Tetrabromocatechol

Base Information

• Chemical Name: Tetrabromocatechol
• CAS No.: 488-47-1
• Molecular Formula: C6H2Br4O2
• Molecular Weight: 425.697
• Hs Code.: 2908199090
• European Community (EC) Number: 207-678-9
• NSC Number: 66414,36929
• UNII: N642CPH23M
• DSSTox Substance ID: DTXSID9060073
• Nikkaji Number: J87.063C
• Wikidata: Q2406707
• Metabolomics Workbench ID: 140327
• ChEMBL ID: CHEMBL506166
• Mol file: 488-47-1.mol

Synonyms:TETRABROMOCATECHOL;488-47-1;Tetrabromopyrocatechol;Pyrocatechol, tetrabromo-;3,4,5,6-tetrabromobenzene-1,2-diol;1,2-Benzenediol, 3,4,5,6-tetrabromo-;3,4,5,6-Tetrabromocatechol;EINECS 207-678-9;NSC 36929;BRN 2051548;UNII-N642CPH23M;N642CPH23M;NSC-36929;4-06-00-05624 (Beilstein Handbook Reference);1, 3,4,5,6-tetrabromo-;NSC36929;Tetrabromocatechol 96%;Tetrabromocatechol, 96%;C6H2Br4O2;SCHEMBL985158;CHEMBL506166;DTXSID9060073;NSC66414;BDBM50386168;MFCD00002189;NSC-66414;3,4,5,6-Tetrabromo-1,2-benzenediol;3,4,5,6-Tetrabromo-1,2-benzenediol #;LS-136472;CS-0206808;FT-0614121;T-1790;Q2406707

Chemical Property of Tetrabromocatechol

Chemical Property:

• Vapor Pressure: 4.73E-05mmHg at 25°C
• Melting Point: 189-193 °C(lit.)
• Refractive Index: 1.737
• Boiling Point: 339.3 °C at 760 mmHg
• PKA: 5.50±0.33(Predicted)
• Flash Point: 159 °C
• PSA: 40.46000
• Density: 2.818 g/cm³
• LogP: 4.14780
• Water Solubility.: It is partly miscible with water.
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 425.67473
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

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

Tetrabromocatechol 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1(=C(C(=C(C(=C1Br)Br)Br)Br)O)O
• Uses: Tetrabromocatechol is used as a pharmaceutical intermediate.

Technology Process of Tetrabromocatechol

There total 36 articles about Tetrabromocatechol 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: 91.0%

6,7,8,9-tetrabromo-3,4-dihydro-2H-benzo[b]1,4-dioxepine (1446354-14-8) → Tetrabromocatechol (488-47-1)

Guidance literature:

With aluminum (III) chloride; In benzene; for 0.7h; Reflux;

DOI:10.1055/s-0032-1318332

Reference yield: 83.0%

o-bromanil (2435-54-3) → Tetrabromocatechol (488-47-1)

Guidance literature:

With 5,6-O-isopropylidene-L-ascorbic acid; In 1,2-dimethoxyethane; for 8h; UV-irradiation;

DOI:10.1039/b005120i

Reference yield: 65.0%

o-bromanil (2435-54-3) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → Tetrabromocatechol (488-47-1) + 6,6'-[1,2-bis(diphenylphosphoryl)ethane-1,2-diyl]bis(2,3,4,5-tetrabromo-6-hydroxycyclohexa-2,4-dien-1-one) (1445314-18-0) + 1,2-bis(diphenylphosphinoyl)ethane (4141-50-8)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.1080/10426507.2012.702822

upstream raw materials:

3-nitrobenzene-1,2-diol

3,4-Dihydroxybenzoic acid

1,2-dihydroxy-4-nitrobenzene

ortoquinone

Downstream raw materials:

o-bromanil

bromanilic acid

tetrabromo-cyclopent-4-ene-1,3-dione

3,4,6-tribromocatechol

Refernces

• 1、 Huang, Wei-Bin,Guo, Ying,Jiang, Jian-An,Pan, Xian-Dao,Liao, Dao-Hua,Ji, Ya-Fei. "An efficient strategy for protecting dihydroxyl groups of catechols". supporting information. p. 741 - 746. Retrieved 2013/05/09.
• 2、 Shoeib, Nagwa A.,Bibby, Michael C.,Blunden, Gerald,Linley, Peter A.,Swaine, David J.,Wheelhouse, Richard T.,Wright, Colin W.. "In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers". . p. 1445 - 1449. Retrieved 2007/10/03.