Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 106727-86-0 | MDL No. : | MFCD18206198 |
Formula : | C10H8Cl2O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 263.07 | Pubchem ID : | - |
Synonyms : |
|
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 |
---|---|---|
100% | With thionyl chloride for 18h; | |
97% | With thionyl chloride at 0 - 25℃; for 49h; Inert atmosphere; | 10 Synthesis Example 1 4, 5-dichlorophthalic acid (4.7 g, 20 mmol) and methanol (40 mL) were put in a 200 mL two-necked round bottom flask under an argon atmosphere and thionyl chloride (6.0 mL, 84 mmol) was added at 0 ° C for 1 hour I dropped it over. Thereafter, the temperature was raised to room temperature and stirred for 48 hours. The reaction mixture was poured into 300 mL of a saturated aqueous solution of sodium bicarbonate, and separated and extracted with dichloromethane (100 mL). The organic layer was concentrated with an evaporator to obtain 4,5-dichlorophthalic acid dimethyl ester as a white solid (5.10 g, yield 97%). |
94% | With thionyl chloride at 20℃; for 72h; |
91% | With thionyl chloride at 0 - 20℃; for 68h; Inert atmosphere; | |
91% | With sulfuric acid for 18.1667h; Reflux; | 3.1.13. General procedure for synthesis of phthalic acids methyl esters 5b-d General procedure: To a stirred slurry of appropriate phthalic acid (0.1 mol) in methanol (200 mL), concentratedsulphuric acid (20 mL) was added dropwise (caution: exothermic). The reaction mixture was stirredfor ten minutes in room temperature which led to the dissolution of phthalic acid. The obtainedsolution was refluxed for 18 h, then the excess of methanol was evaporated under reduced pressureand the remaining residue was poured into water. The pH was adjusted to ca. 8 by the addition ofsolid sodium hydroxide and the reaction product was extracted with ethyl acetate (3 × 100 mL) Theorganic phase was washed with brine (1 × 50 mL) and dried over anhydrous magnesium sulfate. Thedrying agent was filtered off and the resulting filtrate was evaporated under reduced pressure.Evaporation of the solvent gave the crude product which was used in next step without furtherpurification. |
91% | With thionyl chloride at 0℃; Reflux; | |
64% | With thionyl chloride at 0 - 20℃; for 15.5h; | |
With hydrogenchloride | ||
With thionyl chloride at 20℃; | 251 Dimethyl 4,5-Dichlorophthalate (A5):Thionyl chloride (15OmL, 2.05 mol) is added dropwise over 2h to a magnetically stirred solution of 4,5-dichlorophthalic acid (110.43g, 469.8 mmol) in MeOH (IL) at RT. After stirring overnight, the MeOH is removed in vacuo on a rotary evaporator. The residue is dissolved in EtOAc (75OmL) and extracted with water (1 x 50OmL) and saturated aqueous NaHCO3 (1 x 50OmL). The organic layer is separated, dried over MgSO4, filtered and concentrated in vacuo on a rotary evaporator to afford A5 (122.8g) as a pale yellow liquid. [A. Rosowsky, C. M. Vaidya,h. Bader, J. E. Wright, B. A. Teicher, J. Med. Chem. 40, 286-299 (1997); E. J. Hennessy, S. L. Buchwald, J. Org. Chem., 70, 7371-7375 (2005)]1H NMR (CDCl3, 300MHz): δ 3.92 (s, 3H), 7.82 (s, IH) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With methanol; sodium hydride In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4,5-Dichloro- 1 ,2-bis( hydr oxymethvDbenzene (251):A solution of dimethyl 4,5-dichlorophthalate A5 (98.86g, 375.78 mmol) in tetrahydrofuran (15OmL) is added dropwise over Ih to a mechanically stirred suspension of LAH (20.8g,201 <n="203"/>548.1 mmol) in tetrahydrofuran (1.5L). During the addition, the reaction is cooled in an ice- water bath. When the addition is completed, the reaction is stirred overnight at RT. The excess LAH is decomposed by cautious addition of water (2OmL), 10% aqueous NaOH (4OmL) and water (2OmL). The solids are removed by filtration through a celite pad and washed with tetrahydrofuran. The combined filtrate and wash is concentrated in vacuo on a rotary evaporator to afford crude 251 as white solid that is purified by crystallization from acetone (150mL)-heptane (15OmL). The crystals are collected by filtration, washed with heptane and dried to give 4,5-dichloro-l,2-bis(hydroxymethyl)benzene (37.2g). The combined filtrate and wash afforded a second crop of 251 (18.8g, 24.1%). [L. A. Levy, Synth. Commun., U, 639- 648 (1983); O. Farooq, Synthesis, 1035-1036 (1994)]1H NMR (DMSO-d6, 300MHz): delta 4.49 (d, 2H), 5.32 (t, IH), 7.57 (s, IH) EI-MS m/z 209,207Anal. Calcd. for C8H8Cl2O2: C, 46.41;H, 3.89. Found: C, 46.50;H, 3.83 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In methanol at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With sodium hydride In tetrahydrofuran; mineral oil for 18h; Reflux; | 3.1.2. General procedure for synthesis 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones (3a-j) General procedure: To a solution of diamine 4a-f (1 equiv.) and diester 5a-e (1 equiv.) in anhydrous THF (5mL/mmol), 60% sodium hydride in mineral oil (2 equiv.) was added and the resulting mixture wasrefluxed for 18 h. The reaction mixture was poured into water, acidified with concentrated HCl to pH2 and extracted with ethyl acetate. The organic phase was washed with brine and dried overanhydrous magnesium sulfate. The drying agent was filtered off and the resulting filtrate wasevaporated under reduced pressure. The crude product was purified either by crystallization or bycolumn chromatography. |