3',5'-Dibromo-2'-Hydroxyacetophenone

Base Information

• Chemical Name: 3',5'-Dibromo-2'-Hydroxyacetophenone
• CAS No.: 22362-66-9
• Molecular Formula: C8H6Br2O2
• Molecular Weight: 293.942
• Hs Code.: 2914700090
• European Community (EC) Number: 624-898-4
• NSC Number: 115706
• DSSTox Substance ID: DTXSID30297365
• Nikkaji Number: J1.911.023K
• Wikidata: Q72464422
• Mol file: 22362-66-9.mol

Synonyms:22362-66-9;3',5'-Dibromo-2'-Hydroxyacetophenone;1-(3,5-dibromo-2-hydroxyphenyl)ethanone;1-(3,5-dibromo-2-hydroxyphenyl)-1-ethanone;MFCD00191992;1-(3,5-dibromo-2-hydroxyphenyl)ethan-1-one;NSC115706;SCHEMBL2070725;DTXSID30297365;RCKHUOIKVIOMGZ-UHFFFAOYSA-N;STL169029;AKOS000112354;NSC-115706;UPCMLD0ENAT5522483:001;11J-517S;CS-0155148;D4637;FT-0638214;EN300-21493;D90311;1-[3,5-bis(bromanyl)-2-oxidanyl-phenyl]ethanone;A816223;AE-641/03312017;J-503090;Z104500096;InChI=1/C8H6Br2O2/c1-4(11)6-2-5(9)3-7(10)8(6)12/h2-3,12H,1H

Chemical Property of 3',5'-Dibromo-2'-Hydroxyacetophenone

Chemical Property:

• Melting Point: 108-111 °C(lit.)
• Boiling Point: 307.5 °C at 760 mmHg
• PKA: 8.07±0.23(Predicted)
• Flash Point: 139.8 °C
• PSA: 67.51000
• Density: 1.936 g/cm³
• LogP: 3.01620
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 293.87141
• Heavy Atom Count: 12
• Complexity: 184

Purity/Quality:

98%,99%, ^*data from raw suppliers

3'',5''-Dibromo-2’-hydroxyacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C(=CC(=C1)Br)Br)O
• Uses: 3'',5''-Dibromo-2''-hydroxyacetophenone is a useful reagent in organic synthesis.

Technology Process of 3',5'-Dibromo-2'-Hydroxyacetophenone

There total 13 articles about 3',5'-Dibromo-2'-Hydroxyacetophenone 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: 94.0%

5-Bromo-2-hydroxyacetophenone (1450-75-5) → 3,5-dibromo-2-hydroxyacetophenone (22362-66-9)

Guidance literature:

With pyridinium bromochromate; In acetic acid;

DOI:10.1016/S0040-4039(03)01071-2

Reference yield: 79.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) → 3,5-dibromo-2-hydroxyacetophenone (22362-66-9)

Guidance literature:

With N-Bromosuccinimide; at 20 ℃;

Reference yield: 77.0%

o-hydroxyacetophenone (118-93-4,104809-67-8) → 3,5-dibromo-2-hydroxyacetophenone (22362-66-9) + 5-Bromo-2-hydroxyacetophenone (1450-75-5)

Guidance literature:

o-hydroxyacetophenone; In acetonitrile; at 80 ℃; for 0.166667h;

With N-Bromosuccinimide; In acetonitrile; at 80 ℃; for 8h; regioselective reaction;

DOI:10.1021/jo300731z

upstream raw materials:

acetic acid 2,4-dibromophenyl ester

2,2,2-tribromo-1-(3,5-dibromo-2-hydroxyphenyl)ethanone

2,4-dibromophenol

acetic anhydride

Downstream raw materials:

3',5'-dibromo-2'-hydroxy-3,4-methylenedioxy-trans-chalcone

2,4-dibromo-6-ethylphenol

3',5'-dibromo-2'-hydroxychalcone

3',5'-dibromo-2'-hydroxy-4-methoxychalcone

Refernces

• 1、 Bovonsombat, Pakorn,Teecomegaet, Pattaradra,Kulvaranon, Panisanun,Pandey, Aditi,Chobtumskul, Kittithorn,Tungsirisurp, Sireethorn,Sophanpanichkul, Punyanuch,Losuwanakul, Satreerat,Soimaneewan, Dechathon,Kanjanwongpaisan, Patcharida,Siricharoensang, Pornpawit,Choosakoonkriang, Sirirat. "Regioselective monobromination of aromatics via a halogen bond acceptor-donor interaction of catalytic thioamide and N-bromosuccinimide". . p. 6564 - 6572. Retrieved 2017/10/17.
• 2、 Pajtás, Dávid,Dihen, Károly,Patonay, Tamás,Kónya, Krisztina,Villinger, Alexander,Langer, Peter. "Site-Selective Suzuki-Miyaura Reaction of 6,8-Dibromoflavone". . p. 2601 - 2605. Retrieved 2015/11/11.