Adrafinil

Base Information

• Chemical Name: Adrafinil
• CAS No.: 63547-13-7
• Molecular Formula: C15H15NO3S
• Molecular Weight: 289.355
• Hs Code.: 2942000000
• European Community (EC) Number: 264-303-1
• UNII: BI81Z4542G
• DSSTox Substance ID: DTXSID4046498
• Nikkaji Number: J33.368I
• Wikipedia: Adrafinil
• Wikidata: Q366482
• NCI Thesaurus Code: C81369
• ChEMBL ID: CHEMBL93077
• Mol file: 63547-13-7.mol

Synonyms:adrafinil;adrafinyl;benzhydrylsulfinylacetohydroxamic acid;CRL 40028;CRL-40028;Olmifon

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Chemical Property of Adrafinil

Chemical Property:

• Appearance/Colour: White, hygroscopic powder.
• Melting Point: 150-160 °C
• Refractive Index: 1.652
• PKA: 8.22±0.20(Predicted)
• PSA: 85.61000
• Density: 1.342 g/cm³
• LogP: 3.28670
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: 35 mg/mL
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 289.07726451
• Heavy Atom Count: 20
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)NO
• Description: Adrafinil is a centrally-acting, αl-adrenergic agonist useful in the management of vigillance disturbances and depression in the elderly.
• Uses: a-Adrenergic agonist. Treatment of depression α-Adrenergic agonist. Treatment of depression.

Technology Process of Adrafinil

There total 5 articles about Adrafinil 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: 72.0%

2-benzhydrylsulfanyl-N-hydroxyacetamide (63547-44-4) → adrafinil (63547-13-7)

Guidance literature:

With dihydrogen peroxide; acetic acid; at 40 ℃;

DOI:10.1016/j.tetasy.2004.01.039

Reference yield:

1,1-Diphenylmethanol (91-01-0) → adrafinil (63547-13-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / trifluoroacetic acid / 3 h / 20 °C

2: 99 percent / H₂SO₄ / Heating

3: 92 percent / hydroxylamine hydrochloride; KOH / methanol / 0.25 h

4: 72 percent / aq. H₂O₂; acetic acid / 40 °C

With potassium hydroxide; sulfuric acid; hydroxylamine hydrochloride; dihydrogen peroxide; acetic acid; trifluoroacetic acid; In methanol;

DOI:10.1016/j.tetasy.2004.01.039

Reference yield:

(benzhydrylthio)acetic acid (63547-22-8) → adrafinil (63547-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / H₂SO₄ / Heating

2: 92 percent / hydroxylamine hydrochloride; KOH / methanol / 0.25 h

3: 72 percent / aq. H₂O₂; acetic acid / 40 °C

With potassium hydroxide; sulfuric acid; hydroxylamine hydrochloride; dihydrogen peroxide; acetic acid; In methanol;

DOI:10.1016/j.tetasy.2004.01.039

upstream raw materials:

2-benzhydrylsulfanyl-N-hydroxyacetamide

1,1-Diphenylmethanol

(benzhydrylthio)acetic acid

(diphenylmethyl)(ethyl acetate)sulfide

Refernces