5-Amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoesure

5-Aminofluorescein

HCID 76845CAS 3326-34-9

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Grundinformationen

Standard-SMILES: Nc1ccc2c(c1)C(=O)OC21c2ccc(O)cc2Oc2cc(O)ccc21
InChIKey: GZAJOEGTZDUSKS-UHFFFAOYSA-N
Summenformel: C20H13NO5
Durchschnittliche Molmasse: 347,3 g/mol
Monoisotopische Masse: 347,07937252

Überblick

5-aminofluorescein is a primary amino compound that is fluorescein carrying an amino substituent at C-5. Building block/intermediate for the synthesis of the fluorescent dye flourescein; also used to produce N-(fluorescein-5-yl)maleamic acid. It is functionally related to a fluorescein (lactone form).

Namen und Bezeichner

Bevorzugter Name: 5-Aminofluorescein
IUPAC: 6-amino-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
Lokaler Name: 5-Amino-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoesure
Englischer Name: 5-Aminofluorescein
Summenformel: C20H13NO5
Molmasse: 347.32

Namen und Synonyme

5-Aminofluorescein3326-34-95-fluoresceinamineSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 5-amino-3',6'-dihydroxy-YY8M286SWUDTXSID0062979CHEBI:91078Spiro(isobenzofuran-1(3H),9'-(9H)xanthen)-3-one, 5-amino-3',6'-dihydroxy-RefChem:532426DTXCID1038660222-043-6Fluoresceinamine

Weitere Namen anzeigen

5-AFAMINOFLUORESCEIN4-AMINOFLUORESCEIN5-AMF(isoMer I)1-FLUORESCEINAMINE

Fluoresceinamine Isomer IFluoresceinamine, isomer IFluoresceinamine, isomer 15-AFMMFCD00005052fluorescein-5-amine6-amino-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one5-amino-3',6'-dihydroxy-3H-spiro[isobenzofuran-1,9'-xanthen]-3-one

Datenbank-Bezeichner

CAS: 3326-34-9
PubChem CID: 76845
DTXSID: DTXSID0062979
ChEMBL: CHEMBL5284644
ChEBI: CHEBI:91078
UNII: YY8M286SWU
EC Number: 222-043-6
Nikkaji: J205.409D

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 102 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 6
Frei drehbare Bindungen: 0
Schwere Atome: 26
Formalladung: 0
Komplexität: 557

Experimentelle und physikochemische Eigenschaften

Endocrine DisruptorsPotential endocrine disrupting compound

Physikochemische Eigenschaften

Schmelzpunkt: 223 °C · 223 °C (dec.)(lit.)
Siedepunkt: 481.89 °C · 481.89°C (rough estimate)
Dichte: 1.3724 · 1.3724 (rough estimate)
Brechungsindex: 1.518 · 1.5180 (estimate)
storage temp.: room temp
Löslichkeit: 5 mg/ml; · DMF: 5 mg/ml; DMSO: 5 mg/ml
pka: 9.34 · 9.34±0.20(Predicted)
Aggregatzustand: powder
Farbe: red-brown
Wasserlöslichkeit: Soluble in water (partly), methanol (10 mg/ml), and acetone.
BRN: 48395 · 48395
Stabilität: Light and Moisture Sensitive
Major Application: diagnostic assay manufacturinghematologyhistology
InChI: 1S/C20H13NO5/c21-10-1-4-14-13(7-10)19(24)26-20(14)15-5-2-11(22)8-17(15)25-18-9-12(23)3-6-16(18)20/h1-9,22-23H,21H2
InChIKey: GZAJOEGTZDUSKS-UHFFFAOYSA-N
SMILES: Nc1ccc2c(c1)C(=O)OC23c4ccc(O)cc4Oc5cc(O)ccc35
CAS Datenbank: 3326 · 3326-34-9(CAS DataBase Reference)
EPA chemische Informationen: -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 5-amino-3',6'-dihydroxy- (3326-34-9)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (98.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 85 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (98.8%)

Sicherheitsdaten

F: 10
wgk: 3
tsca: TSCA listed
hs_code: 32049090
risk_code: 22-36/37/38
hazard_code: Xn
safety_code: 26
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Verwendung und Herstellung

General Manufacturing InformationSpiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 5-amino-3',6'-dihydroxy-: ACTIVE

Anwendungen

VerwendenGlycosaminoglycuronans react with 5-aminofluorescein to yield fluorescent derivatives. 5-aminofluorescein is also used to prepare FITC Isomer I (F-011, F-020).

Darstellung · 1 Eintrag

synthetischeThe preparation of 5-aminofluorescein is carried out either by first saponification of 5-nitrofluorescein acetates with alcohol alkali, followed by reduction of the obtained 5-nitrofluorescein in a solution of alcohol alkali with hydrazine hydrate on a nickel catalyst to obtain 5-aminofluorescein , Or by boiling in an aqueous solution of sodium sulfide. The restoration of the nitro group and the saponification of acetates in the second case occurs in one stage.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Dinatriumsulfid 4-Nitrophthalsure 1,3-Dihydroxybenzol Natriumhydrogensulfid 4-AMINO-N-METHYLPHTHALIMIDE 6-Amino-3',6'-dihydroxyspiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-on

Nachgelagerte Produkte

3',6'-Dihydroxy-5(oder 6)-isothiocyanatospiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-on azidofluorescein

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

VladaChem GmbH+49-7246-3082843 +86-18411632868 · [email protected]

Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 5-aminofluorescein is a primary amino compound that is fluorescein carrying an amino substituent at C-5. Building block/intermediate for the synthesis of the fluorescent dye flourescein; also used to produce N-(fluorescein-5-yl)maleamic acid. It derives from a fluorescein (lactone form).