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Chemical Structure| 26093-31-2 Chemical Structure| 26093-31-2
Chemical Structure| 26093-31-2

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CAS No.: 26093-31-2

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7-Amino-4-methylcoumarin is a natural product isolated and purified from an endophytic Xylaria fungal species and exhibited strong antibacterial and antifungal activities in vitro against Aspergillus, Candida, Escherichia, Staphylococcus, Salmonella and Vibrio species, among others. It is also a reagent employed in the preparation of fluorogenic AMC-based substrates for the detection of proteolytic enzyme activity. AMC has been utilized as a fluorescent probe to analyze glycoproteins' monosaccharides and N-linked oligosaccharides via chromatography and has been used as a laser dye.

Synonyms: Coumarin 120; AMC; 4-methyl-7-aminocoumarin, 7-Amino-4-methylcoumarin, AMC, Coumarin 120

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Product Details of 7-Amino-4-methylcoumarin

CAS No. :26093-31-2
Formula : C10H9NO2
M.W : 175.18
SMILES Code : O=C1OC2=C(C=CC(N)=C2)C(C)=C1
Synonyms :
Coumarin 120; AMC; 4-methyl-7-aminocoumarin, 7-Amino-4-methylcoumarin, AMC, Coumarin 120
MDL No. :MFCD00006868
InChI Key :GLNDAGDHSLMOKX-UHFFFAOYSA-N
Pubchem ID :92249

Safety of 7-Amino-4-methylcoumarin

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

Application In Synthesis of 7-Amino-4-methylcoumarin

* 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 [ 26093-31-2 ]

[ 26093-31-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 26093-31-2 ]
  • [ 6404-26-8 ]
  • [ 233691-67-3 ]
YieldReaction ConditionsOperation in experiment
65% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 60℃; for 24h; Dipeptide 47 was synthesized by following the above general procedure for HATU peptide coupling (0 - 60C) for 12 hours and purified by silica gel column (0226) chromatography (EtOAc: Hexane - 3: 1) as a white solid (yield: 65%). lH NMR (400 MHz, CDC13) delta ppm: 9.34 (bs, 1 H), 7.69 (s, 1 H), 7.55 - 7.36 (m, 2 H), 6.79 (bs, 1 H), 5.55 (d, J = 7.2 Hz, 1 H), 4.41 - 4.16 (m, 1 H), 3.35 - 3.26 (m, 2 H), 2.39 (s, 3 H), 2.07 (s, 3 H), 2.00 - 1.87 (m, 1 H), 1.74 (dd, J = 4.9, 13.5 Hz, 1 H), 1.65 - 1.54 (m, 3 H), 1.53 - 1.47 (m, 1 H), 1.45 (s, 9 H), 1.30 - 1.20 (m, 1 H), 1.20 - 1.11 (m, 1 H). MS (ESI): found: [M + Na]+, 468.4.
With triethylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 8w in DMF at room temperature was added 7-amino-4-methyl- 2H-chromen-2-one, HATU and triethylamine. The reaction was stirred at room temperature for 2 h. A saturated solution of sodium bicarbonate was added. The product was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by prep-HPLC to afford 9w.
With HATU; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 8w in DMF at room temperature was added 7-amino-4-methyl-2H-chromen-2-one, HATU and triethy247lamine. The reaction was stirred at room temperature for 2 h. A saturated solution of sodium bicarbonate was added. The product was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by prep-HPLC to afford 9w
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 2h; To a solution of 8w in DMF at room temperature was added 7-amino-4-methyl-2H-chromen-2-one, HATU and triethylamine. The reaction was stirred at room temperature for 2 h. A saturated solution of sodium bicarbonate was added. The product was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by prep-HPLC to afford 9w.

  • 2
  • [ 117-21-5 ]
  • [ 26093-31-2 ]
  • 3-chloro-2-((4-methyl-2-oxo-2H-chromene-7-yl)carbamoyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% In dichloromethane; at 30℃; for 3h; 3-Chlorophthalic anhydride (182.5 mg) was dispersed in 1.2 ml of anhydrous dichloromethane and 1 ml of anhydrous tetrahydrofuran. At 30C, (A-5)-NH2( 175mg) and stirred for 3h. Filter the resulting sediment,It was washed with petroleum ether and ethyl acetate to obtain 292 mg of white solid.The yield was 82%.
 

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