SudanI supplier | CasNO.842-07-9

Name
Sudan I
EINECS 212-668-2
CAS No. 842-07-9
Article Data104
CAS DataBase
Density 1.175 g/cm³
Solubility 0.5 g/L (30 °C) in water
Melting Point 131-133 °C
Formula C₁₆H₁₂N₂O
Boiling Point 443.653 °C at 760 mmHg
Molecular Weight 248.284
Flash Point 290.196 °C
Transport Information
Appearance orange-red powder
Safety 61-46-36/37-22
Risk Codes 68-53-43-40
Molecular Structure
Hazard Symbols Xn
Synonyms 2-Naphthalenol,1-(phenylazo)- (9CI);Sudan Yellow (6CI);1-Benzeneazo-2-naphthol;1-Phenylazo-b-naphthol;C.I. 12055;Calcogas Orange NC;Disperse Yellow 97;Enial Orange I;Fast Orange;Fat Orange G;Fat Orange R;Fat Orange RS;Grasal Orange;HidacoOil Orange;Morton Orange Y;OilOrange;Oil Orange 2311;Oil Orange 2B;Oil Orange 5101;Oil Orange E;Oil Orange PEL;Oil Orange R;Oil Orange Z-7078;Oil orange PS;Orange 3RA Soluble inGrease;Orange JLS-PS;Orange Pel;Orange R Fat Soluble;Stearix Orange;Sudan Orange 220;Sudan Orange RA;Tertrogras Orange SV;Waxoline Orange EP-FW;WaxolineYellow I;Waxoline Yellow IP;a-Phenylazo-b-naphthol;
PSA 44.95000
LogP 4.96080

Synthetic route

: 62-53-3
aniline

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.5h;	99%
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 20℃; for 0.333333h; Green chemistry; Stage #2: β-naphthol In water at 20℃; for 0.666667h; Green chemistry;	99%
Stage #1: aniline With hydrogenchloride In water at 0 - 5℃; for 0.0833333h; Stage #2: β-naphthol In water for 0.0833333h;	98%

: 100-34-5
benzene diazonium chloride

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With sodium hydroxide In water at 0℃; for 0.00555556h; Flow reactor; Large scale; Green chemistry;	95%
With sodium hydroxide In ethanol; water for 0.166667h; Ambient temperature;	93%
With sodium hydroxide In water for 0.35h;	89%

: 135-19-3
β-naphthol

: benzenediazonium o-benzenedisulfonimide

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.333333h;	93%

: 62-53-3
aniline

: 135-19-3
β-naphthol

A: 842-07-9
Sudan I

B: 1602-30-8, 93449-60-6
1-phenyl-azo-2-naphthol

Conditions

Conditions	Yield
Stage #1: aniline With hydrogenchloride In water at 0 - 5℃; for 0.0833333h; Stage #2: With 1-(4-(nitrosooxy)butyl)-3-methylimidazolium chloride In water at 0 - 5℃; for 0.416667h; Stage #3: β-naphthol With sodium hydroxide In water at 0℃; for 0.416667h;	A 87% B n/a

...Expand

: 93680-28-5
C7H7N7

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With trifluoroacetic acid In benzene at 65℃; for 3h;	84%

: 135-19-3
β-naphthol

: 29110-75-6
N'-tosyl phenylhydrazine

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 8h;	80%

: {Ru(NO)(NO2)(C5H4N(C6H5N2))2}(2+)*2ClO4(1-) = {Ru(NO)(NO2)(C5H4N(C6H5N2))2}(ClO4)2

: 135-19-3
β-naphthol

A: {Ru(CH3CN)(NO2)(C5H4N(C6H5N2))2}(1+)*ClO4(1-)*H2O = {Ru(CH3CN)(NO2)(C5H4N(C6H5N2))2}(ClO4)*H2O

B: 842-07-9
Sudan I

Conditions

Conditions	Yield
With aniline In acetonitrile added aniline to a soln. of Ru-complex; stirred for 30 min at room temp.; evapd. to dryness; extracted with ice-cold water; filtrated; added β-naphthol with stirring over a period of 15 min; sepd.; recrystd. from methanol; dried residue obtained after water extraction; dissolved in CH2Cl2; added hexane; filtered; dried in vacuo; elem. anal.;	A 60% B n/a

...Expand

: 60285-31-6
N,N'-diphenyl-N-nitroso-urea

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
In benzene for 2h; Heating;	56%
In ethanol for 72h; Product distribution; Ambient temperature; further 1,3 diaryl-1-nitrosoureas;	25.3%
With sodium hydroxide In ethanol for 0.0833333h; Ambient temperature;	58 % Spectr.
In ethanol for 72h; Ambient temperature;	25.3 % Spectr.

: 135-19-3
β-naphthol

: 17478-75-0, 43187-18-4, 127838-75-9
N'-(4-methoxy-phenyl)-N-phenyl-diazene-N-oxide

A: 56661-22-4
2-hydroxy-4-methoxyazobenzene

B: 842-07-9
Sudan I

Conditions

Conditions	Yield
In benzene for 3h; Irradiation;	A 45% B 12%

...Expand

: 104354-92-9, 109577-22-2
1-Phenyl-1-phenylazo-eth-1-yl-hydroperoxide; compound with benzene

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
Product distribution; Mechanism; Ambient temperature; reactions of α-azohydroperoxides with solvents;	44%

: 135-19-3
β-naphthol

: 17478-80-7, 43187-52-6, 416860-44-1
(4-methoxyphenyl)phenyldiazene 1-oxide

A: 56661-22-4
2-hydroxy-4-methoxyazobenzene

B: 842-07-9
Sudan I

C: 2,4'-dimethoxy-4-hydroxy-5-phenylazoazobenzene

D: 13411-91-1
1-(4-methoxyphenylazo)naphthalen-2-ol

Conditions

Conditions	Yield
In benzene for 4h; Irradiation;	A 38% B 8% C 8% D 17%

...Expand

: 17478-80-7, 43187-52-6, 416860-44-1
(4-methoxyphenyl)phenyldiazene 1-oxide

A: 56661-22-4
2-hydroxy-4-methoxyazobenzene

B: 842-07-9
Sudan I

C: 2,4'-dimethoxy-4-hydroxy-5-phenylazoazobenzene

D: 13411-91-1
1-(4-methoxyphenylazo)naphthalen-2-ol

Conditions

Conditions	Yield
With β-naphthol In benzene for 4h; Irradiation;	A 38% B 8% C 8% D 17%

...Expand

: 14580-01-9
4-oxo-4-(2-phenylhydrazinyl)butanoic acid

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
Stage #1: 4-oxo-4-(2-phenylhydrazinyl)butanoic acid With methanol; ammonium cerium(IV) nitrate Stage #2: β-naphthol With sodium carbonate	32%

: 109057-65-0
C16H12N2O

: 135-19-3
β-naphthol

A: 842-07-9
Sudan I

B: 3375-23-3
2-phenylazo-1-naphthol

C: 3651-02-3
4-Phenylazo-1-naphthol

Conditions

Conditions	Yield
In benzene Ambient temperature;	A 26% B n/a C n/a

...Expand

: 110-86-1
pyridine

: 16978-76-0
(E)-1-(phenyldiazenyl)piperidine

: 628-13-7
pyridine hydrochloride

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

...Expand

: 110-86-1
pyridine

: 100-34-5
benzene diazonium chloride

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

...Expand

: 67-56-1
methanol

: 2-ethoxy-1-phenylazo-naphthalene; dinitrate

A: 625-58-1
ethyl nitrate

B: 842-07-9
Sudan I

...Expand

: 1096-84-0
bis(2-hydroxy-1-naphthyl)methane

: 100-34-5
benzene diazonium chloride

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With alkali

: (2-isopropoxy-[1]naphthyl)-phenyl-diazene; hydrochloride

: 842-07-9
Sudan I

: phenyl-(2-propoxy-[1]naphthyl)-diazene; dihydrochloride

: 842-07-9
Sudan I

Conditions

Conditions	Yield
beim Erhitzen auf dem Schmelzpunkt;

: (2-isobutoxy-[1]naphthyl)-phenyl-diazene; hydrochloride

: 842-07-9
Sudan I

: 62-53-3
aniline

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With chloroform; BF3-N2O3 und Behandeln des Reaktionsprodukts mit <2>Naphthol in wss.NaOH;
Multi-step reaction with 2 steps 1: sodium nitrite; hydrogenchloride / water / 0.17 h / 0 °C 2: sodium hydroxide / water / 0.01 h / 0 °C / Flow reactor; Large scale; Green chemistry View Scheme

: 586-96-9
Nitrosobenzene

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With n-Amyl nitrite; trifluoroacetic anhydride anschliessend mit wss.NaHCO3 undi mit <2>Naphthol in wss.NaOH;

: 2684-02-8
benzenediazonium

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
beim Behandeln von Benzoldiazoniumhydroxid;

: N-methoxy-N'-phenyl-diazene-N-oxide

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With benzene

: 2-methyl-2-(N-nitroso-anilino)-cyclohexanone oxime

: furan-2,3,5(4H)-trione pyridine (1:1)

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

...Expand

: N,N'-dinitroso-N,N'-diphenyl-sulfamide

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

: 542-15-4
anilinium nitrate

: 135-19-3
β-naphthol

: 842-07-9
Sudan I

Conditions

Conditions	Yield
With potassium nitrite; ethanol; water

: 135-19-3
β-naphthol

: 622-37-7
Phenyl azide

A: 62-53-3
aniline

B: 842-07-9
Sudan I

...Expand

: 135-19-3
β-naphthol

: 622-37-7
Phenyl azide

: 842-07-9
Sudan I

: 17739-45-6, 59146-56-4
2-(2-bromoethoxy)tetrahydropyran

: 842-07-9
Sudan I

: 201813-17-4
1-phenyl-2-{2-[2-(tetrahydro-2H-2-pyranyloxy)ethoxy]-1-naphthyl}-1-diazene

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; Etherification;	99.5%

: 20398-06-5
thallium (I) ethoxide

: 842-07-9
Sudan I

: Tl(1+)*C10H6ON2C6H5(1-)=TlC10H6ON2C6H5

Conditions

Conditions	Yield
In tetrahydrofuran (Ar), to soln. of ligand in dry THF added dropwise soln. of TlOEt at room temp., stirred for 2 h; filtered;	99%

: 14637-34-4
ammonium tetraphenylborate

: 842-07-9
Sudan I

: (1-phenylazo-2-naphtholato)diphenylboron

Conditions

Conditions	Yield
In toluene byproducts: NH3, C6H6; soln. of B compd. and ligand refluxed for 20 h; filtered, filtrate evapd. to dryness, recrystd. from MeOH; elem. anal.;	92%

: 109-63-7
boron trifluoride diethyl etherate

: 842-07-9
Sudan I

: 1-phenylazo-2-naphthalate difluoroborate

Conditions

Conditions	Yield
With acetic acid at 20℃; for 16h; Inert atmosphere;	92%

: 639-58-7
triphenyltin chloride

: 842-07-9
Sudan I

: (C6H5)3SnCl(C16H12N2O)

Conditions

Conditions	Yield
In methanol anhydrous methanol soln. of Ph3SnCl was added to a hot methanol soln. of the arylazophenol and refluxed for 1 h, the react. mixture was concd. and cooled to room temp.;; obtained crystals were washed with petroleum ether, recrystd. from methanol, dried in vacuum over CaCl2; elem. anal.;;	90%

: 128706-72-9, 658044-18-9, 52462-29-0
[Ru(p-cymene)Cl2]2

: 842-07-9
Sudan I

: 381227-08-3
(η6-p-cymene)RuClC10H6ON2Ph

Conditions

Conditions	Yield
With Na2CO3 In dichloromethane Ru-complex was treated with ligand in the presence of Na2CO3 in CH2Cl2 with stirring for 4 h at 25°C under N2; washed with n-hexane, dried under vac.; elem. anal.;	90%

: [(Pd(μ-Cl)(C6H5CH2NHCH3-C1,N))2]

: 842-07-9
Sudan I

: 192440-59-8
[Pd(C6H4CH2NHCH3)(OC10H6NNC6H5)]

Conditions

Conditions	Yield
With sodium hydroxide In methanol stirring (10 h); filtn., washing (MeOH), recrystallization (CH2Cl2, MeOH); elem. anal.;	90%

: nickel(II) chloride hexahydrate

: 842-07-9
Sudan I

: nickel(II) bis-1-phenylazo-2-naphthol

Conditions

Conditions	Yield
In ethanol; water for 4h; Reflux;	90%

: copper(II) choride dihydrate

: 842-07-9
Sudan I

: copper(II) bis-1-phenylazo-2-naphthol

Conditions

Conditions	Yield
In ethanol; water for 4h; Reflux;	83%

: 1191-47-5
dibutylmagnesium

: 842-07-9
Sudan I

: [Mg{η2-O(C10H6)NN(C6H5)}2]n

Conditions

Conditions	Yield
In toluene at -78 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;	80%

: 842-07-9
Sudan I

: C16H11N2O(1-)*K(1+)

Conditions

Conditions	Yield
With potassium hexamethylsilazane In toluene at -78℃; for 12h; Inert atmosphere;	80%

: 1191-47-5
dibutylmagnesium

: 842-07-9
Sudan I

: C32H22MgN4O2

Conditions

Conditions	Yield
In n-heptane; toluene at -78℃; for 12h; Inert atmosphere;	80%

: {RuC2O4(bpy)2}*4H2O

: sodium perchlorate

: 842-07-9
Sudan I

: 77590-07-9
bis(2,2'-bipyridine)(1-(phenylazo)-2-naphtholato)ruthenium(II) perchlorate

Conditions

Conditions	Yield
With hydrogenchloride In methanol To a soln. of complex in MeOH aq. HCl was added, heated to reflux for 12 h, the ligand and NaOH was added, refluxed for 6 h, filtered, NaClO4 in MeOH was added;; reduced in vol., ppt. was filtered, washed with H2O, ether, dried undervac.; elem. anal.;;	75%

...Expand

: 753-73-1
dimethyltin dichloride

: 842-07-9
Sudan I

: (C6H5NNC10H6OH)2(CH3)2SnCl2

Conditions

Conditions	Yield
In benzene addn. of ligand to Me2SnCl2 in anhyd. benzene, refluxing for 6 h; hot filtn., crystn. by cooling to room temp., filtn., recrystn. from anhyd. benzene, drying in vacuo, elem. anal.;	72%

: 3375-31-3
palladium diacetate

: 842-07-9
Sudan I

: 169778-99-8
bis[1-(phenylazo)-2-naphtholato-Nβ,O]palladium(II)

Conditions

Conditions	Yield
In chloroform stirring stoich. amts. for 12 h; collection (filtration), washing (EtOH), drying (vac.); elem. anal.;	70%

: copper(II) chloride hexahydrate

: 842-07-9
Sudan I

: 15242-79-2
Cu(1-(phenylazo)-2-naphthol)2

Conditions

Conditions	Yield
for 4h; Reflux;	70%

: 31378-26-4, 31378-27-5, 14284-93-6
tris(2,4-pentanedionato)ruthenium(III)

: 842-07-9
Sudan I

: 227000-09-1
[Ru(CH3COCHCOCH3)(C10H6(O)N2C6H5)2]

Conditions

Conditions	Yield
In ethylbenzene stirring (160°C, 6 h); evapn. (vac.), dichloromethane addn., chromy. (silica gel, hexane/benzene, 3/1 and hexane/benzene, 2/1), evapn.; elem. anal.;	68%

: nickel(II) chloride hexahydrate

: 842-07-9
Sudan I

: 24686-53-1, 54975-69-8
bis-1-(phenylazo)-2-naphtholate nickel(II)

Conditions

Conditions	Yield
With sodium carbonate In methanol; water at 60℃; for 0.8h;	67%
With sodium carbonate In methanol at 60℃; for 8h;	67%

: 108-24-7
acetic anhydride

: 842-07-9
Sudan I

: 39781-22-1
1-(phenyldiazenyl)naphthalen-2-yl acetate

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃;	62%
at 200℃;
With sodium acetate

: 6147-53-1
cobalt(II) diacetate tetrahydrate

: 842-07-9
Sudan I

: cobalt(II) bis-1-phenylazo-2-naphthol

Conditions

Conditions	Yield
In ethanol; water for 4h; Reflux;	61%

: 842-07-9
Sudan I

: 4039-32-1
lithium hexamethyldisilazane

: [Li{η2-O(C10H6)NN(C6H5)}]n

Conditions

Conditions	Yield
In toluene at -78 - 20℃; Inert atmosphere; Schlenk technique; Glovebox;	57%

: 842-07-9
Sudan I

: [Li{η2-O(C10H6)NN(C6H5)}]n

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In toluene at -78℃; for 12h; Inert atmosphere;	56%

SudanI 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 Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 8 ,1975,p. 225.(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) . NTP Carcinogenesis Bioassay (feed); Clear Evidence: rat NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-226 ,1982. . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

SudanI Specification

The IUPAC name of SudanI is (1Z)-1-(phenylhydrazinylidene)naphthalen-2-one. With the CAS registry number 842-07-9, it is also named as C.I. Solvent Yellow 14; 2-Hydroxy-1-phenylazonaphthalene. The product's categories are dyes and pigments; organics; solvent dyestuff. It is orange-red powder which is insoluble in water, slightly soluble in ethanol, easily soluble in oil and mineral oil, and soluble in acetone and benzene. This chemical is an azo compound. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. SudanI is incompatible with strong oxidizing agents and strong acids.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.38; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4; (4)ACD/LogD (pH 7.4): 4; (5)ACD/BCF (pH 5.5): 975; (6)ACD/BCF (pH 7.4): 975; (7)ACD/KOC (pH 5.5): 4798; (8)ACD/KOC (pH 7.4): 4798; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.634; (13)Molar Refractivity: 75.596 cm³; (14)Molar Volume: 211.353 cm³; (15)Polarizability: 29.969×10^-24 cm³; (16)Surface Tension: 46.836 dyne/cm; (17)Enthalpy of Vaporization: 72.834 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 4; (21)Exact Mass: 248.094963; (22)MonoIsotopic Mass: 248.094963; (23)Topological Polar Surface Area: 41.5; (24)Heavy Atom Count: 19.

Preparation of SudanI: It can be obtained by naphthalen-2-ol and N-nitroso-N,N'-diphenyl-urea with reagent 1 N sodium hydroxide and solvent ethanol at ambient temperature. The reaction time is 5 min. The yield is 58 % Spectr.

Uses of SudanI: It is not only used for coloring shoe polish, floor wax, grease, etc., but also for the manufacture of fireworks and lacquer. And it is also used as a biological stain and oil stain. In addition, it can react with 2-(2-bromo-ethoxy)-tetrahydro-pyran to get phenyl-{2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-naphthalen-1-yl}-diazene. This reaction which is etherification needs reagent potassium carbonate and solvent dimethylformamide at temperature of 80°C. The reaction time is 12 hours. The yield is 99.5%.

When you are using this chemical, please be cautious about it as the following:
It may cause sensitization by skin contact and may cause long-term adverse effects in the aquatic environment, so people should not breathe dust. If you want to contact this product, you must wear suitable protective clothing and gloves. If swallowed, seek medical advice immediately and show this container or label. Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES: Oc3ccc1ccccc1c3/N=N/c2ccccc2;
2. InChI: InChI=1/C16H12N2O/c19-15-11-10-12-6-4-5-9-14(12)16(15)18-17-13-7-2-1-3-8-13/h1-11,19H/b18-17+.

Product Name

Sudan I

Synthetic route

SudanI Consensus Reports

SudanI Specification

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