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Chemical Structure| 20103-10-0

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Product Details of [ 20103-10-0 ]

CAS No. :20103-10-0
Formula : C6H4Cl2O2
M.W : 179.00
SMILES Code : OC1=C(Cl)C=C(O)C=C1Cl
MDL No. :MFCD00038786

Safety of [ 20103-10-0 ]

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 [ 20103-10-0 ]

* 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 [ 20103-10-0 ]

[ 20103-10-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2314-36-5 ]
  • [ 7722-84-1 ]
  • KOH-solution [ No CAS ]
  • [ 20103-10-0 ]
  • 2
  • [ 2314-36-5 ]
  • [ 20103-10-0 ]
YieldReaction ConditionsOperation in experiment
76% With sulfuric acid; dihydrogen peroxide; In methanol; water; at 17 - 80℃; In a 250 ml round bottom flask, a solution of 0.69 g (0.007 mol) of c.sulphuric acid and 40 ml methanol was prepared. 4.5 g (0.023 mol) of 3,5-dichloro-4-hydroxyl-benzaldehyde were added and stirred to obtain a clear solution. The reaction mass was cooled to 7- 20°C and 5.34 g (0.047 mol) of 30 percent hydrogen peroxide solution were slowly added under stirring (caution: exothermic reaction) over a period of 5-10 minutes under maintaining the temperature at 20-35°C. The mixture was stirred for 30 min at room temperature and at 80°C for 60 min. The completion of reaction was confirmed by TLC. 15 ml of 20 percent sodium dithionite solution were slowly added (5-10 min) under stirring at 20-25°C. The mixture was stirred under nitrogen at 20-25°C for 30 min. 20 ml of aqueous methanol were distilled out at 40-50°C. The reaction mass was cooled to 20-25°C and 45 ml of process water were added over a period of 5 min. The mixture was stirred for 10-15 min under nitrogen. The product was filtered and washed with 25 ml of process water, suck-dried well and then dried under vacuum at 60°C for 2 hrs to afford 3.2 g (76 percent) of 2,6-dichloro-hydroquinone (2,6-dichlorobenzene-1 ,4-diol). Melting point: 110-112°C.
  • 3
  • [ 2100-42-7 ]
  • [ 608-44-6 ]
  • [ 20103-10-0 ]
  • [ 824-69-1 ]
  • [ 123-31-9 ]
  • [ 615-67-8 ]
YieldReaction ConditionsOperation in experiment
0.019 g; 0.048 g; 0.096 g; 0.105 g; 1.17 g With aluminum (III) chloride; sodium chloride; In melt; at 150 - 185℃; for 0.116667h; Substrate 7 (1.73 g, 10.0 mmol) was added to the melt of anhydrous AlCl3 (8.54 g,64.0 mmol) and NaCl (1.87 g, 32.0 mmol) with vigorous stirring at 150 C, the temperature of the mixture was increased to 180-185 C and maintained for 7 min. Then, the mixture was cooled to room temperature, and diluted with 10% aqueous HCl (60 mL) and distilled water (60 mL). The reaction products were extracted with AcOEt (5×20 mL), the combined extracts were washed with saturated aqueous NaCl (3×15 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 2,5-dichlorohydroquinone (14) (0.096 g, 29%), colorless crystals, m.p. 168-170 C, identical to commercial product (Alfa Aesar). 1H NMR (CDCl3), delta: 5.57 (br.s, 2 H, 2 OH); 7.03 (s, 2 H, H(3),H(6)). 13C NMR (CDCl3), delta: 115.0 (C(3), C(6)); 119.9 (C(2),C(5)); 145.7 (C(1), C(4)). 1H NMR (DMSOd6), delta: 6.92 (s, 2 H,H(3), H(6)); 9.75 (s, 2 H, 2 OH). 13C NMR (DMSOd6), delta: 117.0(C(3), C(6)); 118.3 (C(2), C(5)); 145.9 (C(1), C(4)). The elution with the mixture of hexane-acetone (8 : 1) gave2,6dichlorohydroquinone (15) (0.048 g, 14%), colorless crystals,m.p. 163-165 C (Ref. 42: 164 C). IR (CDCl3), nu/cm-1: 3601,3549, 2925, 2861, 1499, 1450, 1336, 1304, 1270, 1237, 1194,1175, 1039. 1H NMR (CDCl3), delta: 5.35 (br.s, 1 H, C(1) OH);5.45 (br.s, 1 H, C(4) OH); 6.81 (s, 2 H, H(3), H(5)). 13C NMR(CDCl3), delta: 115.6 (C(3), C(5)); 121.9 (C(2), C(6)); 142.8 (C(1));148.8 (C(4)). 1H NMR (DMSOd6), delta: 6.75 (s, 2 H, H(3), H(5));9.24 (br.s, 1 H, C(1) OH); 9.57 (br.s, 1 H, C(4) OH). 13C NMR(DMSOd6), delta: 115.4 (C(3), C(5)); 123.2 (C(2), C(6)); 141.7(C(1)); 150.8 (C(4)).The elution with the mixture of hexane-acetone (7 : 1) gave2,3dichlorohydroquinone (16) (0.019 g, 6%), colorless crystals,m.p. 142-144 C (Ref. 43: 144 C). 1H NMR (DMSOd6), delta:6.76 (s, 2 H, H(5), H(6)); 9.25 (s, 2 H, 2 OH). 13C NMR(DMSOd6), delta: 115.3 (C(5), C(6)); 119.0 (C(2), C(3)); 147.3(C(1), C(4)).The elution with the mixture of hexane-acetone (5 : 1) gave2chlorohydroquinone (12) (1.17 g, 81%), colorless crystals,m.p. 101-102 C, identical to commercial product (Alfa Aesar).1H NMR (DMSOd6), delta: 6.56 (dd, 1 H, H(5), J = 9.1 Hz,J = 2.8 Hz); 6.71 (d, 1 H, H(3), J = 2.8 Hz); 6.77 (d, 1 H, H(6),J = 9.1 Hz); 9.01 (br.s, 1 H, C(1) OH); 9.21 (br.s, 1 H, C(4)OH). 13C NMR (DMSOd6), delta: 114.8 (C(5)); 116.1 (C(6)); 117.3(C(3)); 119.6 (C(2)); 145.6 (C(1)); 150.3 (C(4)).The elution with the mixture of hexane-acetone (4 : 1) gavehydroquinone (13) (0.105 g, 50%), colorless crystals, m.p.170-172 C, identical to commercial product (Alfa Aesar).1H NMR (CDCl3), delta: 4.45 (br.s, 2 H, 2 OH); 6.72 (s, 4 H, H(2),H(3), H(5), H(6)). 13C NMR (CDCl3), delta: 116.1 (C(2), C(3),C(5), C(6)); 149.4 (C(1), C(4)). 1H NMR (DMSOd6), delta: 6.56(s, 4 H, H(2), H(3), H(5), H(6)); 8.56 (s, 2 H, 2 OH). 13C NMR(DMSOd6), delta: 115.7 (C(2), C(3), C(5), C(6)); 149.8 (C(1), C(4)).
  • 4
  • [ 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.
 

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