5-Aminofluorescein (HCID 76845)

Overview

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).

Names & identifiers

Preferred name: 5-Aminofluorescein
IUPAC: 6-amino-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one
English name: 5-Aminofluorescein
Molecular formula: C20H13NO5
Molecular weight: 347.32

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 102 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 6
Rotatable bonds: 0
Heavy atoms: 26
Formal charge: 0
Complexity: 557

Experimental & physicochemical properties

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 223 °C · 223 °C (dec.)(lit.)
Boiling point: 481.89 °C · 481.89°C (rough estimate)
Density: 1.3724 · 1.3724 (rough estimate)
refractive index: 1.518 · 1.5180 (estimate)
storage temp.: room temp
solubility: 5 mg/ml; · DMF: 5 mg/ml; DMSO: 5 mg/ml
pka: 9.34 · 9.34±0.20(Predicted)
form: powder
color: red-brown
Appearance: Solid Powder
Water Solubility: Soluble in water (partly), methanol (10 mg/ml), and acetone.
λmax: 496 nm · 496 nm
BRN: 48395 · 48395
Stability: 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 DataBase Reference: 3326 · 3326-34-9(CAS DataBase Reference)
FDA UNII: 8 M286SWU · YY8M286SWU
EPA Substance Registry System: -1 · Spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one, 5-amino-3',6'-dihydroxy- (3326-34-9)
UNSPSC Code: 12171500 · 12171500
NACRES: 47 · NA.47
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22-36/37/38
Safety Statements: 26 · 26
WGK Germany: 3 · 3
F: 10 · 10
TSCA: TSCA listed
HS Code: 32049090 · 32049090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.8%)

Safety data

F: 10
PPE: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk: 3
tsca: TSCA listed
hs_code: 32049090
risk_code: 22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H302-H315-H319-H335
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P270-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Uses & manufacturing

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

Applications · 4 items

Description5-AMF is a fluorescent probe for carboxylic acids and glutamine, and it also can be coupled to aldehydes and ketones.

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

Uses5-aminofluorescein is also used to prepare FITC Isomer I (CDX-F0011, CDX-F0020). It is a chemical used as molecular probe and important as fluorescent dye and for derivatives. Fluorescent labeling reagent for proteins. Used in the fluorescent antibody technique for rapid identification of pathogens.

General DescriptionFluoresceinamine, isomer I belongs to the class of derivatized fluoresceins.

Preparation methods · 1 item

PreparationThe 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.

Upstream & downstream products

Upstream raw materials

Downstream products

Fluorescein isothiocyanate azidofluorescein

Suppliers50 total

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]

Additional notes · 1 item

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).