Hydroxybupropione

Base Information

• Chemical Name: Hydroxybupropione
• CAS No.: 92264-81-8
• Deprecated CAS: 82793-84-8
• Molecular Formula: C13H18ClNO2
• Molecular Weight: 255.744
• Hs Code.: 2922509090
• UNII: V94F513635
• DSSTox Substance ID: DTXSID101002894
• Nikkaji Number: J523.812I
• Wikipedia: Hydroxybupropion
• Wikidata: Q18206601
• Metabolomics Workbench ID: 41935
• ChEMBL ID: CHEMBL3544616
• Mol file: 92264-81-8.mol

Synonyms:Hydroxybupropione;1-(3-Chlorophenyl)-2-[(1-hydroxy-2-methylpropan-2-yl)amino]propan-1-one;

Chemical Property of Hydroxybupropione

Chemical Property:

• Appearance/Colour: Off-White Solid
• Melting Point: 121-123 °C
• Boiling Point: 393.9 °C at 760 mmHg
• PKA: 15.43±0.10(Predicted)
• Flash Point: 192 °C
• PSA: 49.33000
• Density: 1.15 g/cm³
• LogP: 2.66260
• Storage Temp.: ?20°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Sligh
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 255.1026065
• Heavy Atom Count: 17
• Complexity: 268

Purity/Quality:

97% ^*data from raw suppliers

Hydroxybupropion ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xn
• Hazard Codes: F,Xn
• Statements: 11-20/21/22-36
• Safety Statements: 16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)CO
• Uses: A metabolite of Bupropion, an antidepressant. The compound exists mainly as cyclic acetal (2-hydroxy-2-(3?chlorophenyl)-355-trimethylmorpholine). See US Pat. # 6342496

Technology Process of Hydroxybupropione

There total 6 articles about Hydroxybupropione 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: 55.0%

2-bromo-3'-chloropropiophenone (34911-51-8) + 2-Amino-2-methyl-1-propanol (124-68-5) → Hydroxybupropion (92264-81-8,82793-84-8)

Guidance literature:

sodium iodide; In chloroform; Heating / reflux;

Reference yield:

bupropion (34841-39-9,34911-55-2,144445-75-0,144445-76-1) → Hydroxybupropion (92264-81-8,82793-84-8)

Guidance literature:

With NADPH; recombinant human CYP₂B₆; In phosphate buffer; at 37 ℃; pH=7.4; Further Variations:; Catalysts; Enzyme kinetics;

DOI:10.1007/s00228-003-0636-9

Reference yield:

3'-chloro-propiophenone (34841-35-5) → Hydroxybupropion (92264-81-8,82793-84-8)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / chloroform / 20 °C

2: sodium iodide / chloroform / Heating / reflux

With bromine; sodium iodide; In chloroform;

upstream raw materials:

3'-chloro-propiophenone

2-Amino-2-methyl-1-propanol

bupropion

3-chloro-benzonitrile