Description

1-Amino-2,4-dibromoanthraquinone (CAS No. 81-49-2) is a high-purity brominated anthraquinone derivative with the molecular formula C₁₄H₇Br₂NO₂. This compound, also known by its IUPAC name 1-amino-2,4-dibromoanthracene-9,10-dione, is a valuable intermediate in organic synthesis and dye manufacturing. It features a distinctive anthraquinone backbone with amino and bromo functional groups at the 1, 2, and 4 positions, offering unique reactivity for electrophilic substitutions and metal-catalyzed cross-coupling reactions. Our product is rigorously tested for purity (>98% by HPLC) and is supplied as a fine crystalline powder with excellent batch-to-batch consistency. Ideal for research in photodynamic therapy, liquid crystal displays, and advanced material science applications. Available in sealed amber vials or bulk quantities with customizable packaging options under inert atmosphere.

Properties

• CAS Number: 81-49-2
• Complexity: 414
• IUPAC Name: 1-amino-2,4-dibromo-anthracene-9,10-dione
• InChI: InChI=1S/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
• InChI Key: ZINRVIQBCHAZMM-UHFFFAOYSA-N
• Exact Mass: 380.88230
• Molecular Formula: C14H7Br2NO2
• Molecular Weight: 381.02
• SMILES: C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C(=C(C=C3Br)Br)N
• Topological: 60.2
• Monoisotopic Mass: 378.88435
• Physical Description: 1-amino-2,4-dibromoanthraquinone is an odorless red powder.
• Color/Form: Red needles
• Melting Point: 439 °F
• Flash Point: greater than 392 °F
• Solubility: less than 1 mg/mL at 73 °F
• Synonyms: 1-AMINO-2,4-DIBROMOANTHRAQUINONE, 81-49-2, Dibromoaminoanthraquinone, 2,4-Dibromo-1-anthraquinonylamine, 9,10-Anthracenedione, 1-amino-2,4-dibromo-, 1-Amino-2,4-dibromanthrachinon, Anthraquinone, 1-amino-2,4-dibromo-, NCI-C55458, NSC 3529, CCRIS 5884, HSDB 5241, RF75O3IKOZ, EINECS 201-354-0, BRN 1993373, 1-Amino-2,4-dibromanthrachinon [Czech], DTXSID4039235, AI3-16445, NSC-3529, DTXCID9052, NSC3529, 4-14-00-00444 (Beilstein Handbook Reference), 1-AMINO-2,4-DIBROMOANTHRAQUINONE [IARC], 1-Amino-2,4-dibromanthrachinon (Czech), ADBAQ, 1-AMINO-2,4-DIBROMOANTHRAQUINONE (IARC), 1-amino-2,4-dibromo-9,10-Anthracenedione, 1Amino2,4dibromanthrachinon, 2,4Dibromo1anthraquinonylamine, Anthraquinone, 1amino2,4dibromo, 9,10Anthracenedione, 1amino2,4dibromo, CI-55458, 9,10-ANTHRACENEDIONE,1-AMINO-2,4-DIBROMO-, 201-354-0, 1-amino-2,4-dibromoanthracene-9,10-dione, 1-Amino-2,4-dibromo-anthraquinone, 1-amino-2,4-dibromo-9,10-anthraquinone, 1-Amino-2,4-dibromoanthra-9,10-quinone, CHEBI:82304, 1-amino-2,4-dibromo-9,10-dihydroanthracene-9,10-dione, UNII-RF75O3IKOZ, NSC 3529; 1-Amino-2,4-dibromo-9,10-anthracenedione; 1-Amino-2,4-dibromo-9,10-anthraquinone; 1-Amino-2,4-dibromoanthraquinone; 2,4-Dibromo-1-anthraquinonylamine, MFCD00019155, Anthraquinone,4-dibromo-, 9, 1-amino-2,4-dibromo-, CHEMBL559749, SCHEMBL3272427, l-amino-2,4-dibromoanthraquinone, 1-Amino-2, 4-dibromoanthraquinone, Tox21_202582, BBL013158, STK803590, AKOS000668885, CAS-81-49-2, NCGC00260131-01, WLN: L C666 BV IVJ DZ EE GE, AC-13906, AS-61164, 1-AMINO-2,4-DIBROMOANTHRA-QUINONE, DB-056532, CS-0188511, NS00038127, ST50409824, C19211, E76133, AE-641/00127034, Q27155867

Application

1-Amino-2,4-dibromoanthraquinone serves as a key precursor in the synthesis of anthraquinone-based dyes for textile and LCD color filters. Its bromine substituents enable Suzuki-Miyaura coupling reactions to create extended π-conjugated systems for organic semiconductors. Researchers utilize this compound in developing photosensitizers for photodynamic cancer therapy due to its strong absorbance in visible light spectrum. The amino group allows further functionalization for creating specialized polymers with thermal stability.

Safety and Hazards

GHS Hazard Statements

• H350: May cause cancer [Danger Carcinogenicity]

Precautionary Statements

• P203, P280, P318, P405, and P501

Hazard Classes and Categories

• Eye Irrit. 2 (90.9%)
• Carc. 2 (13.6%)

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