2-AMINO ANTHRAQUINONE

2-Amino anthraquinone is used in the production of specialty pigments that provide excellent color strength and durability for industrial applications.
2-Amino anthraquinone is utilized as an intermediate in the manufacture of organic pigments for printing inks, coatings, and paints.
2-Amino anthraquinone is incorporated into research laboratories as a starting material for synthesizing various anthraquinone derivatives with tailored chemical properties.

CAS Number: 117-79-3
EC Number: 204-208-4
Molecular formula: C₁₄H₉NO₂
Molecular weight: 223.23 g/mol

SYNONYMS:
2-Aminoanthraquinone, 2-Amino-9,10-anthraquinone, 2-Amino-9,10-anthracenedione, 2-Aminoanthracene-9,10-dione, 9,10-Anthracenedione, 2-amino-, Anthraquinone, 2-amino-, β-Aminoanthraquinone, Beta-Aminoanthraquinone, β-Anthraquinonylamine, Beta-Anthraquinonylamine, Aminoanthraquinone, 2-Amino-anthraquinone, 2-Aminoanthra-9,10-quinone, 2-AAQ, AAQ, NCI-C01876, NSC-5, NSC 5, CCRIS 23, HSDB 4088, MFCD00001233, EINECS 204-208-4, CAS-117-79-3, Aminoanthraquinone, 2-, 2-amino-9,10-dihydroanthracene-9,10-dione, 2-AMINOANTHRAQUINONE, 117-79-3, 9,10-Anthracenedione, 2-amino-, 2-Amino-9,10-anthraquinone, 2-Amino-9,10-anthracenedione, Anthraquinone, 2-amino-, beta-Aminoanthraquinone, NCI-C01876, beta-Anthraquinonylamine, DTXSID6020068, 2-amino-9,10-dihydroanthracene-9,10-dione, NSC-5, 65Z03V2Z09, DTXCID2068, RefChem:85362, 204-208-4, 2-aminoanthracene-9,10-dione, 2-Amino-anthraquinone, 2-AAQ, NSC 5, .beta.-Aminoanthraquinone, MFCD00001233, 2-Aminoanthra-9,10-quinone, AAQ, CCRIS 23, CAS-117-79-3, HSDB 4088, Aminoanthraquinone, 2-, EINECS 204-208-4, AI3-09063, UNII-65Z03V2Z09, 2-amino anthraquinone, 9, 2-amino-, NSC5, .beta.-Anthraquinonylamine, CBMicro_011266, SCHEMBL40960, MLS002152869, BIDD:ER0316, CHEMBL84685, SCHEMBL8998544, SCHEMBL11262118, SCHEMBL31290097, 2-Aminoanthra-9,10-quinone #, CHEBI:34258, HMS3034D13, WLN: L C666 BV IVJ EZ, 2-AMINOANTHRAQUINONE [HSDB], 2-AMINOANTHRAQUINONE [IARC], ALBB-038852, SMSF0003869, Tox21_201521, Tox21_300101, SBB000619, STK396687, 2-Aminoanthraquinone, technical grade, AKOS000119069, CB14717, EBC-612314, FA41565, NCGC00091610-01, NCGC00091610-02, NCGC00091610-03, NCGC00091610-04, NCGC00091610-05, NCGC00253972-01, NCGC00259071-01, AC-10747, AS-75624, SMR000765637, SY049674, BIM-0011444.P001, A0255, CS-0010171, NS00003496, ST45245356, EN300-16812, E77026, 2-Aminoanthraquinone, technical, 85-90% (HPLC), AO-801/41077416, F236743, Q27115949, F1908-0138, InChI=1/C14H9NO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H,15H, 9,10-Anthracenedione, 2-amino-, β-Aminoanthraquinone, 2-Amino-9,10-anthraquinone, 2-Aminoanthraquinone, AAQ, NCI-C01876, 2-Amino-9,10-anthracenedione, 2-AAQ, β-Anthraquinonylamine, beta-Aminoanthraquinone, NSC 5, 9,10-Anthracenedione, 2-amino-,Anthraquinone, 2-amino-, 9,10-Anthracenedione, 2-amino-, «beta»-Aminoanthraquinone, 2-Amino-9,10-anthraquinone, 2-Aminoanthraquinone, AAQ, NCI-C01876, 2-Amino-9,10-anthracenedione, 2-AAQ, «beta»-Anthraquinonylamine, beta-Aminoanthraquinone, NSC 5

2-Amino anthraquinone is an anthraquinone derivative containing an amino group at the 2-position of the anthraquinone ring system.
2-Amino anthraquinone is also known as 2-amino-9,10-anthracenedione and is an important aromatic intermediate, particularly in the manufacture of anthraquinone dyes and pigments.

2-Amino anthraquinone is a highly conjugated aromatic compound containing three fused benzene-like rings and two ketone groups at the 9,10-positions, together with one amino substituent.
2-Amino anthraquinone's extensive conjugated π-electron system is responsible for its strong color and its usefulness in dye chemistry.

2-Amino anthraquinone is normally encountered as a red, red-brown, orange-brown or dark-brown crystalline solid.
2-Amino anthraquinone is a synthetic, red or orange-brown needle-shaped solid that is insoluble in water and soluble in alcohol, acetone, benzene and chloroform.
2-Amino anthraquinone is an organic compound with the formula C14H9O2N.

2-Amino anthraquinone is one of two monoaminoanthraquinone isomers.
2-Amino anthraquinone is prepared from 2-chloroanthraquinone by treatment with ammonia.
A number of other routes have been described, e.g. using nitrobenzene in the diacylation.

2-Amino anthraquinone exhibits extensive reactivity, e.g. diazotization.
2-Amino anthraquinone is a precursor to indanthrone, a commercial blue dye.
2-Amino anthraquinone (2-AAQ) represents an organic compound classified as an anthraquinone derivative.

2-Amino anthraquinone manifests as a colorless solid and exhibits solubility in most organic solvents.
In scientific research, 2-Amino anthraquinone has been employed across a range of applications.
2-Amino anthraquinone acts as a fluorescent probe for detecting metal ions in aqueous solutions, a fluorescent dye for DNA detection, and a reagent for polymer synthesis.
Notably, 2-Amino anthraquinone functions as a potent inhibitor of the enzyme cytochrome P450 2C9 (CYP2C9).

USES and APPLICATIONS of 2-AMINO ANTHRAQUINONE:
2-Amino anthraquinone is used as intermediate for the synthesis of both anthraquinone dyes and pharmaceutical products.
2-Amino anthraquinone is used in fabrication of high performance electrode of supercapacitor based on chemically modified graphene hydrogel.
2-Amino anthraquinone is primarily used as an intermediate in the manufacture of anthraquinone-based dyes and pigments.

2-Amino anthraquinone serves as a key raw material for producing acid, disperse, reactive, and vat dyes used in the textile industry.
2-Amino anthraquinone is widely employed in the synthesis of colorants for dyeing natural and synthetic fibers, including cotton, wool, silk, polyester, and nylon.
2-Amino anthraquinone is used in the production of specialty pigments that provide excellent color strength and durability for industrial applications.

2-Amino anthraquinone is utilized as an intermediate in the manufacture of organic pigments for printing inks, coatings, and paints.
2-Amino anthraquinone is incorporated into research laboratories as a starting material for synthesizing various anthraquinone derivatives with tailored chemical properties.
2-Amino anthraquinone is used in pharmaceutical and chemical research for developing biologically active anthraquinone-based compounds.

2-Amino anthraquinone serves as a building block in the synthesis of functional organic molecules used in advanced chemical processes.
2-Amino anthraquinone is employed in academic and industrial research investigating the optical, electronic, and photochemical properties of anthraquinone compounds.
2-Amino anthraquinone is used in laboratory-scale organic synthesis for preparing substituted anthraquinone derivatives through further chemical modification.

2-Amino anthraquinone is also applied in the development of specialty chemicals where stable aromatic quinone structures are required.
Its strong aromatic backbone makes 2-Amino anthraquinone a valuable intermediate for producing high-performance organic compounds used in various industrial chemical processes.

-Dye intermediate uses of 2-Amino anthraquinone:
The most important industrial use of 2-Amino anthraquinone is as an intermediate for anthraquinone dyes.
2-Amino anthraquinone is used to introduce an amino functionality into the anthraquinone framework, after which further chemical transformations can generate dyes with specific color, solubility and textile affinity.
Historical industrial information identifies 2-Amino anthraquinone as a precursor/intermediate associated with several anthraquinone dyes and pigments, including Vat Blue 4, Vat Blue 6, Vat Blue 12, Vat Blue 24, Vat Yellow 1 and Pigment Blue 22.

-Vat dyes uses of 2-Amino anthraquinone:
2-Amino anthraquinone is used in the chemistry of vat dyes, an important class of dyes used particularly for textile coloration.
2-Amino anthraquinone's anthraquinone framework provides a strong chromophoric structure, while subsequent chemical modification can produce compounds with desirable vat-dye characteristics.

-Pigment manufacture uses of 2-Amino anthraquinone:
2-Amino anthraquinone can serve as an intermediate in the synthesis of anthraquinone pigments, including derivatives used for high-performance coloration.
The rigid conjugated anthraquinone framework, 2-Amino anthraquinone, is particularly valuable for pigment chemistry because it can contribute to strong color and high chemical stability.

-Pharmaceutical intermediates uses of 2-Amino anthraquinone:
2-Amino anthraquinone is also described as an intermediate in pharmaceutical synthesis.
2-Amino anthraquinone provides an anthraquinone framework containing an amino group that can be further functionalized.
This should be understood as an industrial chemical-intermediate application, not as evidence that 2-Amino anthraquinone itself is an approved pharmaceutical active ingredient.

-Synthesis of other anthraquinone derivatives uses of 2-Amino anthraquinone:
Because the amino group can be transformed into a variety of other functional groups, 2-Amino anthraquinone is useful as a starting material for preparing more complex anthraquinone compounds.
2-Amino anthraquinone's derivatives can be generated through diazotization, substitution, acylation, alkylation and other organic transformations.

-Research applications of 2-Amino anthraquinone:
2-Amino anthraquinone has been investigated in materials science and surface chemistry.
2-Amino anthraquinone's used in the fabrication of high-performance supercapacitor electrodes based on chemically modified graphene hydrogels and in the preparation of ordered molecular assemblies on Au(111) surfaces.
These are research/specialty applications rather than 2-Amino anthraquinone's principal bulk industrial use.

BENEFITS AND INDUSTRIAL VALUE of 2-AMINO ANTHRAQUINONE:
The main value of 2-Amino anthraquinone comes from the combination of its stable anthraquinone chromophore and chemically reactive amino group.
2-Amino anthraquinone structure provides a large conjugated system that can produce intense optical absorption and strong coloration in derivatives.
The amino group provides a convenient site for further chemical modification.

Consequently, 2-Amino anthraquinone can serve as a versatile intermediate from which many structurally different anthraquinone dyes, pigments and specialty chemicals can be prepared.
2-Amino anthraquinone's high melting point, low vapor pressure and rigid aromatic structure are also useful characteristics in chemical processing.

CHARACTERISTICS of 2-AMINO ANTHRAQUINONE:
2-Amino anthraquinone is a high-melting, low-volatility, poorly water-soluble, highly conjugated aromatic solid.
2-Amino anthraquinone's molecular structure combines an anthraquinone chromophore with a reactive amino group.
This combination makes 2-Amino anthraquinone particularly valuable as an intermediate for the synthesis of anthraquinone dyes, vat dyes, pigments and specialty chemicals.

Its rigid, planar and conjugated structure gives 2-Amino anthraquinone strong electronic and optical properties, while the amino group allows further chemical modification through reactions such as diazotization, acylation and alkylation.
2-Amino anthraquinone's principal industrial importance is therefore as a building block for colorants rather than as a final-use chemical.

CHEMICAL STRUCTURE AND CHARACTERISTICS of 2-AMINO ANTHRAQUINONE:
2-Amino anthraquinone consists of an anthraquinone skeleton bearing an amino group at the 2-position.
2-Amino anthraquinone portion contains three fused six-membered carbon rings.

The two outer rings are benzene-like aromatic rings, while the central ring contains the two carbonyl groups at positions 9 and 10.
The simplified structural description is:
Anthraquinone core + NH₂ substituent at C-2

The two carbonyl groups make the molecule a quinone, while the amino group gives it aromatic-amine chemistry.
The extended conjugated π-electron system allows electrons to be delocalized over a large portion of the molecule.
This is an important reason why anthraquinone derivatives can absorb visible light and exhibit intense colors.

The amino group also provides a chemically reactive site.
2-Amino anthraquinone can participate in diazotization, acylation and alkylation reactions, while the anthraquinone ring can undergo electrophilic substitution such as nitration or sulfonation under appropriate conditions.

 
CHEMICAL REACTIVITY of 2-AMINO ANTHRAQUINONE:
2-Amino anthraquinone is chemically reactive at both the amino group and the anthraquinone ring.
The amino group can be diazotized, allowing the preparation of diazonium intermediates that can subsequently undergo further transformations.
This provides a route to structurally diverse anthraquinone derivatives.

The nitrogen atom can undergo acylation and alkylation, producing substituted aminoanthraquinones.
The aromatic ring system can undergo nitration and sulfonation, allowing modification of its electronic properties and water compatibility.
2-Amino anthraquinone can form salts with mineral acids because of the amino functionality.

THERMAL CHARACTERISTICS of 2-AMINO ANTHRAQUINONE:
2-Amino anthraquinone has a high melting/decomposition temperature because its molecular structure is rigid, planar and strongly conjugated.
Its extremely low vapor pressure means that 2-Amino anthraquinone is essentially nonvolatile under ordinary room-temperature conditions.
When heated sufficiently to decomposition, 2-Amino anthraquinone can release nitrogen oxides, carbon monoxide and carbon dioxide.

WHY 2-AMINO ANTHRAQUINONE STRUCTURE IS IMPORTANT
Anthraquinone is one of the most important chromophoric structures in synthetic dye chemistry.
The two carbonyl groups at the 9,10 positions interact electronically with the aromatic system.
This creates an extended conjugated structure capable of absorbing electromagnetic radiation at relatively long wavelengths.

Introducing an amino group at position 2 changes the electronic distribution of the molecule and provides an additional functional group for chemical derivatization.
This makes 2-Amino anthraquinone a useful building block rather than simply a final dye.
2-Amino anthraquinone appears as red needle-like crystals or dark brown granular solid.
2-Amino anthraquinone is an anthraquinone.

SYNTHESIS AND CHEMICAL PRODUCTION of 2-AMINO ANTHRAQUINONE
2-Amino anthraquinone can be prepared by replacing an appropriate substituent on the anthraquinone ring with an amino group.
One established industrial route involves 2-chloroanthraquinone, in which the chlorine substituent is replaced by an amino functionality.
Older processes have also used anthraquinone-2-sulfonic acid as a starting material, replacing the sulfonic-acid group.
Nitroanthraquinone routes followed by reduction are another chemically logical approach and are represented in commercial chemical literature.

PHYSICAL and CHEMICAL PROPERTIES of 2-AMINO ANTHRAQUINONE:
Chemical name: 2-Aminoanthraquinone
IUPAC name: 2-Aminoanthracene-9,10-dione
CAS Number: 117-79-3
EC Number: 204-208-4
EINECS Number: 204-208-4
PubChem CID: 8341
ChemSpider ID: 8038
ChEBI ID: CHEBI:34258
ChEMBL ID: CHEMBL84685
Molecular formula: C₁₄H₉NO₂
Molecular weight: 223.23 g/mol

Exact mass: approximately 223.0633 Da
Monoisotopic mass: approximately 223.0633 Da
InChIKey: XOGPDSATLSAZEK-UHFFFAOYSA-N
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)N
Physical state: Solid
Chemical class: Anthraquinone derivative / aromatic amine / quinone
Functional groups: Aromatic amine, two ketone groups, fused aromatic ring system
ECHA identifies the substance as 2-aminoanthraquinone with EC number 204-208-4, CAS 117-79-3 and molecular formula C₁₄H₉NO₂. 
PubChem gives the same identity information and assigns CID 8341.
Appearance: Red needle-like crystals, red/orange-brown crystalline solid or dark-brown granular solid.

Physical state: Solid.
Color: Brown to red/orange-brown depending on crystal form, purity and observation conditions.
Odor: No strong characteristic odor is generally emphasized in the available database descriptions.
Melting point: Approximately 292–295 °C with decomposition according to ChemicalBook. 
Some references, including Wikipedia, give approximately 302–303 °C, illustrating that reported melting/decomposition temperatures vary between sources and experimental conditions. 
For technical documentation, the supplier's specification should be used.
Boiling point: Approximately 364.5 °C, but this is a rough estimated value, rather than a well-established experimental normal boiling point.
Density: Approximately 1.1814 g/cm³, listed as an estimate by ChemicalBook.
Refractive index: Approximately 1.4700, estimated.

Flash point: Approximately 283 °C is listed by ChemicalBook, although the material is primarily handled as a high-melting solid and actual fire behavior depends on particle size and experimental conditions.
Water solubility: Approximately 0.163 mg/L at 25 °C (163 µg/L), indicating very low water solubility.
Solubility in ethanol: Soluble according to the cited literature entry.
Storage temperature: ChemicalBook recommends approximately 2–8 °C and protection from light for laboratory material.
Vapor pressure: Approximately 5.0 × 10⁻¹¹ mmHg at 25 °C, indicating extremely low volatility at room temperature.
Vapor pressure at elevated temperature: An ILO-WHO/ICSC-derived value reported by PubChem is approximately 1.3 Pa at 180 °C.
Log Kow: Approximately 3.31–3.3, indicating substantially greater affinity for organic phases than for water.
Henry's law constant: Approximately 1.1 × 10⁵ mol/(m³·Pa) at 25 °C according to the ChemicalBook entry.
pKa: Approximately 0.97 ± 0.20, predicted.

Stability: Generally stable under appropriate storage conditions.
Water behavior: Very poorly soluble/essentially insoluble in water.
Thermal decomposition: Heating to decomposition can generate toxic nitrogen oxides and carbon-containing fumes.
Number of carbon atoms: 14
Number of hydrogen atoms: 9
Number of nitrogen atoms: 1
Number of oxygen atoms: 2
Aromatic/conjugated system: Extensive
Aromatic rings: Three fused-ring anthraquinone framework
Carbonyl groups: 2
Primary amino group: 1

Hydrogen-bond donors: 1
Hydrogen-bond acceptors: approximately 3, considering the amino nitrogen and two carbonyl oxygens.
Formal charge: 0 in the neutral molecule.
Rotatable bonds: Very few; the molecule is predominantly rigid and planar.
Ring system: Fused polycyclic aromatic system.
Polarity: Moderately polar for an aromatic hydrocarbon derivative, because of the amino and carbonyl groups.
Volatility: Extremely low at room temperature.
Hydrophobicity: Moderate, consistent with a reported log Kow around 3.3.
The rigid, conjugated structure and relatively planar molecular framework are characteristic of anthraquinone dyes and pigment intermediates.
CAS No.: 117-79-3
EC No.: 204-208-4

Molecular Formula: C₁₄H₉NO₂
Molecular Weight: 223.23 g/mol
PubChem CID: 8341
ChemSpider ID: 8038
ChEBI ID: CHEBI:34258
IUPAC Name: 2-Aminoanthracene-9,10-dione
InChIKey: XOGPDSATLSAZEK-UHFFFAOYSA-N
Physical form: Crystalline solid
Main industrial role: Dye and pigment intermediate
Other role: Pharmaceutical and specialty-chemical intermediate
Water solubility: ~0.163 mg/L at 25 °C
Melting/decomposition range: ~292–295 °C reported by ChemicalBook; other sources report ~302–303 °C

Log Kow: ~3.3
Vapor pressure: ~5 × 10⁻¹¹ mmHg at 25 °C
Molecular Weight: 223.23 g/mol
XLogP3: 2.7
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 0
Exact Mass: 223.063328530 Da
Monoisotopic Mass: 223.063328530 Da
Topological Polar Surface Area: 60.2 Ų
Heavy Atom Count: 17

Formal Charge: 0
Complexity: 352
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Chemical Formula: C14H9NO2
Molar Mass: 223.231 g·mol−1
Appearance: white solid
Melting Point: 302–303 °C (576–577 °F; 575–576 K)
Empirical Formula (Hill Notation): C14H9NO2
CAS Number: 117-79-3

Molecular Weight: 223.23
EC Number: 204-208-4
UNSPSC Code: 12352100
PubChem Substance ID: 24850139
Beilstein/REAXYS Number: 745903
MDL Number: MFCD00001233
Form: powder
Physical State: powder
Color: dark brown
Odor: No data available
Melting Point/Freezing Point: Melting point/range: 292 - 295 °C - dec.
Initial Boiling Point and Boiling Range: No data available
Flammability (Solid, Gas): No data available
Upper/Lower Flammability or Explosive Limits: No data available

Flash Point: 283,00 °C - closed cup
Autoignition Temperature: No data available
Decomposition Temperature: No data available
pH: No data available
Viscosity: Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water Solubility: No data available
Partition Coefficient: n-octanol/water: No data available
Vapor Pressure: No data available
Density: No data available
Relative Density: No data available
Relative Vapor Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: No data available

FIRST AID MEASURES of 2-AMINO ANTHRAQUINONE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation: 
Fresh air.
*In case of skin contact: 
Take off immediately all contaminated clothing. 
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact: 
Rinse out with plenty of water. 
Call in ophthalmologist. 
Remove contact lenses.
*If swallowed:
After swallowing: 
Immediately make victim drink water (two glasses at most). 
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of 2-AMINO ANTHRAQUINONE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains. 
Collect, bind, and pump off spills. 
Observe possible material restrictions. 
Take up dry. 
Dispose of properly. 
Clean up affected area.

FIRE FIGHTING MEASURES of 2-AMINO ANTHRAQUINONE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2) 
Foam 
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of 2-AMINO ANTHRAQUINONE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection. 
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A 
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of 2-AMINO ANTHRAQUINONE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed. 
Dry.

STABILITY and REACTIVITY of 2-AMINO ANTHRAQUINONE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available

For more information, you can contact Ataman Kimya.
İstanbul Head Office: +90 216 577 10 10
Fax: +90 216 577 42 80