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CAS No. : | 131088-03-4 | MDL No. : | MFCD17169948 |
Formula : | C7H5IO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 264.02 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With Iodine monochloride; acetic acid at 20℃; for 5h; Inert atmosphere; | |
51% | With Iodine monochloride; acetic acid In dichloromethane at 20℃; for 5h; Inert atmosphere; | 2,4-Dihydroxy-5-iodobenzaldehyde (4a). To a stirred solution of 2,4-dihydroxybenzaldehyde (20) (1.50 g, 10.9 mmol) in AcOH (7.5 mL) was added slowly ICl (17.32 mL, 17.31 mmol) in CH2Cl2 under nitrogen atmosphere and stirred for 5 h at rt. The reaction was quenched with sodium thiosulfate-H2O (4:1) resulted solid product and the solid was filtered and washed with water resulted the product as brown solid. Yield: 2.87 g (51%); Rf 0.63 (EtOAc/hexane =1/2); mp 167-170 oC; 1H NMR (300 MHz, acetone-d6) δ9.67 (1H, s), 7.95 (1H, s), 6.36 (1H, s); 13C NMR (75 MHz,acetone-d6) δ 193.02, 157.65, 156.77, 143.92, 117.75, 102.05,70.61. |
51% | With Iodine monochloride; acetic acid In dichloromethane for 5h; Inert atmosphere; regioselective reaction; | 1 Synthesis method of Formula 2 from dihydroxybenzaldehyde (I) Dihydroxy-benzaldehyde (2,4-dihydroxybenzaldehyde) (1.50g, 10.9 mmol)Acetic acid (7.5ml) under a nitrogen gas stream after a semi-dissolved iodine (iodine monochloride in CH2Cl2) (17.32ml, 17.31mmol) was gradually put to give stir for 5 hours.After completion of the reaction sodium thiosulfate: H2O = 1: 1.5 and shake slowly to put the (30ml) to give a brown solid of the desired compound (Formula 2). |
With Iodine monochloride; acetic acid at 20℃; for 12h; | 1 Example 1 : Synthesis of the intermediate 2,4-dihydroxy-5-iodobenzaldehyde (1) Example 1 : Synthesis of the intermediate 2,4-dihydroxy-5-iodobenzaldehyde (1): 2,4-Dihydroxy-5-iodobenzaldehyde (6g, 43 mmol.) was dissolved in 50 mL of acetic acid. A solution of iodine monochloride (8,46g, 52 mmol.) in 20 mL of acetic acid was added dropwise. The resulting mixture was stirred for 12 h at room temperature before it was poured into a saturated sodium thiosulfate solution (100 mL). The crude solution was extracted four times with ethyl acetate and the solvents were evaporated in vacuo. The crude residue was purified by silica gel chromatography eluting with CH2CI2/Pet. Ether 1 :1 to CH2CI2 100% leading to compound 1 as white/beige powder (4.6 g, 40%). H NMR (300MHz, d6-acetone) δ (ppm): 1 1 .07 (br s, 1 H, OH), 10.73 (br s, 1 H, OH), 9.76 (s, 1 H, OH), 8.05 (s, 1 H, CH Ar), 6.49 (s, 1 H, CH Ar). 3C NMR (75MHz, d6-acetone) δ (ppm): 195.1 , 164.9, 164.5, 145.7, 1 18.2, 103.1 , 73 |