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Chemical Structure| 3348-03-6 Chemical Structure| 3348-03-6
Chemical Structure| 3348-03-6

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6-CFDA is fluorescent polyanionic probe, and its derivatives such as 2′,7′-bis(2-carboxyethyl)-5(6)-carboxyfluorescein are used to measure changes in intracellular pH (pHi) and processes such as dendrimer aggregation and absorption.

Synonyms: 6-Carboxyfluorescein diacetate

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of 6-CFDA

CAS No. :3348-03-6
Formula : C25H16O9
M.W : 460.39
SMILES Code : O=C(C1=CC(C2(C3=C(OC4=C2C=CC(OC(C)=O)=C4)C=C(OC(C)=O)C=C3)O5)=C(C=C1)C5=O)O
Synonyms :
6-Carboxyfluorescein diacetate
English Name :6-Carboxyfluorescein diacetate
MDL No. :MFCD00036871
InChI Key :QMOGCCYGOPYYNT-UHFFFAOYSA-N
Pubchem ID :151095

Safety of 6-CFDA

Application In Synthesis of 6-CFDA

* 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 [ 3348-03-6 ]

[ 3348-03-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1004524-64-4 ]
  • [ 3348-03-6 ]
  • [ 79955-27-4 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With triethanolamine In N,N-dimethyl-formamide at 31℃; 5 Example 5:; N-[4-(4-Aminopyrimidin-2-yloxymethyl)-benzyl]-diacetylfluorescein-6-carboxamide (6) and N-[4-(4-Aminopyrimidin-2-yloxymethyl)-benzyl]-diacetylfluorescein-5-carboxamide (7); [Show Image] 2-(4-(Aminomethyl)benzyloxy)pyrimidin-4-amine (2) (4.1 mg, 0.018 mmol) and 5(6)-carboxyfluorescein diacetate succinimidyl ester (10 mg, 0.018 mmol) are dissolved in 800 µL DMF with 2.7 µL TEA and heated overnight at 31 °C. The solvent is evaporated under vacuum and the compounds isolated by reversed phase MPLC on a C18 column using a linear gradient of water:acetonitrile (from 95:5 to 20:80 in 20 min, 0.08% TFA). MS (ESI) m/z 673 [M+H]+.
  • 2
  • [ 108-24-7 ]
  • [ 108-46-3 ]
  • [ 552-30-7 ]
  • [ 3348-03-6 ]
  • [ 79955-27-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: recorcinol; trimellitic Anhydride With zinc dibromide at 180℃; for 1.33333h; Stage #2: acetic anhydride for 2h; Reflux; Overall yield = 4.3 g;
1: 161 mg 2: 152 mg Stage #1: recorcinol; trimellitic Anhydride With methanesulfonic acid at 80℃; for 24h; Stage #2: acetic anhydride With pyridine at 80℃; for 0.0833333h; 5 4. SYNTHESIS OF 5-CARBOXYFLUORESCEIN DIPIVALATE (16) Trimellitic anhydride (436 mg, 1 equiv) and resorcinol (500 mg, 2 equiv) were stirred in methanes ulfonic acid (12 mL) at 80 °C for 24 h. The resulted mixture was poured into ice water (thO). The precipitate was collected and washed with water to yield the crude 5 (6) -carboxy fluorescein (15) (820 mg).5(6)-carboxyfluorescein (15): yellow powder; 'H NMR (500 MHz, methanol -d 8.59 (d, J = 1.5 Hz, 1H), 8.37 (dd, J = 8.0, 1.5 Hz, 1H), 8.31 (dd, J = 8.0, 1.5 Hz, 1H), 8.09 (d, J = 8.0 Hz, lH), 7.74 (s, 1H), 7.30 (d, J = 8.0 Hz, 1H), 6.70-6.72 (d, J = 9.7 Hz, 4H), 6.60- 6.42 (br s, 4H), 6.53-6.57 (m, 4H). 5. SYNTHESIS OF 5-CARBOXYFLUORESCEIN DIACETATE (17)5(6)-carboxyfluorescein (15) (320 mg) and pyridine (260 pL) were stirred in acetic anhydride (5 mL) at 80 °C for 5 min. The solvents were removed in vacuo and the residue was purified by preparative HPLC using a Luna 5 pm C18 column (isocratic, 50% MeCN in 0.1% formic acid) to yield 5-carboxyfluorescein diacetate (17) (161 mg) and 6- carboxy fluorescein diacetate (152 mg).[0487] 5-carboxyfluorescein diacetate (17): yellow powder; 'H NMR (400 MHz, methanol-iL): d 8.61 (s, lH), 8.37 (d, J = 8.0 Hz, lH), 7.32 (d, J = 8.0 Hz, lH), 7.18 (br s, 2H), 6.88 (br s, 4H), 2.28 (s, 6H).
 

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