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[ CAS No. 88770-22-3 ] {[proInfo.proName]}

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Chemical Structure| 88770-22-3
Chemical Structure| 88770-22-3
Structure of 88770-22-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 88770-22-3 ]

CAS No. :88770-22-3 MDL No. :MFCD01934527
Formula : C6H5NO4S Boiling Point : -
Linear Structure Formula :- InChI Key :NXVKWUOGNGQZTR-UHFFFAOYSA-N
M.W : 187.17 Pubchem ID :2740231
Synonyms :

Safety of [ 88770-22-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 88770-22-3 ]

* 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 [ 88770-22-3 ]

[ 88770-22-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 22913-26-4 ]
  • [ 88770-22-3 ]
YieldReaction ConditionsOperation in experiment
42% With nitric acid; acetic anhydride; In acetic acid; at 0 - 40℃; for 1h; To a solution of 3-thiophene carboxylic acid methyl ester (1.8g, 12.68mmol) in acetic acid (7.5ml) was added a mixture of nitric acid (0.67ml), acetic acid (7.5ml) and acetic anhydride (4.3ml) at 0-100C. The reaction mixture was stirred at 400C for lhr and then poured into crushed ice. The solid was filtered, washed with cold water and dried. The compound was recrystallised using ether/hexane to give 5-nitro-<strong>[22913-26-4]thiophene-3-carboxylic acid methyl ester</strong> (l.Og, 42%).
2.2 g With nitric acid; acetic anhydride; at -14 - 20℃; A mixture of acetic anhydride (15.7 mL, 166 mmol) and fuming nitric acid (1.8 mL, 44 mmol) was cooled to -14 C and a cold solution of <strong>[22913-26-4]methyl 3-thiophenecarboxylate</strong> (4.8 g, 34 mmol) in acetic anhydride (15.7 mL, 166 mmol) was slowly added to the reaction mixture keeping the temperature at -12 C. The reaction mixture was stirred for 4 h and was allowed to stand overnight at room temperature. The mixture was poured into ice-water (final volume: 150 mL), neutralized with a saturated solution of sodium bicarbonate (150 mL) and extracted with diethyl ether (10 × 30 mL). The combined ethereal phases were washed with cold water (15 mL) and dried over sodium sulfate. The reaction was checked by silica gel TLC (hexane/ethyl acetate 2:1). The nitrated product was visualized by UV light and also by p-dimethylaminobenzaldehyde solution. After some hours subsequent to the heating of the plate, the compound was visualized as a yellow spot; Rf (hexane/ethyl acetate 2:1) = 0.57. Column chromatography over silica gel (hexane/ethyl acetate 10:1) of the evaporation residue gave 10 as a pale yellow solid (yield: 2.2 g, 35%). Identification data: IR (KBr) nu (cm-1): 1343, 1534, 1717; 1H NMR (300 MHz, CDCl3) delta (ppm): 8.28 (1H, d, J = 1.8 Hz), 8.24 (1H, d, J = 1.8 Hz), 3.91 (3H, s); 13C NMR (200 MHz, CDCl3) delta (ppm): 51.6, 131.3, 134.8, 142.7, 153.2, 160.0; MS (EI) m/z 187 (M+), 156 (100), 141, 110, 82.
  • 3
  • [ 88770-22-3 ]
  • [ 192879-33-7 ]
YieldReaction ConditionsOperation in experiment
83% EXAMPLE 42To a solution of the nitro-ester (1.006 g, 5.375 mmol) in TFA (15 mL), Fe powder (1.5135 g, 27.10 mmol) was slowly added to the round bottom flask. The reaction was heated to 60C for 45 min at which time TLC (1 :1 , ethyl acetate to hexanes) showed consumption of starting material. The reaction was diluted with ethyl acetate and the Fe was filtered off. The filtrate was neutralized with aqueous Na2CO3 and allowed to stir for 1 hr. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated to give 0.701 g (83%) of a yellow solid. 1H NMR (400 MHz) CD3OD delta 7.29 (s, 1 H), 6.44 (s, 1 H), 3.79 (s, 3H). Mass calculated for formula C6H7NO2S 157.19; observed MH+ (LCMS) 158.1 (m/z).
24% With iron; acetic acid; In water; for 3h;Heating / reflux; To a solution of S-nitro-thiophene-S-carboxylic acid methyl ester (0.5g, 2.67mmol) in aqueous acetic acid (5ml) was added iron powder (1.04g, 18.6mmol) and the reaction mixture was heated to reflux for 3 hr. The reaction mixture was filtered and triethylamine was added to the filtrate. The compound was extracted with ethyl acetate and the organic layer was washed with water, concentrated and dried to yield crude compound. The compound was purified by silica gel column chromatography, using ethyl acetate/hexane as eluent, to yield 5-amino-thiophene-3-carboxylic acid methyl ester (0. Ig, 24%).
  • 4
  • [ 40357-96-8 ]
  • [ 74-88-4 ]
  • [ 88770-22-3 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h; 41 EXAMPLE 41To a solution of 5-nitrothiophene-3-carboxylic acid (5.00 g, 28.88 mmol) in dimethylformamide (40 mL) was added potassium carbonate (11.98 g, 86.71 mmol) and iodomethane (2.70 mL, 43.37 mmol). The reaction mixture was stirred at RT for 16 hr. After the starting material had been consumed, the reaction was diluted with 50% ethyl acetate/hexanes (350 mL) and extracted with H2O (350 mL). The organic layer was washed with brine (150 mL) and concentrated. Hexanes (50 mL) was added to the solid and concentrated again to yield 5.456 g (99%) of product. 1H NMR (400 MHz) CDCI3 δ 8.30 (s, 1 H), 8.25 (s, 1 H)1 3.93 (s, 3H). Mass calculated for formula C6H5NO4S 187.17; observed M4H+ (MS) 191.15 (m/z)
  • 5
  • [ 88770-22-3 ]
  • [ 6651-43-0 ]
  • [ 22913-25-3 ]
YieldReaction ConditionsOperation in experiment
In benzene at 160℃; Cooling with liquid nitrogen; General procedure for the thermal DA reactions: General procedure: All reactions were carried out in oven-dried glassware. An ampoule containing a solution of 1.0 mmol of the dienophile and the required amount of the diene in 0.5 mL of dry benzene was cooled in liquid nitrogen, sealed and heated in an oil bath. After completion of the reaction, it was cooled once more in liquid nitrogen and opened. The solvent was evaporated in vacuo to give the crude product, which was subjected to TLC and GC-MS spectrometry. For the case in which the reaction yield was moderate (i.e. DA reaction between 10 and 1), column chromatography and NMR analysis were also performed.
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