8-Aminonaphthalene-1,3,5-trisulfonic acid

HCID 87355CAS 17894-99-4

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Basic information

Standard SMILES: Nc1ccc(S(=O)(=O)O)c2cc(S(=O)(=O)O)cc(S(=O)(=O)O)c12
InChIKey: RQVVDWMOCSOAJS-UHFFFAOYSA-N
Molecular formula: C10H9NO9S3
Average molar mass: 383.4 g/mol
Monoisotopic mass: 382.94394387

Names & identifiers

Preferred name: 8-Aminonaphthalene-1,3,5-trisulfonic acid
IUPAC: 8-aminonaphthalene-1,3,5-trisulfonic acid
English name: 1-Naphthylamine-4,6,8-trisulfonic acid
Molecular formula: C10H9NO9S3
Molecular weight: 383.37

Names & synonyms

8-aminonaphthalene-1,3,5-trisulfonic acid17894-99-48-amino-1,3,5-naphthalenetrisulfonic acid8-Aminonaphthalene-1,3,5-trisulphonic acid1,3,5-Naphthalenetrisulfonic acid, 8-amino-EINECS 241-837-3SCHEMBL229199SCHEMBL8508622SCHEMBL30901433DTXSID201706181-Naphthylamin-4,6,8-trisulfosaureMFCD00035848

Show more names

1-NAPHTHYLAMINE-4,6,8-TRISULFONIC ACID8-aminonaphthalene-1,3,5-trisulfonicaci8-azanylnaphthalene-1,3,5-trisulfonic acid8-AMINO-NAPHTHALENE-1,3,5-TRISULFONIC ACID

AKOS015960656H7785R978N8-aminonaphthalene-1,3,5-trisulfonicacidAC-11886SY254105CS-0145918NS00025895

Database identifiers

CAS: 17894-99-4
PubChem CID: 87355
DTXSID: DTXSID20170618
UNII: H7785R978N
EC Number: 241-837-3
Nikkaji: J173.263C

Properties

Computed structural properties

XLogP: -1.3
Topological polar surface area: 214 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 10
Rotatable bonds: 3
Heavy atoms: 23
Formal charge: 0
Complexity: 756

Physicochemical properties

Density: 1.974 · 1.974±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
pka: -1.75 · -1.75±0.40(Predicted)
InChI: InChI=1S/C10H9NO9S3/c11-7-1-2-8(22(15,16)17)6-3-5(21(12,13)14)4-9(10(6)7)23(18,19)20/h1-4H,11H2,(H,12,13,14)(H,15,16,17)(H,18,19,20)
InChIKey: RQVVDWMOCSOAJS-UHFFFAOYSA-N
SMILES: C1(S(O)(=O)=O)=C2C(C(S(O)(=O)=O)=CC=C2N)=CC(S(O)(=O)=O)=C1

Chemistry & industry

Applications · 1 item

UsesAlkali fusion of B acid yields K acid. A special outlet for purified B acid is in the synthesis of the drug suramin sodium (Bayer 205) . 1-Aminonaphthalene-4,6,8-trisulfonic acid is acylated with 2-nitrotoluyl chloride, and this product is reduced and acylated with mnitrobenzoyl chloride. This intermediate is reduced and finally phosgenated to give suramin sodium, which has been used to treat trypanosomiasis and onchocerciasis.