Sudan Brown RR

Base Information

• Chemical Name: Sudan Brown RR
• CAS No.: 6416-57-5
• Molecular Formula: C₁₆H₁₄N₄
• Molecular Weight: 262.314
• Hs Code.: 2927000090
• European Community (EC) Number: 229-127-1
• UNII: 0AL30EZ5L1
• DSSTox Substance ID: DTXSID0064339
• Nikkaji Number: J33.574F
• Wikidata: Q27156048
• Mol file: 6416-57-5.mol

Synonyms:Fat Brown RR;Sudan Brown RR;6416-57-5;Solvent Brown 1;C.I. Solvent Brown 1;Typogen Brown N;Hexatype Brown N;Lithofor Brown A;Resinol RRN;Sudan Brown YR;Organol 2R;C.I. 11285;Organol Brown 2R;Resinol Brown RRN;Fat Brown 2G;Fat Brown 2R;Silotras Brown TRN;Grasan Brown DT new;4-(naphthalen-1-yldiazenyl)benzene-1,3-diamine;Hned sudan RR [Czech];C.I. Solvent Brown PR;Hned sudan RR;1,3-Benzenediamine, 4-(1-naphthalenylazo)-;4-(1-Naphthylazo)benzene-1,3-diamine;Hned rozpoustedlova 1 [Czech];Hned rozpoustedlova 1;EINECS 229-127-1;4-(1-Naphthylazo)-m-phenylenediamine;1-Naphthalenazo-2',4'-diaminobenzene;BRN 0658518;UNII-0AL30EZ5L1;0AL30EZ5L1;4-(1-Naphthalenylazo)-1,3-phenylenediamine;m-Phenylenediamine, 4-(1-naphthylazo)-;1,3-Benzenediamine, 4-(2-(1-naphthalenyl)diazenyl)-;1,3-Benzenediamine, 4-[2-(1-naphthalenyl)diazenyl]-;FAT BROWN;SCHEMBL592568;SUDAN BROWN RR [IARC];DTXSID0064339;CHEBI:82536;Fat Brown RR, Dye content 95 %;MFCD00009689;1-(2,4-diaminophenylazo) naphthalene;AKOS015894768;C.I.11285;LS-105873;Fat brown RR (C.I. 11285) for microscopy;C19528;4-[2-(1-Naphthalenyl)diazenyl]-1,3-benzenediamine;Q27156048

Chemical Property of Sudan Brown RR

Chemical Property:

• Vapor Pressure: 5.68E-11mmHg at 25°C
• Melting Point: 147-158 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 521.4°C at 760 mmHg
• Flash Point: 269.2°C
• PSA: 76.76000
• Density: 1.26g/cm³
• LogP: 5.58200
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 262.121846464
• Heavy Atom Count: 20
• Complexity: 343

Purity/Quality:

99% ^*data from raw suppliers

4-(1-NAPHTHALENYLAZO)-1,3-BENZENEDIAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2N=NC3=C(C=C(C=C3)N)N
• General Description: FAT BROWN RR is an azo dye used as a key component in the synthesis of a colorimetric anion sensor, where it functions as a signaling group alongside a nitrophenyl moiety. The resulting receptor demonstrates selective recognition of fluoride and acetate ions through distinct color changes, supported by spectroscopic shifts in absorption bands. The dye's incorporation into the sensor highlights its utility in developing optical detection systems for specific anions, particularly in DMSO solutions. No significant interaction was observed with other common anions, emphasizing its selectivity for fluoride and acetate.

Refernces

A new colorimetric anion sensor which have both a fat brown RR dye and a nitrophenyl group as signaling group

10.1007/s10847-010-9813-5

The study presents the development of a new colorimetric anion sensor 1, synthesized using Fat Brown RR dye and a nitrophenyl group as signaling components, and an amide moiety as the binding site. The receptor 1 is designed to selectively recognize fluoride and acetate ions through color changes observable both via spectroscopic methods and to the naked eye. The receptor was synthesized by reacting Fat Brown RR with 4-nitrobenzoyl chloride, yielding a red solid in 76.3% yield. In DMSO, the receptor displayed strong absorption at 412 nm, which shifted upon addition of tetrabutylammonium fluoride, indicating complex formation. Excess fluoride ions led to deprotonation, evidenced by a new absorption band at 531 nm. Similar behavior was observed with acetate ions. The receptor did not bind to other anions like chloride, bromide, iodide, perchlorate, hydrogensulfate, or nitrate. The association constants for fluoride and acetate were determined through UV–vis and 1H NMR titrations, confirming the receptor's selectivity and efficiency as a naked-eye detector for these anions.