74532-85-7

Basic information

• Product Name: (R)-1-(2-broMophenyl)propan-1-ol
• Synonyms: (R)-1-(2-broMophenyl)propan-1-ol
• CAS NO: 74532-85-7
• Molecular Formula: C10H11Br
• Molecular Weight: 215.09
• Mol File: 74532-85-7.mol

Chemical Properties

• CAS DataBase Reference: (R)-1-(2-broMophenyl)propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(2-broMophenyl)propan-1-ol(74532-85-7)
• EPA Substance Registry System: (R)-1-(2-broMophenyl)propan-1-ol(74532-85-7)

Safety Data

• Hazardous Substances Data: 74532-85-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(R)-1-(2-bromophenyl)propan-1-ol is used as a key intermediate in the organic synthesis of various compounds, including pharmaceuticals, agrochemicals, and perfumes. Its unique structure and reactivity make it a valuable building block for creating complex molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (R)-1-(2-bromophenyl)propan-1-ol is used as an intermediate for the production of various drugs. Its chiral nature allows for the creation of enantiomerically pure compounds, which can have different biological activities and are essential in drug development.
Used in Agrochemicals:
(R)-1-(2-bromophenyl)propan-1-ol is also utilized in the agrochemical industry as an intermediate for the synthesis of pesticides and other agricultural chemicals. Its versatility in chemical reactions enables the development of new compounds with improved efficacy and selectivity.
Used in Perfumery:
In the perfume industry, (R)-1-(2-bromophenyl)propan-1-ol is used as a starting material for the synthesis of various fragrance components. Its ability to undergo chemical transformations allows for the creation of a wide range of scent molecules.
Used in Stereochemistry Research:
(R)-1-(2-bromophenyl)propan-1-ol has potential applications in the study of stereochemistry, which is the branch of chemistry that deals with the three-dimensional arrangement of atoms in molecules. Its chiral nature makes it an ideal candidate for investigating the effects of molecular geometry on chemical reactions and biological activities.
Used in Drug Candidate Development:
Due to its unique structural features, (R)-1-(2-bromophenyl)propan-1-ol is also used in the development of new drug candidates. Its potential applications in this area include the creation of novel therapeutic agents with improved pharmacological properties and reduced side effects.

Upstream product

• 74-96-4 ethyl bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 925-90-6 ethylmagnesium bromide 
• 557-20-0 diethylzinc 
• 811-49-4 ethyllithium 
• 927-77-5 n-propylmagnesium bromide 
• 7154-66-7 2-bromobenzoic acid chloride 
• 62403-86-5 2-bromopropiophenone 
• 18982-54-2 o-bromobenzyl alcohol 
• 123-38-6 propionaldehyde 
• 583-53-9 2,3-dibromobenzene 
• 2386-64-3 ethylmagnesium chloride 

Downstream Products

• 958633-19-7 (Z)-4,4,5,5-tetramethyl-2-(2-phenyl-1-buten-1-yl)-1,3,2-dioxaborolane 
• 1354364-38-7 3-(2-bromophenyl)pentan-3-ol 
• 1200767-94-7 1-(2-bromophenyl)propyl acetate 
• 134024-26-3 4-Methoxy-4-[((Z)-2-propenyl)-phenyl]-cyclohexa-2,5-dienone 
• 92628-24-5 triethyl 4-(2-bromophenyl)-5-methylpyridine-2,3,6-tricarboxylate 
• 70913-13-2 (E)-1-(propen-1-yl)-2-(1-methyl-2,3-diphenyl-2-cyclopropen-1-yl)benzene 
• 70968-46-6 (Z)-1-bromo-2-(2-methylethenyl)benzene 
• 637-50-3 1-phenylpropene 

Relevant articles and documents

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations

A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).

Asymmetric Synthesis and Application of Chiral Spirosilabiindanes

Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.

Synthesis of Carbamates from Alkyl Bromides and Secondary Amines Using Silver Carbonate

Synthesis of alkyl carbamates from alkyl bromides and secondary amines using silver carbonate as a carbonate source under mild condition is described. Various secondary amines and bromo derivatives were converted into alkyl carbamate derivatives in 33 to 62 % yield.

Synthesis of fluorenyl alcohols: Via cooperative palladium/norbornene catalysis

Herein, we report a novel catalytic synthesis of substituted 9H-fluoren-9-ols starting from aryl iodides and secondary ortho-bromobenzyl alcohols in the presence of palladium/norbornene as a catalytic system. The present protocol exhibits high functional

NBS-mediated synthesis of β-keto sulfones from benzyl alcohols and sodium arenesulfinates

An efficient synthetic route towards the synthesis of β-keto sulfones has been developed from secondary benzyl alcohols using N-bromosuccinimide (NBS). The present protocol utilizes NBS as oxidant as well as brominating agent, readily accessible benzyl alcohols and sodium arenesulfinates as the sulfonylating reagent under mild conditions. The control experiments revealed that the reaction proceeds via oxidation of alcohol to ketone, α-bromination of ketone and nucleophilic substitution by sodium arenesulfinate. Furthermore, the efficiency of the methodology was tested with a gram scale reaction and also shown the synthetic utility.

Phosphine- and water-promoted pentannulative aldol reaction

Herein, an efficient metal-free intramolecular aldol reaction for the synthesis of an unusual class of cyclopentanoids is described. The reaction of α-substituted dienones tethered with ketones in the presence of tributylphosphine and water provided aldols. The role of water was realised to be crucial for this transformation. Furthermore, isotopic labeling experiments provided vital information about the reaction mechanism.

Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones

A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.

One-Pot Asymmetric Synthesis of Alkylidene 1-Alkylindan-1-ols Using Br?nsted Acid and Palladium Catalysis

A one-pot catalytic enantioselective allylboration/Mizoroki-Heck reaction of 2-bromoaryl ketones has been developed for the asymmetric synthesis of 3-methyleneindanes bearing a tertiary alcohol center. Br?nsted acid-catalyzed allylboration with a chiral BINOL derivative was followed by a palladium-catalyzed Mizoroki-Heck cyclization, resulting in selective formation of the exo-alkene. This novel protocol provides a concise and scalable approach to 1-alkyl-3-methyleneindan-1-ols in high enantiomeric ratios (up to 96:4 er). The potential of these compounds as chiral building blocks was demonstrated with efficient transformation to optically active diol and amino alcohol scaffolds.

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.