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Chemical Structure| 15012-64-3 Chemical Structure| 15012-64-3

Structure of 15012-64-3

Chemical Structure| 15012-64-3

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Product Details of [ 15012-64-3 ]

CAS No. :15012-64-3
Formula : C10H2Cl4O4
M.W : 327.93
SMILES Code : OC1=C(Cl)C(Cl)=C(O)C(C(C(Cl)=C2Cl)=O)=C1C2=O

Safety of [ 15012-64-3 ]

Application In Synthesis of [ 15012-64-3 ]

* 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 [ 15012-64-3 ]

[ 15012-64-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1122-17-4 ]
  • [ 2100-42-7 ]
  • [ 608-44-6 ]
  • [ 20103-10-0 ]
  • [ 32741-27-8 ]
  • [ 824-69-1 ]
  • [ 14918-69-5 ]
  • [ 15012-64-3 ]
  • [ 123-31-9 ]
  • [ 615-67-8 ]
YieldReaction ConditionsOperation in experiment
1%; 3%; 42%; 5%; 2%; 2.5%; 10%; 20% With aluminum (III) chloride; iron(III) chloride; sodium chloride; In melt; at 150 - 185℃; for 0.166667h; General procedure: A mixture of substrate 7 (1.38 g, 8.0 mmol) and anhydride 9 (2.67 g, 16.0 mmol) was added to the melt of anhydrous AlCl3 (8.54 g, 64.0 mmol), NaCl (1.87 g, 32.0 mmol) and anhydrous FeCl3 (1.30 g, 8.0 mmol) with vigorous stirring at 150 C, the temperature of the mixture was increased to 180-185 C and maintained for 10 min. Then, the reaction mixture was cooled to room temperature, treated with 10% aqueous HCl (60 mL), and allowed to stand for 12 h. The product formed was separated, washed with hot (55-60 C) water (10×40 mL), dried to the constant weight, and subjected to chromatography on a column with SiO2. The elution with the mixture of hexane-benzene (10 : 1) gave compound 2 (0.066 g, 2.5%), the elution with the mixture of hexane-benzene (4 : 1) gave compound 1 (0.99 g, 42%), the elution with benzene gave compound 10 (0.045 g, 2%) identical to the sample described above. The combined acidic mother liquor and washing water (460 mL) were extracted with AcOEt (6×50 mL), the combined extracts were washed with saturated aqueous NaCl (3×50 mL), and dried with Na2SO4. The solvent was evaporated at reduced pressure, the residue was subjected to chromatography on a column with SiO2. The elution with the mixture of hexane-acetone (9 : 1) gave compound 14 (0.057 g, 5%), the elution with the mixture of hexane-acetone (8 : 1) gave compound 15 (0.034 g, 3%), the elution with the mixture of hexane-acetone (7 : 1) gave compound 16 (0.011 g, 1%), the elution with the mixture of hexane-acetone (5 : 1) gave compound 12 (0.232 g, 20%), and the elution with the mixture of hexane-acetone (4 : 1) gave compound 13 (0.07 g, 10%) identical to the sample described above.
  • 2
  • [ 1122-17-4 ]
  • [ 39542-66-0 ]
  • [ 608-94-6 ]
  • [ 32741-27-8 ]
  • [ 15012-64-3 ]
  • [ 615-67-8 ]
YieldReaction ConditionsOperation in experiment
34%; 34%; 32%; 1% With aluminum (III) chloride; sodium chloride; In melt; at 150 - 180℃; for 0.025h; General procedure: A mixture of substrate 8 (2.07 g, 10.0 mmol) and anhydride 9 (3.34 g, 20.0 mmol) was added to the melt of anhydrous AlCl3 (8.54 g, 64.0 mmol) and NaCl (8.54 g, 64.0 mmol) with vigorous stirring at 150 C, the temperature of the mixture was increased to 175-180 C and maintained for 1.5 min. The workup similar to that described above for cycloacylation of substrate 7 gave a mixture of products, which was subjected to chromatography on a column with SiO2. The elution with the mixture of hexane-benzene (10 : 1) gave compound 2 (1.05 g, 32%), the elution with the mixture of hexane-benzene (4 : 1) gave compound 1 (0.34 g, 34%) identical to the sample described above. The combined acidic mother liquor and washing water (460 mL) were extracted according to procedure described above for cycloacylation of substrate 7 in the presence of FeCl3 to isolate a mixture of products, which was subjected to chromatography on a column with SiO2. The elution with the mixture of hexane-acetone (10 : 1) gave hydroquinone 17 (0.238 g, 34%), the elution with the mixture of hexane-acetone (5 : 1) gave hydroquinone 12 (0.01 g, 1%) identical to the sample described above. The same amount of the reagents heated at 175-180 C for the longer time of 3 min led to the formation of a mixture of products, which was subjected to chromatography on a column with SiO2. The elution with the mixture of hexane-benzene (10 : 1) gave compound 2 (0.033 g, 1%), the elution with the mixture of hexane-benzene (4 : 1) gave compound 1 (1.51 g, 52%), the elution with benzene gave compound 10 (0.152 g, 6%), and the elution with the mixture of benzene-acetone 1 : 1 gave compound 11 (0.014 g, 0.5%) identical to the sample described above.
 

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