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Allyl bromide

Base Information Edit
  • Chemical Name:Allyl bromide
  • CAS No.:106-95-6
  • Deprecated CAS:2581909-73-9
  • Molecular Formula:C3H5Br
  • Molecular Weight:120.977
  • Hs Code.:2903.30
  • European Community (EC) Number:203-446-6
  • NSC Number:7596
  • UN Number:1099
  • UNII:FXQ8X2F74Z
  • DSSTox Substance ID:DTXSID8024442
  • Nikkaji Number:J4.040A
  • Wikipedia:Allyl_bromide
  • Wikidata:Q223062
  • ChEMBL ID:CHEMBL1429506
  • Mol file:106-95-6.mol
Allyl bromide

Synonyms:allyl bromide

Suppliers and Price of Allyl bromide
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • AllylBromide(StabilizedwithPropyleneOxide)
  • 500g
  • $ 155.00
  • TRC
  • AllylBromide(StabilizedwithPropyleneOxide)
  • 250g
  • $ 120.00
  • TCI Chemical
  • Allyl Bromide >98.0%(GC)
  • 500g
  • $ 83.00
  • TCI Chemical
  • Allyl Bromide >98.0%(GC)
  • 25g
  • $ 21.00
  • SynQuest Laboratories
  • Allyl bromide 99.0%
  • 50 g
  • $ 15.00
  • SynQuest Laboratories
  • Allyl bromide 99.0%
  • 1 kg
  • $ 65.00
  • SynQuest Laboratories
  • Allyl bromide 99.0%
  • 250 g
  • $ 25.00
  • Sigma-Aldrich
  • 3-Bromo-1-propene (stabilised) for synthesis
  • 1 L
  • $ 148.00
  • Sigma-Aldrich
  • 3-Bromo-1-propene (stabilised) for synthesis. CAS No. 106-95-6, EC Number 203-446-6., (stabilised) for synthesis
  • 8010211000
  • $ 143.00
  • Sigma-Aldrich
  • Allyl bromide reagent grade, 97%, contains ≤1000 ppm propylene oxide as stabilizer
  • 1l
  • $ 135.00
Total 4 raw suppliers
Chemical Property of Allyl bromide Edit
Chemical Property:
  • Appearance/Colour:Colorless liquid 
  • Vapor Pressure:153mmHg at 25°C 
  • Melting Point:-119 ºC 
  • Refractive Index:n20/D 1.469(lit.)  
  • Boiling Point:68.107 ºC at 760 mmHg 
  • Flash Point:-1 ºC 
  • PSA:0.00000 
  • Density:1.398 g/cm3 
  • LogP:1.56730 
  • Storage Temp.:2-8°C 
  • Sensitive.:Light Sensitive 
  • Water Solubility.:insoluble 
  • XLogP3:1.8
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:0
  • Rotatable Bond Count:1
  • Exact Mass:119.95746
  • Heavy Atom Count:4
  • Complexity:17.2
  • Transport DOT Label:Flammable Liquid Poison
Purity/Quality:

99%min *data from raw suppliers

AllylBromide(StabilizedwithPropyleneOxide) *data from reagent suppliers

Safty Information:
  • Pictogram(s): FlammableF,ToxicT,Dangerous
  • Hazard Codes:F,T,N 
  • Statements: 11-23/25-34-50-25-46-45 
  • Safety Statements: 16-26-36/37/39-45-60-61-53 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Halogenated Aliphatics, Unsaturated
  • Canonical SMILES:C=CCBr
  • Uses Allyl Bromide is used as a reagent in the synthesis of Resveratrol derivatives. Resveratrol (R150000) is a minor constituent of wine, correlated with serum lipid reduction and inhibition of platelet a ggregation. Resveratrol is a specific inhibitor of COX-1, and it also inhibits the hydroperoxidase activity of COX-1. It has been shown to inhibit events associated with tumor initiation, promotion a nd progression. manufacture of synthetic perfumes, other allyl compounds. Allyl bromide is used as an alkylating agent in the synthesis of pharmaceuticals, polymers, adhesives, perfumes, biochemicals and other allylic compounds. It is used as precursor for the preparation of allyliczinc bromide by reacting it with zinc. It is also used in the preparation of allylethers like allyl decyl ether, allyl benzyl ether and allyl geranyl ether. It is also used in the preparation of R enantiomer of allyl phenyl carbinol (APC) such as 1-phenyl-3-butene, which is a valuable intermediate for drugs and agro-chemicals.
Technology Process of Allyl bromide

There total 76 articles about Allyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With piperazine; hydrogen; In ethanol; at 80 ℃; for 24h; under 4500.45 Torr;
DOI:10.1039/c9cy02016k
Guidance literature:
With silica bromide; In dichloromethane; at 20 ℃; for 0.0833333h;
DOI:10.2174/157017812802850285
Guidance literature:
In [D3]acetonitrile; Irradiation (UV/VIS); Degasses condition, 298 K, 33 h;; detected by NMR-spectroscopy;; Kinetics;
DOI:10.1021/om00145a020
Refernces Edit

Intramolecular cyclization of 1-[1-alkylsulfanyl-2-phenyl- 2-(phenylhydrazono)ethylidene]-pyrrolidinium salts

10.1007/s10593-010-0647-2

The study focuses on the intramolecular cyclization of 1-[1-alkylsulfanyl-2-phenyl-2-(phenylhydrazono)ethylidene]pyrrolidinium salts, which are synthesized by the alkylation of thioamide with benzyl, allyl, and propargylsulfanyl groups in the presence of cesium carbonate in DMF at room temperature. These pyrrolidinium salts can be efficiently converted into 1,3-diphenyl-6,7,8,8a-tetrahydro-1H-pyrrolo[2,1-c]-1,2,4-triazine-4-thione derivatives in good yields. The research demonstrates that this cyclization method is general for alkyl derivatives of arylhydrazonothioacetamides, expanding the scope of this reaction type. The synthesized pyrrolotriazines are of practical interest due to their potential high antitumor activity, making them promising candidates for biological investigation. The study was financially supported by the Russian Basic Research Fund and includes detailed experimental procedures, characterization data, and comparison of the reaction outcomes with different bases and solvents.

Sequential Birch reduction-allylation and Cope rearrangement of o-anisic acid derivatives

10.1016/j.tetlet.2004.09.025

The study presents a novel approach for constructing quaternary centers on cycloalkane rings, which is a significant challenge in synthetic chemistry. The researchers utilized a combination of Birch reduction-allylation and Cope rearrangement on o-anisic acid derivatives to synthesize 2-acyl-3-cyclohexenone derivatives. They successfully generated rearrangement substrates and achieved high yields of 2-cyclohexenone products through thermal equilibration in 1,2-dichlorobenzene. Notably, the Cope rearrangement of a specific substrate resulted in the formation of a new quaternary center with excellent yield, marking the first example of such synthesis on a cycloalkenone ring via Cope rearrangement. This method could serve as a powerful tool for creating substituted 2-cyclohexenones, offering a potentially versatile synthetic intermediate with potential for 1,3-chirality transfer and access to enantiomerically pure products.

Studies on indium-mediated additions to lactones: Synthesis of 2-deoxy-2-substituted-3-ulosonic acids

10.1016/j.tetasy.2010.07.011

The research focuses on the indium-mediated Reformatsky reaction of sugar lactones, specifically the synthesis of 2-deoxy-2-substituted-3-ulosonic acids, which are important for creating biologically active compounds and new biopolymers. The experiments involved the reaction of a mannose-derived lactone with various ethyl 2-bromo-alkanoates and 2-bromo-lactones in the presence of indium powder and under ultrasonic waves. Reactants included D-mannose-derived lactone, different bromo-alkanoates, and 2-bromo-lactones. Allyl bromide 22 was used in the indium-mediated allylation reaction to produce addition adduct 23. The analyses used to characterize the products comprised of techniques such as single crystal X-ray analysis, NMR spectroscopy, and mass spectrometry, which confirmed the stereochemistry at the newly created stereogenic center and provided information on the structure and purity of the synthesized ulosonic acid esters. The study proposed a mechanistic explanation for the reaction's stereoselectivity and discussed the potential applications of the synthesized branched chain sugars.

A simple and direct method for converting thioamides into thioesters

10.1016/S0040-4020(98)01096-5

The research aimed to develop a simple, direct, and efficient method for converting thioamides into thioesters, which are activated carboxylic acid derivatives with applications in synthetic chemistry. The study addressed the need for a reliable, multi-gram synthesis of thioesters and proposed a new route from thioamides that is mild, inexpensive, and experimentally straightforward. The method involved warming thioamides in an aqueous tetrahydrofuran (THF) solution containing an alkylating agent, leading to high yields and being scalable to multi-gram levels. The reactions were found to be tolerant of aryl ethers and acetals, and when volatile alkyl halides were used, products of approximately 95% purity could be obtained without chromatographic purification. Key chemicals used in the process included various thioamides, alkyl iodides, dialkyl sulfates, and activated alkyl bromides as alkylating agents, with methyl iodide (MeI), ethyl iodide (EtI), allyl bromide (allyl-Br), and benzyl bromide (BnBr) being specific examples. The study concluded that the developed method was effective for preparing thioesters from thioamides, offering a practical alternative to existing methods.

Synthesis of Substituted 2,6-Dioxabicyclo<3.1.1>heptanes. 1,3-Anhydro-2,4,6-tri-O-benzyl- and 1,3-Anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose

10.1021/jo00317a030

The study investigates the synthesis and properties of substituted 2,6-dioxabicyclo[3.1.1]heptanes, specifically focusing on the compounds 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-mannopyranose and 1,3-anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose. These compounds are synthesized through a series of reactions involving various reagents such as dibutyltin oxide, allyl bromide, benzyl chloride, and p-bromobenzyl bromide. The synthesis process includes steps like acetylation, benzylation, and ring closure using strong bases like sodium hydride (NaH) and potassium tert-butoxide (t-BuOK). The study aims to produce these anhydro sugars as precursors for the synthesis of 1,3-mannopyranans by ring-opening polymerizations, which are of interest for their potential applications in immunological and biochemical investigations. The compounds' structures are confirmed through mass spectrometry, 1H NMR, and 13C NMR spectroscopy, and their stability and purity are assessed through various analytical techniques.

Reaction with aqueous alkali of diammonium salts with a 1,1-dimethylbut-2-yne-1,4-diyl common group

10.1023/A:1023419530311

The study in the provided document investigates the reaction of quaternary ammonium salts with a 1,1-dimethylbut-2-yne-1,4-diyl common group with aqueous alkali. The research focuses on the intermediate formation of 1,2-cleavage products rather than 1,4-cleavage products. When both nitrogen atoms have allylic groups, a rearrangement followed by cleavage and substitution occurs, leading to the formation of methyl isopropyl ketones. Salts with two 3-methylbut-2-en-1-yl groups result in the cleavage of isoprene. The study also explores the reactions of 1,4-diammonium salts with two methyl substituents in the but-2yne-1,4-diyl common group under the influence of aqueous alkali, detailing the products and mechanisms involved in these chemical transformations.

Total synthesis of the marine polypropionates, siphonarienal, siphonarienone, and pectinatone

10.1016/j.tetasy.2009.08.021

The research focuses on the total synthesis of marine polypropionates—siphonarienal, siphonarienone, and pectinatone—employing a desymmetrization strategy to create three consecutive stereogenic centers. The synthesis involves a series of chemical reactions starting from known precursors, utilizing reactants such as allyl bromide, LHMDS, LAH, 2,2-dimethoxypropane, CSA, Bn-Br, TsCl, Et3N, DMAP, LiAlH4, DDQ, and others as detailed in the experimental section. The synthesis steps include allylation, reductive ring opening, protection of hydroxyl groups, selective tosylation, reductive cleavage, and oxidation, among others. The synthesized compounds were analyzed using techniques like TLC, NMR, MS, and HRMS to confirm their structures and purities. The study also compares the efficiency of this strategy to previous methods, highlighting its advantage of creating three stereogenic centers in a single reaction, which is more efficient than the approximately 10 steps required by other methods.

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