3,4,5-TRICHLOROPHENOL Chemical Properties

Melting point:

118-119℃

Boiling point:

275℃

Density 

1.5701 (rough estimate)

refractive index 

1.5300 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly, Heated)

pka

pK1:7.839 (25°C)

Appearance

Light brown to brown Solid

Stability:

Stable. Probably combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides.

InChI

InChI=1S/C6H3Cl3O/c7-4-1-3(10)2-5(8)6(4)9/h1-2,10H

InChIKey

GBNHEBQXJVDXSW-UHFFFAOYSA-N

SMILES

C1(O)=CC(Cl)=C(Cl)C(Cl)=C1

EPA Substance Registry System

3,4,5-Trichlorophenol (609-19-8)

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

20/21/22-36/37/38-50/53-41-37/38

Safety Statements 

26-36-61-60

RIDADR 

UN3077 9/PG 3

WGK Germany 

3

RTECS 

SN1650000

Hazardous Substances Data

609-19-8(Hazardous Substances Data)

3,4,5-TRICHLOROPHENOL Usage And Synthesis

Chemical Properties

off-white crystalline solid

Uses

3,4,5-Trichlorophenol is a chlorinated phenol found in fungus. It also has possible toxic effects.

General Description

Needles (from ligroin) or off-white solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3,4,5-TRICHLOROPHENOL may be incompatible with acid chlorides, acid anhydrides and oxidizing agents. .

Fire Hazard

Flash point data for 3,4,5-TRICHLOROPHENOL are not available; however, 3,4,5-TRICHLOROPHENOL is probably combustible.

Synthesis

3,4,5-Trichlorobenzenediazonium tetrafluoroborate (CAS: 2106-38-9, 9.62 g, 32.6 mmol, 1 eq.) was added to an aqueous solution (3.5 L) containing copper (II) nitrate trihydrate (450 g, 1.86 mol, 57 eq.) and copper(I) oxide (14.03 g, 98.1 mmol, 3 eq.) ) in water. The reaction mixture was stirred vigorously for 1 h at room temperature. After completion of the reaction, the solid was collected by filtration and washed with dichloromethane. The filtrate was extracted three times with dichloromethane, the organic phases were combined and dried with anhydrous magnesium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of ethyl acetate/hexane ranging from 0 to 20%, resulting in 3,4,5-trichlorophenol as an orange-brown solid (3.199 g, 49% yield).1H NMR (CDCl3) δ 6.91 (s, 2H), 4.95 (br s, 1H).

Purification Methods

Crystallise the phenol from pet ether/*benzene mixture. [Beilstein 6 III 729.]

References

[1] Patent: WO2005/92835, 2005, A1. Location in patent: Page/Page column 38

3,4,5-TRICHLOROPHENOL(609-19-8)Related Product Information

• L-PYROGLUTAMIC ACID PENTACHLOROPHENYL ESTER
• 2,3,4,5-TETRACHLOROANISOLE
• PENTACHLOROPHENOL DODECANOATE
• Pentachlorophenol
• 2,3,4,5-TETRACHLOROPHENOL
• PENTACHLOROANISOLE
• 3,4,5-TRICHLOROPHENOL
• TETRACHLOROCATECHOL
• Pentachlorophenol sodium salt hydrate
• PENTACHLOROPHENOL-UL-14C
• 2-amino-3,4,6-trichlorophenol
• 2,3,5-TRICHLOROPHENOL
• 2,4,5-Trichlorophenol
• Sodium 2,4,6-trichlorophenolate
• 2,4,6-TRICHLOROPHENOL ACETATE
• Hexachlorophene
• TRICHLOROPHENOL(2,4,6-),1,3,5-Trichlorophenol
• 2,3,6-trichlorophenol