585-79-5

Basic information

• Product Name: 3-Bromonitrobenzene
• Synonyms: m-Nitrobromobenzene;1-bromo-3-nitro-benzen;1-Nitro-3-brombenzen;1-Nitro-3-bromobenzene;3-Bromo-1-nitrobenzene;Benzene,1-bromo-3-nitro-;BROMONITROBENZENE-3;M-BROMONITROBENZENE
• CAS NO: 585-79-5
• Molecular Formula: C₆H₄BrNO₂
• Molecular Weight: 202.01
• EINECS: 209-563-9
• Product Categories: Aromatic Halides (substituted);Benzene derivates;Bromine Compounds;Nitro Compounds;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks;Aromatics;Aliphatics;Isotope Labelled Compounds;Quinolines
• Mol File: 585-79-5.mol
• Article Data: 60

Chemical Properties

• Melting Point: 51-54 °C
• Boiling Point: 256 °C
• Flash Point: 113 °C
• Appearance: white to light yellow crystal powder
• Density: 1.704
• Vapor Pressure: 0.0299mmHg at 25°C
• Refractive Index: 1.6050 (estimate)
• Storage Temp.: Refrigerator
• Solubility: 10g/l
• BRN: 2043212
• CAS DataBase Reference: 3-Bromonitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromonitrobenzene(585-79-5)
• EPA Substance Registry System: 3-Bromonitrobenzene(585-79-5)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 36/37/38-20/21/22-33-23/24/25
• Safety Statements: 36/37/39-26-22-45-37-28A-28-37/39
• RIDADR: 2732
• WGK Germany: 3
• RTECS: CY9040500
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 585-79-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Labelled glycerol kinase substrate specificity

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 2169, 1981 DOI: 10.1021/jo00323a039

Purification Methods

Crystallise it twice from pet ether, using charcoal before the first crystallisation. [Beilstein 5 III 618, 5 IV 729.]

InChI:InChI=1/C6H5NO2.BrH/c8-7(9)6-4-2-1-3-5-6;/h1-5H;1H

Upstream product

• 827-94-1 2,6-dibromo-4-nitroaniline 
• 99-09-2 3-nitro-aniline 
• 554-84-7 meta-nitrophenol 
• 552-16-9 ortho-nitrobenzoic acid 
• 55215-57-1 1-amino-3-bromo-5-nitrobenzene 
• 51516-96-2 3-nitrophenylhydrazine hydrochloride 
• 591-19-5 m-Bromoaniline 
• 16518-62-0 3-bromo-N,N-dimethylaniline 
• 87961-72-6 (3-nitrophenyl)(triphenyl-λ5-phosphanyl)gold 
• 36372-59-5 4-bromo-2-nitrophenyl-cyclopropane 
• 411235-57-9 cyclopropylboronic acid 
• 100-01-6 4-nitro-aniline 
• 32578-25-9 trifluoromethanesulfonic acid 3-nitrophenyl ester 
• 68716-48-3 4,4,5,5-tetramethyl-2-(3-nitrophenyl)-1,3,2-dioxaborolane 

Downstream Products

• 586-76-5 4-Bromobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 63213-03-6 1,2-bis(3-bromophenyl)diazene 
• 107920-34-3 acetic acid-[4-(3-nitro-phenoxy)-anilide] 
• 873983-25-6 [2-(3-nitro-anilino)-phenyl]-arsonic acid 
• 38490-83-4 3,3'-dinitrodiphenyl ether 
• 2914-72-9 1-nitro-3-(4-nitrophenoxy)benzene 
• 50829-58-8 3-(4-methylphenoxy)nitrobenzene 
• 107622-63-9 1-methoxy-2-(3-nitro-phenoxy)-benzene 
• 37984-01-3 1nitro-3-(3-(trifluoromethyl)phenoxy)benzene 
• 4531-79-7 3-nitro-N-phenylaniline 
• 136476-19-2 1-nitro-3-(1,1,1-trifluoroprop-2-en-2-yl)benzene 
• 105018-28-8 2-(2-bromo-6-nitro-phenyl)acetonitrile 
• 105003-96-1 (4-bromo-2-nitro)phenylacetonitrile 

Relevant articles and documents

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Poly-N-bromosulfonamide-melamine as a novel brominating reagent for regioselective ipso-bromination of arylboronic acids

A practical synthetic method for the synthesis of aryl bromide was developed through regioselective bromination of boronic acid in the presence of poly-N-bromosulfonamide-melamine (PBBSM). In this regard, a novel heterogeneous support, cross-linked poly sulfonamide-melamine, has been successfully synthesized to stabilize bromine with high surface functional group density (6.6?mmol Br+/g). The prepared reagent is a novel brominating reagent that combines the effective functions of N-bromosulfonamide, N-bromosulfonamide-melamine, and melamine groups. The structure of PBBSM was characterized using XRD, FT–IR, 1H NMR, TGA, FE-SEM, EDX, and TGA analysis. Graphic abstract: [Figure not available: see fulltext.]

Metal- and base-free synthesis of aryl bromides from arylhydrazines

An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.