No renderable structure data available
CSC1=CC=C(C=C1)IChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 4-Iodothioanisole |
|---|---|
| IUPAC Name | — |
| CAS Number | 35371-03-0 |
| Database ID | 2759374 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
4-Iodothioanisole (CAS 35371-03-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 2759374
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
7 reactions · 7 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0c573d61b79044c7a2ef1282aeada72eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f0658168fe284f5b82031806a1ad99a6Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask was charged with 10 g of 4-iodothioanisole and 5.5 mL of dimethylsulfate and warmed to ca. 90° C. for 10 min. The resulting solution was dissolved in conc. sulfuric acid (30 mL) and cooled to ca. 0-4° C., whereupon it was treated, with extreme caution, slowly with conc. HNO3 (ca. 2 mL) while maintaining the reaction temperature below 4° C. After stirring it for ca. 10 min, the reaction mixture was stirred at ca. 90° C. for ca. 3 d. The reaction was monitored with HPLC, TLC, and LC-MS, and if needed, smaller portions of nitric acid were added to the reaction mixture to force it to completion. Use of fuming sulfuric acid is also helpful. After the complete consumption of the aromatic starting material, the reaction mixture was cooled, poured over crushed ice, treated with 30% aq. perchloric acid at 4° C. The light colored precipitate was filtered, washed thoroughly with water, and dried under vacuum. The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h. Upon cooling to room temperature, the precipitate was filtered, washed thoroughly with water to get rid of any inorganic salts, and dried under vacuum to obtain 4-iodo-3-nitrothioanisole in >80% yield. cooled to ca. 0-4° C., whereupon it while maintaining the reaction temperature below 4° C the reaction mixture was stirred at ca. 90° C. for ca. 3 d After the complete consumption of the the reaction mixture was cooled poured over crushed ice treated with 30% aq. perchloric acid at 4° C The light colored precipitate was filtered washed thoroughly with water dried under vacuum The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h Upon cooling to room temperature the precipitate was filtered washed thoroughly with water to get rid of any inorganic salts dried under vacuum
Source ID: ord-cb905cb02d1e4e19951ca9d1f23ecf9fConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0c573d61b79044c7a2ef1282aeada72eConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-f0658168fe284f5b82031806a1ad99a6Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask was charged with 10 g of 4-iodothioanisole and 5.5 mL of dimethylsulfate and warmed to ca. 90° C. for 10 min. The resulting solution was dissolved in conc. sulfuric acid (30 mL) and cooled to ca. 0-4° C., whereupon it was treated, with extreme caution, slowly with conc. HNO3 (ca. 2 mL) while maintaining the reaction temperature below 4° C. After stirring it for ca. 10 min, the reaction mixture was stirred at ca. 90° C. for ca. 3 d. The reaction was monitored with HPLC, TLC, and LC-MS, and if needed, smaller portions of nitric acid were added to the reaction mixture to force it to completion. Use of fuming sulfuric acid is also helpful. After the complete consumption of the aromatic starting material, the reaction mixture was cooled, poured over crushed ice, treated with 30% aq. perchloric acid at 4° C. The light colored precipitate was filtered, washed thoroughly with water, and dried under vacuum. The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h. Upon cooling to room temperature, the precipitate was filtered, washed thoroughly with water to get rid of any inorganic salts, and dried under vacuum to obtain 4-iodo-3-nitrothioanisole in >80% yield. cooled to ca. 0-4° C., whereupon it while maintaining the reaction temperature below 4° C the reaction mixture was stirred at ca. 90° C. for ca. 3 d After the complete consumption of the the reaction mixture was cooled poured over crushed ice treated with 30% aq. perchloric acid at 4° C The light colored precipitate was filtered washed thoroughly with water dried under vacuum The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h Upon cooling to room temperature the precipitate was filtered washed thoroughly with water to get rid of any inorganic salts dried under vacuum
Source ID: ord-122290786c8149acbb0e9815bd9073bcConditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A flask was charged with 10 g of 4-iodothioanisole and 5.5 mL of dimethylsulfate and warmed to ca. 90° C. for 10 min. The resulting solution was dissolved in conc. sulfuric acid (30 mL) and cooled to ca. 0-4° C., whereupon it was treated, with extreme caution, slowly with conc. HNO3 (ca. 2 mL) while maintaining the reaction temperature below 4° C. After stirring it for ca. 10 min, the reaction mixture was stirred at ca. 90° C. for ca. 3 d. The reaction was monitored with HPLC, TLC, and LC-MS, and if needed, smaller portions of nitric acid were added to the reaction mixture to force it to completion. Use of fuming sulfuric acid is also helpful. After the complete consumption of the aromatic starting material, the reaction mixture was cooled, poured over crushed ice, treated with 30% aq. perchloric acid at 4° C. The light colored precipitate was filtered, washed thoroughly with water, and dried under vacuum. The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h. Upon cooling to room temperature, the precipitate was filtered, washed thoroughly with water to get rid of any inorganic salts, and dried under vacuum to obtain 4-iodo-3-nitrothioanisole in >80% yield. cooled to ca. 0-4° C., whereupon it while maintaining the reaction temperature below 4° C the reaction mixture was stirred at ca. 90° C. for ca. 3 d After the complete consumption of the the reaction mixture was cooled poured over crushed ice treated with 30% aq. perchloric acid at 4° C The light colored precipitate was filtered washed thoroughly with water dried under vacuum The perchlorate salt was stirred with saturated aq. NaCl solution at 95° C. for 3-6 h Upon cooling to room temperature the precipitate was filtered washed thoroughly with water to get rid of any inorganic salts dried under vacuum
Source ID: ord-cb905cb02d1e4e19951ca9d1f23ecf9fPubChem References
These sources are listed in the compound's public database record.
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