3,4-Dichloroiodobenzene Chemical Properties

Melting point:

27-29 °C (lit.)

Boiling point:

116-118 °C (12 mmHg)

Density 

1.9882 (estimate)

refractive index 

1.6480

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to lump to clear liquid

color 

White or Colorless to Yellow

Sensitive 

Light Sensitive

BRN 

2245136

CAS DataBase Reference

20555-91-3(CAS DataBase Reference)

EPA Substance Registry System

Benzene, 1,2-dichloro-4-iodo- (20555-91-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant/Light Sensitive

TSCA 

Yes

HS Code 

29039990

MSDS

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

3,4-Dichloroiodobenzene Usage And Synthesis

Chemical Properties

beige low melting solid

Uses

3,4-Dichloroiodobenzene may be used in the preparation of:

• tetrachloromethoxybiphenyls
• 1-(3,4-dichlorophenyl)-2-trimethylsilylacetylene
• 2-(3,4-dichlorocinnamyl)isoindoline-1,3-dione

General Description

3,4-Dichloroiodobenzene undergoes Stille coupling reaction with vinyltributyltin in the presence of Pd(0)precursors to furnish styrene derivative.

Synthesis

General procedure for the synthesis of 3,4-dichloroiodobenzene from 3,4-dichloroaniline: 3,4-dichloroaniline (15 g) was added to a stirred aqueous solution (350 mL) of concentrated H2SO4 (27.2 g). The mixture was heated to 80°C and stirred at this temperature for 10 minutes. Subsequently, the mixture was cooled to below 5°C and an aqueous solution of NaNO2 (6.4 g) (40 mL) was slowly added dropwise. After the dropwise addition, stirring was continued for 1 hour, and then an aqueous solution of KI (15.4 g) (40 mL) was slowly added. The reaction mixture was stirred for an additional 30 min, followed by heating in a 40 °C water bath for 30 min. After the reaction was completed, the mixture was extracted with CH2Cl2. The CH2Cl2 extracts were combined, dried and concentrated with CaCl2. Finally, the residue was purified by column chromatography using petroleum ether as eluent to give 20 g of the target product 3,4-dichloroiodobenzene in 79% yield.

References

[1] Patent: US2005/234046, 2005, A1. Location in patent: Page/Page column 59
[2] Recueil des Travaux Chimiques des Pays-Bas, 1930, vol. 49, p. 1082,1087
[3] Journal of Organometallic Chemistry, 1977, vol. 136, p. 185 - 200
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1982, p. 1593 - 1598

3,4-Dichloroiodobenzene(20555-91-3)Related Product Information

• 1,2-Diiodobenzene
• 1,3-Dichloropropene
• Chlorobenzene
• Iodobenzene
• 2-Iodobenzoic acid
• Methyl 2-iodobenzoate
• Bromobenzene
• (Diacetoxyiodo)benzene
• Dichloroethane
• 4-Iodobenzoic acid
• 1,4-Diiodobenzene
• 2,3,5-Triiodobenzoic acid
• Thionyl chloride
• 1-Chloro-3-iodobenzene
• 1-IODO-2,4,5-TRICHLOROBENZENE
• 1-Chloro-4-iodobenzene
• 2,5-DICHLOROIODOBENZENE
• 2,4-DICHLOROIODOBENZENE