24070-52-8

Basic information

• Product Name: 4-bromobutyrophenone
• Synonyms: 1-Phenyl-4-bromo-1-butanone;γ-Bromobutyrophenone
• CAS NO: 24070-52-8
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.0977
• EINECS: 246-005-3
• Mol File: 24070-52-8.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 300.3°C at 760 mmHg
• Flash Point: 77.9°C
• Appearance: /
• Density: 1.358g/cm³
• Vapor Pressure: 0.00113mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 4-bromobutyrophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-bromobutyrophenone(24070-52-8)
• EPA Substance Registry System: 4-bromobutyrophenone(24070-52-8)

Safety Data

• Hazardous Substances Data: 24070-52-8(Hazardous Substances Data)

Usage

General Description

4-bromobutyrophenone, also known as 1-(4-bromobutyl)-1H-inden-3-ol, is a chemical compound with the molecular formula C10H11BrO. It is a white to off-white crystalline solid that is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 4-bromobutyrophenone is also used as a building block in the manufacture of various organic compounds and as a reagent in organic synthesis. It is important to handle 4-bromobutyrophenone with care, as it is a potential irritant to the skin, eyes, and respiratory system, and may have harmful effects if ingested or inhaled.

InChI:InChI=1/C10H11BrO/c11-8-4-7-10(12)9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2

Upstream product

• 927-58-2 4-bromobutyroyl chloride 
• 71-43-2 benzene 
• 10229-11-5 4-phenyl-but-3-yn-1-ol 
• 79172-43-3 1-benzoylcyclopropanecarboxylic acid 
• 10035-10-6 hydrogen bromide 
• 3481-02-5 cyclopropyl phenyl ketone 
• 64-19-7 acetic acid 
• 21034-21-9 α-benzoyl-γ-butyrolactone 
• 56489-06-6 4-bromobutyryl bromide 
• 5332-06-9 4-bromobutanenitrile 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 3365-26-2 1-phenylcyclobutene 
• 591-51-5 phenyllithium 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 100388-04-3 2-(3-bromo-propyl)-2-phenyl-[1,3]dioxolane 
• 343810-59-3 4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-phenyl-butan-1-one 
• 151091-46-2 VUF 4592 
• 4170-67-6 1-methyl-5-phenyl-2,3-dihydro-pyrrole 
• 3481-02-5 cyclopropyl phenyl ketone 
• 700-91-4 2-phenyl-1-pyrroline 
• 1304688-79-6 4-(4-acetylphenyl)-1-phenylbutan-1-one 
• 69573-41-7 γ-azidobutyrophenone 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 42330-80-3 4-(p-methylphenylthio)-1-phenylbutan-1-ol 
• 82777-36-4 Picrateethyl-(4-methoxy-phenyl)-(4-oxo-4-phenyl-butyl)-sulfonium; 

Relevant articles and documents

Transition-Metal-Free Ring-Opening Reaction of 2-Halocyclobutanols through Ring Contraction

The present work describes the preparation of halohydrins from 2-halocyclobutanones by means of reactions with Grignard reagents at ?78 °C. We discovered that the prepared cyclobutanols underwent a thermal ring-opening reaction. Depending on the structure of the starting cyclobutanol, different products were formed. More specifically, 1-substituted 2-bromocyclobutan-1-ol was found to open to γ-substituted butyrophenones. A novel 1,3-dihydro-2H-inden-2-ylidene derivative was obtained for indene-derived cyclobutanols. Based on the outcomes of the performed experiments, a mechanism for the ring-opening of cyclobutanols can be proposed.

Boron tribromide as a reagent for anti-Markovnikov addition of HBr to cyclopropanes

Although radical formation from a trialkylborane is well documented, the analogous reaction mode is unknown for trihaloboranes. We have discovered the generation of bromine radicals from boron tribromide and simple proton sources, such as water ortert-butanol, under open-flask conditions. Cyclopropanes bearing a variety of substituents were hydro- and deuterio-brominated to furnish anti-Markovnikov products in a highly regioselective fashion. NMR mechanistic studies and DFT calculations point to a radical pathway instead of the conventional ionic mechanism expected for BBr3

Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines

A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.