1,3,5-Tribromobenzene Chemical Properties

Melting point:

117-121 °C (lit.)

Boiling point:

271 °C (lit.)

Density 

2.3515 (estimate)

refractive index 

1.6340 (estimate)

Flash point:

271°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in benzene, chloroform, and ether (Weast, 1986)

form 

Powder

color 

Almost white to orange-brown

Water Solubility 

Soluble in hot ethanol and acetic acid. Insoluble in water.

BRN 

1858917

InChI

1S/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3H

InChIKey

YWDUZLFWHVQCHY-UHFFFAOYSA-N

SMILES

Brc1cc(Br)cc(Br)c1

CAS DataBase Reference

626-39-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,3,5-tribromo-(626-39-1)

EPA Substance Registry System

1,3,5-Tribromobenzene (626-39-1)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-53

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

RTECS 

DC1957200

TSCA 

TSCA listed

HS Code 

29036990

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Chronic 4

MSDS

• Language:English Provider:Tribromobenzene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,3,5-Tribromobenzene Usage And Synthesis

Chemical Properties

Lump powder; Vapour pressure of 1,3,5-tribromobenzene between 295 and 389 K (solid) and 397 and 410 K (liquid). The enthalpies of sublimation and vaporisation were derived from the relationship between vapour pressure and temperature: ΔH°SUB(334.78 K) = 83.54 ± 2 kJ/mol and ΔH°vap(403.23 K) = 58.68 ± 1.5 kJ/mol.

Uses

Intermediate in drug manufacturing; organic synthesis; internal standard in analysis of aqueous samples.

Uses

1,3,5-Tribromobenzene, is a reagent that can be used in the preparation of different inhibitors. It is also a substituted Bromobenzene, a general reagent in palladium-catalyzed reactions and in the synthesis of Grignard reagents.

General Description

• 1,3,5-Tribromobenzene(TBB) acts as internal standard during derivatization step in determination of cyanide in human plasma and urine by gas chromatography-mass spectrometry.
• TBB forms molecular complexes of 1:2 stoichiometry with [60]-and [70] fullerenes.
• TBB reacts with perfluoroalkenylzinc reagent in the presence of Pd(Ph₃)₄ catalyst to yield a novel trifunctional monomer 1,3,5-tris(α, β, β-trifluorovinyl)benzene.

Synthesis

Pour 10 mol of benzene into a 500 ml three-necked bottle, add 200 ml of trichloromethane and 0.4 g of iron powder, stirring to dissolve, ice bath until the system is about 0 ??, protected from light, slowly add 35 mol of liquid bromine and 80 ml of trichloromethane mixture, the reaction is at room temperature for 10 hours, a large number of yellow-brown solid precipitation. At the end of the reaction, saturated aqueous sodium bisulfite was added to remove excess unreacted bromine. The crude product was washed twice with saturated aqueous sodium bisulfite solution, dried, and purified by recrystallization to obtain a light yellow-brown powder.

Environmental Fate

Photolytic. Peijnenburg et al. (1992) investigated the photodegradation of a variety of substituted aromatic halides using a Rayonet RPR-208 photoreactor equipped with 8 RUL 3,000- ? lamps (250–350 nm). The reaction of 1,3,5-tribromobenzene (initial concentration 10-5 M) was conducted in distilled water and maintained at 20 °C. Though no products were identified, the investigators reported photohydrolysis was the dominant transformation process. The measured pseudo-first-order reaction rate constant and corresponding half-life were 0.005/min and 140.5 min., respectively.
Chemical/Physical. 1,3,5-Tribromobenzene will not hydrolyze to any reasonable extent.

Purification Methods

Crystallise it from glacial acetic acid/water (4:1), then wash with chilled EtOH and dry in air. [Beilstein 5 H 213, 5 IV 685.]

1,3,5-Tribromobenzene(626-39-1)Related Product Information

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• 2,4,6-TRIBROMORESORCINOL
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