81-50-5

Basic information

• Product Name: 1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE
• Synonyms: 1-amino-4-bromo-2-methylanthracene-9,10-dione;1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE, TECH., 95%;1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE, 9 9%;1-Amino-4-bromo-2-methyl-9,10-anthracenedione;1-Amino-4-bromo-2-methylanthraquinone,95%;1-Amino-2-methyl-4-bromoanthraquinone;1-amino-4-bromo-2-methyl-10-anthracenedione;1-Amino-4-bromo-2-methylanthra-9,10-quinone
• CAS NO: 81-50-5
• Molecular Formula: C₁₅H₁₀BrNO₂
• Molecular Weight: 316.15
• EINECS: 201-355-6
• Product Categories: Anthraquinones, Hydroquinones and Quinones;C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 81-50-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 245 °C (dec.)(lit.)
• Boiling Point: 526.5 °C at 760 mmHg
• Flash Point: 272.2 °C
• Appearance: Orange to red crystalline powder
• Density: 1.631 g/cm³
• Vapor Pressure: 3.56E-11mmHg at 25°C
• Refractive Index: 1.706
• CAS DataBase Reference: 1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE(81-50-5)
• EPA Substance Registry System: 1-AMINO-4-BROMO-2-METHYLANTHRAQUINONE(81-50-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 81-50-5(Hazardous Substances Data)

Usage

Uses

1-Amino-4-bromo-2-methylanthraquinone has been used in the synthesis of 4-substituted 1-amino-2-methylanthraquinone derivatives:1-amino-2-methyl-4-phenylaminoanthraquinone1-amino-2-methyl-4-(3-methylphenylamino)anthraquinone1-amino-2-methyl-4-(4-methylphenylamino)anthraquinone1-amino-2-methyl-4-(1-naphthylamino)anthraquinone

InChI:InChI=1/C15H10BrNO2/c1-7-6-10(16)11-12(13(7)17)15(19)9-5-3-2-4-8(9)14(11)18/h2-6H,17H2,1H3

Upstream product

• 82-28-0 disperse orange 11 
• 21301-46-2 1-azido-2-methylanthraquinone 
• 7732-18-5 water 
• 860729-43-7 N-(4-bromo-2-methyl-9-oxo-9,10-dihydro-[1]anthryl)-acetamide 
• 858847-97-9 2-(5-amino-2-bromo-4-methyl-benzyl)-benzoic acid 
• 7664-93-9 sulfuric acid 
• 140-89-6 potassium ethyl xanthogenate 
• 92629-25-9 3-Methyl-5-bromoanthra<1,9-cd>-6-isoxazolone 
• 871-58-9 potassium butylxanthate 
• 2667-20-1 potassium methylxanthate 
• 110-83-8 cyclohexene 
• 101575-99-9 N-(4-bromo-2-methyl-9,10-dioxo-9,10-dihydro-[1]anthryl)-acetamide 

Downstream Products

• 63723-54-6 1-acetyl-6-bromo-2-hydroxy-4-methyl-naphtho[1,2,3-de]quinolin-7-one 
• 95163-94-3 1-amino-2-methyl-4-(toluene-4-sulfonylamino)-anthraquinone 
• 75313-86-9 N-(4-amino-3-methyl-9,10-dioxo-9,10-dihydro-[1]anthryl)-sulfanilic acid 
• 501075-77-0 1-amino-4-{[3-(dimethylamino)propyl]amino}-2-methylanthra-9,10-quinone 
• 733748-40-8 C₂₂H₁₈N₂O₂ 
• 1052088-32-0 C₂₇H₂₁N₃O₅S 
• 67499-51-8 C₂₃H₁₆BrNO₃ 
• 94176-30-4 1-amino-2-methyl-4-(4-tert.-butylphenylmercapto)-anthraquinone 
• 1052088-02-4 sodium 1-amino-2-methyl-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene 
• 858842-12-3 3-methyl-1-(toluene-4-sulfonylamino)-anthraquinone 

Relevant articles and documents

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.

SYNTHESIS AND STRUCTURE OF 5-ACYLTHIO- AND 5-ACYLAMINO-6-OXO-6H-ANTHRAISOXAZOLES

The action of 5-halogeno-6-oxo-6H-anthraisoxazoles on xanthates gave the corresponding 5-alkoxythiocarbonylthio-6-oxo-6H-anthraisoxazoles, for which the 1,10-quinonoid structure was confirmed.The initial product from the reaction of 5-chloro-6-oxo-6H-anthraisoxazole with potassium thiobenzoate, i.e., 5-benzoylthio-6-oxo-6H-anthraisoxazole, is unstable and was only detected spectrally.The acyl group in the obtained 5-acylamino-6-oxo-6H-anthraisoxazoles is also incapable of migration to the oxygen atom, and they therefore also exist in the 1,10-quinonoid form.

Polymeric red colors

Polymeric red colors having the structure STR1 wherein R1 and R2 are independently selected from among hydrogen, halos, lower alkyls, lower alkoxies, nitros, and sulfonates, R3 is selected from hydrogens, alkyls and alkylsulfonates, and R4 is an alkyl-containing polymer linking a plurality (n) of anthraquinones into a polymeric colorant are disclosed to be used as nonabsorbable colorants for edibles and cosmetics. They may also be used in such substrates as lakes.