76334-36-6

Basic information

• Product Name: 3-Bromo-3-buten-1-ol
• Synonyms: 3-Bromo-3-buten-1-ol, stabilized with copper;3-BROMO-3-BUTEN-1-OL;3-Bromo-3-buten-1-ol, 97+%;3-BroMo-3-buten-1-ol, 97+% 10GR;3-BroMo-3-buten-1-ol, 97%, stab. with copper;3-broMobut-3-en-1-ol;3-BROMO-2-BUTEN-1-OL
• CAS NO: 76334-36-6
• Molecular Formula: C₄H₇BrO
• Molecular Weight: 151
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 76334-36-6.mol

Chemical Properties

• Boiling Point: 64-65 °C9 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear brown/liquid (clear)
• Density: 1.522 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.412mmHg at 25°C
• Refractive Index: n20/D 1.499(lit.)
• PKA: 14.86±0.10(Predicted)
• Sensitive: Light Sensitive
• BRN: 1737671
• CAS DataBase Reference: 3-Bromo-3-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-3-buten-1-ol(76334-36-6)
• EPA Substance Registry System: 3-Bromo-3-buten-1-ol(76334-36-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41-43
• Safety Statements: 26-36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 76334-36-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Bromo-3-buten-1-ol is used as a building block in the synthesis of various organic compounds due to its reactive nature and functional groups. It plays a crucial role in the formation of α-methylene lactones, which are important intermediates in the synthesis of numerous pharmaceuticals and natural products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Bromo-3-buten-1-ol is used as a key intermediate for the synthesis of tricyclic sesquiterpenes. These complex organic compounds have been found to possess a range of biological activities, including anti-inflammatory, antifungal, and anticancer properties.
Used in Chemical Research:
3-Bromo-3-buten-1-ol is also utilized in chemical research for various cyclization and alkylation reactions. Its unique structure allows for the development of new synthetic routes and the creation of novel compounds with potential applications in various fields, such as materials science, agrochemistry, and environmental science.

InChI:InChI=1/C4H7BrO/c1-4(5)2-3-6/h6H,1-3H2

Upstream product

• 55030-57-4 2,4-dibromo-1-butene 
• 127-08-2 potassium acetate 
• 21031-50-5 ethyl α-(bromomethyl)acrylate 
• 927-74-2 3-Butyn-1-ol 
• 109-87-5 Dimethoxymethane 
• 513-31-5 2-bromoallyl bromide 
• 50-00-0 formaldehyd 
• 2117-12-6 4-(trimethylsilyl)but-3-yn-1-ol 
• 35804-44-5 ethyl 4-bromo-4-pentenoate 

Downstream Products

• 927-74-2 3-Butyn-1-ol 
• 910819-14-6 3-(3-chlorophenyl)but-3-en-1-ol 
• 29123-91-9 3-(4-fluorophenyl)-3-buten-1-ol 
• 1134201-53-8 3-(4-isopropylphenyl)but-3-en-1-ol 
• 1134201-46-9 3-(o-tolyl)-3-butene-1-ol 
• 29123-93-1 3-m-methylphenyl-3-buten-1-ol 
• 29128-22-1 3-(4-methylphenyl)-3-buten-1-ol 
• 29123-92-0 3-(4-chlorophenyl)but-3-en-1-ol 
• 1134201-59-4 C₁₂H₁₆O 
• 1134201-55-0 3-(4-(tert-butyl)phenyl)but-3-en-1-ol 
• 1134201-61-8 C₁₂H₁₆O₃ 
• 1134201-51-6 C₁₄H₂₀O 
• 1134201-63-0 C₁₂H₁₆O 
• 1459714-30-7 8-methyl-3-methylenenon-4-yn-1-ol 

Relevant articles and documents

Domino Prins/pinacol reaction for the stereoselective synthesis of spiro[pyran-4,4′-quinoline]-2′,3′-dione derivatives

A wide array of aldehydes undergo smooth cross-coupling with 3-hydroxy-3-(4-hydroxybut-1-en-2-yl)-1-methylindolin-2-one in the presence of 10 mol% BF3·OEt2 at 0 °C in dichloromethane to afford the corresponding 2,3,5,6-tetrahydro-1′H-spiro[pyran-4,4′-quinoline]-2′,3′-dione derivatives in good yields with excellent diastereoselectivity. This is the first report on the synthesis of tetrahydro-1′H-spiro[pyran-4,4′-quinoline]-2′,3′-dione scaffolds through a cascade of Prins/pinacol reactions.

BORONIC ACID DERIVATIVES AND THERAPEUTIC USES THEREOF

Disclosed herein are antimicrobial compounds, compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to boronic acid derivatives and their use a therapeutic agents.

Photoredox-Catalyzed Cyclopropanation of 1,1-Disubstituted Alkenes via Radical-Polar Crossover Process

The photoredox-neutral catalyzed cyclopropanation of 1,1-disubstituted alkenes via radical addition-anionic cyclization cascade has been successfully developed. Another new protocol based on photocatalytic allylation and cyclopropanation cascade was also described between allylic halide and halomethyl radical. In addition to the successful use of bis-catecholato silicates as the alkyl radical precursors, the acyl and alkyl radicals derived from 1,4-dihydropyridines were also engaged in this radical-polar crossover process. The competing experiments displayed that the 3-exo-tet mode of cyclization preferred over 4-exo and 5-exo cyclization modes, allowing for the selective 3-exo-tet cyclization. The superior nucleofuge character of bromide over chloride and tosylate has been demonstrated in the reaction of bromomethyl radical with homoallylic (pseudo)halides. This new protocol is characterized by its redox-neutral process, broad substrate scope, mild conditions, and good functional-group compatibility. (Figure presented.).

Ring strain-dictated divergent fluorinating Prins cyclization or semipinacol rearrangement

We have developed ring-strain dictated divergent diastereoselective fluorinating Prins cyclization reactions or semipinacol rearrangement reactions to access tetrahydropyrans containing a fluorohydrin or a carbonyl moiety at quaternary carbon centers under mild conditions, respectively.

Hydroalumination of terminal β-acetylene alcohols with lithium aluminum hydride

Hydrogenation of terminal β-acetylene alcohols with lithium aluminum hydride in THF has afforded homoallylic alcohols. Decomposition of the intermediate organoaluminum complex with deuterated water, iodine, or pyridinium dibromide has evidenced about the non-regioselective hydride attack at the triple bond.

Ynamide Carbopalladation: A Flexible Route to Mono-, Bi- and Tricyclic Azacycles

Bromoenynamides represent precursors to a diversity of azacycles by a cascade sequence of carbopalladation followed by cross-coupling/electrocyclization, or reduction processes. Full details of our investigations into intramolecular ynamide carbopalladation are disclosed, which include the first examples of carbopalladation/cross-coupling reactions using potassium organotrifluoroborate salts; and an understanding of factors influencing the success of these processes, including ring size, and the nature of the coupling partner. Additional mechanistic observations are reported, such as the isolation of triene intermediates for electrocyclization. A variety of hetero-Diels-Alder reactions using the product heterocycles are also described, which provide insight into Diels-Alder regioselectivity.

Tandem Prins/pinacol reaction for the synthesis of oxaspiro[4.5]decan-1-one scaffolds

A novel Lewis acid catalyzed Prins/pinacol cascade process has been developed for the synthesis of 7-substituted-8-oxaspiro[4.5]decan-1-ones in good yields with excellent selectivity. This is the first example of the synthesis of oxaspirocycles from aldehydes and 1-(4-hydroxybut-1-en-2-yl)cyclobutanol through a cascade of Prins/pinacol rearrangement. This method is applicable to a wide range of aldehydes such as aromatic, aliphatic, heteroaromatic, and α,β-unsaturated aldehydes. This journal is the Partner Organisations 2014.

Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N -allylcarboxamides

A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)2 as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with u

Reductive cyclization of bromoenynamides with alcohols as hydride source: Synthesis and reactions of 2-amidodienes

Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles. Copyright

SnCl2/KI-mediated allylation reactions of formaldehyde in water

An efficient procedure for SnCl2/KI-mediated allylation reactions of formaldehyde with a variety of allylic bromides in aqueous solution is reported. Under conditions developed in this effort, various homoallylic alcohols and 2-halohomoallylic alcohols are produced in good to excellent yields. Georg Thieme Verlag Stuttgart New York.