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| CAS No.: | 60-09-3 |
|---|---|
| Name: | 4-Aminoazobenzene |
| Article Data: | 137 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H11N3 |
| Molecular Weight: | 197.239 |
| Synonyms: | Benzenamine,4-(phenylazo)- (9CI);C.I. Solvent Yellow 1 (7CI,8CI);4-(Phenylazo)aniline;4-(Phenylazo)benzenamine;4-Aminoazobenzol;Aniline yellow;Brasilazina Oil Yellow G;C.I. 11000;Cellitazol R;Ceres Yellow R;Fast SpiritYellow;Fat Yellow AAB;NSC 2032;Oil Soluble Aniline Yellow;Oil Yellow AAB;Oil Yellow AB;Oil Yellow AN;Oil Yellow B;Organol Yellow 2A;Solvent Yellow1;Somalia Yellow 2G;Sudan Yellow R;p-(Phenylazo)aniline;p-Aminoazobenzene;p-Aminoazobenzol;p-Aminodiphenylimide; |
| EINECS: | 200-453-6 |
| Density: | 1.12 g/cm3 |
| Melting Point: | 123-126 °C(lit.) |
| Boiling Point: | 360.7 °C at 760 mmHg |
| Flash Point: | 171.9 °C |
| Solubility: | 29.59mg/L(25 oC) |
| Appearance: | powder |
| Hazard Symbols: |
 T;  N;  C
|
| Risk Codes: | 45-50/53 |
| Safety: | 53-45-60-61 |
| Transport Information: | UN 3077 9/PG 3 |
| PSA: | 50.74000 |
| LogP: | 4.26540 |
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- 99170-93-1N-Methyl-2-oxazolamine
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- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
- 297766-64-4
1,3-Diphenyltriazen
- 60-09-3
aniline yellow
| Conditions | Yield |
|---|---|
| With K10-montmorillonite-H+ at 20℃; for 3h; Product distribution; Isomerization; | 100% |
| Mechanism; | |
| With sodium hydroxide at 50℃; pH=8; | |
| With hydrogenchloride In methanol; water at 40℃; for 2h; Temperature; Solvent; |
- 19689-52-2
4-(N'-phenyl-hydrazino)-aniline
- 60-09-3
aniline yellow
| Conditions | Yield |
|---|---|
| With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In ethanol at 60℃; for 12h; Green chemistry; | 95% |
| Conditions | Yield |
|---|---|
| Stage #1: With bentonite GB clay; sodium nitrite at 0 - 5℃; for 1h; Stage #2: aniline at 0 - 20℃; | 94% |
| With hydrogenchloride; sodium nitrite In water at 0 - 5℃; | 80% |
| Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.16667h; Stage #2: aniline With hydrogenchloride In water at 0 - 5℃; for 3h; Stage #3: With ammonia In water | 71% |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol at 30℃; for 48h; | A 75% B 8.2% |
| With hydrogenchloride In methanol at 30℃; for 48h; Product distribution; var. solvents; | A 64% B 5.8% |
| With hydrogenchloride In tert-butyl alcohol at 30℃; for 48h; | A 61% B 14% |
| Conditions | Yield |
|---|---|
| Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: aniline hydrochloride In water at 0 - 5℃; for 3h; Stage #3: With ammonia In water | 73% |
| Conditions | Yield |
|---|---|
| With sodium dithionite; 1,1′-dioctyl-4,4′-bipyridinium; potassium carbonate In water; acetonitrile at 35℃; for 1h; | A 20% B 62% |
| Conditions | Yield |
|---|---|
| at 40 - 45℃; for 1h; Inert atmosphere; | 62% |
- 95-53-4
o-toluidine
- 297766-64-4
1,3-Diphenyltriazen
A
- 60-09-3
aniline yellow
B
- 1142-13-8
2-methyl-4-phenylazo-aniline
| Conditions | Yield |
|---|---|
| With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition; | A 5% B 42% |
- 106-49-0
p-toluidine
- 297766-64-4
1,3-Diphenyltriazen
A
- 60-09-3
aniline yellow
B
- 313485-86-8
4-methyl-2-phenylazoaniline
| Conditions | Yield |
|---|---|
| With K10-montmorillonite at 20℃; for 6h; Product distribution; Addition; | A 21% B 36% |
- 108193-68-6
N,N-diethyl-4-phenylazoaniline N-oxide
A
- 60-09-3
aniline yellow
B
- 2058-67-5
N-ethyl-4-aminoazobenzene
C
- 2481-94-9
4-(diethylamino)azobenzene
| Conditions | Yield |
|---|---|
| In benzene at 17℃; for 5h; Irradiation; | A 23% B 10% C 28% |
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Chemistry
Molecule structure of 4-Aminoazobenzene (CAS NO.60-09-3) :
IUPAC Name: 4-phenyldiazenylaniline
Molecular Weight: 197.23584 g/mol
Molecular Formula: C12H11N3
Density: 1.12 g/cm3
Melting Point: 127 deg C
Boiling Point: 360.7 °C at 760 mmHg
Flash Point: 171.9 °C
Molar Volume: 174.9 cm3
Polarizability: 24.09*10-24 cm3
Surface Tension: 45.6 dyne/cm
Enthalpy of Vaporization: 60.64 kJ/mol
pKa Dissociation Constant: 2.82
log P (octanol-water): 3.41
Water Solubility: 32 mg/L
Henry's Law Constant: 8.70E-11 atm-m3/mole
Atmospheric OH Rate Constant: 4.34E-11 cm3/molecule-sec
XLogP3: 3.4
H-Bond Donor: 1
H-Bond Acceptor: 3
Rotatable Bond Count: 2
Tautomer Count: 2
Exact Mass: 197.095297
MonoIsotopic Mass; 197.095297
Topological Polar Surface Area: 50.7
Heavy Atom Count: 15
Complexity: 201
Canonical SMILES: C1=CC=C(C=C1)N=NC2=CC=C(C=C2)N
InChI: InChI=1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2
InChIKey: QPQKUYVSJWQSDY-UHFFFAOYSA-NEINECS: 200-453-6
Product Categories: Intermediates of Dyes and Pigments; Solvent Dyestuff
Uses
4-Aminoazobenzene (CAS NO.60-09-3) is used as dye intermediates. And it is used for the synthesis of azo dyes, disperse dyes, oxazine dyes; also used in the system paints and pigments, as well as alcohol-soluble yellow and pH indicator.
Production
Inputs phenlyaniline and sodium nitrite solution to the reactor, at 30-40 °C stirring, at 2.5-3h to add 30% hydrochloric acid, then heated to 50-55 °C for translocation.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 200mg/kg (200mg/kg) | National Technical Information Service. Vol. AD277-689, |
Safety Profile
Hazard Codes: 
T, 
N, 
Xi
Risk Statements: 45-50/53
R45: May cause cancer
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements: 53-45-60-61
S53: Avoid exposure - obtain special instructions before use
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible)
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR: UN 3077 9/PG 3
WGK Germany: 3
RTECS: BY8225000
Hazardous Substances Data: 60-09-3(Hazardous Substances Data)
Specification
4-Aminoazobenzene (CAS NO.60-09-3) is also called 4-(Phenylazo)aniline ; 4-(Phenylazo)benzenamine ; 4-Amino-1,1'-azobenzene ; 4-Aminoazobenzol ; 4-Benzeneazoaniline ; Aminoazobenzene ; Aniline Yellow ; Aniline, p-(phenylazo)- ; Azobenzene, 4-amino- ; Benzenamine, 4-(phenylazo)- ; Brasilazina Oil Yellow G . 4-Aminoazobenzene (CAS NO.60-09-3) is odorless brownish-yellow needles with bluish coating, or an orange powder. It is insoluble in water and soluble in ethanol, ether, chloroform, benzene and oil. Dust may form an explosive mixture in air. 4-Aminoazobenzene can detonate, particularly if sensitized by the presence of metal salts or strong acids. May form toxic gases with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. May form flammable gases with alkali metals. May react explosively with strong oxidizing agents, metal salts, peroxides, and sulfides. Emits toxic fumes of oxides of nitrogen when heated to decomposition (over 350 °C) . Flash point data for 4-Aminoazobenzenecan are not available; however, 4-Aminoazobenzenecan is probably combustible.