1643-30-7

Usage

Chemical Properties

White to light yellow or beige crystalline powder

InChI:InChI=1/C9H9BrO2/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5H,3,6H2,(H,11,12)

Upstream product

• 39109-67-6 3-(4-bromo-phenyl)-1,1-dichloro-propene 
• 823-78-9 meta-bromobenzyl bromide 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 501-52-0 3-Phenylpropionic acid 
• 92013-18-8 2-[(4-bromophenyl)methyl]propanedioic acid 
• 7726-95-6 bromine 
• 7732-18-5 water 
• 25574-11-2 3-(4-bromophenyl)propanol 
• 1772-43-6 2,4,4-trimethyl oxazoline 
• 198494-75-6 5-(4-bromo-benzyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 1122-91-4 4-bromo-benzaldehyde 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 4489-22-9 (+/-)-1-(4-bromophenyl)propanol 

Downstream Products

• 75567-84-9 methyl 3-(4-bromopehynl)propanoate 
• 586-76-5 4-Bromobenzoic acid 
• 14548-39-1 6-bromoindan-1-one 
• 52168-41-9 3‐(4‐bromophenyl)‐1‐phenylpropan‐1‐one 
• 1211311-93-1 3-(4-bromo-3-nitro-phenyl)-propionic acid 
• 55394-81-5 3-(4-bromophenyl)propanoyl chloride 
• 351014-59-0 vinyl 3-(4-bromophenyl)propanoate 
• 25574-11-2 3-(4-bromophenyl)propanol 
• 326496-52-0 tert-butyl 3-(4-bromophenyl)propanoate 
• 866815-84-1 4-(3-((tert-butyldimethylsilyl)oxy)propyl)benzaldehyde 
• 866815-86-3 {[4-(3-hydroxy-propyl)-phenyl]-phenyl-methyl}-carbamic acid tert-butyl ester 
• 866815-87-4 {[4-(3-azido-propyl)-phenyl]-phenyl-methyl}-carbamic acid tert-butyl ester 
• 866815-92-1 (S)-2-{[1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-phenyl}-meth-(E)-ylidene]-amino}-2-phenyl-ethanol 

Relevant academic research and scientific papers

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.

Regioselectivity inversion tuned by iron(iii) salts in palladium-catalyzed carbonylations

Impactful regioselectivity control is crucial for cost-effective chemical synthesis. By using cheap and abundant iron(iii) salts, the hydroxycarbonylations of both aromatic and aliphatic alkenes were significantly enhanced in both reactivity and selectivity (iso/n or n/iso up to >99:1). Moreover, Pd-catalyzed carbonylation selectivity can be switched from branched to linear by using different Fe(iii) salts. In addition, similar results were obtained for the carbonylation of secondary alcohols.

Pd-Catalyzed β-C(sp3)?H Arylation of Propionic Acid and Related Aliphatic Acids

A generally applicable Pd-catalyzed protocol for the β-C(sp3)?H arylation of propionic acid and related α-branched aliphatic acids is reported. Enabled by the use of N-acetyl-β-alanine as ligand our protocol delivers a broad range of arylation products. Notably, the highly challenging substrate, propionic acid, which lacks any acceleration through the Thorpe–Ingold effect, can be employed as substrate with synthetically useful yields. Furthermore, the scalability and synthetic applicability of the protocol are demonstrated.

Hydrocarboxylation of olefins by supported aqueous-phase catalysis

Pd-TPPTS complexes supported on acidic macro-porous resins (Pd-TPPTS/resin) have been employed for the hydrocarboxylation of 1-hexene and styrene derivatives by supported aqueous phase catalysis (SAPC). Acidic macroporous resins acted as substitutes for both heterogeneous acids and supports of Pd-TPPTS complexes afforded many advantages, such as easy separation from organic products and good reusability. The prepared Pd-TPPTS/resin catalysts were characterized by FT-IR, TG, SEM and N2 physisorption, which demonstrated that the Pd-TPPTS complexes were loaded on the resin. Compared with homogeneous analogue, the present SAP catalyst offered higher total acid yield and selectivity towards linear acid in the hydrocarboxylation of 1-hexene. Moreover, it was found that water had a significant influence on the catalytic activity and selectivity toward linear acid over the SAP catalyst. Optimum water/resin ratio at about 66.7% in the SAP catalyst afforded maximum activity under the given reaction temperature. The present SAP catalyst was highly Pd-leaching resistant and can be reused at least four times without obvious loss in activity.

SUBSTITUTED BENZAMIDES AND THEIR USES

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

A robust and simple protocol for the synthesis of arylfluorophosphonates

Fluorophosphonates represent powerful probes for the identification and analysis of active serine hydrolases in activity based protein profiling. Although alkylphosphonofluoridates are widely used for such purposes, little is known about the synthesis and purification of arylphosphonofluoridates, which may be useful tools for screening enzyme activities toward aromatic esters. Our optimized route makes this subclass of transition state inhibitors broadly accessible for a diverse series of phosphonic acid derivatives using a combination of selective monoesterification with EDC·HCl and subsequent mild fluorination with DAST. All compounds were isolated as pure materials using a simple acid-base extraction protocol in 76-93% yields over two steps. These probes can be stored under an inert atmosphere at -24 °C for several months without significant degradation.

SUBSTITUTED BENZAMIDES AND THEIR USES

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

A simple and straightforward approach toward selective C=C bond reduction by hydrazine

A simple and straightforward method for reducing the C=C double bond with hydrazine is described. A number of representative C=C bonds in various steric and electronic environments were examined. Substituted alkenes can be selectively reduced in EtOH in the presence of hydrazine to give the corresponding products in up to 100% yields.

Rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acrylic acid in water: One-step preparation of 3-arylpropionic acids

A practical method for the one-step preparation of 3-arylpropionic acids through rhodium-catalyzed 1,4-addition of arylboronic acids to acrylic acid is reported. The method is applicable to a broad scope of aryl boronic acids and displays a wide functional group tolerance operating in water as the optimal reaction medium. Georg Thieme Verlag Stuttgart · New York.

Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp 2 and sp3 carbon-hydrogen bonds

We have developed a method for auxiliary-directed, palladium-catalyzed β-arylation and alkylation of sp3 and sp2 C-H bonds in carboxylic acid derivatives. The method employs a carboxylic acid 2-methylthioaniline- or 8-aminoquinoline amide substrate, aryl or alkyl iodide coupling partner, palladium acetate catalyst, and an inorganic base. By employing 2-methylthioaniline auxiliary, selective monoarylation of primary sp3 C-H bonds can be achieved. If arylation of secondary sp 3 C-H bonds is desired, 8-aminoquinoline auxiliary may be used. For alkylation of sp3 and sp2 C-H bonds, 8-aminoquinoline auxiliary affords the best results. Some functional group tolerance is observed and amino- and hydroxy-acid derivatives can be functionalized. Preliminary mechanistic studies have been performed. A palladacycle intermediate has been isolated, characterized by X-ray crystallography, and its reactions have been studied.