Bromohydroquinone

Base Information

• Chemical Name: Bromohydroquinone
• CAS No.: 583-69-7
• Molecular Formula: C6H5BrO2
• Molecular Weight: 189.008
• Hs Code.: 29081990
• European Community (EC) Number: 209-516-2
• NSC Number: 3977
• UNII: B33BAR0J2E
• DSSTox Substance ID: DTXSID6060397
• Nikkaji Number: J95.607D
• Wikidata: Q926579
• Metabolomics Workbench ID: 168535
• Mol file: 583-69-7.mol

Synonyms:2-bromohydroquinone

Chemical Property of Bromohydroquinone

Chemical Property:

• Appearance/Colour: beige to brown fine crystalline powder
• Vapor Pressure: 0.00255mmHg at 25°C
• Melting Point: 112-116 °C(lit.)
• Refractive Index: 1.657
• Boiling Point: 278.3 °C at 760 mmHg
• PKA: 9.14±0.18(Predicted)
• Flash Point: 122.1 °C
• PSA: 40.46000
• Density: 1.844 g/cm³
• LogP: 1.86030
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 187.94729
• Heavy Atom Count: 9
• Complexity: 97.1

Purity/Quality:

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

Bromohydroquinone >90.0%(GC) ^*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

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC(=C(C=C1O)Br)O
• Uses: Bromohydroquinone was used in the synthesis of Π-conjugated polymers composed of alkyl carbazole/dialkoxyphenylene and squaraine units via Sonogashira cross-coupling reactions. It was used in the preparation of 2-bromobenzoquinone.

Technology Process of Bromohydroquinone

There total 24 articles about Bromohydroquinone 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: 95.0%

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

Guidance literature:

With sodium azide; In water; acetone; at 20 ℃;

DOI:10.1080/00397910600639760

Reference yield: 90.0%

2-bromo-1,4-phenylene diacetate (52376-16-6) → 2-bromobenzene-1,4-diol (583-69-7)

Guidance literature:

With sodium hydroxide; for 12h; Ambient temperature;

DOI:10.1055/s-1990-27058

Reference yield: 88.0%

1,4-Cyclohexanedione (637-88-7) → 2-bromobenzene-1,4-diol (583-69-7)

Guidance literature:

With oxygen; copper diacetate; trifluoroacetic acid; lithium bromide; In acetonitrile; at 80 ℃; for 10h; under 760.051 Torr; Sealed tube;

DOI:10.1002/ejoc.201400158

upstream raw materials:

2-hydroxybromobenzene

3-bromo-4-hydroxybenzylaldehyde

quinhydrone

hydroquinone

Downstream raw materials:

2-methoxyphenazine

1,4-O-di-propanoylbromohydroquinone

bromobenzene

1-(4-Bromo-2,5-dihydroxy-phenyl)-propan-1-one

Refernces

• 1、 Babel, Lucille,Baudet, Karine,Besnard, Céline,Kale, Vishal,Mirzakhani, Mohsen,Naseri, Soroush,Nozary, Homayoun,Piguet, Claude. "Neutral Heteroleptic Lanthanide Complexes for Unravelling Host-Guest Assemblies in Organic Solvents: The Law of Mass Action Revisited". supporting information. p. 62 - 75. Retrieved 2020/02/20.
• 2、 Hemati, Roya,Shahvelayati, Ashraf S.,Yadollahzadeh, Khadijeh. "o-xylylene bis(triethyl ammonium tribromide) as a mild and recyclable reagent for rapid and regioselective bromination of anilines and phenols". . p. 682 - 687. Retrieved 2018/07/14.