Product Name

  • Name

    Solvent Red 23

  • EINECS 201-638-4
  • CAS No. 85-86-9
  • Article Data6
  • CAS DataBase
  • Density 1.22 g/cm3
  • Solubility
  • Melting Point 199 °C
  • Formula C22H16N4O
  • Boiling Point 584.6 °C at 760 mmHg
  • Molecular Weight 352.395
  • Flash Point 398.1 °C
  • Transport Information
  • Appearance reddish brown powder
  • Safety 22-24/25-36-26
  • Risk Codes 10-20-36/38-36/37/38
  • Molecular Structure Molecular Structure of 85-86-9 (Solvent Red 23)
  • Hazard Symbols IrritantXi
  • Synonyms Red No. 225;Red Zh;Silotras Scarlet TB;Somalia Red III;Stearix Scarlet;Sudan 3;Sudan III;Sudan P III;Sudan Red III;Tetrazobenzene-b-naphthol;Toney Red;SudanⅢ;2-Naphthalenol,1-[[4-(phenylazo)phenyl]azo]- (9CI);2-Naphthol, 1-(p-phenylazophenylazo)-(6CI);C.I. Solvent Red 23 (8CI);1-(p-Phenylazophenylazo)-2-naphthol;111440Red;Brasilazina Oil Scarlet;C.I. 26100;Certiqual Oil Red;D and C Red No.17;D&;C Red No. 17;DC Red 17;FD And C Red No. 17;Fast Oil Scarlet III;Fat Red Bluish;Fat Red HRR;Fat Red R;Fat Red RS;Fat Scarlet LB;Grasal Brilliant Red G;Grasan Brilliant Red G;NSC 65825;NSC 8995;Oil Red DR 126;OilRed Extra;
  • PSA 69.67000
  • LogP 7.37620

Synthetic route

aniline yellow
60-09-3

aniline yellow

β-naphthol
135-19-3

β-naphthol

Sudan III
85-86-9

Sudan III

Conditions
ConditionsYield
In ethanol65%
Stage #1: aniline yellow With hydrogenchloride; sodium nitrite Cooling;
Stage #2: β-naphthol With sodium hydroxide
β-naphthol
135-19-3

β-naphthol

diazotized 4-amino-azobenzene

diazotized 4-amino-azobenzene

Sudan III
85-86-9

Sudan III

Conditions
ConditionsYield
With alkali
iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

Sudan III
85-86-9

Sudan III

[Fe(sud)Cl3H2O]

[Fe(sud)Cl3H2O]

Conditions
ConditionsYield
In ethanol; N,N-dimethyl-formamide for 2h; Reflux;88%
Sudan III
85-86-9

Sudan III

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}cobalt(II)

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}cobalt(II)

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol for 1h; Reflux;87%
Sudan III
85-86-9

Sudan III

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}nickel(II)

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}nickel(II)

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol for 1h; Reflux;81%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

Sudan III
85-86-9

Sudan III

[Ni(sudan III)(1,10-phenanthroline)Cl2]

[Ni(sudan III)(1,10-phenanthroline)Cl2]

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; nickel(II) chloride hexahydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
79%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

iron(III) chloride hexahydrate

iron(III) chloride hexahydrate

Sudan III
85-86-9

Sudan III

[Fe(sudan III)(1,10-phenanthroline)Cl2]Cl*H2O

[Fe(sudan III)(1,10-phenanthroline)Cl2]Cl*H2O

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; iron(III) chloride hexahydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
79%
copper diacetate
142-71-2

copper diacetate

Sudan III
85-86-9

Sudan III

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}copper(II)

bis{1-[4-(phenyldiazenyl)phenyldiazenyl]naphthalen-2-olato}copper(II)

Conditions
ConditionsYield
In N,N-dimethyl-formamide; isopropyl alcohol for 1h; Reflux;76%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

zinc(II) chloride dihydrate

zinc(II) chloride dihydrate

Sudan III
85-86-9

Sudan III

[Zn(sudan III)(1,10-phenanthroline)Cl2]

[Zn(sudan III)(1,10-phenanthroline)Cl2]

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; zinc(II) chloride dihydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
74%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

cadmium(II) chloride dihydrate

cadmium(II) chloride dihydrate

Sudan III
85-86-9

Sudan III

[CdCl(sudan III)(1,10-phenanthroline)(H2O)]Cl*0.5H2O

[CdCl(sudan III)(1,10-phenanthroline)(H2O)]Cl*0.5H2O

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; cadmium(II) chloride dihydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
74%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

copper(II) choride dihydrate

copper(II) choride dihydrate

Sudan III
85-86-9

Sudan III

[Cu(sudan III)(1,10-phenanthroline)Cl2]*1.5H2O

[Cu(sudan III)(1,10-phenanthroline)Cl2]*1.5H2O

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; copper(II) choride dihydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
73%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

chromium(III) chloride hexahydrate

chromium(III) chloride hexahydrate

Sudan III
85-86-9

Sudan III

[Cr(sudan III)(1,10-phenanthroline)Cl2]Cl*H2O

[Cr(sudan III)(1,10-phenanthroline)Cl2]Cl*H2O

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; chromium(III) chloride hexahydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
72%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

manganese(II) chloride tetrahydrate

manganese(II) chloride tetrahydrate

Sudan III
85-86-9

Sudan III

[MnCl(sudan III)(1,10-phenanthroline)(H2O)]Cl

[MnCl(sudan III)(1,10-phenanthroline)(H2O)]Cl

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; manganese(II) chloride tetrahydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
70%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

Sudan III
85-86-9

Sudan III

[Co(sudan III)(1,10-phenanthroline)Cl2]

[Co(sudan III)(1,10-phenanthroline)Cl2]

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; cobalt(II) chloride hexahydrate; Sudan III With ammonium hydroxide In ethanol; N,N-dimethyl-formamide at 60℃;
Stage #2: In ethanol; N,N-dimethyl-formamide for 2h; Reflux;
68%
Sudan III
85-86-9

Sudan III

A

aniline
62-53-3

aniline

B

1,4-phenylenediamine
106-50-3

1,4-phenylenediamine

Conditions
ConditionsYield
With sodium hydroxide; sodium dithionite In water at 100℃; for 1h; Product distribution; Further Variations:; Temperatures; Solvents; pH-values; reflux condenser;
acryloyl chloride
814-68-6

acryloyl chloride

Sudan III
85-86-9

Sudan III

acrylic acid 1-(4-phenylazo-phenylazo)-naphthalen-2-yl ester

acrylic acid 1-(4-phenylazo-phenylazo)-naphthalen-2-yl ester

Conditions
ConditionsYield
Stage #1: Sudan III With triethylamine at 21℃; for 0.166667h; Inert atmosphere;
Stage #2: acryloyl chloride at 55℃; for 18h; Inert atmosphere;
96 mg

Solvent Red 23 Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 8 ,1975,p. 241.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Solvent Red 23 Specification

The IUPAC name of Oil Red is (1Z)-1-[(4-phenyldiazenylphenyl)hydrazinylidene]naphthalen-2-one. With the CAS registry number 85-86-9, it is also named as C.I. Solvent Red 23; 2-Naphthalenol, 1-((4-(phenylazo)phenyl)azo)-. The product's categories are organics; solvent dyestuff. It is reddish brown powder which is toxic, flammable, stable and incompatible with strong oxidizing agents. And Oil Red will produce toxic nitrogen oxide fumes when buring, so the storage environment should be ventilate, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 5.74; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.74; (4)ACD/LogD (pH 7.4): 5.74; (5)ACD/BCF (pH 5.5): 13495.4; (6)ACD/BCF (pH 7.4): 13495.38; (7)ACD/KOC (pH 5.5): 31475.66; (8)ACD/KOC (pH 7.4): 31475.63; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.661; (13)Molar Refractivity: 106.81 cm3; (14)Molar Volume: 288.6 cm3; (15)Polarizability: 42.34×10-24 cm3; (16)Surface Tension: 50.4 dyne/cm; (17)Enthalpy of Vaporization: 90.58 kJ/mol; (18)Vapour Pressure: 2.9E-14 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Tautomer Count: 5; (21)Exact Mass: 352.132411; (22)MonoIsotopic Mass: 352.132411; (23)Topological Polar Surface Area: 66.2; (24)Heavy Atom Count: 27.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation. And it is irritating to eyes, respiratory system and skin, so people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

People can use the following data to convert to the molecule structure. 
1. SMILES: Oc4ccc1ccccc1c4/N=N/c3ccc(\N=N/c2ccccc2)cc3;
2. InChI: InChI=1/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23-,26-25+.

The following are the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LDLo intraperitoneal 250mg/kg (250mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
Journal of Pathology and Bacteriology. Vol. 87, Pg. 317, 1964.
 
rabbit LDLo intrapleural 500mg/kg (500mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
Journal of Pathology and Bacteriology. Vol. 87, Pg. 317, 1964.
 
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
Journal of Pathology and Bacteriology. Vol. 87, Pg. 317, 1964.
 

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