2-Chloroanthraquinone is used in the manufacture of specialty organic pigments that provide high color stability and durability.
2-Chloroanthraquinone is employed as a chemical intermediate for producing pharmaceutical and fine chemical compounds.
2-Chloroanthraquinone is used in laboratory research for the synthesis of substituted anthraquinone derivatives.
CAS Number: 131-09-9
EC Number: 205-010-0
Molecular Formula: C₁₄H₇ClO₂
Molecular Weight: 242.65 g/mol
SYNONYMS:
2-Chloroanthraquinone, 2-Chloroanthra-9,10-quinone, 2-Chloro-9,10-anthraquinone, 2-Chloro-9,10-anthracenedione, 2-Chloroanthracene-9,10-dione, 9,10-Anthracenedione, 2-chloro-, Anthraquinone, 2-chloro-, β-Chloroanthraquinone, Beta-Chloroanthraquinone, .beta.-Chloroanthraquinone, 2-Chloroanthraquinone, 2-Chloroanthra-9,10-dione, Anthraquinone, 2-chloro-, 2-Chloro-9,10-anthracenedione, EINECS 205-010-0, CAS 131-09-9, NSC 1702, AI3-00064, 2-Chloroanthraquinone, 2-Chloroanthracene-9,10-dione, 9,10-Anthracenedione, 2-chloro-, 131-09-9, 2-Chloro-9,10-anthracenedione, beta-Chloroanthraquinone, 2-Chloro-9,10-anthraquinone, EINECS 205-010-0, NSC 1702, 2-chloro-9, 10-anthracenedione β-chloroanthrapuinone 10-Anthracenedione 2-chloro-9, 2-Chloroanthracene-9,10-dione, Anthraquinone, 2-chloro-, beta-Chloroanthraquinone, β-chloroanthraquinone, 2-Chloro-9,10-anthracenedione, anthraquinone,2-chloro-, β-chloroanthrapuinone, Melting point standard 2-chloroanthraquinone, 2-Chloroanthraqukinone, MELTING POINT STANDARD 2-CHLORO- &, 2-Chloranthrachinon, 2-Chloroanthraquinone,99%, 2-Chloroanthraquinone,97%
2-Chloroanthraquinone is an organic compound with the formula C14H7O2Cl.
2-Chloroanthraquinone is one of two monochlorinated anthraquinone isomers.
2-Chloroanthraquinone is prepared by diacylation of chlorobenzene with phthalic anhydride, a standard route to anthraquinones.
Heating 2-chloroanthraquinone under pressure with ammonia gives 2-aminoanthraquinone, which in turn is a precursor to indanthrone, a commercial blue dye.
2-Chloroanthraquinone is a pale yellow needle crystal.
2-Chloroanthraquinone is insoluble in water, soluble in hot benzene, nitrobenzene, concentrated sulfuric acid.
2-Chloroanthraquinone is an important dye intermediate that can be used to make alizarin and aminoanthraquinone.
2-Chloroanthraquinone has been evaluated as a photo-reagent for the analysis of ginsenosides using photoreduction fluorescence (PRF) detection method.
2-Chloroanthraquinone is a compound of Organic Building Blocks research chemicals for sale.
2-Chloroanthraquinone's CAS No. is 131-09-9, molecular formula is C14H7ClO2 and its molecular weight is 242.66 g/mol.
2-Chloroanthraquinone is a chlorinated anthraquinone derivative consisting of an anthraquinone nucleus bearing one chlorine atom at the 2-position.
2-Chloroanthraquinone is also called 2-chloroanthracene-9,10-dione or β-chloroanthraquinone.
2-Chloroanthraquinone is an aromatic quinone with an extended, highly conjugated three-ring system and two ketone groups at the 9- and 10-positions.
2-Chloroanthraquinone is primarily important as a chemical intermediate for the manufacture of anthraquinone dyes and other anthraquinone derivatives.
One particularly important transformation is 2-Chloroanthraquinone's conversion to 2-aminoanthraquinone, which is itself an important intermediate for dyes such as indanthrone.
2-Chloroanthraquinone belongs to the anthraquinone family of aromatic quinones.
2-Chloroanthraquinone framework contains three fused rings and two carbonyl groups positioned at C-9 and C-10.
In 2-chloroanthraquinone, a hydrogen atom on one of the outer aromatic rings is replaced by chlorine at position 2.
The combination of the rigid anthraquinone skeleton and the chlorine substituent gives 2-Chloroanthraquinone useful chemical reactivity for further functionalization.
In particular, the chlorine atom can be replaced by nucleophilic groups under suitable reaction conditions, allowing 2-chloroanthraquinone to serve as a versatile starting material for the preparation of substituted anthraquinones.
USES and APPLICATIONS of 2-CHLOROANTHRAQUINONE:
Research chemical: 2-Chloroanthraquinone is also used as a laboratory/research intermediate for preparing and studying substituted anthraquinones.
2-Chloroanthraquinone's greatest industrial importance is therefore as a building block/intermediate, rather than as a final-use chemical.
It is an important dye intermediate; 2-chloroanthraquinone is used to prepare alizarin and aminoanthraquinone.
2-Chloroanthraquinone is widely used as an intermediate in the production of anthraquinone-based dyes and pigments.
2-Chloroanthraquinone serves as a key raw material in the synthesis of disperse, vat, and solvent dyes for the textile industry.
2-Chloroanthraquinone is used in the manufacture of specialty organic pigments that provide high color stability and durability.
2-Chloroanthraquinone is employed as a chemical intermediate for producing pharmaceutical and fine chemical compounds.
2-Chloroanthraquinone is used in laboratory research for the synthesis of substituted anthraquinone derivatives.
2-Chloroanthraquinone is applied in organic synthesis because the chlorine atom can be readily replaced by other functional groups through substitution reactions.
2-Chloroanthraquinone is used in the preparation of advanced aromatic compounds for industrial chemical processes.
2-Chloroanthraquinone is utilized in research involving anthraquinone derivatives with potential biological and functional material applications.
2-Chloroanthraquinone is also used in the development of specialty chemicals for coatings, inks, and colorant formulations where anthraquinone chemistry is required.
-Dye intermediate uses of 2-Chloroanthraquinone:
The principal application of 2-chloroanthraquinone is as a dye intermediate.
2-Chloroanthraquinone is used as a starting material for producing other anthraquinone compounds that can subsequently be converted into dyes and pigments.
2-Chloroanthraquinone is an important dye intermediate.
-2-Chloroanthraquinone is used production of 2-aminoanthraquinone
One of its most important synthetic applications is the preparation of 2-aminoanthraquinone.
The chlorine atom is replaced by an amino group through ammonolysis.
The resulting 2-aminoanthraquinone is an important intermediate in the production of anthraquinone dyes, including indanthrone-related chemistry.
The overall relationship can be summarized as:
2-Chloroanthraquinone → 2-Aminoanthraquinone → further anthraquinone dye intermediates
Alizarin-related chemistry
2-chloroanthraquinone is an intermediate that can be used in the production of alizarin and aminoanthraquinone.
-Anthraquinone dyes and pigments uses of 2-Chloroanthraquinone:
Because chlorine can be replaced by other functional groups, 2-chloroanthraquinone provides a convenient route to a variety of substituted anthraquinones that can be used in dye and pigment synthesis.
The anthraquinone chromophore is particularly valuable in color chemistry because of its strong conjugation and optical properties.
-Photochemical applications of 2-Chloroanthraquinone:
2-Chloroanthraquinone has been evaluated as a photoreagent for photoreduction fluorescence detection of ginsenosides.
This is a specialized analytical application rather than its principal commercial use.
BENEFITS AND INDUSTRIAL IMPORTANCE of 2-CHLOROANTHRAQUINONE:
The principal benefit of 2-chloroanthraquinone is its synthetic versatility.
2-Chloroanthraquinone framework is already an advanced aromatic structure, while the chlorine atom provides a convenient position for subsequent functionalization.
This makes 2-Chloroanthraquinone possible to use the compound as a platform for synthesizing many other anthraquinone derivatives.
2-Chloroanthraquinone's major industrial value comes from:
High-value anthraquinone skeleton
Useful chlorine substitution site
Ability to form aminoanthraquinone derivatives
Application in dye and pigment synthesis
Useful photochemical properties
High thermal stability relative to low-molecular-weight aromatic compounds
Availability as a crystalline solid that can be weighed and processed in laboratory/industrial operations
WHY THE CHLORINE ATOM IS IMPORTANT:
The chlorine atom is not simply an inert substituent.
Its position at carbon 2 is chemically useful because the neighboring anthraquinone carbonyl system changes the electronic environment of the aromatic ring.
Under suitable reaction conditions, nucleophiles can replace the chlorine atom.
This makes the compound a useful electrophilic substrate for preparing substituted anthraquinones.
For example:
Cl → NH₂ gives 2-aminoanthraquinone.
This particular transformation is one of the reasons 2-chloroanthraquinone is an important intermediate in anthraquinone dye chemistry.
CHEMICAL PROPERTIES of 2-CHLOROANTHRAQUINONE:
2-Chloroanthraquinone contains an anthraquinone quinone system with two ketone groups and a chlorine substituent on the aromatic ring.
The two carbonyl groups provide the characteristic chemical behavior of anthraquinones.
The extended conjugated system gives the molecule substantial electronic stability and allows 2-Chloroanthraquinone to participate in redox chemistry.
The chlorine atom at the 2-position is particularly useful synthetically.
Under appropriate conditions, 2-Chloroanthraquinone can undergo nucleophilic substitution, allowing the chlorine to be replaced by groups such as amino, hydroxyl or alkoxy functionalities.
This property is important because 2-Chloroanthraquinone permits the preparation of a range of substituted anthraquinones from a single intermediate.
2-Chloroanthraquinone is relatively rigid and planar.
There are essentially no freely rotating aliphatic chains, and the three fused aromatic rings provide a large conjugated π-electron system.
2-Chloroanthraquinone is poorly soluble in water but can dissolve in certain organic solvents, particularly when heated.
STRUCTURAL CHARACTERISTICS of 2-CHLOROANTHRAQUINONE:
The basic structure can be represented conceptually as:
Anthraquinone core + chlorine substituent at the 2-position
The anthraquinone portion can be represented as:
C₁₄H₈O
Replacing one aromatic hydrogen with chlorine gives:
C₁₄H₇ClO₂
This substitution increases molecular weight and modifies the electronic characteristics of the anthraquinone system without destroying its overall conjugated structure.
2-Chloroanthraquinone's rigid structure is one of its most important physical characteristics.
The fused aromatic system restricts molecular flexibility and contributes to 2-Chloroanthraquinone's crystalline nature and relatively high melting point.
CHEMICAL REACTIVITY of 2-CHLOROANTHRAQUINONE:
The most important reactive feature of 2-chloroanthraquinone is the C–Cl bond on the anthraquinone ring.
Because 2-Chloroanthraquinone carbonyl groups withdraw electron density from the aromatic system, the chlorine-bearing carbon can be susceptible to nucleophilic substitution under appropriate conditions.
This makes 2-chloroanthraquinone useful for preparing:
2-aminoanthraquinone
2-hydroxyanthraquinone derivatives
2-alkoxy derivatives
Other substituted anthraquinones
The transformation to 2-aminoanthraquinone is especially important.
Heating 2-chloroanthraquinone with ammonia under pressure can replace chlorine with an amino group.
2-Aminoanthraquinone can then be used in further dye synthesis, including the chemistry of indanthrone.
2-Chloroanthraquinone nucleus can also undergo other aromatic chemical transformations, including reactions involving nitration, sulfonation and halogenation under suitable controlled conditions.
REDOX CHARACTERISTICS of 2-CHLOROANTHRAQUINONE:
Anthraquinones are quinone compounds and can participate in reversible oxidation-reduction chemistry.
2-Chloroanthraquinone carbonyl groups can be reduced to corresponding hydroquinone/anthrahydroquinone-type states and subsequently oxidized again.
This redox behavior is one reason anthraquinone derivatives have attracted interest beyond dyes, including in organic electronic materials, photochemistry and redox-active molecular systems.
For 2-chloroanthraquinone specifically, the anthraquinone core is the principal redox-active portion of the molecule, while chlorine primarily serves as a substituent that provides a useful synthetic reaction site.
THERMAL PROPERTIES of 2-CHLOROANTHRAQUINONE:
2-Chloroanthraquinone melts at approximately 209–211 °C.
2-Chloroanthraquinone's high melting point is consistent with:
The rigid fused-ring structure,
Strong intermolecular interactions,
Large planar aromatic surface,
Extended π-conjugation,
and relatively high molecular weight.
2-Chloroanthraquinone is therefore normally handled as a crystalline solid rather than as a liquid.
2-Chloroanthraquinone's estimated boiling point of approximately 345.65 °C should be interpreted cautiously because high-temperature behavior of aromatic quinones can involve decomposition rather than clean atmospheric boiling.
SOLUBILITY CHARACTERISTICS of 2-CHLOROANTHRAQUINONE:
2-Chloroanthraquinone is insoluble in water.
This is expected from 2-Chloroanthraquinone's molecular structure because the molecule has:
A large hydrophobic aromatic surface,
No hydrogen-bond donor groups,
Only two hydrogen-bond acceptor sites,
and a rigid planar structure.
2-Chloroanthraquinone is reported to dissolve in hot benzene, nitrobenzene and concentrated sulfuric acid.
The low water solubility is also environmentally relevant because 2-Chloroanthraquinone does not readily dissolve and disperse in water in the same way as highly water-soluble organic chemicals.
PREPARATION / SYNTHESIS of 2-CHLOROANTHRAQUINONE:
A known preparation route involves the Friedel–Crafts-type condensation of phthalic anhydride with chlorobenzene, producing an intermediate chlorobenzoylbenzoic acid, followed by cyclization to form the anthraquinone ring system.
The preparation as condensation of phthalic anhydride and chlorobenzene to form p-chlorobenzoylbenzoic acid followed by sulfuric-acid cyclization.
The simplified sequence is:
Phthalic anhydride + chlorobenzene → chlorobenzoylbenzoic acid → cyclization → 2-chloroanthraquinone
The exact industrial process can involve different catalysts, solvents, temperatures and purification steps.
RELATIONSHIP of 2-CHLOROANTHRAQUINONE WITH 2-AMINOANTHRAQUINONE:
This is particularly relevant because you previously asked about 2-aminoanthraquinone.
The two compounds are directly related:
2-Chloroanthraquinone: C₁₄H₇ClO₂, MW 242.65 g/mol
2-Aminoanthraquinone: C₁₄H₉NO₂, MW 223.23 g/mol
In 2-chloroanthraquinone, the substituent at position 2 is Cl.
In 2-aminoanthraquinone, that substituent is NH₂.
Under suitable ammonolysis conditions, the chlorine can be replaced by an amino group.
Thus, 2-chloroanthraquinone is an important precursor to 2-aminoanthraquinone.
This makes 2-chloroanthraquinone an important intermediate in the synthesis chain leading to several anthraquinone dyes.
CHARACTERISTICS of 2-CHLOROANTHRAQUINONE:
2-Chloroanthraquinone is a pale-yellow, high-melting, crystalline anthraquinone derivative with very low water solubility and low volatility.
2-Chloroanthraquinone's molecular formula is C₁₄H₇ClO₂, its molecular weight is 242.65 g/mol, its CAS number is 131-09-9, and its EC number is 205-010-0.
2-Chloroanthraquinone's most important chemical characteristic is the combination of a strongly conjugated anthraquinone chromophore and a reactive chlorine substituent.
The 2-chloroanthraquinone portion provides the characteristic quinone/redox and optical properties, while the chlorine atom provides a useful site for further substitution.
2-Chloroanthraquinone's principal commercial importance is as a dye and pigment intermediate, especially for preparing other substituted anthraquinones.
2-Chloroanthraquinone's conversion to 2-aminoanthraquinone is particularly important because 2-aminoanthraquinone is subsequently used in the synthesis of anthraquinone dyes, including indanthrone-related colorants.
PREPARATION of 2-CHLOROANTHRAQUINONE:
2-Chloroanthraquinone is prepared by condensing phthalic anhydride and chlorobenzene into p-chlorobenzoylbenzoic acid, and then cyclizing it with sulfuric acid.
PHYSICAL and CHEMICAL PROPERTIES of 2-CHLOROANTHRAQUINONE:
Chemical name: 2-Chloroanthraquinone
IUPAC name: 2-Chloroanthracene-9,10-dione
CAS Number: 131-09-9
EC Number: 205-010-0
EINECS Number: 205-010-0
PubChem CID: 8553
ChemSpider ID: 8235
Molecular Formula: C₁₄H₇ClO₂
Molecular Weight: 242.65 g/mol (often rounded to 242.66 g/mol in supplier databases)
Exact Mass: approximately 242.0134 Da
Monoisotopic Mass: approximately 242.0134 Da
Chemical class: Chlorinated anthraquinone / quinone / aromatic halogen compound
Physical state: Solid
Appearance: Pale yellow to yellow crystalline solid or needles
Main industrial role: Dye intermediate and synthetic intermediate
InChI: InChI=1S/C14H7ClO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H
InChIKey: FPKCTSIVDAWGFA-UHFFFAOYSA-N
Canonical SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)Cl
Physical state: Solid
Appearance: Pale yellow needle-shaped crystals; supplier descriptions also include white, light-orange to yellow crystalline material.
Color: Pale yellow to yellow
Form: Powder to crystalline solid
Odor: No strong characteristic odor is generally reported.
Melting point: 209–211 °C
Boiling point: Approximately 345.65 °C, listed as a rough estimated value.
Density: Approximately 1.2377 g/cm³, estimated.
Refractive index: Approximately 1.5380, estimated.
Water solubility: Insoluble
Solubility in hot benzene: Soluble
Solubility in nitrobenzene: Soluble
Solubility in concentrated sulfuric acid: Soluble
Vapor pressure: Very low at ordinary temperature because of its high melting point and rigid aromatic structure.
Volatility: Very low at room temperature.
Storage: Sealed, dry, room-temperature storage is commonly specified; laboratory suppliers may provide additional light-protection recommendations.
Melting behavior: The relatively high melting point is consistent with its rigid, planar, highly conjugated molecular structure.
The reported physical properties are particularly useful for distinguishing 2-chloroanthraquinone from lower-molecular-weight chlorinated aromatic compounds: it is a high-melting crystalline solid rather than a volatile liquid.
Carbon atoms: 14
Hydrogen atoms: 7
Chlorine atoms: 1
Oxygen atoms: 2
Nitrogen atoms: 0
Carbonyl groups: 2
Chlorine substituents: 1
Aromatic/conjugated system: Extensive
Fused rings: Three
Formal charge: 0
Hydrogen-bond donors: 0
Hydrogen-bond acceptors: 2
Rotatable bonds: Essentially 0
Aromatic rings: Three fused aromatic rings
Molecular geometry: Predominantly rigid and planar
Polarity: Moderate, due primarily to the two carbonyl groups
Hydrophobic character: Relatively significant because of the large aromatic framework and low water solubility.
The absence of hydrogen-bond donor groups and the large hydrophobic aromatic surface contribute to the compound's very low water solubility.
Empirical Formula (Hill Notation): C14H7ClO2
CAS Number: 131-09-9
Molecular Weight: 242.66
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24849604
EC Number: 205-010-0
Beilstein/REAXYS Number: 2051842
MDL Number: MFCD00001227
Assay: 97%
Form: powder
Chemical Formula: C14H7ClO2
Molar Mass: 242.66 g·mol−1
Appearance: yellow solid
Melting Point: 210 °C (410 °F; 483 K)
Physical State: solid
Color: No data available
Odor: No data available
Melting Point/Freezing Point: Melting point/range: 209 - 211 °C - lit.
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: No data available
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 Vapour Density: No data available
Particle Characteristics: No data available
Explosive Properties: No data available
Oxidizing Properties: No data available
Other Safety Information: No data available
Melting Point: 209-211 °C (lit.)
Boiling Point: 345.65°C (rough estimate)
Density: 1.2377 (rough estimate)
Refractive Index: 1.5380 (estimate)
Storage Temperature: Sealed in dry, Room Temperature
Form: powder to crystal
Color: White to Light orange to Yellow
Water Solubility: insoluble
BRN: 2051842
Henry's Law Constant: 4.2×103 mol/(m3Pa) at 25℃, Zhang et al. (2010)
InChI: InChI=1S/C14H7ClO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H
InChIKey: FPKCTSIVDAWGFA-UHFFFAOYSA-N
SMILES: C1=C2C(C(=O)C3=C(C2=O)C=CC=C3)=CC=C1Cl
CAS Database Reference: 131-09-9(CAS Database Reference)
NIST Chemistry Reference: 2-Chloroanthraquinone(131-09-9)
EPA Substance Registry System: 9,10-Anthracenedione, 2-chloro- (131-09-9)
Molecular Formula / Molecular Weight: C14H7ClO2 = 242.66
Physical State (20 deg.C): Solid
Storage Temperature: Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 131-09-9
Reaxys Registry Number: 2051842
PubChem Substance ID: 87565303
SDBS (AIST Spectral DB): 122
MDL Number: MFCD00001227
Density: 1.4±0.1 g/cm3
Boiling Point: 425.7±34.0 °C at 760 mmHg
Melting Point: 209-211 °C(lit.)
Molecular Formula: C14H7ClO2
Molecular Weight: 242.657
Flash Point: 179.7±26.2 °C
Exact Mass: 242.013458
PSA: 34.14000
LogP: 4.11
Vapour Pressure: 0.0±1.0 mmHg at 25°C
Index of Refraction: 1.666
InChIKey: FPKCTSIVDAWGFA-UHFFFAOYSA-N
SMILES: O=C1c2ccccc2C(=O)c2cc(Cl)ccc21
Water Solubility: insoluble
FIRST AID MEASURES of 2-CHLOROANTHRAQUINONE:
-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-CHLOROANTHRAQUINONE:
-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-CHLOROANTHRAQUINONE:
-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-CHLOROANTHRAQUINONE:
-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-CHLOROANTHRAQUINONE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of 2-CHLOROANTHRAQUINONE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
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