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

Chemical Properties

1-Amino-2,4-dibromoanthraquinone is a red powder or a red solid needles. Odorless

Uses

ADBAQ and other aminoanthraquinones are key intermediates in the production of almost all anthraquinone dyes (HSDB 2009). Anthraquinones, including ADBAQ, are widely used as starting material for the manufacture of vat dyes, which are a class of water-insoluble dyes that can easily be reduced to a water-soluble and usually colorless form. In this form, they are readily impregnated into fibers and textiles. Oxidation then produces an insoluble colored form that is remarkably fast to washing, light, and chemicals. Vat dyes typically are used with cotton, wool, and cellulose acetate (NTP 1996).

General Description

Odorless red powder.

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

• 82-45-1 1-amino-9,10-anthracenedione 
• 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 
• 83-62-5 1-aminoanthraquinone-2-sulfonic acid 
• 7732-18-5 water 
• 82840-40-2 3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 103-73-1 Phenetole 
• 74386-37-1 1-azido-4-bromoanthraquinone 
• 2372-45-4 sodium butanolate 
• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 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 

Downstream Products

• 26868-32-6 1-amino-2-bromo-4-(toluene-4-sulfonylamino)-anthraquinone 
• 116-82-5 1-amino-2-bromo-4-hydroxyanthraquinone 
• 82840-40-2 3,5-dibromo-6-oxo-6H-anthra<1,9-cd>isoxazole 
• 75753-36-5 6H-6-oxo-3-bromo-5-(p-toluidino)anthra<1,9-cd>isoxazole 

Relevant articles and documents

SMALL MOLECULE BASED ANTIBODY-RECRUITING COMPOUNDS FOR CANCER TREATMENT

The present invention relates to chimeric (including bifunctional) compounds, compositions comprising those compounds and methods of treating cancer in a patient or subject, especially including metastatic cancer where cancer cells exhibit overexpression (heightened expression) of cell surface urokinase-type plasminogen activator receptor (urokinase receptor) compared to normal (non-cancerous) cells. The compounds bind to the urokinase-type plasminogen activator receptor (uPAR) on the surface of a cancer cell, including a metastatic cancer cell, and consequently recruit native antibodies of the patient or subject where the antibodies can selectively degrade and/or deactivate targeted cancer cells through antibody-dependent cellular phagocytosis and antibody-dependent cellular cytotoxicity (ADCC) and/or complement dependent cytotoxicity (CDC) against a large number and variety of cancers, thus providing cancer cell death and an inhibition of growth, elaboration and/or metastasis of the cancer, including remission and cure of the patient's cancer.

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.

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.