1,3-diethyl 2-(6-chloro-9H-carbazol-2-yl)-2-(2H3)methylpropanedioate

• ChemBase ID: 167325
• Molecular Formular: C20H20ClNO4
• Molecular Mass: 373.8301
• Monoisotopic Mass: 373.10808581
• SMILES: c1c(cc2c(c1)[nH]c1c2ccc(c1)C(C(=O)OCC)(C(=O)OCC)C)Cl
• Canonical SMILES: CCOC(=O)C(c1ccc2c(c1)[nH]c1c2cc(cc1)Cl)(C(=O)OCC)C
• InChI: InChI=1S/C20H20ClNO4/c1-4-25-18(23)20(3,19(24)26-5-2)12-6-8-14-15-11-13(21)7-9-16(15)22-17(14)10-12/h6-11,22H,4-5H2,1-3H3
• InChIKey: VCWSZWDBRMAJJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-(6-chloro-9H-carbazol-2-yl)-2-(^2H₃)methylpropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-(6-chloro-9H-carbazol-2-yl)-2-(^2H₃)methylpropanedioate
• Synonyms: (6-Chloro-9H-carbazol-2-yl)methyl-propanedioic Acid Diethyl Ester; Diethyl-(6-chloro-2-carbazolyl)methyl-d3 Malonate

Database IDs

• CAS Number: 1189473-03-7
• PubChem SID: 162261458
• PubChem CID: 45039001

CALCULATED PROPERTIES

• Acid pKa: 14.7494545
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.628776
• LogD (pH = 7.4): 4.628776
• Log P: 4.628776
• Molar Refractivity: 99.4127 cm^3
• Polarizability: 41.145687 Å^3
• Polar Surface Area: 68.39 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 134-135°C

DETAILS

Toronto Research Chemicals - D444027

A labelled intermediate in the synthesis of Caprofen-d3.

REFERENCES

• Randall, L.O., et al.: Arch. Int. Pharmacodyn., 220,94 (1976)
• Yu, T.F., et al.: J. Clin. Pharmacol., 20, 347 (1976)
• O’Brien, W.M., et al.: Pharmacotherapy, 7, 16 (1976)