2227-64-7

Basic information

• Product Name: 3-Nitrophenacylbromide
• Synonyms: 2-Bromo-3'-nitroacetophenone,97%;2-Bromo-3'-nitroacetophenone, 2-Bromo-1-(3-nitrophenyl)ethan-1-one;2-BroMo-3&priMe;3-Nitro-ɑ-broMoacetophenone;2-Bromo-3'-nitroacetophenone 97%;2-BROMO-3'-NITROACETOPHENONE;2-BROMO-1-(3-NITRO-PHENYL)-ETHANONE;2-bromo-1-(3-nitrophenyl)ethan-1-one
• CAS NO: 2227-64-7
• Molecular Formula: C₈H₆BrNO₃
• Molecular Weight: 244.04
• EINECS: 218-764-0
• Product Categories: Building Blocks;C7 to C8;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Pharmaceutical Intermediates
• Mol File: 2227-64-7.mol
• Article Data: 76

Chemical Properties

• Melting Point: 90-96 °C(lit.)
• Boiling Point: 288.6 °C at 760 mmHg
• Flash Point: 128.3 °C
• Appearance: Beige-orange to yellow-green/Crystalline Powder
• Density: 1.8033 (rough estimate)
• Refractive Index: 1.6090 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Soluble in methanol.
• BRN: 610594
• CAS DataBase Reference: 3-Nitrophenacylbromide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitrophenacylbromide(2227-64-7)
• EPA Substance Registry System: 3-Nitrophenacylbromide(2227-64-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-28-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2227-64-7(Hazardous Substances Data)

Usage

Chemical Properties

beige-orange to yellow-green crystalline powder

Uses

2-Bromo-3′-nitroacetophenone may be used in the preparation of 2-bromo-3′-nitroacetophenone. It may be used in the preparation of 2-hydroxy-ethyl-1-[(3-nitro-phenyl)-2-oxoethyl]-piperidinium bromide.

General Description

Debromination of 2-bromo-3′-nitroacetophenone in various solvents has been reported.

Upstream product

• 70-11-1 α-bromoacetophenone 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 86440-77-9 1-bromo-2-(3-nitrophenyl)acetylene 
• 5400-78-2 1-(3-nitrophenyl)ethanol 
• 121-89-1 3-Nitroacetophenone 
• 99-47-8 2-chloro-1-(3-nitrophenyl)ethanone 
• 7697-37-2 nitric acid 
• 98-86-2 acetophenone 
• 67-56-1 methanol 

Downstream Products

• 26031-71-0 1-(2-(3-nitrophenyl)-2-oxoethyl)pyridin-1-ium bromide 
• 7496-74-4 2-(3-nitro-phenyl)-indolizine 
• 34658-67-8 2-(3-nitrophenyl)imidazo[1,2-a]pyridine 
• 6277-56-1 3-bromo-1-(3-nitro-phenacyl)-pyridinium; bromide 
• 7477-72-7 3,5-dibromo-1-(3-nitro-phenacyl)-pyridinium; bromide 
• 6625-24-7 6-chloro-1-(3-nitro-phenacyl)-quinolinium; bromide 
• 7477-81-8 2-(3,4-dihydro-2H-[1]quinolyl)-1-(3-nitro-phenyl)-ethanone 
• 7469-58-1 4-(3-nitro-phenacyl)-4-phenethyl-morpholinium; bromide 
• 357627-44-2 7-methyl-2-(3-nitro-phenyl)-indolizine 
• 27996-91-4 2-(4-chloro-anilino)-1-(3-nitro-phenyl)-ethanone 
• 40511-41-9 4-(3-nitrophenyl)-1H-imidazole 
• 90945-65-6 2-acetoxy-1-(3-nitrophenyl)ethanone 
• 57493-24-0 4-(3-nitrophenyl)thiazol-2-ylamine 
• 5021-44-3 2-(3-nitrophenyl)quinoxaline 

Relevant articles and documents

Design, synthesis and SAR analysis of potent BACE1 inhibitors: Possible lead drug candidates for Alzheimer's disease

We have identified potent isophthalic acid derivatives armed with imidazol and indolyl groups as potent β-secretase inhibitors. The most effective analogs demonstrated low nano-molar potency for the BACE1 (β-secretase cleaving enzyme) as measured by FRET (Fluorescence Resonance Energy Transfer) and cell-based (ELISA) assays. Our design strategy followed a traditional SAR approach and was supported by molecular modeling studies based on previously reported hydroxyethylene transition state inhibitor derived from isophthalic acid I. In the FRET assay, the most potent compound, 10a, displayed an IC50value for BACE1 of 75 nM, and exhibited cellular activity with an EC50 value of 0.81 μM. On the other hand, compound 11b was found to be the most potent compound in the cell-based assay with an EC50value of 0.29 μM.

An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers

An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.