Basic information
- CAS
82-76-8- Standard SMILES
O=S(=O)(O)c1cccc2cccc(Nc3ccccc3)c12- InChIKey
FWEOQOXTVHGIFQ-UHFFFAOYSA-N- Molecular formula
- C16H13NO3S
- Average molar mass
- 299.3 g/mol
- Monoisotopic mass
- 299.06161445
Overview
8-anilinonaphthalene-1-sulfonic acid is a naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8. It has a role as a fluorescent probe. It is a naphthalenesulfonic acid and an aminonaphthalene.
Names & identifiers
- Preferred name
- 8-Anilino-1-naphthalenesulfonic acid
- IUPAC
- 8-anilinonaphthalene-1-sulfonic acid
- English name
- 8-Anilino-1-naphthalenesulfonic acid
- Molecular formula
- C16H13NO3S
- Molecular weight
- 299.34
Names & synonyms
8-Anilino-1-naphthalenesulfonic acid82-76-88-anilinonaphthalene-1-sulfonic acidPhenylperi acid1-Anilino-8-naphthalenesulfonate1-Anilino-8-naphthalenesulfonic acid1-(Phenylamino)-8-naphthalenesulfonic acid1-Naphthalenesulfonic acid, 8-(phenylamino)-1,8-ANSAnilinonaphthalenesulfonic acidNSC-1746630I4V6051
Show more names
PHENYL PERI ACIDANSA1-ANILINONAPHTHALENE-8-SULFONIC ACIDPHENYL ACIDANSA/1,8-ANSN-PHENYL PERI ACIDfluorescent probes
DTXSID7058882CHEBI:397088-ANSA cpdRefChem:429462DTXCID1048259201-438-78-(phenylamino)naphthalene-1-sulfonic acidANS
Database identifiers
- CAS
82-76-8- PubChem CID
- 1369
- DTXSID
DTXSID7058882
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 74.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 439
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
PolymersNitrogen Compounds -> Amines, Polyaromatic
Physical DescriptionGray powder; [Aldrich MSDS]
Physicochemical properties
- Melting point
- 215 · 215-217 °C (dec.)(lit.)
- Density
- 1.409 · 1.409±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 50 mg/mL · DMF: soluble50mg/mL
- pka
- 0.19 · 0.19±0.40(Predicted)
- form
- Powder
- color
- Dark green to brown to black
- Appearance
- Dark Grey to Black Solid
- Merck
- 13 · 13,664
- BRN
- 1843887 · 1843887
- Major Application
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (78.6%): 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 14 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 1-Naphthalenesulfonic acid, 8-(phenylamino)-
REACH registered substance: 8-anilinonaphthalene-1-sulphonic acid (EC: 201-438-7)
1-Naphthalenesulphonic acid, 8-(phenylamino)-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryAn irritant; Targets the liver and kidney; [Aldrich MSDS] See 8-Anilino-1-naphthalenesulfonic acid hemimagnesium.
Hazard Classes and CategoriesAcute Tox. 4 (78.6%)
Safety data
- wgk
- -
- tsca
- TSCA listed
- hs_code
- 29214980
- risk_code
- 36-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.
Uses & manufacturing
UsesUsed as a fluorescent probe for protein studies; Was used to make aniline dyes; [Merck Index]
General Manufacturing Information1-Naphthalenesulfonic acid, 8-(phenylamino)-: ACTIVE
Applications
Description1,8-ANS is a fluorescent dye that binds with high affinity to hydrophobic surfaces of proteins. 1,8-ANS has an excitation maximum of 350 nm. It has an emission maximum of 520 nm when free in solution but undergoes a blue shift with an increase in fluorescence intensity when bound to protein; for example, when bound to intestinal fatty acid binding protein (FABP2) it has emission maxima of 468-477 nm. 1,8-ANS binds to low polarity regions of protein surfaces making it well suited for determining the affinity of hydrophobic ligands to their corresponding binding proteins, such as the binding of free fatty acids to FABPs. 1,8-ANS binds to FABP2 with a Kd value of approximately 9.7 μM at 24.5°C.
UsesIntermediate of dyestuff
Uses8-Anilino-1-naphthalenesulfonic Acid is used as a fluorescent probe to identify hydrophobic sites. Dyes and metabolites.
Upstream & downstream products
Upstream raw materials
Related reactions
1 records
Compound notes
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