Chloramphenicol base

• CAT Number: R015617
• CAS Number: 716-61-0
• Molecular Formula: C9H12N2O4
• Molecular Weight: 212.205
• Purity: 99%
• Synonyms: D-threo-(1R,2R)-1-p-Nitrophenyl-2-amino-1,3-propanediol; D-threo-2-Amino-1-(4-nitrophenyl)-1,3-propanediol; D-threo-2-Amino-1-(p-nitrophenyl)-1,3-propanediol; Levoamine; [R-(R*,R*)]-2-Amino-1-(4-nitrophenyl)-1,3-propanediol
• Appearance: White solid
• Storage: -20°C
• Analysis method: HPLC
• InChI: InChI=1S/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2/t8-,9-/m1/s1
• InChIKey: OCYJXSUPZMNXEN-RKDXNWHRSA-N
• SMILES: C1=CC(=CC=C1C(C(CO)N)O)[N+](=O)[O-]

Chloramphenicol base is the parent 4-nitrophenylpropylamine formed by the hydrolysis of the dichloroacetamide of
chloramphenicol and is a degradation product commonly encountered with commercial production of chloramphenicol.
Chloramphenicol base has no antibiotic activity but has played an integral role in the synthesis and SAR of new generation
antibiotics, notably thiamphenicol and experimental analogues, bromamphenicol and methamphenicol.

Reference

1. Chloramphenicol (chloromycetin). IV. Chemical studies. Rebstock M.C. et al., J. Am. Chem. Soc. 1949, 71,
2458.
2. Chloramphenicol (chloromycetin). VI. A synthetic approach. Long L.M. & Troutman H.D. J. Am. Chem. Soc.
1949, 71, 2469.
3. Biochemical studies on chloramphenicol. III. Isolation and identification of metabolic products in urine. Glazko
A.J. et al., J. Biol. Chem. 1950, 183, 679.
4. Structure-activity relationships of chloramphenicols. Hansch C. et al., J. Med. Chem. 1973, 16, 917.