N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide

• ChemBase ID: 167294
• Molecular Formular: C13H20N2O2
• Molecular Mass: 236.3101
• Monoisotopic Mass: 236.15247789
• SMILES: c1c(cc(c(c1)O)CN(CC)CC)NC(=O)C
• Canonical SMILES: CCN(Cc1cc(ccc1O)NC(=O)C)CC
• InChI: InChI=1S/C13H20N2O2/c1-4-15(5-2)9-11-8-12(14-10(3)16)6-7-13(11)17/h6-8,17H,4-5,9H2,1-3H3,(H,14,16)
• InChIKey: BOUCRWJEKAGKKG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide
• IUPAC Traditional name: N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide
• Synonyms: N-[3-[(Diethylamino)methyl]-4-hydroxyphenyl]acetamide; α-(Diethylamino)-4'-hydroxy-m-acetotoluidide; 4-Acetamido-2-[(diethylamino)methyl]phenol; NSC 12479; NSC 51970; 3-Diethylamino Acetaminophen

Database IDs

• CAS Number: 121-78-8
• PubChem SID: 162261427
• PubChem CID: 224175

CALCULATED PROPERTIES

• Acid pKa: 8.219101
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.6704358
• LogD (pH = 7.4): -0.16001381
• Log P: 0.5731159
• Molar Refractivity: 70.9418 cm^3
• Polarizability: 26.538921 Å^3
• Polar Surface Area: 52.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D443180

An impurity of Amodiaquine (A634200). 3-Diethylamino Acetaminophen is an important precursor in preparation of anti-tuberculosis drugs.

REFERENCES

• Agrawal, V.K. et al.: Ind. J. Chem., Sec. B Org. Chem. Med. Chem., 19B, 1084 (1980)
• Latif, T. et al.: Aus. J. Med. Chem., 52, 909 (1980)