Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 89-57-6 | MDL No. : | MFCD00007877 |
Formula : | C7H7NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KBOPZPXVLCULAV-UHFFFAOYSA-N |
M.W : | 153.14 | Pubchem ID : | 4075 |
Synonyms : |
Mesalamine;5-ASA;MAX-002;AJG-501;Z-206;Asacol;Mesalazine
|
Chemical Name : | 5-Amino-2-hydroxybenzoic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
5-Aminosalicylic Acid (CAS: 89-57-6) can be used in the preparation of Sulfasalazine (Azulfidine) (CAS: 599-79-1). Sulfasalazine is indicated for managing inflammatory diseases such as ulcerative colitis and rheumatoid arthritis (RA).
* 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 |
---|---|---|
77% | With polyphopshoric acid; at 180 - 200℃; for 4h; | A mixture of 2-aminophenol (0.436g, 4 mmol) and 5-aminosalicylic acid (0.612g, 4 mmol) was stirred in 15 mL PPA at 200 oC for 4 h. Then the reaction mixture was cooled down, and poured into 400 mL cold water to give a yellow precipitate. After filtered, the yellow precipitate was washed by 10% Na2CO3. The obtained crude product was separated by silica gel column chromatography (silica gel, CH2Cl2 as eluent) to get compound 2 (yellow solid, yield 0.702 g, 77%). TLC (CH2Cl2): Rf ? 0.1; m.p.: 188.2~190.0 oC(Lit. 190~190.5 oC [S1]). FT-IR spectrum(KBr pellet, cm-1):3410, 3325, 3051, 2361, 1635, 1597, 1496, 1438,1311, 1275, 1252, 1194, 995, 912, 830, 793, 756, 724, 696, 640; 1H NMR (DMSO-d6, 600 MHz) (ppm): 11.90(s, 1H), 7.97 (d, 1H, J = 7.8 Hz), 7.88 (d, 1H, J = 7.8 Hz), 7.49 (t, 1H, J = 7.8Hz), 7.39 (t, 1H, J = 7.8 Hz), 7.01 (d, 1H, J = 3.0 Hz), 6.95 (d, 1H, J = 8.4Hz), 6.80 (dd, 1H, J1 = 8.4 Hz , J2 = 2.4 Hz); 13CNMR (150 MHz, CDCl3) delta 169.78, 154.96, 151.26, 144.87, 137.30,129.79, 128.32, 125.34, 125.25, 123.38, 120.98, 115.45. |
53% | With polyphosphoric acid; at 170℃; for 5h; | In a general way, the precursors were obtained byreaction of an equimolar amount of 5-aminosalicylicacid (3) (4.0 g, 26.12 mmol) and 2-aminophenol (4)(2.8 g, 26.12 mmol) or 2-aminothiophenol (5) (2.76 mL,26.12 mmol) in polyphosphoric acid (PPA) (60 mL) at170 C for 5 h. The reaction was followed by TLC usingdichloromethane as the eluent. The reaction mixture waspoured onto crushed ice and neutralized with NaHCO3(20%). The precipitate was filtered and dried at 60 oC.The obtained compounds were purified by columnchromatography eluted with dichloromethane. |
49% | With polyphosphoric acid; at 180℃; for 3h; | Compound 2 (2-aminothiophenol, 2 g, 16 mmol), compound 3 (4-amino salicylic acid, 2.45 g, 16 mmol) and polyphosphoric acid (35 mL) were added into a 100 mL round-bottom flask. The mixture was heated to 180 oC and stirred for 3 h, which was turned from colorless to atrovirens. The mixture was poured into a beaker with 30 g ice immediately, and pH was adjustedby NaOH. Compound 4 (1.9 g, 7.84 mmol) was obtained by filtration in 49% yield as green solid. |
at 160℃; for 8h; | General procedure: HBZ and HBT were synthesized according to the procedure reported by Hein et al. [30]. HBZ was prepared by heating equimolar ratio of 1,2-phenylenediamine (1.08g, 0.01mol) and 5-amino-2-hydroxybenzoic acid (1.37g, 0.01mol) at 160C for 8h in 3.5mL polyphosphoric acid. After the completion of the reaction (as indicated by the TLC analysis of small aliquot) the reaction mixture was quenched in ice and neutralized using 10% Na2CO3 solution. Excess base was removed by washing with ice-cold water. The precipitate was dried overnight and recrystallized in methanol to obtain 4-amino-2-(1H-benzimidazol-2-yl)phenol (HBZ). Similarly, 4-amino-2-(benzothiazol-2-yl)phenol (HBT) was synthesized by using 2-aminothiophenol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Synthesis Example 3 Preparation of 2-hydroxy-5-[2-(4-nitrophenyl)ethylamino]-benzoic acid According to the similar procedure to Synthesis Example 1, by using 5-aminosalicylic acid (500 mg, 3.26 mmole) and 4-nitrophenylethyl bromide (900 mg, 3.92 mmole), 890 mg (50% yield) of 2-hydroxy-5-[2-(4-nitrophenyl)ethylamino]-benzoic acid was obtained as a pale yellow solid. Melting point 234-236 C. Elemental analysis of C15H14N2O5 |