Chloramphenicol

Base Information

• Chemical Name: Chloramphenicol
• CAS No.: 56-75-7
• Deprecated CAS: 137731-90-9,15313-32-3,55172-72-0,59112-59-3,85666-84-8,15313-32-3,55172-72-0,59112-59-3,85666-84-8
• Molecular Formula: C11H12Cl2N2O5
• Molecular Weight: 323.133
• Hs Code.: 2941400000
• European Community (EC) Number: 200-287-4
• NSC Number: 3069
• UNII: 66974FR9Q1
• DSSTox Substance ID: DTXSID7020265
• Nikkaji Number: J2.802I
• Wikipedia: Chloramphenicol
• Wikidata: Q274515
• NCI Thesaurus Code: C363
• RXCUI: 2348
• Metabolomics Workbench ID: 42801
• ChEMBL ID: CHEMBL130
• Mol file: 56-75-7.mol

Synonyms:Amphenicol;Amphenicols;Chloramphenicol;Chlornitromycin;Chlorocid;Chloromycetin;Cloranfenicol;Detreomycin;Kloramfenikol;Levomycetin;Ophthochlor;Syntomycin

Chemical Property of Chloramphenicol

Chemical Property:

• Appearance/Colour: White to grey-white crystalline powder
• Vapor Pressure: 1.63E-17mmHg at 25°C
• Melting Point: 148-150 °C(lit.)
• Refractive Index: 20 ° (C=5, EtOH)
• Boiling Point: 644.913 °C at 760 mmHg
• PKA: 11.03±0.46(Predicted)
• Flash Point: 343.831 °C
• PSA: 115.38000
• Density: 1.547 g/cm³
• LogP: 1.82310
• Storage Temp.: 2-8°C
• Solubility.: absolute ethanol: soluble5-20mg/mL (as a stock solution)
• Water Solubility.: 2.5 g/L (25 º C)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 322.0123269
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

98%-102% ^*data from raw suppliers

D-threo- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,F
• Statements: 45-11-39/23/24/25-23/24/25
• Safety Statements: 53-45-16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antiinfective Agents
• Canonical SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Recent ClinicalTrials: Repeated Bone Marrow Transplantation in Treating Women With Advanced Breast Cancer
• Antibiotic Properties: Chloramphenicol is a broad-spectrum antibiotic effective against a wide range of bacterial infections, including conjunctivitis, meningitis, plague, cholera, and typhoid fever. It inhibits protein synthesis in bacteria by binding to the bacterial ribosomal subunit, leading to bacterial death.; Effective against both gram-positive and gram-negative bacteria, as well as anaerobic bacteria in both humans and animals.
• Usage and Regulation: Widely accepted for usage in developing countries due to its relatively low production cost and stability. Used to treat infections in animals, but many countries have regulations prohibiting its presence in foods for human consumption.
• Medical Applications: Used in the management and treatment of superficial eye infections like bacterial conjunctivitis and otitis external. Also employed in the treatment of systemic infections such as typhoid and cholera.; Classified as an antibiotic that inhibits protein synthesis.
• Toxicity and Detection: Prolonged accumulation of chloramphenicol in the human body can lead to irreversible aplastic anemia and hematopoietic toxicity.; Various analytical techniques, including electrochemical and optical sensors, are developed for the rapid detection of chloramphenicol in animal products and related processed foods.; Optical sensors typically contain a recognition unit that interacts specifically with chloramphenicol, providing high sensitivity, simplicity in operation, and fast analysis speed.

Technology Process of Chloramphenicol

There total 165 articles about Chloramphenicol 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: 79.0%

(2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (100381-03-1) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ol901784m

Reference yield:

chloramphenicol (26367-75-9) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01145a523

Reference yield:

(+/-)-threo-2-amino-1-phenyl-1,3-propanediol (3306-06-7,5285-86-9,28143-91-1,36391-67-0,36391-68-1,46032-98-8,55057-81-3,105452-39-9,119364-52-2) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

Multi-step reaction with 5 steps

2: pyridine

3: amidosulfuric acid; nitric acid

4: aqueous hydrochloric acid

With pyridine; hydrogenchloride; aminosulfonic acid; nitric acid;

DOI:10.1021/ja01175a066

upstream raw materials:

dichloroacethyl chloride

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

chloral hydrate

potassium cyanide

Downstream raw materials:

(1R,2R)-3-bromoacetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol

(1R,2R)-3-dichloroacetoxy-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-propan-1-ol

(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-nitro-phenyl)-3-pentylcarbamoyloxy-propan-1-ol

chloramphenicol

Refernces

• 1、 -. "Method for continuously preparing chloramphenicol by using micro-reaction system". Paragraph 0030-0044. . Retrieved 2021/08/19.
• 2、 Prasad,Reddi,Sudalai. "Oxidant controlled regio- and stereodivergent azidohydroxylation of alkenes via I2 catalysis". supporting information. p. 10276 - 10279. Retrieved 2015/06/25.