1-(3-Chlorophenyl)-1-hydroxypropan-2-one

Base Information

• Chemical Name: 1-(3-Chlorophenyl)-1-hydroxypropan-2-one
• CAS No.: 857233-13-7
• Molecular Formula: C9H9ClO2
• Molecular Weight: 184.622
• UNII: ZH3TKS3HJR
• DSSTox Substance ID: DTXSID20434106
• Nikkaji Number: J711.159B
• ChEMBL ID: CHEMBL4590340
• Mol file: 857233-13-7.mol

Synonyms:857233-13-7;1-(3-Chlorophenyl)-1-hydroxypropan-2-one;1-(3-CHLOROPHENYL)-1-HYDROXY-2-PROPANONE;ZH3TKS3HJR;2-Propanone, 1-(3-chlorophenyl)-1-hydroxy-;UNII-ZH3TKS3HJR;1-(m-Chlorophenyl)-1-hydroxy-2-propanone;CHEMBL4590340;SCHEMBL12658713;DTXSID20434106;USP Bupropion Related Compound C;Buprion Related Compound F (USP);MFCD16251305;AKOS023431128;2-propanona, 1-(3-clorofenil)-1-hidroxi-;FT-0664887;EN300-219586;J-008962;Z1255467340

Chemical Property of 1-(3-Chlorophenyl)-1-hydroxypropan-2-one

Chemical Property:

• Boiling Point: 106-108 °C(Press: 0.5 Torr)
• PKA: 12.06±0.20(Predicted)
• PSA: 37.30000
• Density: 1.240 g/cm3
• LogP: 1.96240
• Storage Temp.: Hygroscopic, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Ethyl Acetate (Slig
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 184.0291072
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

98%Min ^*data from raw suppliers

1-(3-Chlorophenyl)-1-hydroxy-2-propanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)C(C1=CC(=CC=C1)Cl)O
• Uses: Bupropion intermediate. Bupropion hydrochloride related compound F. Bupropion intermediate. Bupropion USP Related Compound F.

Technology Process of 1-(3-Chlorophenyl)-1-hydroxypropan-2-one

There total 10 articles about 1-(3-Chlorophenyl)-1-hydroxypropan-2-one 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: 75.0%

(+/-)-1-[(tert-butyldimethylsilyl)oxy]-1-(3-chlorophenyl)propan-2-one (1038432-36-8) → 1-(3-chlorophenyl)-1-hydroxy-2 propanone (857233-13-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In methanol; at 20 ℃; for 2h;

DOI:10.1590/S0103-50532011000800022

Reference yield:

BUPROPION HYDROCHLORIDE (31677-93-7) → 1-(3-chlorophenyl)-1-hydroxy-2 propanone (857233-13-7) + 3-chlorobenzoate (535-80-8)

Guidance literature:

With hydrogenchloride; dihydrogen peroxide; In methanol; water; at 25 ℃; for 48h; Reagent/catalyst; Temperature; Kinetics;

DOI:10.1039/c5ra07716h

Reference yield:

(±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate (1038432-24-4) → 1-(3-chlorophenyl)-1-hydroxy-2 propanone (857233-13-7)

Guidance literature:

Multi-step reaction with 6 steps

1: water; lithium hydroxide / acetonitrile / 4 h / 50 - 60 °C

2: triethylamine / acetone / 0.08 h / 0 °C

3: sodium azide / acetone / 2 h / 20 °C

4: toluene / 2 h / Reflux; Inert atmosphere

5: water / 2 h / Reflux

6: tetrabutyl ammonium fluoride / methanol / 2 h / 20 °C

With sodium azide; tetrabutyl ammonium fluoride; water; triethylamine; lithium hydroxide; In methanol; acetone; toluene; acetonitrile; 4: Curtius rearrangement;

DOI:10.1590/S0103-50532011000800022

upstream raw materials:

methyl magnesium iodide

3-chloro-mandelic acid-amide

(±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate

(+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid