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Chemical Structure| 379711-35-0 Chemical Structure| 379711-35-0

Structure of 379711-35-0

Chemical Structure| 379711-35-0

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Product Details of [ 379711-35-0 ]

CAS No. :379711-35-0
Formula : C8H4Br2O4
M.W : 323.92
SMILES Code : O=C(C1C(Br)=C(C(=O)O)C=C(Br)C=1)O
MDL No. :MFCD28719346

Safety of [ 379711-35-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 379711-35-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 379711-35-0 ]

[ 379711-35-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 121-91-5 ]
  • [ 379711-35-0 ]
  • [ 379711-34-9 ]
  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
0 - 4.9%; 0 - 23.5%; 11.9 - 80.1% With sulfuric acid; sulfur trioxide; bromine; at 110 - 150℃; for 7 - 22h; Into a 50 ml pressure and sealable glass tube, 1.66 g (10 mmol) of isophthalic acid, 6.00 g of 10 wt percent fuming sulfuric acid and 1.6 g (10 mmol) of bromine were charged, and the content was stirred at 130° C. for 22 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 2.41 g (purity: 83.5percent) of a crude crystal of the aimed product (yield: 81.9percent). Then, the crystals were solved in 10 g of methanol at 60° C., cooled to room temperature, and thereafter filtered off to give 1.61 g (purity: 100percent) of a white crystal (yield of recrystallization: 80.1percent). This crystal was identified as 5-bromopisophthalic acid by MASS, 1H-NMR and melting point. EXAMPLES 2 TO 7 [0033] Procedures were carried out similarly to that of Example 1 except that the reaction temperature, the concentration of fuming sulfuric acid and the amount of bromine were changed. The results on the resulting monobromo products were shown in Table 1. [TABLE-US-00001] TABLE 1 Concentration of Fuming Quantitative Yield (percent) Ex. Sulfuric Acid Bromine Tempera- Time 4,5- 2,5- No. (wt percent)-(g) g(mmol) ture(° C.) (h.) 5BIP IP DBIP DBIP 2 10-6 1.6(10) 110 22 34.5 58.0 trace - 3 20-6 1.6(10) 110 22 48.6 43.2 trace - 4 30-6 1.6(10) 110 22 62.8 24.6 2.3 - 5 10-6 1.6(10) 150 22 77.0 4.1 8.0 - 6 20-6 1.6(10) 150 7 53.8 46.5 0.7 - 7 10-6 3.2(20) 150 7 79.1 6.4 5.8 trace IP: Isophthalic Acid, 5BIP:5-Bromoisophthalic Acid, 4,5-DBIP: 4,5-Dibromoisophthalic Acid 2,5-DBIP: 2,5-Dibromoisophthalic Acid EXAMPLE 8 [0034] Into a 50 ml pressure and sealable glass tube, 1.66 g (10 mmol) of isopthalic acid, 6.00 g of 30 wt percent fuming sulfuric acid and 1.6 g (10 mmol) of bromine were charged, and the content was stirred at 150° C. for 22 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. Then, the resulting solid was filtered off, washed with cooling, and further purified by column chromatography on silica gel (chloroform/methanol=6/1, v/v) to give 0.51 g (yield: 20.7percent) of 5-bromoisophthalic acid, 0.76 g (yield: 23.5percent) of 4,5-dibromoisophthalic acid and 0.07 g (yield: 2.1percent) of 2,5-dibromoisophthalic acid. These crystals were identified by MASS, 1H-NMR and melting point. EXAMPLES 9 TO 16 [0035] Procedures were carried out similarly to that of Example 8 except that the reaction temperature, the concentration of fuming sulfuric acid and the amount of bromine were changed. The results on the resulting monobromo and dibromo products were shown in Table 2. [TABLE-US-00002] TABLE 2 Concentration of Fuming Quantitative Yield (percent) Ex. Sulfuric Acid Bromine Tempera- Time 4,5- 2,5- No. (wt percent)-(g) g(mmol) ture(° C.) (h.) 5BIP IP DBIP DBIP 9 60-6 1.6(10) 110 22 45.0 1.4 18.7 1.0 10 20-6 1.6(10) 130 22 49.2 0.0 15.3 trace 11 30-6 1.6(10) 130 22 53.1 0.8 13.6 1.0 12 20-6 1.6(10) 150 22 43.1 0.0 20.0 0.8 13 20-6 3.2(20) 150 7 37.5 0.0 23.3 1.5 14 10-12 1.6(10) 150 7 47.0 0.6 18.1 1.2 15 20-12 1.6(10) 150 7 49.8 0.7 20.3 1.4 16 20-12 3.2(10) 150 7 11.9 0.0 26.2 4.9 IP: Isophthalic Acid, 5BIP:5-Bromoisophthalic Acid, 4,5-DBIP: 4,5-Dibromoisophthalic Acid 2,5-DBIP: 2,5-Dibromoisophthalic Acid
  • 2
  • [ 1459-93-4 ]
  • dimethyl 2,5-dibromoisophthalate [ No CAS ]
  • [ 379711-35-0 ]
  • [ 379711-34-9 ]
  • [ 244768-63-6 ]
  • [ 121-91-5 ]
  • [ 51760-21-5 ]
  • [ 23351-91-9 ]
YieldReaction ConditionsOperation in experiment
0.9%; 4.9%; 7.2%; 0.2%; 19.6%; 7.0%; 50.4% With sulfuric acid; sulfur trioxide; bromine; at 120℃; for 7h; Into a 100 ml pressure and sealable glass tube, 9.70 g (50 mmol) of dimethyl isophthalate, 30.00 g of 10 wt percent fuming sulfuric acid and 10.40 g (100 mmol) of bromine were charged, and the content was stirred at 120° C. for 7 hours. After the conclusion of the reaction, the content was cooled to room temperature, and placed in a beaker containing ice water to give a solid. The resulting solid was filtered off, washed with cooling, and further dried under reduced pressure to give 11.95 g of a crude crystal of the aimed product (reaction yield: 50.4percent 5-bromoisophthalic acid, 19.6percent isophthalic acid, 4.9percent 2,5-dibromoisophthalic acid, 7.2percent 4,5-dibromoisophthalic acid, 7.0percent dimethyl 5-bromoisophthalate, 1.5percent dimethyl isophthalate, 0.9percent dimethyl 2,5-dibromoisophthalate and 0.2percent dimethyl 4,5-dibromoisophthalate). Then, dimethyl esters were derived from the crystal by heating and stirring it with 65.50 g (2.04 mol) of methanol and 1.75 g (30 mol percent) of sulfuric acid in an autoclave at 120° C. [0038] In succession, the esters were subjected to rectification to give 6.73 g (yield: 49.3percent, vacuum boiling point: 159° C./4.8mmHg) of aimed dimethyl 5-bromoisophthalate and 1.67 g (yield: 17.2percent, vacuum boiling point: 133° C./4.8mmHg) of dimethyl isophthalate corresponding to a raw material. The resulting crystals were identified as dimethyl 5-bromoisophthalate and 5-bromoisophthalic acid by MASS, 1H-NMR and melting point.
  • 3
  • [ 100189-84-2 ]
  • [ 379711-35-0 ]
 

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