85666-84-8

Basic information

• Product Name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• Synonyms: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• CAS NO: 85666-84-8
• Molecular Formula: C11H12Cl2N2O5
• Molecular Weight: 0
• Mol File: 85666-84-8.mol
• Article Data: 33

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide(85666-84-8)
• EPA Substance Registry System: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide(85666-84-8)

Safety Data

• Hazardous Substances Data: 85666-84-8(Hazardous Substances Data)

Upstream product

• 79-36-7 dichloroacethyl chloride 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 872302-03-9 dichloroacetyl-phosphorous acid diethyl ester 
• 3018-12-0 dichloroacetonitrile 
• 100-58-3 phenylmagnesium bromide 
• 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 
• 10318-17-9 (1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate 
• 86022-41-5 (2S,3R)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 1424360-99-5 (1S,2R,5S,8R,1'R)-5-(1'-hydroxy-p-nitrobenzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 129446-45-3 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 
• 116-54-1 dichloroacetic acid methyl ester 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Downstream Products

• 33485-16-4 isonicotinic acid-[(2R,3R)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propyl ester] 
• 34718-53-1 (1R,2R)-3-dichloroacetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol 
• 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 
• 115052-25-0 (1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-3-octanoyloxy-propan-1-ol 
• 124109-27-9 (1R,2R)-2-(2,2-dichloro-acetylamino)-3-myristoyloxy-1-(4-nitro-phenyl)-propan-1-ol 
• 2242-25-3 dichloroacetic acid-[(5R)-2ξ-methyl-4c-(4-nitro-phenyl)-[1,3]dioxan-5r-ylamide] 
• 59005-99-1 threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-butanoate 
• 100847-18-5 2,2-Dichloro-N-[(7R,8R)-7-(4-nitro-phenyl)-6,10-dioxa-spiro[4.5]dec-8-yl]-acetamide 
• 1676076-87-1 C₈H₁₅N₂⁽¹⁺⁾*C₁₁H₁₁Cl₂N₂O₅^(1-) 
• 10318-16-8 (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl acetate 

Relevant articles and documents

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride

The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.

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.