Phenacetin

Base Information

• Chemical Name: Phenacetin
• CAS No.: 62-44-2
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 29251995
• European Community (EC) Number: 200-533-0,695-035-7
• NSC Number: 757401,7651
• UN Number: 3077
• UNII: ER0CTH01H9
• DSSTox Substance ID: DTXSID1021116
• Nikkaji Number: J2.348E
• Wikipedia: Phenacetin
• Wikidata: Q419175
• NCI Thesaurus Code: C44432
• Metabolomics Workbench ID: 53354
• ChEMBL ID: CHEMBL16073
• Mol file: 62-44-2.mol

Synonyms:Acetophenetidin;Phenacetin

Chemical Property of Phenacetin

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.21E-05mmHg at 25°C
• Melting Point: 133-136 °C(lit.)
• Refractive Index: 1.548
• Boiling Point: 355.1 °C at 760 mmHg
• PKA: pKa 2.2(H2O) (Uncertain);3.5(aqueous acetone) (Uncertain)
• Flash Point: 168.5 °C
• PSA: 38.33000
• Density: 1.099 g/cm³
• LogP: 2.11670
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 0.076 g/100 mL
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

99.8%,99%, ^*data from raw suppliers

Phenacetin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,F
• Statements: 45-22-20/21/22-36-11
• Safety Statements: 53-45-36/37-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)NC(=O)C
• Uses: Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years. It was introduced into therapy in 1887 and was extensively used in analgesic mixtures until it was implicated in kidney disease (nephropathy) due to abuse of analgesics (Flower et al. 1985) and was withdrawn from the U.S. market in 1983 (Ronco and Flahault 1994, FDA 1998, 1999). Phenacetin also was previously used as a stabilizer for hydrogen peroxide in hair-bleaching preparations (IARC 1980, HSDB 2009). Analgesic, antipyretic. Component of APC tablets, analgesic mixture also containing aspirin and caffeine. Phenacetin is reasonably anticipated to be a human carcinogen; analgesic mixtures containing Phenacetin are listed as known human carcinogens. glycosylation inhibitor Phenacetin was used as an analgesic and fever-reducing drug in both human and veterinary medicine for many years until it was implicated in kidney disease (nephropathy) due to abuse of analgesics and was withdrawn from the market. Phenacetin also was previously used as a stabilizer for hydrogen peroxide in hair-bleaching preparations.
• Description: Phenacetin, a painkiller, was the world’s first synthetic pharmaceutical drug. It was one of the first painkillers that was not derived from opium while at the same time being absent of antiinflammatory qualities. Phenacetinwas developed in 1878 by an American chemist, Harmon Northrop Morse. It was introduced into the pharmaceutical market in 1887. However, it was withdrawn in 1983 in the United States due to unacceptable levels of interstitial nephritis in patients and potential risks of tumorigenicity. Like in the United States, most Western countries did not ban phenacetin from marketing until 1983. Phenacetin is a component of APC (aspirin-phenacetin-caffeine).
• Therapeutic Function: Analgesic

Technology Process of Phenacetin

There total 54 articles about Phenacetin 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: 99.0%

carbonic acid dimethyl ester (616-38-6) + 1-ethoxy-4-nitrobenzene (100-29-8) → 4-ethoxyacetanilide (62-44-2,105931-34-8)

Guidance literature:

With di(rhodium)tetracarbonyl dichloride; tungsten hexacarbonyl; 1,3-bis-(diphenylphosphino)propane; sodium phosphate; sodium iodide; In water; at 120 ℃; for 24h;

Reference yield: 95.5%

4-ethoxyanilinium dihydrogenphosphate + acetic anhydride (108-24-7) → 4-ethoxyacetanilide (62-44-2,105931-34-8)

Guidance literature:

In aq. acetate buffer; at 95 - 100 ℃; for 6h; pH=4 - 5; Large scale;

Reference yield: 95.0%

(4-nitrobenzylidene)(4-ethoxyphenyl)amine (15485-31-1,97221-16-4) + acetic anhydride (108-24-7) → 4-ethoxyacetanilide (62-44-2,105931-34-8) + 4-nitrobenzaldehdye (555-16-8)

Guidance literature:

With water; sodium dodecyl-sulfate; at 25 - 30 ℃; for 0.0833333h;

DOI:10.1080/00397910701459571

upstream raw materials:

ethyl bromide

4-acetaminophenol

potassium ethyl sulfate

1-(4-ethoxy-phenyl)-ethanone oxime

Downstream raw materials:

acetic acid-(N-chloro-p-phenetidide)

5-acetamido-2-hydroxyacetophenone

bis-(2-acetylamino-5-ethoxy-phenyl)-methane

2,5-dichloro-4-ethoxyacetanilide

Refernces

• 1、 -. "Preparation method of acetamide compound". Paragraph 0035-0047. . Retrieved 2021/05/19.
• 2、 Gurjar, Jitendra,Fokin, Valery V.. "Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement". supporting information. p. 10402 - 10405. Retrieved 2020/07/25.