Basic information
- Standard SMILES
O=C1OC2(OC=C(c3ccccc3)C2=O)c2ccccc21- InChIKey
ZFKJVJIDPQDDFY-UHFFFAOYSA-N- Molecular formula
- C17H10O4
- Average molar mass
- 278.26 g/mol
- Monoisotopic mass
- 278.0579088
Overview
A nonfluorescent reagent for the detection of primary amines, peptides and proteins. The reaction products are highly fluorescent.
Names & identifiers
- Preferred name
- Fluorescamine
- IUPAC
- 4'-phenylspiro[2-benzofuran-3,2'-furan]-1,3'-dione
- English name
- Fluorescamine
- Molecular formula
- C17H10O4
- Molecular weight
- 278.26
Names & synonyms
Fluorescamine38183-12-9FluramSpiro[furan-2(3H),1'(3'H)-isobenzofuran]-3,3'-dione, 4-phenyl-Y6859V58YWDTXSID50872017Spiro(furan-2(3H),1'(3'H)-isobenzofuran)-3,3'-dione, 4-phenyl-RO-20-7234RefChem:388984DTXCID30819622253-814-54'-phenylspiro[2-benzofuran-3,2'-furan]-1,3'-dione
Show more names
FluaramFLURAM(R)FluorescaminFluorescamineA.R.Fluorescamine, pureFLURAMANALYTICAL GRADEFluorescamine Labeling
4-Phenylspiro[furan-2(3H),1-phthalan]-3,3'-dioneMFCD00005928EINECS 253-814-5FLUORESCAMINE [MI]4-phenyl-3H,3'H-spiro[furan-2,1'-isobenzofuran]-3,3'-dioneRo 20-7234CS-3522AS-14756
Database identifiers
- CAS
38183-12-9- PubChem CID
- 37927
- DTXSID
DTXSID50872017- UNII
- Y6859V58YW
- EC Number
- 253-814-5
- Nikkaji
- J22.287I
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 503
Experimental & physicochemical properties
Chemical ClassesDyes -> Indicator Dyes
Physical DescriptionOff-white odorless powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 153 · 153-157 °C (lit.)
- Boiling point
- 381.08 °C · 381.08°C (rough estimate)
- Density
- 1.2661 · 1.2661 (rough estimate)
- refractive index
- 1.5447 · 1.5447 (estimate)
- Flash point
- -17 °C · -17 °C
- storage temp.
- room temp
- solubility
- acetonitrile: soluble
- form
- powder
- color
- off-white to yellow
- Water Solubility
- Soluble in acetone, ethanol, chloroform, dimethylsulfoxide and acetonitrile. Slightly soluble in water.
- Merck
- 14 · 14,4158
- BRN
- 921143 · 921143
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C17H10O4/c18-15-13(11-6-2-1-3-7-11)10-20-17(15)14-9-5-4-8-12(14)16(19)21-17/h1-10H
- InChIKey
- ZFKJVJIDPQDDFY-UHFFFAOYSA-N
- SMILES
- O=C1OC2(OC=C(C2=O)c3ccccc3)c4ccccc14
- CAS DataBase Reference
- 38183 · 38183-12-9(CAS DataBase Reference)
- FDA UNII
- 6859 V58YW · Y6859V58YW
- NIST Chemistry Reference
- -2 · Spiro[furan-2(3h),1'(3'h)-isobenzofuran]-3,3'-dione, 4-phenyl-(38183-12-9)
- UNSPSC Code
- 12352204 · 12352204
- NACRES
- 32 · NA.32
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 280 · P280-P302+P352-P305+P351+P338
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/38-66-67-36-36/37/38
- Safety Statements
- 22 · 22-24/25-36/37-33-29-26-16-9-37/39
- RIDADR
- 1090 · UN 1090 3/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- HS Code
- 29322090 · 29322090
- Storage Class
- 13 · 13 - Non Combustible Solids
Safety & regulation
GHS classification
GHS Classification
Warning
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P261, P264+P265, P271, P280, P304+P340, P305+P351+P338, P319, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Regulatory InformationSpiro[furan-2(3H),1'(3'H)-isobenzofuran]-3,3'-dione, 4-phenyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryMay cause irritation; [Alfa Aesar MSDS]
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- ridadr
- UN 1090 3/PG 2
- hs_code
- 29322090
- risk_code
- 11-36/38-66-67-36-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- F,Xi
- safety_code
- 22-24/25-36/37-33-29-26-16-9-37/39
- Storage Class
- 13 - Non Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Uses & manufacturing
UsesUsed as an analytical reagent; [Merck Index]
Applications
UsesFor fluorescent detection of amino acids, peptides and proteins.Fluorescamine plays an important role as a reagent for the detection of amines, peptides and proteins. It is also used as a substrate for measuring protease activity. It is utilized in the detection and quantitation of residual aminopenicillins and sulfonamides in honey by HPLC. It finds application in the determination of lisinopril in human plasma and urine.
UsesFluorescamine is a non-fluorescent reagent that reacts readily under mild conditions with primary amines in amino acids and peptides to form stable, highly fluorescent compounds. Reaction takes place under mild conditions. Low background due to hydrolysis.
UsesAnalytical reagent.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
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Related reactions
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