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686859

Sigma-Aldrich

1,3,5-Tris(4-carboxyphenyl)benzene

greener alternative

≥98%, ≤20 wt. % solvent

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Synonym(s):
4,4′,4′′,-Benzene-1,3,5-triyl-tris(benzoic acid), H3BTB
Empirical Formula (Hill Notation):
C27H18O6
CAS Number:
50446-44-1
Molecular Weight:
438.43
MDL number:
MFCD10000888
UNSPSC Code:
26111700
PubChem Substance ID:
329761077
NACRES:
NA.23

Quality Level

100

Assay

≥98%

form

solid

greener alternative product characteristics

Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

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impurities

≤20 wt. % solvent

mp

322-327 °C

greener alternative category

Enabling,

SMILES string

OC(=O)c1ccc(cc1)-c2cc(cc(c2)-c3ccc(cc3)C(O)=O)-c4ccc(cc4)C(O)=O

InChI

1S/C27H18O6/c28-25(29)19-7-1-16(2-8-19)22-13-23(17-3-9-20(10-4-17)26(30)31)15-24(14-22)18-5-11-21(12-6-18)27(32)33/h1-15H,(H,28,29)(H,30,31)(H,32,33)

InChI key

SATWKVZGMWCXOJ-UHFFFAOYSA-N

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for energy efficiency. Find details here.

Application

1,3,5-Tris(4-carboxyphenyl)benzene (H3BTB) is a star-shaped two-dimensional molecule that forms a self-assembled monolayer (SAM) on a variety of substrates. It can be used as a tritopic bridging ligand that facilitates the functionalization of polyoxometalate-based metal organic frameworks (MOFs) for potential usage in gas storage, gas separation, and catalysis.
1,3,5-Tris(4-carboxyphenyl)benzene (BTB) is a building block for Metal Organic Frameworks (MOFs). MOFs are 3D-microporous materials with potential applications in gas adsorption and separation technologies. BTB has been recently used as a linker to make MOFs with extremely high surface area such as MOF-177 (~ 5000 m2/g), a hydrogen absorbing material with an extremely high hydrogen storage capacity of 7.5% at 77K.

Signal Word

Danger

Hazard Statements

H228,H315,H319,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

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  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. What residual solvents are present in Product 686859, Benzoic acid?

    Possible residual solvents present in this material are dimethyl sulfoxide and acetic acid. Both impurities are quantified on a batch-to-batch basis and the levels reported on the certificate of analysis.

  6. Is a protocol available for using Product 686859, Benzoic acid, to produce Metal Organic Frameworks (MOFs) with high surface area?

    Unfortunately, Sigma-Aldrich does not manufacture MOFs and do not have a protocol for using this material for a similar application. However, a synthesis method for preparing MOF-177 (a MOF with high surface area) can be obtained from the following reference: Chae, H. K.; Siberio-Perez, D. Y.; Kim, J.; Go, Y.-B.; Eddaoudi, M.; Matzger, A. J.; O’Keeffe, M.; Yaghi, O. M. Nature 2004, 427, 523-527. In addition to product #686859, Zinc (II) nitrate hexahydrate (e.g. product #96482) and N,N-Diethylformamide (e.g. product #186317) would be required to prepare the MOF in this reference.

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    Ask a Scientist here.

Chong Liu et al.
Faraday discussions, 201, 163-174 (2017-06-18)
Gradient MOFs contain directional gradients of either structure or functionality. We have successfully prepared two ternary gradient MOFs based on bMOF-100 analogues, namely bMOF-100/102/106 and bMOF-110/100/102, via cascade ligand exchange reactions. The cubic unit cell parameter discrepancy within an individual
Two-dimensional 1, 3, 5-tris (4-carboxyphenyl) benzene self-assembly at the 1-phenyloctane/graphite interface revisited
Silly F
The Journal of Physical Chemistry C, 116(18), 10029-10032 (2012)
The first tritopic bridging ligand 1, 3, 5-tris (4-carboxyphenyl)-benzene (H 3 BTB) functionalized porous polyoxometalate-based metal-organic framework (POMOF): from design, synthesis to electrocatalytic properties
Dong BX, et al.
Dalton Transactions, 44(3), 1435-1440 (2015)
Meng-Yao Chao et al.
Dalton transactions (Cambridge, England : 2003), 47(38), 13722-13729 (2018-09-15)
The two-dimensional (2D) metal-organic framework (MOF) [Cd2.25Co0.75(BTB)2(DEF)4]·2(DEF)0.5 (1a, BTB = benzene-1,3,5-tribenzolate; DEF = N,N'-diethylformamide) featuring linear trimetallic cluster secondary building units (SBUs) and replaceable DEF solvates reacts smoothly with dipyridyl ligands DPS, DPDS, and BIPY (DPS = 4,4'-dipyridyl sulfide; DPDS
Ram R R Prasad et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 24(57), 15309-15318 (2018-07-07)
Post-synthetic modification of the hafnium metal-organic framework MOF-808(Hf) to include triarylphosphine ligands is reported. Sulfonated phenylphosphines are incorporated without oxidation to give a "MOF ligand" that can complex late transition metals such as Ir and Rh to give a bifunctional
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