7384-89-6

Basic information

• Product Name: L-erythro-Chloramphenicol
• Synonyms: Acetamide, 2,2-dichloro-N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-;Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,S*)]-;Acetamide, 2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-, L-erythro-(+)- (8CI);L-(+)-erythro-Chloramphenicol;L-erythro-(1R,2S)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol;L-erythro-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]acetamide;L-erythro-Chloramphenicol
• CAS NO: 7384-89-6
• Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular Weight: 323.13
• Mol File: 7384-89-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 644.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.547±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 11.03±0.46(Predicted)
• CAS DataBase Reference: L-erythro-Chloramphenicol(CAS DataBase Reference)
• NIST Chemistry Reference: L-erythro-Chloramphenicol(7384-89-6)
• EPA Substance Registry System: L-erythro-Chloramphenicol(7384-89-6)

Safety Data

• Hazardous Substances Data: 7384-89-6(Hazardous Substances Data)

Usage

Description

L-erythro-Chloramphenicol, also known as threo-chloramphenicol, is a synthetic broad-spectrum antibiotic derived from the bacterium Streptomyces venezuelae. It is characterized by its ability to inhibit bacterial protein synthesis by targeting the 50S subunit of the bacterial ribosome. L-erythro-Chloramphenicol is distinguished from other isomers by its specific optical rotation and can be identified through reversed phase and chiral liquid chromatography combined with tandem mass spectrometric detection.

Uses

Used in Pharmaceutical Industry:
L-erythro-Chloramphenicol is used as an antibiotic for the treatment of various bacterial infections, particularly those caused by gram-positive and some gram-negative bacteria. Its broad-spectrum activity makes it effective against a wide range of bacterial pathogens.
Used in Biological Studies:
In the field of biological research, L-erythro-Chloramphenicol serves as a potent inhibitor of electron transport in the mitochondria. This property makes it a valuable tool for studying mitochondrial function and the mechanisms of oxidative phosphorylation.
Used in Analytical Chemistry:
L-erythro-Chloramphenicol is used as a chiral reference compound in the development and validation of analytical methods for the separation and identification of enantiomers. Its distinct optical rotation and chromatographic properties make it a useful standard for chiral liquid chromatography and tandem mass spectrometric detection.

Upstream product

• 116-54-1 dichloroacetic acid methyl ester 
• 2792-51-0 (1R,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol 
• 884595-44-2 (1R,2S)-2-benzoylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 116181-53-4 (1R,2S)-2-benzoylamino-3-benzoyloxy-1-(4-nitro-phenyl)-propan-1-ol 
• 116181-52-3 (1S,2S)-2-benzoylamino-3-benzoyloxy-1-(4-nitro-phenyl)-propan-1-ol 
• 112322-24-4 (4S)-4r-benzoyloximethyl-5c-(4-nitro-phenyl)-2-phenyl-4,5-dihydro-oxazole 
• 513-96-2 3,3,3-trichloro-2-hydroxy-propionitrile 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 872302-03-9 dichloroacetyl-phosphorous acid diethyl ester 
• 26367-75-9 chloramphenicol 
• 6158-95-8 (S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one 
• 907579-60-6 dichloroacetic acid-[(5R)-4c-(4-nitro-phenyl)-2-oxo-[1,3]dioxan-5r-ylamide] 
• 115082-34-3 dichloroacetic acid-[(5R)-4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 

Downstream Products

• 56-75-7 chloramphenicol 
• 134-90-7 L-threo-chloramphenicol 
• 115082-34-3 dichloroacetic acid-[4t-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 
• 115082-34-3 dichloroacetic acid-[4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 
• 24223-54-9 (RS)-((RS)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 492-79-5 (1RS,2RS)-3-benzoyloxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 492-79-5 (1RS,2SR)-3-benzoyloxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 10318-16-8 (1RS,2SR)-3-acetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 530-43-8 (1RS,2RS)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-3-palmitoyloxy-propan-1-ol 
• 906366-48-1 (2R,3R)-2-[N-(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propanoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 

Relevant articles and documents

Oxidant controlled regio- and stereodivergent azidohydroxylation of alkenes via I2 catalysis

A novel, I2 catalyzed regio- and stereodivergent vicinal azidohydroxylation of alkenes leading to 1,2-azidoalcohols in high yields (up to 92%) and excellent dr (up to 98%) has been developed. This unprecedented transformation employs NaN3 and DMF as N- and O-nucleophiles respectively. The role of DMF as the O-source in the reaction has been unequivocally proven by 18O labelling studies.

Organocatalytic aziridine synthesis using F+ salts

This paper describes a unique application of the fluoronium cation (F +) as an organocatalyst for mediating the reaction between N-substituted imines and ethyl diazoacetate affording excellent yields of N-substituted aziridines.

REGIOSELECTIVE ACYLATIVE CLEAVAGE OF CYCLIC FORMAL OF CHLORAMPHENICOL

The amide 6 has been synthesised by reacting the amine 3 with dichloroketene in situ.This amide 6 on nitration gave formal 7, which when reacted with acetic anhydride and p-toluene sulfonic acid underwent regioselective cleavage of the dioxane ring to furnish the hemiacetal 11.This on treatment with methanol-water-ammonia yielded chloramphenicol 2.