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Sigma-Aldrich

1,3,5-Tris(bromomethyl)benzene

97%

Synonym(s):

2,4,6-Tri(bromomethyl)benzene, Tribromomesitylene

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About This Item

Linear Formula:
C9H9Br3
CAS Number:
18226-42-1
Molecular Weight:
356.88
MDL number:
MFCD00182500
UNSPSC Code:
12352103
PubChem Substance ID:
24884279
NACRES:
NA.23

Assay

97%

form

solid

mp

94-99 °C

SMILES string

BrCc1cc(CBr)cc(CBr)c1

InChI

1S/C9H9Br3/c10-4-7-1-8(5-11)3-9(2-7)6-12/h1-3H,4-6H2

InChI key

GHITVUOBZBZMND-UHFFFAOYSA-N

General description

1,3,5-Tris(bromomethyl)benzene has three bromo substituents around an aromatic ring that can be used as a cross-linker. It is mainly utilized in the synthesis of ligands and dendrimeric monomers.

Application

1,3,5-Tris(bromomethyl)benzene can be crosslinked with triptycene monomers by using Friedel-Crafts alkylation reaction to form microporous polymers for selective adsorption of CO2 and H2. Proton exchange membranes (PEMs) can be fabricated by covalently linking polybenzimidazole (PBI) and 1,3,5-tris(bromomethyl)benzene as part of the tri-functional bromomethyls for fuel cell applications. It is also used in the synthesis of trifluoroacetamide derivative triaza[33]cyclophane.
A monomer for synthesizing dendrimers and light emitting oligomers.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis, 39-39 (2008)
Fabrication of crosslinked polybenzimidazole membranes by trifunctional crosslinkers for high temperature proton exchange membrane fuel cells
Yang J, et al.
International Journal of Hydrogen Energy, 43(6), 3299-3307 (2018)
Triptycene based microporous polymers (TMPs): Efficient small gas (H2 and CO2) storage and high CO2/N2 selectivity
Bera R, et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 257(6), 253-261 (2018)
1, 3, 5-Tris (bromomethyl) benzene
Fernandes J, et al.
Acta Crystallographica Section C, Structural Chemistry, 67(6), o198-o200 (2011)
Papri Sutar et al.
Inorganic chemistry, 56(16), 9417-9425 (2017-08-10)
The recent upsurge in research on coordination polymer gels (CPGs) stems from their synthetic modularity, nanoscale processability, and versatile functionalities. Here we report self-assembly of an amphiphilic, tripodal low-molecular weight gelator (L) that consists of 4,4',4-[1,3,5-phenyl-tri(methoxy)]-tris-benzene core and 2,2':6',2″-terpyridyl termini
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