99-81-0

Basic information

• Product Name: 2-Bromo-4'-nitroacetophenone
• Synonyms: ASISCHEM D48949;4'-NITROPHENACYL BROMIDE;4-NITROPHENACYL BROMIDE;AKOS BBS-00003952;ALPHA-BROMO-P-NITROACETOPHENONE;ALPHA-BROMO-4-NITROACETOPHENONE;A-BROMO-P-NITROACETOPHENONE;2-BROMO-4'-NITROACENTOPHENONE
• CAS NO: 99-81-0
• Molecular Formula: C₈H₆BrNO₃
• Molecular Weight: 244.04
• EINECS: 202-789-9
• Product Categories: Aromatic Halides (substituted);B;Bioactive Small Molecules;Building Blocks;C7 to C8;Carbonyl Compounds;Cell Biology;Chemical Synthesis;Ketones;Organic Building Blocks
• Mol File: 99-81-0.mol

Chemical Properties

• Melting Point: 94-99 °C(lit.)
• Boiling Point: 325.2 °C at 760 mmHg
• Flash Point: 150.5 °C
• Appearance: Yellow to orange/Crystalline Powder
• Density: 1.8033 (rough estimate)
• Vapor Pressure: 0.000233mmHg at 25°C
• Refractive Index: 1.6090 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• BRN: 393567
• CAS DataBase Reference: 2-Bromo-4'-nitroacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4'-nitroacetophenone(99-81-0)
• EPA Substance Registry System: 2-Bromo-4'-nitroacetophenone(99-81-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 19
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 99-81-0(Hazardous Substances Data)

Usage

Uses

2-Bromo-4′-nitroacetophenone was used to study the pKa of the histidine-34 imidazole.

Synthesis Reference(s)

Synthesis, p. 487, 1980 DOI: 10.1055/s-1980-29067

Purification Methods

Crystallise it from *C6H6/pet ether. [Beilstein 7 IV 661.]

InChI:InChI=1/C8H6BrNO3/c9-5-8(11)6-1-3-7(4-2-6)10(12)13/h1-4H,5H2

Upstream product

• 838-57-3 ethyl 4-nitrobenzoylacetate 
• 59777-30-9 [1,2-dibromo-1-(4-nitro-phenyl)-ethyl]-methyl ether 
• 101291-55-8 bis-[1-(4-nitro-phenyl)-vinyl]-ether 
• 101091-01-4 (4-nitro-benzoyl)-oxalacetic acid diethyl ester 
• 7402-45-1 α,α,α-tribromoacetophenone 
• 100-19-6 (4-nitrophenyl)ethanone 
• 19922-82-8 2-bromo-1-(4-nitrophenyl)ethanol 
• 59938-04-4 4-nitro-1-(1-ethoxyvinyl)benzene 
• 586-78-7 para-nitrophenyl bromide 
• 122-04-3 4-nitro-benzoyl chloride 
• 3440-23-1 1-(1-methoxyvinyl)-4-nitrobenzene 
• 100-13-0 4-nitrostyrene 
• 100-12-9 4-ethylnitrobenzene 
• 67-56-1 methanol 

Downstream Products

• 33707-92-5 1-(4-nitro-phenyl)-2-piperidin-1-yl-ethanone 
• 25357-42-0 4-methyl-1-(4-nitro-phenacyl)-pyridinium; bromide 
• 109015-66-9 3-hydroxy-1-(4-nitro-phenacyl)-pyridinium; bromide 
• 7120-14-1 6-p-nitrophenylimidazo<2,1-b>thiazole 
• 3323-26-0 2-(4-nitrophenyl)imidazo[1,2-a]pyridine 
• 103503-25-9 3-methyl-6-p-nitrophenylimidazo<2,1-b>thiazole 
• 91974-40-2 1-(2-(4-nitrophenyl)-2-oxoethyl)pyrrolidine-2,5-dione 
• 14247-81-5 7-methyl-2-(4-nitro-phenyl)-imidazo[1,2-a]pyrimidine 
• 100382-31-8 1-(4-nitro-phenyl)-2-(pyridine-3-sulfonyl)-ethanone 
• 5397-95-5 1-(4-nitro-phenacyl)-4-pentyl-pyridinium; bromide 
• 60477-38-5 2-(4-nitrophenyl)-5,6,7,8-tetrahydrobenzo[d]imidazo[2,1-b]thiazole 
• 106735-84-6 1-(3-methyl-6-(4-nitrophenyl)imidazo[2,1-b]thiazol-2-yl)ethanone 
• 860260-68-0 ethyl 3-methyl-6-(4-nitrophenyl)imidazo[2,1-b]thiazole-2-carboxylate 

Relevant articles and documents

Synthesis of a New Phorbazole and Its Derivatives

Phorbazoles are chlorinated marine alkaloids containing pyrrole, oxazole and phenol ring units, and differ in the number and positions of chlorine atoms. They are isolated from sea sponges and nudibranchs. In this work, a convenient synthetic method leading to a new phorbazole and its derivatives is developed. This synthesis of synthetic phorbazole G and its derivatives is achieved in seven steps in good overall yields of 26-52%. It involves formation of the pyrrole-oxazole skeleton followed by chlorination. The pyrrole-oxazole skeleton is synthesized from pyrrole and substituted acetophenones, and the key step involves cyclodehydration of amide intermediates to give protected oxazoles, followed by hydrolysis.

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives

In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.

Synthesis of Novel Heterocycles by Amide Activation and Umpolung Cyclization

Herein, we report a metal-free synthesis of cyclic amidines, oxazines, and an oxazinone under mild conditions by electrophilic amide activation. This strategy features an unusual Umpolung cyclization mode and enables the smooth union of α-aryl amides and diverse alkylazides, effectively rerouting our previously reported α-amination transform.

Facile Synthesis of α-Haloketones by Aerobic Oxidation of Olefins Using KX as Nonhazardous Halogen Source

An operationally simple and safe synthesis of α-haloketones using KBr and KCl as nonhazardous halogen sources is reported. It involves an iron-catalysed reaction of alkenes with KBr/KCl using O2 as terminal oxidant under the irradiation of visible-light. This strategy avoids the risks associated with handling halo-contained electrophiles (Cl2, Br2, NCS, NBS). The process is tolerant to several functional groups, and extended to a range of substituted styrenes in up to 89% yield. A radical reaction pathway is proposed based on control experiments and spectroscopy studies.

Reaction of ketone hydrazones with TeCl4: Isolation and reactions of novel divinyl telluride

The reaction of acetophenone hydrazones with TeCl4 in the presence of DBU gave a mixture of divinyl ditellurides and divinyl tellurides, which easily reacted with Cu powder in refluxing toluene to afford divinyl tellurides in good yields. The reaction of divinyl tellurides with bromine (1.2 eq.) gave the corresponding tellurium dibromide rather than the addition of the double bond whereas 3 molar amount of bromine gave excess brominated and oxidized products. The reaction of divinyl tellurides with 2-(trimethylsilyl)phenyl triflate in the presence of CsF gave (E)-2-alkenyldiaryl tellurides in good yields.

Application of poly(vinylphenyltrimethylammonium tribromide) resin as an efficient polymeric brominating agent in the α-bromination and α-bromoacetalization of acetophenones

The applications of a new supported tribromide reagent based on poly(vinylbenzyltrimethylammonium hydroxide) resin (Amberlite 717) were reported. This supported tribromide resin was used directly in α-bromination and α-bromoacetalization of acetophenones without any other catalyst under mild conditions. The effects of solvents and the amount of the supported tribromide resin on the reactions were investigated. Under the optimal conditions, most of α-bromo and α-bromoacetal of acetophenones were selectively obtained in excellent yields.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

High-bromine-atom-utilization-rate method for preparing alpha-monobrominated aromatic ketones

The invention belongs to the technical field of chemical engineering, and particularly relates to a high-bromine-atom-utilization-rate method for preparing alpha-monobrominated aromatic ketones. The method comprises the following steps: taking an aromatic

Novel arylimino thiazole compound, preparation method and uses thereof

The present invention relates to a compound with antibacterial synergy activity, a preparation and uses thereof, particularly to a novel arylimino thiazole compound, a preparation method and uses thereof, and specifically discloses a class of compounds represented by a formula (I) or optical isomers, cis-trans isomers or pharmaceutically acceptable salts thereof, a preparation method and uses thereof. The invention further discloses a pharmaceutical composition containing the compound. The compound of the present invention can effectively enhance the antibacterial activity of antibiotics, andcan be used for treating antibiotic-resistant bacteria. The formula (I) is defined in the specification.

Antibacterial synergist, preparation method and uses thereof

The present invention relates to an antibacterial synergist, a preparation method and uses thereof, and specifically discloses a compound represented by a formula (I) and having antibacterial synergyactivity, or an optical isomer, a cis-trans isomer or a pharmaceutically acceptable salt thereof, and a preparation method thereof. The present invention further discloses a medical composition containing the compound, and uses thereof. According to the present invention, the compound can effectively enhance the antibacterial activity of polymyxin B against Acinetobacter baumannii and Klebsiella pneumoniae, and can be used for the antibacterial treatment of pathogenic bacteria insensitive to polymyxin or having low bacterial inhibition activity. The formula (I) is defined in the specification.