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

Base Information

• Chemical Name: 1-(3-Chlorophenyl)-2-hydroxypropan-1-one
• CAS No.: 152943-33-4
• Molecular Formula: C9H9ClO2
• Molecular Weight: 184.622
• European Community (EC) Number: 642-246-7
• UNII: HLG232MS8B
• DSSTox Substance ID: DTXSID00592793
• Mol file: 152943-33-4.mol

Synonyms:152943-33-4;1-(3-Chlorophenyl)-2-hydroxypropan-1-one;1-(3-CHLOROPHENYL)-2-HYDROXY-1-PROPANONE;HLG232MS8B;1-Propanone, 1-(3-chlorophenyl)-2-hydroxy-;UNII-HLG232MS8B;SCHEMBL2070613;DTXSID00592793;AKOS011305887;DB-237653;CS-0447038;EN300-205498

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

Chemical Property:

• Boiling Point: 301.7±22.0 °C(Predicted)
• PKA: 12.71±0.20(Predicted)
• PSA: 37.30000
• Density: 1.253±0.06 g/cm3(Predicted)
• LogP: 1.90350
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• 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:

> 95% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 16 articles about 1-(3-Chlorophenyl)-2-hydroxypropan-1-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: 96.2%

3'-chloro-propiophenone (34841-35-5) → (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one (152943-33-4)

Guidance literature:

3'-chloro-propiophenone; With 1-benzyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide salt; In 2-methyltetrahydrofuran; N,N-dimethyl-formamide; at 55 ℃; for 0.283333h;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 2-methyltetrahydrofuran; N,N-dimethyl-formamide; at 55 ℃; for 3h; Reagent/catalyst; Solvent;

Reference yield: 85.0%

(+/-)-1-(3-chlorophenyl)propane-1,2-diol → (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one (152943-33-4)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 30h;

DOI:10.1016/j.tetlet.2008.04.040

Reference yield:

acetaldehyde (75-07-0,9002-91-9) + m-Chlorobenzaldehyde (587-04-2) → (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one (152943-33-4)

Guidance literature:

With benzoyl formate decarboxylase; thiamine diphosphate; In water; at 20 ℃; for 20h; pH=7.0; Enzymatic reaction;

DOI:10.1002/1099-0690(200006)2000:11<2161::AID-EJOC2161>3.0.CO;2-6

upstream raw materials:

acetaldehyde

m-Chlorobenzaldehyde

rac-1-(3-chlorophenyl)-2-acetoxypropan-1-one

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

Downstream raw materials:

bupropion

Refernces

• 1、 -. "Green preparation method α - hydroxyketone". Paragraph 0047-0050. . Retrieved 2020/08/27.
• 2、 -. "Synthesis method of hydroxyketone compounds". Paragraph 0044; 0045; 0046, 0047; 0048. . Retrieved 2016/10/08.