl O-Methylphosphoramidate-d6; 4-tert-Butyl-2-chlorophenyl Methyl N-Methylphosphoramidate-d6; Amidofos-d6; Amidophos-d6; Crufomat-d6; Dowco 132-d6; Montrel-d6; NSC 253463-d6; Ruelene-d6; Crufomate-d6

Database IDs

• PubChem SID: 162259177
• PubChem CID: 71315011

CALCULATED PROPERTIES

• Acid pKa: 10.704875
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.1916747
• LogD (pH = 7.4): 3.1914866
• Log P: 3.191677
• Molar Refractivity: 73.2969 cm^3
• Polarizability: 29.020954 Å^3
• Polar Surface Area: 47.56 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C825502

Labelled Crufomate, an organophosphate pesticide. Crufomate is an anthelmintic that functions as a potent inhibitor of an acetylcholinesterase in the anterior end of the worms. Crufomate is also used to combat bovine hypodermatosis.

REFERENCES

• Knowles, C.O. et al.: J. Agric. Food Chem., 14, 566 (1966)
• Drummond, R.O. et al.: J. Econ. Entomol., 77, 402 (1966)
• Khan, M.A. et al.: Res. Vet. Sci., 15, 180 (1966)