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Chemical Structure| 3326-34-9 Chemical Structure| 3326-34-9
Chemical Structure| 3326-34-9

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CAS No.: 3326-34-9

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Synonyms: 5-AF

4.5 *For Research Use Only !

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Product Details of [ 3326-34-9 ]

CAS No. :3326-34-9
Formula : C20H13NO5
M.W : 347.32
SMILES Code : O=C1OC2(C3=C(OC4=C2C=CC(O)=C4)C=C(O)C=C3)C5=C1C=C(N)C=C5
Synonyms :
5-AF
MDL No. :MFCD00005052
InChI Key :GZAJOEGTZDUSKS-UHFFFAOYSA-N
Pubchem ID :76845

Safety of [ 3326-34-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis [ 3326-34-9 ]

* 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 [ 3326-34-9 ]

[ 3326-34-9 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 652-12-0 ]
  • [ 3326-34-9 ]
  • [ 209540-90-9 ]
YieldReaction ConditionsOperation in experiment
With pyridine; hydrogenchloride; In sodium hydrogencarbonate; N,N-dimethyl-formamide; Example 27 Preparation of 5-(2'-carboxy-3',4',5',6'-tetrafluorobenzoylamino)fluorescein (27): 5-Aminofluorescein (1 g, 2.9 mmol) is dissolved in 10 mL of anhydrous N,N-dimethylformamide (DMF) that contains anhydrous pyridine (0.47 mL, 5.8 mmol). To the solution is added tetrafluorophthalic anhydride (660 mg, 3.0 mmol) in 5 portions over 5 h. The resulting mixture is stirred overnight. This reaction mixture is concentrated in vacuo, and the residue is poured into water (200 mL). The precipitate thus formed is collected by filtration and washed by water. The crude solid is taken up in 1M aqueous NaHCO3 solution (100 mL), and the resulting mixture is filtered. The filtrate is washed with ether (3*100 mL). The aqueous layer is carefully neutralized to pH 7.5 with 10% HCl and the resulting precipitate is collected by filtration and air-dried to give Compound 27 (939 mg, yield: 59%).
  • 2
  • [ 5926-51-2 ]
  • [ 3326-34-9 ]
  • [ 1266664-71-4 ]
YieldReaction ConditionsOperation in experiment
73% With acetic acid; at 20 - 150℃; for 15h;Sealed tube; Reference Example 30 Preparation of N-Fluorescein Bromomaleimide Di<strong>[5926-51-2]bromomaleic anhydride</strong> (346 mg, 1.95 mmol) was added in one portion to a solution of fluoresceinamine isomer 1 (678 mg, 1.95 mmol) in acetic acid (65 mL) and the reaction mixture was stirred for 12 hours at room temperature in a sealed tube. The reaction mixture was then heated to 150° C. for 3 h. Upon cooling to room temperature the solid was filtered and dried (toluene azeotrope) to afford the desired compound as an orange solid (722 mg, 1.43 mmol, 73percent yield). 1H NMR (600 MHz, DMSO) delta 7.99 (d, 1H, J=1.7, 1H, H-11), 7.77 (dd, 1H, J=1.9 and 8.2, 1H, H-7), 7.73 (s, 1H, H-3), 7.43 (d, J=8.2, 1H, H-8), 6.69 (m, 6H, 2*H-16, 2*H-17, 2*H-18); 13C NMR (175 MHz, DMSO) delta 167.93 (C=O), 167.63 (C=O), 164.48 (C=O), 159.62 (2*C18), 151.79 (2*C20), 151.52 (C6), 133.68 (C7), 133.02 (Ar), 132.90 (C3), 131.23 (C), 129.15 (2*Ar-H), 126.73 (C), 124.82 (C11), 122.29 (C8), 112.77 (2*Ar-H), 109.08 (2*Ar), 102.30 (2*Ar-H), 83.36 (C14); IR (solid, cm-1) 3064 (w), 1726 (s); MS (ES+) m/z, (relative intensity): 508 ([81M], 95), 506([79M], 100); Exact mass calcd for [C24H13O7N79Br] requires 505.9875 Found 505.9833 (ES+).
  • 3
  • [ 1122-12-9 ]
  • [ 3326-34-9 ]
  • N-fluorescein-3,4-dibromomaleimide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With acetic acid; at 20℃; for 12h;Reflux; Reference Example 31 Preparation of N-Fluorescein Dibromomaleimide Dibromomaleic anhydride (77.0 mg, 0.30 mmol) was added in one portion to a solution of fluoresceinamine isomer 1 (105 mg, 0.30 mmol) in acetic acid (10 mL) and the reaction mixture was stirred for 6 h at room temperature. The solid was then filtered off, washed with ethyl acetate, and redissolved in acetic acid (10 mL). The reaction mixture was then heated to reflux for 3 h. Upon cooling to room temperature toluene (10 ml) was added and the solvent removed in vacuo, affording the desired compound as an orange solid (148 mg, 0.25 mmol, 84percent yield). delta 1H NMR (400 MHz, CD3OD) delta 8.07 (d, 1H, J=1.5, H-11), 7.81 (dd, 1H, J=1.5 and 8.0, H-7), 7.34 (d, 1H, J=8.5, H-8), 6.71-6.58 (m, 6H, 6*Ar-H); 13C NMR (100 MHz, CD3OD) delta 170.23 (C=O), 164.34 (2*C=O), 161.63 (2*C), 154.18 (2*C), 152.93 (C), 134.59 (C), 134.19 (Ar-H), 131.01 (C), 130.35 (Ar-H), 129.25 (2*C), 126.25 (2*Ar-H), 123.63 (Ar-H), 113.84 (2*Ar-H), 111.02 (2*C), 103.55 (2*Ar-H); IR (solid, cm-1) 3064 (w), 1732 (s); MS (ES+) m/z, (relative intensity): 586 ([81+81M], 30), 584 ([79+81M], 100), 582 ([79+79M], 100); Exact mass calcd for [C24H10O7N79Br2] requires 581.8824 Found 581.8824 (ES+).
 

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