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

Description

[S-(R,R)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide is a complex organic compound with a unique stereochemistry and functional groups. It is characterized by its dichloro-substituted acetamide structure, which includes a nitrobenzene ring, an amide bond, and two alcohol functions. [S-(R,R)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide has potential applications in various fields due to its antimicrobial and protein synthesis inhibitory properties.

Uses

Used in Pharmaceutical Industry:
[S-(R,R)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide is used as an antimicrobial agent for its broad-spectrum activity against both Gram-positive and Gram-negative bacteria. Its ability to inhibit protein synthesis makes it a valuable compound in the development of new antibiotics to combat bacterial infections.
Used in Research and Development:
In the field of research, this compound serves as a valuable tool for studying the mechanisms of bacterial resistance and the development of new strategies to overcome these resistances. Its unique structure and properties allow scientists to investigate its interactions with bacterial cells and identify potential targets for novel antimicrobial therapies.
Used in Drug Synthesis:
The compound's structural features make it a potential candidate for the synthesis of new drugs with improved properties, such as enhanced efficacy, reduced side effects, or targeted delivery. Its ability to inhibit protein synthesis could be harnessed to develop drugs for various therapeutic applications, including the treatment of bacterial infections and other diseases.
Used in Drug Resistance Studies:
[S-(R,R)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide can be employed in studies aimed at understanding the mechanisms of drug resistance in bacteria. By examining the compound's interactions with bacterial cells and its effects on protein synthesis, researchers can gain insights into the development of resistance and design strategies to counteract it.

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

• 116-54-1 dichloroacetic acid methyl ester 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 67-56-1 methanol 
• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 56-75-7 chlorampenicol 
• 57-24-9 strychnidin-10-one 
• 123410-35-5 (-)-(2R,3S)-N-(Dichloroacetyl)-3-(4-nitrophenyl)serine methyl ester 
• 15917-27-8 (+/-)-methyl (βR)-β-hydroxy-4-nitro-1-phenylalaninate 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 56-75-7 2-(2,2-dichloroacetylamino)-1-(4-nitrophenyl)propane-1,3-diol 
• 108943-99-3 N-(1-acetoxy-3-oxo-3-phenylpropyl)acetamide 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 3509-75-9 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 33485-02-8 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 

Downstream Products

• 56-75-7 chloramphenicol 
• 134-90-7 L-threo-chloramphenicol 
• 6158-95-8 (S)-2-(2,2-dichloro-acetylamino)-3-hydroxy-1-(4-nitro-phenyl)-propan-1-one 
• 26367-75-9 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 
• 56-75-7 chlorampenicol 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 

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.

Synthesis of Some Selectively N-Protected (1S,2S)-p-Nitrophenylserinol-Based Diamino-1,3-dioxanes and Tripodands

The unconventional methodology for the non-epimerizable cycloacetalization of optically active (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol) (condensed H2SO4 96% as solvent and catalyst, i.e., sulfuric transacetalization) producing (2R,4S,5S) diamino-1,3-dioxanes was enlarged by the use of N-protected forms of 2,2-dimethoxyethylamine (DMEA, aminoacetaldehyde dimethylacetal). Conversely, N-protected derivatives of p-nitrophenylserinol were successfully cyclocondensed with DMEA in the same sulfuric conditions. N-Functionalization of DMEA upon treatment with trimesic acid trichloride and cyanuric chloride yielded the corresponding triple amide and melamine, respectively. Their adapted sulfuric transacetalization in triplicate in reaction with arylserinols (aryl: phenyl, p-nitrophenyl) afforded a new series of optically active tripodands.