55394-81-5

Usage

Chemical compound

3-(4-bromophenyl)propanoyl chloride

Family

Acyl chloride

Structure

3-(4-bromophenyl)propanoyl group attached to a chloride atom

Use

Intermediate in organic synthesis, particularly for pharmaceuticals and agrochemicals

Building block

Key in the synthesis of biologically active compounds, including drugs and insecticides

Reactivity

Highly reactive compound

Handling

Should be handled with care in a well-ventilated, controlled environment

Upstream product

• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 92013-18-8 2-[(4-bromophenyl)methyl]propanedioic acid 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 1122-91-4 4-bromo-benzaldehyde 
• 1200-07-3 trans-4-bromocinnamic acid 
• 1643-30-7 3-(4-bromophenyl)propionic acid 
• 157134-36-6 dimethyl 2-(4-bromobenzyl)malonate 

Downstream Products

• 76689-78-6 3-(4-Bromo-phenyl)-propionic acid N'-methyl-N'-phenyl-hydrazide 
• 924627-87-2 methyl 4-[3-(4-bromophenyl)propanoylamino]thiophene-3-carboxylate 
• 607744-36-5 4-(3-(4-bromophenyl)propyl)morpholine 
• 607744-33-2 3-(4-bromophenyl)-1-morpholinopropan-1-one 
• 342373-40-4 3-(4-bromophenyl)-N-hydroxypropanamide 
• 3279-90-1 6-bromo-3,4-dihydro-1H-quinolin-2-one 
• 259099-03-1 3-(4-bromophenyl)-N-methoxy-N-methylpropanamide 
• 1609209-15-5 (6R,7R)-7-(3-(4-bromophenyl)propanamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Relevant academic research and scientific papers

Ruthenium-catalyzed intramolecular arene C(sp2)-H amidation for synthesis of 3,4-dihydroquinolin-2(1 H)-ones

We report the [Ru(p-cymene)(l-proline)Cl] ([Ru1])-catalyzed cyclization of 1,4,2-dioxazol-5-ones to form dihydroquinoline-2-ones in excellent yields with excellent regioselectivity via a formal intramolecular arene C(sp2)-H amidation. The reactions of the 2- and 4-substituted aryl dioxazolones proceeds initially through spirolactamization via electrophilic amidation at the arene site, which is para or ortho to the substituent. A Hammett correlation study showed that the spirolactamization is likely to occur by electrophilic nitrenoid attack at the arene, which is characterized by a negative ρ value of -0.73.

A solid-phase synthetic route to N-acylated α-alkyl-D,L-homoserine lactones

A synthetic route to N-acylated α-alkyl-D,L-homoserine lactones was established using solid-phase unnatural peptide synthesis (UPS) and combinatorial chemistry. The application of UPS methodology allowed access to racemic N-acylated homoserine lactones (D,L-AHLs) and their α-alkyl structural analogs (α-R1-D,L-AHLs). The synthesis and characterization of a library of five D,L-AHLs and ten α-R1-D,L-AHLs prepared from resin-bound amino acids is reported.

Decarboxylative Borylation of mCPBA-Activated Aliphatic Acids

A decarboxylative borylation of aliphatic acids for the synthesis of a variety of alkylboronates has been developed by mixing m-chloroperoxybenzoic acid (mCPBA)-activated fatty acids with bis(catecholato)diboron in N,N-dimethylformamide (DMF) at room temperature. A radical chain process is involved in the reaction which initiates from the B-B bond homolysis followed by the radical transfer from the boron atom to the carbon atom with subsequent decarboxylation and borylation.

Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams

β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method

Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores

The synthesis of a series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores is presented. The biological activity of such imidazolium salts was further evaluated in vitro against a panel of human tumor cell lines. The results suggest that the electron-withdrawing group on the aza-brazilan moiety, substituted 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methylbenzyl group were essential for modulating the cytotoxic activity. Compounds 55 and 39, bearing a 4-methylbenzyl substituent at position-3 of 5,6-dimethyl-benzimidazole, were found to be the most potent compounds with IC50 values of 0.52-1.30 μM and 0.56-1.51 μM against four human tumor cell lines investigated. Particularly, compound 57 exhibited inhibitory activity against the MCF-7 cell line with an IC50 value of 0.35 μM and was 56-fold more sensitive than DDP. Moreover, compound 55 inhibited cell proliferation through inducing G0/G1 cell cycle arrest and apoptosis in SMMC-7721 cells.

Cyclohexyl-Fused, Spirobiindane-Derived, Phosphine-Catalyzed Synthesis of Tricyclic ?3-Lactams and Kinetic Resolution of ?3-Substituted Allenoates

A C2-symmetric chiral phosphine catalyst, NUSIOC-Phos, which can be easily derived from cyclohexyl-fused spirobiindane, was introduced. A highly enantioselective domino process involving pyrrolidine-2,3-diones and γ-substituted allenoates catalyzed by NUSIOC-Phos has been disclosed. Diastereospecific tricyclic γ-lactams containing five contiguous stereogenic centers were obtained in high yields and with nearly perfect enantioselectivities. A kinetic resolution process of racemic γ-substituted allenoates was developed for the generation of optically enriched chiral allenoates.

Ligand-Assisted Palladium(II)/(IV) Oxidation for sp3C H Fluorination

The direct functionalization of inert sp3C H bonds is limited to a few bond types. Although the activation of sp3C H bonds can be accomplished under mild conditions using palladium catalysts, the subsequent functionalization is not trivial due to the high energy required to convert palladium(II) to palladium(IV). We have systematically studied the palladium oxidation using computation-guided experiments for reactions involving strong chelation control. We find that a mild external ligand could significantly accelerate the oxidation of palladium(II) to palladium(IV) for strong bidentate directing groups. The acceleration is believed to be a result of ligand stabilization of both the palladium(II) and palladium(IV) intermediates. (Figure presented.) .

SUBSTITUTED BENZAMIDES AND THEIR USES

Provided herein are Substituted Benzamides, compositions, and method of their manufacture and use.

Synthesis of Alkyl-Substituted Pyridines by Directed Pd(II)-Catalyzed C-H Activation of Alkanoic Amides

A general alkylation protocol for substituted iodopyridines was developed (32 examples, 44-97% yield). The reaction is based on the Pd(II)-catalyzed C-H activation of 8-aminoquinoline-derived alkanoic amides and it employs a catalyst cocktail of Pd(OAc)2 (10 mol%), NaI (30 mol%), and (BuO)2POOH (20 mol%), with Ag2CO3 as base.

SUBSTITUTED BENZAMIDES AND THEIR USES

Provided herein are Substituted Benzamides, compositions, and method of their manufacture and use.