5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one

Base Information

• Chemical Name: 5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one
• CAS No.: 3172-00-7
• Molecular Formula: C7H5BrO2
• Molecular Weight: 201.019
• Hs Code.: 2914700090
• DSSTox Substance ID: DTXSID90498452
• Nikkaji Number: J355.826F
• Mol file: 3172-00-7.mol

Synonyms:5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one;3172-00-7;5-Bromo-2-hydroxycyclohepta-2,4,6-trienone;5-bromotropolone;2,4,6-Cycloheptatrien-1-one, 5-bromo-2-hydroxy-;SCHEMBL21465807;DTXSID90498452;MFCD08166335;FT-0692684;A901918;(2E,4E,6Z)-5-bromo-2-hydroxycyclohepta-2,4,6-trienone

Chemical Property of 5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 189-190 °C
• Boiling Point: 269.098oC at 760 mmHg
• PKA: 5.71±0.10(Predicted)
• Flash Point: 116.546oC
• PSA: 37.30000
• Density: 1.863g/cm3
• LogP: 1.51490
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 199.94729
• Heavy Atom Count: 10
• Complexity: 248

Purity/Quality:

97% ^*data from raw suppliers

5-BROMO-2-HYDROXYCYCLOHEPTA-2,4,6-TRIEN-1-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)C(=CC=C1Br)O
• General Description: 5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one (also known as 5-bromotropolone) is a brominated derivative of tropolone, which serves as a key intermediate in the synthesis of colchicine. It participates in palladium-catalyzed cross-coupling reactions with aryl siloxane derivatives to form aryl-tropolone bonds, a crucial step in constructing the carbocyclic framework of colchicine. 5-BROMO-2-HYDROXYCYCLOHEPTA-2,4,6-TRIEN-1-ONE demonstrates utility in methodologies comparing siloxane and boronic acid coupling technologies for generating functionalized biaryl products.

Technology Process of 5-Bromo-2-hydroxycyclohepta-2,4,6-trien-1-one

There total 3 articles about 5-Bromo-2-hydroxycyclohepta-2,4,6-trien-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: 92.0%

5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one (33816-51-2) → 5-bromotropolone (3172-00-7)

Guidance literature:

With water; sodium hydroxide; In methanol; for 13h; Reflux; Inert atmosphere;

DOI:10.1002/hc.21201

Reference yield: 22.0%

5-bromo-2-(p-tolylmethoxy)tropone (77367-75-0) → 5-bromotropolone (3172-00-7) + 5-bromo-3-(p-tolylmethyl)tropolone (77367-82-9)

Guidance literature:

In decalin; at 190 ℃; for 10h;

DOI:10.1246/cl.1981.73

Reference yield:

→ 5-bromotropolone (3172-00-7) + 3-bromo-2-hydroxy-2,4,6-cycloheptatrien-1-one (4584-68-3)

Guidance literature:

With chloroform; bromine;

upstream raw materials:

5-bromo-2-(p-tolylmethoxy)tropone

5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one

Downstream raw materials:

5-bromo-2-methoxycyclohepta-2,4,6-trien-1-one

5-styryltropolone

5-<3-(3,4-dimethoxyphenyl)-1-propenyl>tropolone

5-phenyltropolone

Refernces

Efforts directed toward the synthesis of colchicine: Application of palladium-catalyzed siloxane cross-coupling methodology

10.1021/jo051636h

The study focuses on the synthesis of colchicine, a naturally occurring compound with therapeutic properties, using a palladium-catalyzed siloxane cross-coupling methodology. The key chemicals involved in this approach include 5-bromotropolone, various aryl siloxane derivatives, and a palladium catalyst with a high degree of phosphine ligand coordination. These chemicals serve to form the aryl-tropolone bond, which is a critical step in the synthesis of colchicine. The study investigates and optimizes the coupling conditions for a range of highly functionalized aryl siloxane derivatives, aiming to develop an efficient method for constructing the carbocyclic framework of colchicine and its derivatives. The research also provides a direct comparison between siloxane and boronic acid coupling technologies, demonstrating their efficiency in producing highly functionalized biaryl products.

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