81-49-2

Basic information

• Product Name: 1-Amino-2,4-dibromoanthraquinone
• Synonyms: 1-Amino-2,4-dibromanthrachinon;1-amino-2,4-dibromanthrachinon(czech);1-amino-2,4-dibromo-10-anthracenedione;1-Amino-2,4-dibromoanthra-9,10-quinone;1-amino-2,4-dibromo-anthraquinon;9,10-Anthracenedione, 1-amino-2,4-dibromo-;Anthraquinone, 1-amino-2,4-dibromo-;NCI-C55458
• CAS NO: 81-49-2
• Molecular Formula: C₁₄H₇Br₂NO₂
• Molecular Weight: 381.02
• EINECS: 201-354-0
• Product Categories: Intermediates of Dyes and Pigments;Anthraquinones, Hydroquinones and Quinones;Aldehyde;Steroids
• Mol File: 81-49-2.mol

Chemical Properties

• Melting Point: 226°C
• Boiling Point: 550.4 °C at 760 mmHg
• Flash Point: 286.7 °C
• Appearance: red powder
• Density: 1.8218 (rough estimate)
• Vapor Pressure: 3.64E-12mmHg at 25°C
• Refractive Index: 1.6220 (estimate)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: -3.09±0.20(Predicted)
• Water Solubility: <0.1 g/100 mL at 23℃
• Stability: Stable.
• CAS DataBase Reference: 1-Amino-2,4-dibromoanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-2,4-dibromoanthraquinone(81-49-2)
• EPA Substance Registry System: 1-Amino-2,4-dibromoanthraquinone(81-49-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• TSCA: Yes
• Hazardous Substances Data: 81-49-2(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
1-Amino-2,4-dibromoanthraquinone is used as a key intermediate for the production of anthraquinone dyes, which are essential in the textile industry. These dyes are particularly favored for their ability to impart vibrant and long-lasting colors to fibers and textiles, such as cotton, wool, and cellulose acetate.
As a starting material for the manufacture of vat dyes:
ADBAQ is used as a starting material for the production of vat dyes, a class of water-insoluble dyes that can be easily reduced to a water-soluble and colorless form. This property allows the dyes to be readily impregnated into fibers and textiles. Upon oxidation, the dyes form an insoluble colored form that exhibits remarkable fastness to washing, light, and chemicals, making them highly desirable for use in the textile industry.

Air & Water Reactions

1-Amino-2,4-dibromoanthraquinone is sensitive to long term exposure to air and light . Insoluble in water.

Fire Hazard

1-Amino-2,4-dibromoanthraquinone is probably combustible.

Potential Exposure

A halide-and amine-substituted aromatic compound. (halogenated amine). Intermediate in the production of dyes.

Carcinogenicity

1-Amino-2,4-dibromoanthraquinone (ADBAQ) is reasonably anticipated to be a human carcinogen based on sufficient evidence from studies in experimental animals.

Shipping

UN3259 Amines, solid, corrosive, n.o.s, or Polyamines, solid, corrosive, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required. UN2735 Amines, liquid, corrosive, n.o.s, or Polyamines, liquid, corrosive, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required.

Incompatibilities

May be combustible. Powder mixture with air may be explosive. Sensitive to air and light exposure, long term. A chemical base: will neutralize acids to form salts plus water with an exothermic reaction. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents such as hydrides, nitrides, alkali metals, and sulfides.

Waste Disposal

Dispose of contents and container to an approved waste disposal plant. Use a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed

InChI:InChI=1/C14H7Br2NO2/c15-8-5-9(16)12(17)11-10(8)13(18)6-3-1-2-4-7(6)14(11)19/h1-5H,17H2

Upstream product

• 83-62-5 1-aminoanthraquinone-2-sulfonic acid 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 82-45-1 1-amino-9,10-anthracenedione 
• 82840-40-2 3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 103-73-1 Phenetole 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 7664-93-9 sulfuric acid 
• 4095-85-6 1,4-diamino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 24429-49-0 sodium 1-amino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 129-43-1 1-hydroxyanthraquinone 
• 74386-37-1 1-azido-4-bromoanthraquinone 
• 2372-45-4 sodium butanolate 

Downstream Products

• 55448-07-2 N-(4-amino-3-bromo-9,10-dioxo-9,10-dihydro-[1]anthryl)-benzenesulfonamide 
• 102184-28-1 1-amino-2-bromo-4-phenoxy-9,10-antraquinone 
• 116-82-5 1-amino-2-bromo-4-hydroxyanthraquinone 
• 602-72-2 1,3-dibromo-anthraquinone 
• 53773-31-2 1-amino-2,4-diphenoxy-anthraquinone 
• 313498-69-0 4,6-dibromo-2-methyl-7-oxo-7H-naphtho[1,2,3-de]quinoline-1-carboxylic acid ethyl ester 
• 128-83-6 1-amino-2-bromo-4-(p-toluidino)-9,10-anthraquinone 
• 83929-40-2 2-((4-amino-3-bromo-9,10-dioxo-9,10-dihydroanthracen-1-yl)amino)benzoic acid 
• 26868-32-6 1-amino-2-bromo-4-(toluene-4-sulfonylamino)-anthraquinone 
• 1564-71-2 1-amino-2-bromo-4-phenylaminoanthraquinone 
• 1564-68-7 1-amino-2-bromo-4-p-phenetidino-anthraquinone 
• 76382-24-6 1-amino-4-p-anisidino-2-bromo-anthraquinone 
• 82840-40-2 3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 86397-46-8 1-amino-2-phenoxy-4-anilinoanthraquinone 

Relevant articles and documents

PROCESS OF PREPARING TYROSINE KINASE INHIBITOR

The invention relates to a process for preparing sodium 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzoate.

Efficient, facile metal free protocols for the bromination of commercially important deactivated aminoanthracene-9,10-diones

Highly efficient, mild synthetic protocols were developed for the oxidative bromination of deactivated aminoanthracene-9,10-diones by using H2O2-HBr and m-CPBA-HBr in methanolic medium. Both the protocols offer excellent bromine atom economy, good conversion (100%) along with high yield (82–93%) and high purity of desired product. The N-alkylated amines undergo regio-selective bromination to give selective p-bromo product. The commercial availability of all the starting materials, simple reaction procedure and ease of work up, and easily amenable for scale up demonstrated commercial feasibility of both the protocols.

PROCESS FOR PREPARING SUBSTITUTED 9,10-DIOXO-9,10-DIOXO-9,10-DIHYDROANTHRECENES AND 6H-ANTHRA(1,9-CD)ISOXAZOL-6-ONES

The disclosure provides processes of preparing compounds of Formula (I) and Formula (IV), their salts, and intermediates thereof, wherein R1, R2, R3, and R7 are defined as set forth in the specification.

SMALL MOLECULE BASED ANTIBODY-RECRUITING COMPOUNDS FOR CANCER TREATMENT

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Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) - Precursors for dyes and drugs

Anthraquinone (AQ) derivatives play a prominent role in medicine and also in textile industry. Bromaminic acid (1-amino-4-bromoanthraquinone-2-sulfonic acid) is an important precursor for obtaining dyes as well as biologically active compounds through the replacement of the C4-bromo substituent with different (ar)alkylamino residues. Here we report methods for the synthesis of bromaminic acid analogues bearing different substituents at the 2-position of the anthraquinone core. 1-Aminoanthraquinone was converted to its 2-hydroxymethyl-substituted derivative which, under different reaction conditions, yielded the corresponding carbaldehyde, carboxylic acid, and nitrile derivatives. The latter was further reacted to obtain 1-amino-2-tetrazolylanthraquinone. Subsequent bromination using bromine in DMF led to the corresponding bromaminic acid derivatives in excellent isolated yields (>90%) and high purities. Alternatively, 1-amino-4-bromo-2-hydroxymethylanthraquinone could be directly converted to the desired 2-substituted bromaminic acid analogues in high yields (85-100%). We additionally report the preparation of bromaminic acid sodium salt and 1-amino-2,4-dibromoanthraquinone directly from 1-aminoanthraquinone in excellent yields (94-100%) and high purities. The synthesized brominated AQs are valuable precursors for the preparation of AQ drugs and dyes.

COMPOSITIONS OF COMPOUNDS AND USES THEREOF

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POLYMERIZABLE DICHROIC DYES

The present invention relates to new dichroic dyes, their composition with slave materials and their use for a dichroic polymer network, a dichroic liquid crystalline polymer film (LCP film) or a dichroic liquid crystalline polymer gel, which for instance find application as electro- optical or optical devices.

Nonanebis(peroxoic acid): A stable peracid for oxidative bromination of aminoanthracene-9,10-dione

A new protocol for the oxidative bromination of aminoanthracene-9,10-dione, which is highly deactivated towards the electrophilic substitution is investigated. The peracid, nonanebis(peroxoic acid), possesses advantages such as better stability at room temperature, it is easy to prepare and non-shock sensitiv as compared to the conventional peracids. The present protocol has a broad scope for the bromination of various substituted and unsubstituted aminoanthracene-9,10-diones.

CRYSTALLINE FORMS OF TRYOSINE KINASE INHIBITORS AND THEIR SALTS

The invention relates to various polymorphic forms and amorphous form of sodium 4-((3-(4-cyclohexylpiperazin-1-yl)-6-oxo-6H-anthra[1,9-cd]isoxazol-5-yl)amino)benzate, including the polymorphic form A, mixtures of the polymorphs, process for the preparation thereof and the use thereof in a pharmaceutical composition containing thereof.

Anthroneamine based chromofluorogenic probes for Hg2+ detection in aqueous solution

Anthroneamine derivatives 1-3 (H2O:DMSO; 9:1, HEPES buffer, pH 7.0 ± 0.1) undergo highly selective fluorescence quenching with Hg 2+. The observed linear fluorescence intensity change allows the quantitative detection of Hg2+ between 200 nM/40 ppb - 12 μM/2.4 ppm even in the presence of interfering metal ions viz. Na+, K +, Mg2+, Ca2+, Ba2+, Cr 3+, Fe2+, Co2+, Ni2+, Cu 2+, Zn2+, Ag+, Cd2+, Pb 2+. Probes 1-3 and their Hg2+ complexes also show the broad pH resistance for their practical applicability.