(1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

Base Information

• Chemical Name: (1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol
• CAS No.: 716-61-0
• Molecular Formula: C₉H₁₂N₂O₄
• Molecular Weight: 212.205
• Hs Code.: 29221990
• European Community (EC) Number: 211-938-7,222-997-3
• DSSTox Substance ID: DTXSID80221832
• Nikkaji Number: J193.088E
• Wikidata: Q27147894
• ChEMBL ID: CHEMBL4561142
• Mol file: 716-61-0.mol

Synonyms:1-(4'-nitrophenyl)-2-aminopropane-1,3-diol;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol mono-hydrochloride, (S-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (R*,R*)-(+-)-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (R*,S*)-(+-)-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (R-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (R-(R*,S*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (S)-hydroxybutanedioate (2:1) (S-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, (S-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, L-(+)-tartrate(S-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, mono-HCl(R*,R*)-(+-)-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, mono-hydrochloride, (1R,2R)-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, mono-L-(+)-tartrate(R-(R*,R*))-isomer;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, mononitrate;1-(4'-nitrophenyl)-2-aminopropane-1,3-diol, sulfate(S-(R*,R*))-isomer;1-(4-nitrophenyl)-1,3-dihydroxypropylamine;2-amino-1-nitrophenylpropane-1,3-diol;chloramphenicol base;para-nitrophenylserinal

Chemical Property of (1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

Chemical Property:

• Appearance/Colour: light yellow powder
• Vapor Pressure: 5.92E-09mmHg at 25°C
• Melting Point: 163-165 °C(lit.)
• Refractive Index: -30.5 ° (C=1, 6mol/L HCl)
• Boiling Point: 451.9 °C at 760 mmHg
• PKA: 10.98±0.45(Predicted)
• Flash Point: 227.1 °C
• PSA: 112.30000
• Density: 1.41 g/cm³
• LogP: 1.17130
• Storage Temp.: −20°C
• Water Solubility.: almost transparency in hot Water
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 212.07970687
• Heavy Atom Count: 15
• Complexity: 211

Purity/Quality:

99% ^*data from raw suppliers

D-threo-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-45
• Safety Statements: 26-45-53-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(CO)N)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO)N)O)[N+](=O)[O-]
• Uses: D-threo-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol is an impurity of Chloramphenicol (C325030), a broad spectrum antibiotic agent obtained from cultures of the soil bacterium Streptomyces venezuel ae. 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. (1R,2R)-(-)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol may be used in the preparation of (1R,2R)-(-)-2-dimethylamino-1-(4-nitrophenyl)-1,3-propanediol via N,N-dimethylation. It may also be used as a starting material to synthesize (1R,2R)-1,3-diacetoxy-1-(4-nitrophenyl)-2-propylisothioeyanate [(R,R)-DANI].

Technology Process of (1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol

There total 191 articles about (1R,2R)-2-amino-1-(4-nitrophenyl)propane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

chloramphenicol (56-75-7,85666-84-8) → (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01175a065

Reference yield:

(2S,3S)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (1194757-37-3) → (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0)

Guidance literature:

ueber mehrere Stufen;

Reference yield:

(2S,3R)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (582295-24-7) → (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol (119-62-0,716-61-0,2792-51-0,2792-52-1,2964-48-9,3689-55-2,63526-31-8,71115-69-0,140694-64-0)

Guidance literature:

With tetrahydrofuran; lithium borohydride;

upstream raw materials:

(+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol

(2S,3S)-2-amino-3-methoxy-3-(4-nitro-phenyl)-propan-1-ol

(1R,2S)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol

(1S,2S)-2-acetamido-1-phenylpropane-1,3-diyl diacetate

Downstream raw materials:

(1S,2S)-1-(4-nitro-phenyl)-2-[2]pyridylmethylenamino-propane-1,3-diol

N,N'-bis-[2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-oxalamide

[(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-oxalamic acid methyl ester

(1S,2S)-2-benzoylamino-1-(4-nitro-phenyl)-propane-1,3-diol

Refernces

• 1、 Abad, Etna,Antonenko, Yuri N.,Bogdanov, Alexey A.,Kajiwara, Susumu,Khairullina, Zimfira Z.,Konevega, Andrey L.,Lukianov, Dmitrii A.,Lyakhovich, Alex,Makarov, Gennady I.,Murayama, Somay Y.,Nazarov, Pavel A.,Osterman, Ilya A.,Paleskava, Alena,Pavlova, Julia A.,Skvortsov, Dmitry A.,Sumbatyan, Natalia V.,Tereshchenkov, Andrey G.,Volynkina, Inna A.. "Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents". . . Retrieved 2021/05/10.
• 2、 -. "ENGINEERED POLYPEPTIDES AND THEIR APPLICATIONS IN SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS". . . Retrieved 2019/01/04.