1,4-Dibromo-2,5-dihexylbenzene

Base Information

• Chemical Name: 1,4-Dibromo-2,5-dihexylbenzene
• CAS No.: 117635-21-9
• Molecular Formula: C18H28 Br2
• Molecular Weight: 404.228
• Hs Code.: 2903999090
• DSSTox Substance ID: DTXSID20390910
• Nikkaji Number: J671.740C
• Wikidata: Q82188048
• Mol file: 117635-21-9.mol

Synonyms:1,4-dibromo-2,5-dihexylbenzene;117635-21-9;2,5-Bis(hexyl)-1,4-dibromobenzene;2,5-DIHEXYL-1,4-DIBROMOBENZENE;C18H28Br2;MFCD01318993;Benzene, 1,4-dibromo-2,5-dihexyl-;SCHEMBL351893;DTXSID20390910;1,4-Dibromo-(2,5-dihexyl)benzene;AKOS015839667;AS-61278;CS-0134087;D5829;FT-0676594;C71568;A852192

Chemical Property of 1,4-Dibromo-2,5-dihexylbenzene

Chemical Property:

• Vapor Pressure: 8.25E-07mmHg at 25°C
• Refractive Index: 1.524
• Boiling Point: 418°Cat760mmHg
• Flash Point: 241.7°C
• PSA: 0.00000
• Density: 1.265g/cm³
• LogP: 7.45720
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 9.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 10
• Exact Mass: 404.05373
• Heavy Atom Count: 20
• Complexity: 206

Purity/Quality:

97% ^*data from raw suppliers

2,5-Bis(hexyl)-1,4-dibromobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC1=CC(=C(C=C1Br)CCCCCC)Br

Technology Process of 1,4-Dibromo-2,5-dihexylbenzene

There total 4 articles about 1,4-Dibromo-2,5-dihexylbenzene 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: 90.0%

1,4-dihexylbenzene (22588-73-4) → 1,4-dibromo-2,5-di-n-hexylbenzene (117635-21-9)

Guidance literature:

With bromine; iodine; for 24h; Ambient temperature;

DOI:10.1055/s-1988-27583

Reference yield:

para-dichlorobenzene (106-46-7,84348-21-0) → 1,4-dibromo-2,5-di-n-hexylbenzene (117635-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 1,3-bis(triphenylphosphanyl)propanenickel(II) chloride / diethyl ether / Heating

2: 82 percent / bromine; iodine / 24 h / 20 °C

With 1,3-bis(triphenylphosphanyl)propanenickel(II) chloride; bromine; iodine; In diethyl ether;

DOI:10.1002/ejoc.200600796

Reference yield:

n-hexylmagnesium bromide (3761-92-0) → 1,4-dibromo-2,5-di-n-hexylbenzene (117635-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / <1,3-bis(diphenylphosphino)propane>Cl₂Ni / diethyl ether / 24 h / Heating

2: 90 percent / Br₂, I₂ / 24 h / Ambient temperature

With bromine; iodine; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether;

DOI:10.1055/s-1988-27583

upstream raw materials:

1,4-dihexylbenzene

para-dichlorobenzene

n-hexylmagnesium bromide

Downstream raw materials:

2,5-Dihexyl-terephthalonitrile

(4-Bromo-2,5-dihexyl-phenyl)-trimethyl-silane

1-bromo-2,5-dihexyl-4-iodobenzene

4-bromo-2,5-dihexyl-benzaldehyde

Refernces

Synthesis and Characterization of Monodisperse Oligo(phenyleneethynylene)s

10.1021/jo970548x

The research focuses on the synthesis and characterization of monodisperse oligo(phenyleneethynylene)s (oligoPPEs), which are oligomers of significant interest due to their potential use as models for polymers and as building blocks for nanoscopic architectures. The study employs an iterative convergent/divergent synthesis strategy based on the bromine-iodine selectivity of the Pd-catalyzed alkyne-aryl-coupling, the conversion of bromine to iodine via halogen metal exchange, and the use of trimethylsilyl (TMS) as an acetylene protecting group. Key chemicals used in the process include 1,4-dibromo-2,5-diisopentoxybenzene, 1,4-dibromo-2,5-dihexylbenzene, TMS-acetylene, n-BuLi, 1,2-diiodoethane, Pd(PPh3)2Cl2, and CuI. The synthesis was efficient, yielding gram amounts of octamers, and further derivatization to esters and carboxylic acids was described. The compounds were fully characterized using 1H and 13C NMR, UV/vis spectroscopy, and elemental analysis, with the results indicating a bathochromic shift in the UV/vis data and a linear relationship between chemical shift and concentration for the oligomers, suggesting potential aggregation effects. The successful synthesis and characterization of these monodisperse oligoPPEs with various functional groups open up possibilities for their use in constructing nanoarchitectures.