| Identification | More | [Name]
4-Iodo-1,2-dimethylbenzene | [CAS]
31599-61-8 | [Synonyms]
1,2-DIMETHYL-4-IODOBENZENE
1-IODO-3,4-DIMETHYLBENZENE
3,4-DIMETHYL-1-IODOBENZENE
3,4-DIMETHYLIODOBENZENE
4-IODO-1,2-DIMETHYLBENZENE
4-IODO-2-XYLENE
4-IODO-O-XYLENE
1,2-DIMETHYL-4-IODOBENZENE, 98+%
4-Iodo-o-xylene, 98+%
3,4-Dimethjyliodobenzene
3,4-Dimethylphenyl iodide | [EINECS(EC#)]
200-208-3 | [Molecular Formula]
C8H9I | [MDL Number]
MFCD00040989 | [Molecular Weight]
232.06 | [MOL File]
31599-61-8.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to red-brown liquid | [Melting point ]
-2.9°C (estimate) | [Boiling point ]
106-108 °C13 mm Hg(lit.) | [density ]
1.633 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.603(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
clear liquid | [color ]
Colorless to Brown | [Sensitive ]
Light Sensitive | [BRN ]
1905729 | [InChI]
InChI=1S/C8H9I/c1-6-3-4-8(9)5-7(6)2/h3-5H,1-2H3 | [InChIKey]
CSFRCLYFVINMBZ-UHFFFAOYSA-N | [SMILES]
C1(C)=CC=C(I)C=C1C | [CAS DataBase Reference]
31599-61-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzene, 4-iodo-1,2-dimethyl-(31599-61-8) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29039990 |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellow to red-brown liquid | [Uses]
1-Iodo-3,4-dimethylbenzene (4-iodo-o-xylene, 3,4-dimethyliodobenzene) may be used in the synthesis of the following:
- 3-arylacrylamide
- 3,3-diaryl substituted acrylamide
- 3-arylpropylamine
- di-tert-butyl 1-(3,4-dimethylphenyl)hydrazine-1,2-dicarboxylate
- 2,3,7,8-tetramethyldibenzofuran
- N-(3-(3,4-Dimethylphenyl)-2-phthalimidopropionyl)-2-methylthioaniline
| [General Description]
1-Iodo-3,4-dimethylbenzene (4-iodo-o-xylene, 3,4-dimethyliodobenzene) is an aryl halide. Its synthesis, NMR and IR spectra has been reported. Its nitration reaction and copper catalyzed trifluoromethylation reaction has been studied. | [Synthesis]
GENERAL STEPS: To a solution of 1,2-dimethylbenzene (o-xylene, 0.106 g, 1 mmol) in acetonitrile (10 mL) was sequentially added iodine (1 mmol, 0.126 g) and polymer-loaded periodate (0.6 g, 1.05 mmol). The reaction mixture was stirred at 40 °C for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a solvent mixture of ethyl acetate and hexane (1:9, v/v). After completion of the reaction, the mixture was cooled to room temperature and filtered. Excess iodine in the filtrate was removed by adding sodium bisulfite solution (1 M) dropwise. The organic layer was separated, dried with anhydrous magnesium sulfate, filtered and evaporated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography, the eluent being a solvent mixture of hexane and ethyl acetate. The final product was 3,4-dimethyl iodobenzene in 95% isolated yield with a boiling point of 235 °C (literature value: 234 °C). | [References]
[1] Bulletin of the Chemical Society of Ethiopia, 2014, vol. 28, # 2, p. 305 - 308
[2] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2413 - 2414
[3] Advanced Synthesis and Catalysis, 2005, vol. 347, # 15, p. 1925 - 1928
[4] Patent: EP1595862, 2005, A1. Location in patent: Page/Page column 9
[5] European Journal of Organic Chemistry, 2017, vol. 2017, # 22, p. 3234 - 3239 |
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