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
• Article Data: 16

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

Description

1-Amino-2,4-dibromoanthraquinone (ADBAQ) is an organic compound that belongs to the anthraquinone family. It is characterized by the presence of an amino group and two bromine atoms attached to the anthraquinone structure. This unique molecular structure endows ADBAQ with specific chemical and physical properties, making it a valuable intermediate in various industrial applications.

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

Downstream Products

• 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 
• 116-82-5 1-amino-2-bromo-4-hydroxyanthraquinone 
• 75753-36-5 6H-6-oxo-3-bromo-5-(p-toluidino)anthra<1,9-cd>isoxazole 

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.

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.

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.