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715298

Sigma-Aldrich

1,2,4,5-Tetrakis(4-carboxyphenyl)benzene

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contains up to 6 wt. % water, ≥98%

Synonym(s):

4,4′,4′′,4′′′-benzene-1,2,4,5-tetrayltetrabenzoic acid, H4TCPB

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About This Item

Empirical Formula (Hill Notation):
C34H22O8
Molecular Weight:
558.53
MDL number:
UNSPSC Code:
26111700
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

≥98%

form

powder

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SMILES string

OC(=O)c1ccc(cc1)-c2cc(-c3ccc(cc3)C(O)=O)c(cc2-c4ccc(cc4)C(O)=O)-c5ccc(cc5)C(O)=O

InChI

1S/C34H22O8/c35-31(36)23-9-1-19(2-10-23)27-17-29(21-5-13-25(14-6-21)33(39)40)30(22-7-15-26(16-8-22)34(41)42)18-28(27)20-3-11-24(12-4-20)32(37)38/h1-18H,(H,35,36)(H,37,38)(H,39,40)(H,41,42)

InChI key

SRTQKANXPMBQCX-UHFFFAOYSA-N

General description

1,2,4,5-Tetrakis(4-carboxyphenyl)benzene (H4TCPB) is an organic linker with a molecular structure that has four carboxyl phenyl groups that are symmetrically attached to the central benzene core. It can be synthesized by using a Suzuki coupling reaction.
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Application

(H4TCPB) can be used for a variety of applications such as:
  • the formation of supramolecular heterostructures to functionalize black phosphorus
  • synthesis of microporous metal-organic frameworks (MOFs) for potential usage in hydrogen storage, gas separation, and catalysis.

[1,1′:4′,1]Terphenyl- 3,3″,5,5″-tetracarboxylic acid (H4TPTC) is used as a linker molecule for the synthesis of high performance metal-organic frameworks (MOFs).

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

185.0 °F - closed cup

flash_point_c

85 °C - closed cup


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Near-critical water, a cleaner solvent for the synthesis of a metal-organic framework
Ibarra IA, et al.
Green Chemistry, 14(1), 117-122 (2012)
Synthesis and structure of Zr (iv)-and Ce (iv)-based CAU-24 with 1, 2, 4, 5-tetrakis (4-carboxyphenyl) benzene
Lammert M, et al.
Dalton Transactions, 45(47), 18822-18826 (2016)
Lilia S Xie et al.
Chemical reviews, 120(16), 8536-8580 (2020-04-11)
Metal-organic frameworks (MOFs) are intrinsically porous extended solids formed by coordination bonding between organic ligands and metal ions or clusters. High electrical conductivity is rare in MOFs, yet it allows for diverse applications in electrocatalysis, charge storage, and chemiresistive sensing
Selected Applications of Metal-Organic Frameworks in Sustainable Energy Technologies?.
Caskey SR and Matzger AJ.
Material Matters, 4(4), 111-111 (2009)
Singlet oxygen-mediated selective C--H bond hydroperoxidation of ethereal hydrocarbons
Sagadevan A, et al.
Nature Communications, 8(1), 1-8 (2017)

Articles

Metal-organic frameworks, a subset of coordination polymers, represent a powerful new tool for a plethora of alternative energy applications. MOFs are readily available using simple synthetic strategies that supply tailored, high surface area materials.

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