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Chemical Structure| 2100-42-7 Chemical Structure| 2100-42-7

Structure of 2100-42-7

Chemical Structure| 2100-42-7

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Product Details of [ 2100-42-7 ]

CAS No. :2100-42-7
Formula : C8H9ClO2
M.W : 172.61
SMILES Code : COC1=CC=C(OC)C(Cl)=C1
MDL No. :MFCD00008356
InChI Key :QMXZSRVFIWACJH-UHFFFAOYSA-N
Pubchem ID :246724

Safety of [ 2100-42-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 2100-42-7 ]

* 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 [ 2100-42-7 ]

[ 2100-42-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 77-78-1 ]
  • [ 615-67-8 ]
  • [ 2100-42-7 ]
  • 2
  • [ 615-67-8 ]
  • [ 74-88-4 ]
  • [ 2100-42-7 ]
  • 3
  • [ 2100-42-7 ]
  • [ 76-05-1 ]
  • [ 90064-48-5 ]
YieldReaction ConditionsOperation in experiment
47% With hexamethylenetetramine; In tetrahydrofuran; at 90 - 95℃; for 2.0h; To a mixture of compound 4 (1.0 g, 5.79 mmol) and hexamethylenetetramine (893mg, 6.37 mmol) in THF, TFA (12.89 mg, 113 mmol) was added slowly. The reactionmixture was then refluxed for 2 hours. After that, the hot reaction liquid was pouredinto ice and its pH was adjusted to 7 with NaHCO3 powder. The mixture was extractedwith ethyl acetate and the organic phase was collected, washed with brine, dried overNa2SO4, and concentrated under reduced pressure to get the reaction crude. Thereaction crude was then purified with silica gel to give 543 mg compound 5 as a whitesolid in 47 % yield.
  • 5
  • [ 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)).
  • 6
  • [ 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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