2-Bromo-1,4-benzoquinone

Base Information

• Chemical Name: 2-Bromo-1,4-benzoquinone
• CAS No.: 3958-82-5
• Molecular Formula: C6H3BrO2
• Molecular Weight: 186.993
• Hs Code.: 2914700090
• European Community (EC) Number: 678-013-1
• DSSTox Substance ID: DTXSID90192701
• Nikkaji Number: J435.418D
• Wikidata: Q72451706
• ChEMBL ID: CHEMBL4171141
• Mol file: 3958-82-5.mol

Synonyms:2-bromo-1,4-benzoquinone;2-bromoquinone

Chemical Property of 2-Bromo-1,4-benzoquinone

Chemical Property:

• Melting Point: 55°C
• Boiling Point: 229.4 °C at 760 mmHg
• Flash Point: 103.4 °C
• PSA: 34.14000
• Density: 1.9 g/cm³
• LogP: 0.97320
• Storage Temp.: Refrigerator
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 185.93164
• Heavy Atom Count: 9
• Complexity: 225

Purity/Quality:

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

2-Bromocyclohexa-2,5-diene-1,4-dione ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C(=CC1=O)Br

Technology Process of 2-Bromo-1,4-benzoquinone

There total 21 articles about 2-Bromo-1,4-benzoquinone 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: 99.0%

2-bromobenzene-1,4-diol (583-69-7) → 2-bromo-1,4-benzoquinone (3958-82-5)

Guidance literature:

With oxygen; Nitrogen dioxide; In dichloromethane; at -10 ℃; for 10h;

DOI:10.1016/S0040-4039(00)76211-3

Reference yield: 94.0%

p-benzoquinone (106-51-4) → 2-bromo-1,4-benzoquinone (3958-82-5)

Guidance literature:

With aluminum oxide; bromine; for 2.5h; Ambient temperature; other reagents: iodine monobromide, acetic acid;

DOI:10.1080/00397919608003692

Reference yield: 87.0%

2-bromo-4-methoxyphenol (17332-11-5) → 2-bromo-1,4-benzoquinone (3958-82-5)

Guidance literature:

With μ-Oxo-I,I'-bis(trifluoroacetato-O)-I,I'-diphenyldiiodine(III); In water; acetonitrile; at 0 ℃; for 2h;

DOI:10.1055/s-0031-1290579

upstream raw materials:

2-bromobenzene-1,4-diol

2,4-dibromo-aniline

5,6-dibromo-cyclohex-2-ene-1,4-dione

5-bromo-6-chlorocyclohex-2-ene-1,4-dione

Downstream raw materials:

2-[bis-(2-chloro-ethyl)-amino]-5-bromo-[1,4]benzoquinone

2-Bromo-4-(5,6-dihydro-4H-pyran-2-yl)-4-hydroxy-cyclohexa-2,5-dienone

5-Bromo-2-methyl-1,3-diphenyl-2H-isoindole-4,7-dione

1,4-bis(trimethylsilyloxy)-2-trimethylsilylbenzene

Refernces

• 1、 Cantekin, Seda,Baran, Arif,Caliskan, Rasit,Balci, Metin. "Synthesis of bromo-conduritol-B and bromo-conduritol-C as glycosidase inhibitors". . p. 426 - 431. Retrieved 2009.
• 2、 Wood, James M.,Satam, Nishikant S.,Almeida, Renata G.,Cristani, Vinicius S.,de Lima, Dênis P.,Dantas-Pereira, Luiza,Salom?o, Kelly,Menna-Barreto, Rubem F.S.,Namboothiri, Irishi N.N.,Bower, John F.,da Silva Júnior, Eufranio N.. "Strategies towards potent trypanocidal drugs: Application of Rh-catalyzed [2?+?2?+?2] cycloadditions, sulfonyl phthalide annulation and nitroalkene reactions for the synthesis of substituted quinones and their evaluation against Trypanosoma cruzi". . . Retrieved 2020/06/23.
• 3、 Tahmouresilerd, Babak,Moody, Michael,Agogo, Louis,Cozzolino, Anthony F.. "The impact of an isoreticular expansion strategy on the performance of iodine catalysts supported in multivariate zirconium and aluminum metal-organic frameworks". supporting information. p. 6445 - 6454. Retrieved 2019/05/24.