134-90-7

Basic information

• Product Name: [S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
• Synonyms: [S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide;(1S,2S)-2-(2,2-Dichloroacetamido)-1-(4-nitrophenyl)-1,3-propanediol;Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [S-(R*,R*)]-;Acetamide, 2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-, L-threo-(+)- (8CI);Dextramycin;Dextromycetin;L-(+)-threo-Chloramphenicol;L-threo-(1S,2S)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediol
• CAS NO: 134-90-7
• Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular Weight: 323.12938
• EINECS: 205-161-2
• Product Categories: Amines;Aromatics;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Aromatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 134-90-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 150-151 °C
• Boiling Point: 527.51°C (rough estimate)
• Flash Point: 343.8°C
• Appearance: /
• Density: 1.2886 (rough estimate)
• Vapor Pressure: 1.63E-17mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Ethanol (Sparingly, Sonicated), Methanol (Slightly)
• PKA: 11.03±0.46(Predicted)
• CAS DataBase Reference: [S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: [S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide(134-90-7)
• EPA Substance Registry System: [S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide(134-90-7)

Safety Data

• Hazardous Substances Data: 134-90-7(Hazardous Substances Data)

Usage

Uses

The S,S-stereoisomer of Chloramphenicol (C325030). Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial.

Definition

ChEBI: Chloramphenicol is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli metabolite, a Mycoplasma genitalium metabolite and a geroprotector. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide.

InChI:InChI=1/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m0/s1

Upstream product

• 67-56-1 methanol 
• 116-54-1 dichloroacetic acid methyl ester 
• 872302-03-9 dichloroacetyl-phosphorous acid diethyl ester 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 26367-75-9 chloramphenicol 
• 115082-34-3 dichloroacetic acid-[(5R)-4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide] 
• 6158-95-8 (S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one 
• 683-60-3 sodium isopropylate 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 76738-28-8 (R)-((R)-2-dichloromethyl-4,5-dihydro-oxazol-4-yl)-(4-nitro-phenyl)-methanol 
• 100381-03-1 (2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 119-62-0 (1RS,2SR)-2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 13916-40-0 bis-dichloroacetyl-amine 

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 
• 56-75-7 chlorampenicol 
• 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 
• 6158-95-8 (S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one 
• 108717-03-9 (1RS,2SR)-3-benzoyloxy-1-chloro-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propane 
• 575-17-7 (+/-)-[2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazol-4r-yl]-methanol 
• 103854-92-8 (+/-)-4r-chloromethyl-2-dichloromethyl-5t-(4-nitro-phenyl)-4,5-dihydro-oxazole 
• 33485-06-2 dichloroacetic acid-[(1RS,2SR)-2-chloro-1-chloromethyl-2-(4-nitro-phenyl)-ethylamide] 

Relevant articles and documents

Generating cis-aza-diaryl and triaryl ethers via organoBr?nsted acid catalysed aza-Darzens chemistry

We report the efficient combination of SNAr and organic Br?nsted acid catalysis protocols for the construction of cis-aziridine-derived biaryl and triaryl ethers. Using aza-Darzens chemistry mono-cis-aziridine-biaryl and bis-(cis-aziridine)-triaryl ethers have been generated; these motifs have significant potential as easily synthesised, functionalised precursors of a glycopeptide backbone.

Chiral Br?nsted Acid-Catalyzed Asymmetric Synthesis of N-Aryl-cis-aziridine Carboxylate Esters

We report a multi-component asymmetric Br?nsted acid-catalyzed aza-Darzens reaction which is not limited to specific aromatic or heterocyclic aldehydes. Incorporating alkyl diazoacetates and, important for high ee's, ortho-tert-butoxyaniline our optimized reaction (i.e. solvent, temperature and catalyst study) affords excellent yields (61–98 %) and mostly >90 % optically active cis-aziridines. (+)-Chloramphenicol was generated in 4 steps from commercial starting materials. A tentative mechanism is outlined.

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.