1,3,5-Tri(4-carboxyphenyl)benzene Chemical Properties

Melting point:

322-327 °C

Boiling point:

711.0±60.0 °C(Predicted)

Density 

1.357±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in tetrahydrofuran.

form 

solid

pka

3.46±0.10(Predicted)

color 

white to yellow

InChI

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)

InChIKey

SATWKVZGMWCXOJ-UHFFFAOYSA-N

SMILES

C1(C2=CC(C3=CC=C(C(O)=O)C=C3)=CC(C3=CC=C(C(O)=O)C=C3)=C2)=CC=C(C(O)=O)C=C1

Safety Information

Hazard Codes 

F,Xn,N,Xi

Risk Statements 

10-48/20-50/53-63-65-67-36/38

Safety Statements 

36/37-60-61-62-26

RIDADR 

UN 3175 4.1/PG 2

WGK Germany 

3

HazardClass 

9

HS Code 

29173990

1,3,5-Tri(4-carboxyphenyl)benzene Usage And Synthesis

Chemical Properties

White solid

Uses

1,3,5-Tri(4-carboxyphenyl)benzene is used as a building block for metal organic frameworks, which is a 3D-microporous material and finds applications in gas adsorption and separation technologies.

General Description

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.

Synthesis

3.485 g (0.01 mol) of 1,3,5-tris(4-methylphenyl)benzene was added to 0.0029 g (1 mol%) of cobalt nitrate, 0.005482 g (1 eq.) of ammonium ceric nitrate, 0.0106 g (0.1 eq.) of sodium carbonate as an additive, 0.04 mol of 30% hydrogen peroxide, 5 mL of dimethyl succinate as a solvent, and 7.971 mg (0.1 equiv) of indole ligand in a dry clean pressure resistant tube. The reaction mixture was heated to 110 °C and reacted at 2.0 MPa (gauge pressure) for 6 hours. Upon completion of the reaction, the heating was stopped and the reaction system was extracted three times with ethyl acetate. The organic phases were combined and concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by column chromatography to give 4.2469 g of 1,3,5-tris(4-carboxyphenyl)benzene in 97% yield.

References

[1] Patent: CN108218685, 2018, A. Location in patent: Paragraph 0028; 0030; 0031; 0032
[2] Patent: CN107759460, 2018, A. Location in patent: Paragraph 0071-0093
[3] Patent: CN108484380, 2018, A. Location in patent: Paragraph 0031; 0033; 0035; 0037; 0038; 0039
[4] Journal fuer Praktische Chemie (Leipzig), 1890, vol. <2> 41, p. 414
[5] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 47, p. 420

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