| Identification | More | [Name]
3,4-Dichloroiodobenzene | [CAS]
20555-91-3 | [Synonyms]
1,2-DICHLORO-4-IODOBENZENE
3,4-DICHLOROIODOBENZENE
1,2-dichloro-4-iodo-benzen
Benzene,1,2-dichloro-4-iodo-
3,4-Dichloro-1-iodobenzene
3,4-Dichlorophenyl iodide
4-Iodo-o-dichlorobenzene | [EINECS(EC#)]
243-874-0 | [Molecular Formula]
C6H3Cl2I | [MDL Number]
MFCD00019014 | [Molecular Weight]
272.9 | [MOL File]
20555-91-3.mol |
| Chemical Properties | Back Directory | [Appearance]
beige low melting solid | [Melting point ]
27-29 °C (lit.) | [Boiling point ]
116-118 °C (12 mmHg) | [density ]
1.9882 (estimate) | [refractive index ]
1.6480 | [Fp ]
>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]
20555-91-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant/Light Sensitive | [TSCA ]
Yes | [HS Code ]
29039990 |
| Hazard Information | Back Directory | [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 |
|
|