170859-80-0

Basic information

• Product Name: 3-(3-BROMOPHENYL)PROP-2-YN-1-OL
• Synonyms: 3-(3-BROMOPHENYL)PRO-2-YN-1-OL;3-(3-BROMOPHENYL)PROP-2-YN-1-OL;AKOS PRN-0010
• CAS NO: 170859-80-0
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• Mol File: 170859-80-0.mol

Chemical Properties

• Boiling Point: 304.2 °C at 760 mmHg
• Flash Point: 137.8 °C
• Appearance: /
• Density: 1.58g/cm³
• Vapor Pressure: 0.000389mmHg at 25°C
• Refractive Index: 1.638
• PKA: 13.02±0.10(Predicted)
• CAS DataBase Reference: 3-(3-BROMOPHENYL)PROP-2-YN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-BROMOPHENYL)PROP-2-YN-1-OL(170859-80-0)
• EPA Substance Registry System: 3-(3-BROMOPHENYL)PROP-2-YN-1-OL(170859-80-0)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 170859-80-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(3-BROMOPHENYL)PROP-2-YN-1-OL is used as a key intermediate in the synthesis of various pharmaceuticals due to its ability to be readily modified and incorporated into complex molecular structures. Its unique properties facilitate the development of new drugs with specific therapeutic targets.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(3-BROMOPHENYL)PROP-2-YN-1-OL is utilized as a building block for the creation of new pesticides and other agrochemicals, capitalizing on its reactivity and structural diversity to enhance crop protection and yield.
Used in Research and Development:
3-(3-BROMOPHENYL)PROP-2-YN-1-OL is employed as a starting material in research laboratories for the preparation of innovative organic molecules with potential applications in various fields. Its role in the synthesis of new compounds with biological activities makes it an essential tool in drug discovery and the development of new chemical entities.

InChI:InChI=1/C9H7BrO/c10-9-5-1-3-8(7-9)4-2-6-11/h1,3,5,7,11H,6H2

Upstream product

• 19070-80-5 n-<(trimethylsiloxy)methyl>phthalimide 
• 3989-13-7 2-(3-bromophenyl)ethynyltrimethylsilane 
• 108-36-1 1,3-dibromobenzene 
• 107-19-7 propargyl alcohol 
• 591-18-4 1-Bromo-3-iodobenzene 

Downstream Products

• 86610-63-1 (E)-1-bromo-3-(3-chloroprop-1-en-1-yl)benzene 
• 1333171-03-1 (6S)-6-({3-[4'-(difluoromethoxy)[1,1'-biphenyl]-3-yl]-2-propynyl}oxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 
• 1333171-02-0 (6S)-2-nitro-6-[(3-{3-[6-trifluoromethyl-3-pyridinyl]phenyl}-2-propynyl)oxy]-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine 

Relevant articles and documents

One-pot synthesis of 3-substituted-4H-[1,2,3] triazolo[5,1-c][1,4]oxazin-6(7H)-ones from propargyl alcohols, chloroacetyl chloride, and sodium azide

An efficient, one-pot synthesis of 3-substituted-4H-[1,2,3]triazolo[5,1-c][1,4]oxazin-6(7H)-ones is developed via sequential esterification, substitution, and 1,3-dipolar cycloaddition processes of various propargyl alcohols, chloroacetyl chloride, and so

Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes

Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.

When Gold Meets Perfumes: Synthesis of Olfactive Compounds via Gold-Catalyzed Cycloisomerization Reactions

An efficient, and mild synthetic route for the preparation of functionalized volatile oxa-bicyclo[4.1.0]-hept-4-ene (29 compounds, 44-98% isolated yields) has been developed relying on the association of IPrAuCl with NaBArF. The remarkable selectivity was demonstrated on a 1 g and 25 g scale with low catalyst loadings. The synthetic utility of these low-molecular-weight enols was further demonstrated by the derivatization of some adducts and by the unprecedented olfactory evaluation of all bicyclic derivatives.

Copper-Catalyzed Propargylation of Nitroalkanes

Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Applications of Thermal Activation, Ball-milling and Aqueous Medium in Stereoselective Michael Addition of Nitromethane to Enynones Catalyzed by Chiral Squaramides

Stereoselective addition of nitromethane to conjugated en-ynones was performed through the application of chiral squaramides. Three non-classical approaches to promote the addition reaction were tested, including activation of the nucleophile by inorganic base in a biphasic aqueous system, thermal activation, and ball-milling. Hydrogen-bonding catalysis was effective in all these methods, providing 1,4-addition products in high yields and stereoselectivities of up to 98% requiring 1–5 mol% of Cinchona alkaloid squaramide. (Figure presented.).

Catalytic asymmetric synthesis of 2,5-dihydrofurans using synergistic bifunctional Ag catalysis

We report a bifunctional Ag catalyst promoted intramolecular capture of oxonium ylides with alkynes for the enantioselective synthesis of 2,5-dihydrofurans. This represents unprecedented synergistic catalysis of a bifunctional Ag catalyst. Mechanistic studies revealed that [(R)-3,5-DM-BINAP](AgSbF6)2 (9) is likely to be the active catalytic species and that the reaction involves second order kinetics with respect to 9, suggesting that two molecules of 9 are involved in the intramolecular trapping of a Ag-associated oxonium ylide with a Ag-activated alkyne. Based on our mechanistic hypothesis, we further optimized the reaction, rendering a facile approach to 2,5-dihydrofurans in good to excellent yields in a highly chemo- and enantioselective fashion.

Sodium Phenoxide Mediated Hydroxymethylation of Alkynylsilanes with N-[(Trimethylsiloxy)methyl]phthalimide

The hydroxymethylation of alkynylsilanes with formaldehyde generated in situ from N-[(trimethylsiloxy)methyl]phthalimide proceeds in the presence of a stoichiometric amount of NaOPh. The reaction occurs at room temperature by using an operationally simple one-step procedure. A variety of alkynylsilanes possessing electron-donating, electron-withdrawing, and halogen groups (including heteroaryl-substituted alkynylsilanes) provide hydroxymethylated products.

Pd(ii)-catalyzed formal [4+1] cycloaddition reactions of diazoacetates and aryl propargyl alcohols to form 2,5-dihydrofurans

A Pd(ii)-catalyzed formal [4+1] cycloaddition of aryl diazoacetates and aryl propargyl alcohols is reported to afford 2,5-dihydrofuran derivatives as the dominant product over other traditional ones. The auto-tandem catalytic process is proposed to occur via Pd(ii)-catalyzed intermolecular oxonium ylide formation and subsequent intramolecular trapping of the ylide with Pd(ii)-activated alkynes.

AMINE COMPOUND AND PHARMACEUTICAL USE THEREOF

Provided is a novel amine compound represented by the following formula (I) having a superior peripheral blood lymphocyte decreasing action and superior in the immunosuppressive action, rejection suppressive action and the like, which shows decreased side effects of, for example, bradycardia and the like, or a pharmaceutically acceptable acid addition salt thereof, or a hydrate thereof, or a solvate thereof. wherein each symbol is as defined in the specification.