2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(3-nitrophenyl)propan-2-yl]acetamide

• ChemBase ID: 157384
• Molecular Formular: C11H12Cl2N2O5
• Molecular Mass: 323.12938
• Monoisotopic Mass: 322.01232685
• SMILES: c1cc(cc(c1)[N+](=O)[O-])[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
• Canonical SMILES: OC[C@H]([C@@H](c1cccc(c1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-2-1-3-7(4-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
• InChIKey: FTMJFHVKAXPFIY-RKDXNWHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(3-nitrophenyl)propan-2-yl]acetamide
• IUPAC Traditional name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(3-nitrophenyl)propan-2-yl]acetamide
• Synonyms: [R-(R*,R*)]-2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(3-nitrophenyl)ethyl]acetamide; D-2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-m-nitrophenethyl]acetamide; D-threo-(1R,2R)-1-m-Nitrophenyl-2-dichloroacetamido-1,3-propanediol; m-threo-Chloramphenicol; D-(-)-threo-2-Dichloroacetamido-1-(3-nitrophenyl)-1,3-propanediol; m-Chloramphenicol; D-(-)-苏-2-二氯乙酰胺基-1-(3-硝基苯基)-1,3-丙二醇; 间氯霉素

Database IDs

• CAS Number: 7411-65-6
• MDL Number: MFCD07370152
• PubChem SID: 24860765; 162251521
• PubChem CID: 16212183

CALCULATED PROPERTIES

• Acid pKa: 7.494812
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.8748314
• LogD (pH = 7.4): 0.66058975
• Log P: 0.8787035
• Molar Refractivity: 73.2007 cm^3
• Polarizability: 27.81797 Å^3
• Polar Surface Area: 115.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Product Information

• Grade: VETRANAL™, analytical standard
• Description: threo-form
• Empirical Formula (Hill Notation): C11H12Cl2N2O5

DETAILS

Sigma Aldrich - 34005

General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706024
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - C325020

The D-threo-stereoisomer of the m-nitro analog of (+/-)-Chloramphenicol.

REFERENCES

• Cammarata, A., et al.: J. Med. Chem., 10, 525 (1967)