1,4-Diiodobenzene Chemical Properties

Melting point:

131-133 °C (lit.)

Boiling point:

285 °C (lit.)

Density 

2.350

refractive index 

1.6212

Flash point:

285°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Crystalline Powder

color 

White to beige

Water Solubility 

Soluble in ether and ethanol. Insoluble in water.

Sensitive 

Light Sensitive

BRN 

1904546

Dielectric constant

2.8799999999999999

InChI

1S/C6H4I2/c7-5-1-2-6(8)4-3-5/h1-4H

InChIKey

LFMWZTSOMGDDJU-UHFFFAOYSA-N

SMILES

Ic1ccc(I)cc1

CAS DataBase Reference

624-38-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,4-diiodo-(624-38-4)

EPA Substance Registry System

Benzene, 1,4-diiodo- (624-38-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

F 

8

TSCA 

TSCA listed

HS Code 

29036990

Storage Class

11 - Combustible Solids

MSDS

• Language:English Provider:1,4-Diiodobenzene
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

1,4-Diiodobenzene Usage And Synthesis

Chemical Properties

1,4-Diiodobenzene appears as white to light orange crystals or powder. Its melting point is 131–132 °C, and it boils at 285 °C (sublimes). The compound is readily soluble in ether and ethanol, but insoluble in water.

Uses

1,4-Diiodobenzene is used in Suzuki reaction. It is used as a precursor in the preparation of martinellic acid and 1,4-bis(p-R-phenylethynyl)benzenes. Further, it is employed in the preparation of 1,4-diiodo-2,5-didodecylbenzene , which is a starting reagent for the synthesis of oligo(1,4-phenylene ethynylene). It is also used in human and animal nutrition products including antiseptics and disinfectants. In addition to this, it used in polarizing films for liquid crystal display chemicals.

Preparation

1,4-Diiodobenzene is obtained by diazotising p-iodoaniline followed by substitution. An alternative preparation method involves diazotising p-phenylenediamine hydrochloride, followed by substitution with potassium iodide.

Purification Methods

Crystallise it from EtOH or boiling MeOH, then dry it in air. [Beilstein 5 IV 700.]

References

[1] JENS CARDINALE  Heinz H C  Johannes Ermert. Convenient preparation of (4-iodophenyl)aryliodonium salts[J]. Tetrahedron, 2012, 68 22: Pages 4112-4116. DOI:10.1016/j.tet.2012.03.113.
[2] ROEL S. SÁNCHEZ-CARRERA. Charge-Transport Properties of the 1,4-Diiodobenzene Crystal: A Quantum-Mechanical Study[J]. Chemistry of Materials, 2008, 20 18: 5832-5838. DOI:10.1021/cm801108c.
[3] DU ZONG-DA   Yang C X  Cui Yuan Yuan. Synthesis of silica amino-functionalized microporous organic network composites for efficient on-line solid phase extraction of trace phenols from water.[J]. Journal of Chromatography A, 2020, 1616: 460791. DOI:10.1016/j.chroma.2019.460791.

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