allyl bromide

1-bromo-2-propene

CAS: 106-95-6 C3 H5 Br MW: 120.97685000

Identification

Nameallyl bromide
IUPAC3-bromoprop-1-ene
CAS Number106-95-6
EINECS203-446-6
FDA UNIIFXQ8X2F74Z
Molecular FormulaC3 H5 Br
Molecular Weight120.97685000
MDL NumberMFCD00000244
Nikkaji NumberJ4.040A
Beilstein0605308
XlogP31.80 (est)

Regulatory

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.39800 @ 25.00 °C.
Melting Point -11.90 °C. @ 760.00 mm Hg
Boiling Point 70.10 °C. @ 760.00 mm Hg
Vapor Pressure 153.455002 mmHg @ 25.00 °C. (est)
Vapor Density 4.17 ( Air = 1 )
Flash Point 28.00 °F. TCC ( -2.22 °C. )
logP (o/w) 1.790
Soluble in water, 3830 mg/L @ 25 °C (exp)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 48 mg/kg
Dermal ToxicityNot determined
Inhalation Toxicityinhalation-mammal (species unspecified) LC50 4110 mg/m3

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
IFRA Purity Specification< 0.1% free allyl alcohol
Recommendation for allyl bromide usage levels up tonot for fragrance use.
Recommendation for allyl bromide flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

allylbromide bromallylene 1- bromo-2-propene 3- bromo-propene 3- bromoprop-1-ene 3- bromopropene 3- bromopropylene 1- propene, 3-bromo- PubMed: Nematicidal activity of allyl bromide and dibromo(nitro)methane under laboratory conditions PubMed: Toxicology studies of allyl bromide (CAS No. 106-95-6) in genetically modified (FVB Tg.AC hemizygous) mice and carcinogenicity studies of allyl bromide in genetically modified [B6.129-Trp53tm1Brd (N5) Hapl PubMed: Retraction: Belta‹ef et al. An expeditious synthesis of [1,2]isoxazolidin-5-ones and [1,2]oxazin-6-ones from functional allyl bromide derivatives. Molecules 2010, 15, 4094-4101 PubMed: Indium-Mediated Stereoselective Allylation PubMed: Design, synthesis, and SAR study of isopropoxy allylbenzene derivatives as 15-lipoxygenase inhibitors PubMed: Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin PubMed: Rotation-Triggered Transmetalation on a Heterobimetallic Cu/Al N-Phosphine-Oxide-Substituted Imidazolylidene Complex PubMed: Hyperbranched Poly(ether-siloxane)s Containing Ammonium Groups: Synthesis, Characterization and Catalytic Activity PubMed: Direct and Delayed Dynamics in Electron-Induced Surface Reaction PubMed: Synthesis of Quaternary-Substituted Thiazolines via Halocyclization of S-Allyl Thioimidate Salts PubMed: Bioconversion of ethyl 4-chloro-3-oxobutanoate by permeabilized fresh brewer's yeast cells in the presence of allyl bromide PubMed: Palladium-catalyzed allyl cross-coupling reactions with in situ generated organoindium reagents PubMed: Synthesis of novel tri- and tetrasubstituted C18 furan fatty esters PubMed: The Role Ionic Liquid [BMIM][PF(6)] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier-Prins Reaction PubMed: Chromium(III)-Catalyzed C(sp(2))-H Alkynylation, Allylation, and Naphthalenation of Secondary Amides with Trimethylaluminum as Base PubMed: An expeditious synthesis of [1,2]isoxazolidin-5-ones and [1,2]oxazin-6-ones from functional allyl bromide derivatives PubMed: Mannan-based conjugates as a multimodal imaging platform for lymph nodes PubMed: In-situ synthesis of acylated sodium alginate-g-(tetrahydrofuran(5)-b-polyisobutylene) terpolymer/Ag-NPs nanocomposites PubMed: Total synthesis of alotaketal A PubMed: ?-Cyclodextrin functionalized polystyrene porous monoliths for separating phenol from wastewater PubMed: Novel Quaternary Ammonium-Functionalized Covalent Organic Frameworks/Poly(2,6-dimethyl-1,4-phenylene oxide) Hybrid Anion Exchange Membranes with Enhanced Ion Conductivity and Stability PubMed: B-B Bond Nucleophilicity in a Tetraaryl ?-Hydridodiborane(4) Anion PubMed: Redox-Active Ligand-Assisted Two-Electron Oxidative Addition to Gallium(II) PubMed: A mild synthesis of new aryl vinyl ethers and diethyl 1-[(alkyl)(cyano)methyl]vinylphosphonates via the substitution of a 2,3-difunctional allyl bromide PubMed: Allylic compounds bind directly to DNA: investigation of the binding mechanisms in vitro PubMed: Synthesis of a spirocyclic indoline lactone PubMed: Organic impurity profiling of 3,4-methylenedioxymethamphetamine (MDMA) synthesised from catechol PubMed: N,N,N-trimethylchitosan modified with well defined multifunctional polymer modules used as pDNA delivery vector PubMed: Structures and Reactivities of Sodiated Evans Enolates: Role of Solvation and Mixed Aggregation on the Stereochemistry and Mechanism of Alkylations PubMed: An efficient asymmetric synthesis of diacylglycerols PubMed: Synthesis and antimicrobial evaluation of novel pyrazolones and pyrazolone nucleosides PubMed: Preparation of (+)-trans-isoalliin and its isomers by chemical synthesis and RP-HPLC resolution PubMed: Gas-phase synthesis of [Ag4H]+ and its mediation of the C--C coupling of allyl bromide PubMed: Expeditious synthesis of the fused hexacycle of puberuline C via a radical-based cyclization/translocation/cyclization process PubMed: Synthesis and anticancer activity of some new s-glycosyl and s-alkyl 1,2,4-triazinone derivatives PubMed: Direct synthesis of B-allyl and B-allenyldiisopinocampheylborane reagents using allyl or propargyl halides and indium metal under Barbier-type conditions PubMed: Design and synthesis of modular oxazoline ligands for the enantioselective chromium-catalyzed addition of allyl bromide to ketones PubMed: Oxidation state, aggregation, and heterolytic dissociation of allyl indium reagents PubMed: Kinetic and spectroscopic characterization of the isomers of the allyl bromide molecular ion PubMed: Preparation of cis-?-hydroxycarvone derivatives for synthesis of sesterterpenoid natural products: total synthesis of phorbin A PubMed: Pharmacological actions of levallorphan allyl bromide (CM 32191), a new peripheral narcotic antagonist PubMed: Per-O-(3-hydroxy)propyl-beta-cyclodextrin: a cyclodextrin derivative bearing only primary hydroxyl groups PubMed: Rapid detection of avian influenza A virus by immunochromatographic test using a novel fluorescent dye PubMed: Reactions of atoms and free radicals in solution; the reaction of allyl bromide with bromotrichloromethane PubMed: Structure and reactivity of the cysteine methyl ester radical cation PubMed: Structure and Reaction Chemistry of Magnesium Organocuprates Derived from Magnesiacyclopentadienes and Copper(I) Salts PubMed: Asymmetric syntheses of epohelmins A and B by In-mediated allylation PubMed: Mutagenicity of vinyl compounds in Salmonella typhimurium PubMed: Metal-free activation in the anionic ring-opening polymerization of cyclopropane derivatives PubMed: One-pot preparation of trifluoromethylated homoallylic N-acylhydrazines or à-methylene-?-lactams from acylhydrazines, trifluoroacetaldehyde methyl hemiacetal, allyl bromide and tin PubMed: Secondary deuterium kinetic isotope effects in irreversible additions of allyl reagents to benzaldehyde PubMed: Copper-catalyzed regioselective fluorination of allylic halides PubMed: [Investigation on isotopic exchange of bromine between sodium bromide and allyl bromide in alcohol solution] PubMed: Role of Hydrogen Bonding on the Reactivity of Thiyl Radicals: A Mass Spectrometric and Computational Study Using the Distonic Radical Ion Approach PubMed: Fractionation of whey proteins with high-capacity superparamagnetic ion-exchangers PubMed: Pressure dependent product formation in the photochemically initiated allyl + allyl reaction PubMed: New (99m)Tc(CO)(3) mannosylated dextran bearing S-derivatized cysteine chelator for sentinel lymph node detection PubMed: Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids PubMed: [Molecular toxicological mechanism of the lethal interactions of the new antiviral drug, sorivudine, with 5-fluorouracil prodrugs and genetic deficiency of dihydropyrimidine dehydrogenase] PubMed: 7-Bromo-4b-methyl-7,8-dihydro-4bH-9-thia-8a-aza-fluorene 9,9-dioxide PubMed: Kinetics and mechanisms of the unimolecular elimination of 2,2-diethoxypropane and 1,1-diethoxycyclohexane in the gas phase: experimental and theoretical study PubMed: Aromatic allylation via diazotization: variation of the allylic moiety and a short route to a benzazepine derivative PubMed: Highly efficient formal synthesis of cephalotaxine, using the Stevens rearrangement--acid lactonization sequence as a key transformation PubMed: Gastragogue effect of laxatives and allyl-bromide-mixture PubMed: Indium-catalyzed reduction of allyl bromide with gallium or aluminum. Formation of allylgallium and allylaluminum sesquibromides PubMed: A synthetic macromolecule for sentinel node detection: (99m)Tc-DTPA-mannosyl-dextran PubMed: Photodissociation dynamics of allyl bromide at 234, 265, and 267 nm PubMed: Synthesis and antibacterial activity of 2, 3-dehydro-3-O-(3-aryl-E-prop-2-enyl)-10, 11-anhydroclarithromycin derivatives PubMed: The design and synthesis of 9-phenylcyclohepta[d]pyrimidine-2,4-dione derivatives as potent non-nucleoside inhibitors of HIV reverse transcriptase PubMed: Synthesis of halogenated 4-quinolones and evaluation of their antiplasmodial activity PubMed: Directed hydrozirconation of propargylic alcohols PubMed: Kinetics and mechanisms of the thermal decomposition of 2-methyl-1,3-dioxolane, 2,2-dimethyl-1,3-dioxolane, and cyclopentanone ethylene ketal in the gas phase. Combined experimental and DFT study PubMed: Selective palladium(ii)-mediated oxidation of homoallylic N-tert-butanesulfinyl amine derivatives PubMed: Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs PubMed: Stereochemical Study of the Allylation of Aldehydes with Allyl Halides in Cosolvent/Water(Salt)/Zn and in Cosolvent/Water(Salt)/Zn/Haloorganotin Media PubMed: Indium and zinc-mediated Barbier-type addition reaction of 2,3-allenals with allyl bromide: an efficient synthesis of 1,5,6-alkatrien-4-ols PubMed: Stereoselective synthesis of pyroglutamate natural product analogs from à- aminoacids and their anti-cancer evaluation PubMed: Titanocene(III) chloride mediated radical induced allylation of aldimines: formal synthesis of C-linked 4'-deoxy aza-disaccharide PubMed: DFT computational study of the mechanism of allyl halides carbonylation catalyzed by nickel tetracarbonyl PubMed: Low energy electron-induced decomposition of (?(3)-C(3)H(5))Ru(CO)(3)Br, a potential focused electron beam induced deposition precursor with a heteroleptic ligand set PubMed: Stereoselective à-aminoallylation of aldehydes with chiral tert-butanesulfinamides and allyl bromides PubMed: Synthesis and evaluation of 3-salicyloylpyridine derivatives as cytotoxic mitochondrial apoptosis inducers PubMed: Mechanism-based inactivation of human dihydropyrimidine dehydrogenase by (E)-5-(2-bromovinyl)uracil in the presence of NADPH PubMed: Stereospecific 7à-alkylation of 20-hydroxyecdysone in a lithium-ammonia solution PubMed: 2-(chromon-3-yl)imidazole derivatives as potential antimicrobial agents: synthesis, biological evaluation and molecular docking studies PubMed: Enantioselective synthesis and preliminary metabolic studies of the optical isomers of 2-n-propyl-4-pentenoic acid, a hepatotoxic metabolite of valproic acid PubMed: Palladium complexes with a tridentate PNO ligand. Synthesis of eta1-allyl complexes and cross-coupling reactions promoted by boron compounds PubMed: Synthesis of a deoxy analogue of ADP L-glycero-D-manno-heptose PubMed: [Alkylation of gem-dibromocyclopropanes with higher-order organocuprates] PubMed: Synthesis of the oxepinochromone natural products ptaeroxylin (desoxykarenin), ptaeroxylinol, and eranthin PubMed: N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation PubMed: Total synthesis of antillatoxin PubMed: Aromatic allylation via diazotization: metal-free C-C bond formation PubMed: Addition of organochromium reagents to heteroaryl aldehydes. Synthesis of heteroaryl substituted bis-allyl ethers and homoallyl ethers PubMed: [Biotransformation of 4-methyl-7-allyloxy coumarin by transgenic hairy roots of Polygonum multiflorum] PubMed: Preparation of 4'-substituted thymidines by substitution of the thymidine 5'-esters PubMed: Indium-mediated asymmetric barbier-type allylations: additions to aldehydes and ketones and mechanistic investigation of the organoindium reagents PubMed: Polar reactions of acyclic conjugated bisallenes PubMed: Chiral Diarylmethanes via Copper-Catalyzed Asymmetric Allylic Arylation with Organolithium Compounds PubMed: A novel palladium-catalyzed coupling of epoxides with allyl bromide mediated by indium(I) chloride: a cascade epoxide rearrangement-carbonyl allylation PubMed: Experimental and theoretical studies of the homogeneous, unimolecular gas-phase elimination kinetics of trimethyl orthovalerate and trimethyl orthochloroacetate PubMed: An advance on exploring N-tert-butanesulfinyl imines in asymmetric synthesis of chiral amines PubMed: Copper-free asymmetric allylic alkylation with a Grignard reagent: design of the ligand and mechanistic studies PubMed: Synthesis of acyclovir and HBG analogues having nicotinonitrile and its 2-methyloxy 1,2,3-triazole PubMed: Preparation of 1,3-bis(allyloxy)benzene under a new multi-site phase-transfer catalyst combined with ultrasonication--a kinetic study PubMed: Sensory irritating effects of allyl halides and a role for hydrogen bonding as a likely feature at the receptor site PubMed: Joint experimental and DFT study of the gas-phase unimolecular elimination kinetic of methyl trifluoropyruvate PubMed: Investigation into the regiochemistry of some isoxazoles derived from 1,3-dipolar cycloaddition of 4-nitrobenzonitrile oxide with some dipolarophiles: a combined theoretical and experimental studies PubMed: Modified glycogen as construction material for functional biomimetic microfibers PubMed: Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine PubMed: Reactions of atoms and free radicals in solution; decomposition of diacetyl peroxide in allyl bromide PubMed: Manganese-Mediated Carbon-Carbon Bond Formation in Aqueous Media: Chemoselective Allylation and Pinacol Coupling of Aryl Aldehydes PubMed: Synthesis and anti-HIV-1 activity of novel 2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-ones PubMed: Glucopyranosylidene-spiro-iminothiazolidinone, a new bicyclic ring system: synthesis, derivatization, and evaluation for inhibition of glycogen phosphorylase by enzyme kinetic and crystallographic methods PubMed: Structure-activity relationships of alpha, beta-unsaturated carbonylic compounds PubMed: Reactivity and enantioselectivity in the reactions of scalemic stereogenic alpha-(N-carbamoyl)alkylcuprates PubMed: Frequency of C-allylations on oligoglycinates via N-ylides PubMed: Reactivity of alkynylzirconates towards allyl bromides: selective formation of ?-allyl-zirconacyclopentadienes PubMed: Metal-mediated allylation of enzymatically oxidized methyl à-D-galactopyranoside PubMed: Cotton functionalized with peptides: characterization and synthetic methods PubMed: Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers PubMed: Synthesis and anticholinesterase activity of (-)-N1-norphysostigmine, (-)-eseramine, and other N(1)-substituted analogues of (-)-physostigmine PubMed: P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of à-Keto Esters PubMed: Vinylic C--H borylation of cyclic vinyl ethers with bis(pinacolato)diboron catalyzed by an Iridium(I)-dtbpy complex PubMed: Aliphatic analogues of nucleotides: synthesis and affinity towards nucleases PubMed: Enantioselective allylic alkylation of stereodefined polysubstituted copper enolates as an entry to acyclic quaternary carbon stereocentres PubMed: Mono(cycloheptatrienyl) tantalum chemistry: synthesis and characterization of new tantalum halide, hydride, and alkyl species PubMed: Indium-mediated asymmetric Barbier-type allylation of aldimines in alcoholic solvents: synthesis of optically active homoallylic amines PubMed: Synthesis of Six-Membered Spiro Azacyclic Oxindole Derivatives via a One-Pot Process of Umpolung Allylation/Aza-Prins Cyclization PubMed: Structural and oxo-transfer reactivity differences of hexacoordinate and pentacoordinate (nitro)(tetraphenylporphinato)cobalt(III) derivatives PubMed: A convenient procedure for bismuth-mediated Barbier-type allylation of aldehydes in water containing fluoride ions PubMed: Synthesis of 2,5-Diaryl-1,5-dienes from Allylic Bromides Using Visible-Light Photoredox Catalysis PubMed: [Effects of ATP-regulated potassium channels modulators, N-(2-pyridyl)-N'-(4-toluol) sulfonylcarbamides, on electromechanical activity in guinea pig myocardium] PubMed: An enantiospecific approach to tricyclic sesquiterpenes mayurone and thujopsenes PubMed: Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes. Application To the stereocontrolled synthesis of fused tricyclic beta-lactams via intramolecular diels-alder reaction of 2-azetidinone-tethered PubMed: Analytical application of poly{methyl[3-(2-hydroxy-3,4-difluoro)phenyl]propyl siloxane} as a QCM coating for DMMP detection PubMed: An approach to the total synthesis of the marine ascidian metabolite perophoramidine via a halogen-selective tandem Heck/carbonylation strategy PubMed: Toward a protecting-group-free halogen-metal exchange reaction: practical, chemoselective metalation of functionalized aromatic halides using dianion-type zincate, tBu4ZnLi2 PubMed: A versatile synthesis of ?-lactam-fused oxacycles through the palladium-catalyzed chemo-, regio-, and diastereoselective cyclization of allenic diols PubMed: Monomeric and dimeric nickel complexes derived from a pincer ligand featuring a secondary amine donor moiety PubMed: Elimination of HX (X = Cl, Br) from haloalkenes on the Ru2Q2 (Q = S, Se) core complex PubMed: Generation of chiral boron enolates by rhodium-catalyzed asymmetric 1,4-addition of 9-aryl-9-borabicyclo[3.3.1]nonanes (B-Ar-9BBN) to alpha,beta-unsaturated ketones PubMed: [bmim][Br] as a solvent and activator for the Ga-mediated Barbier allylation: direct formation of an N-heterocyclic carbene from Ga metal PubMed: Syntheses, derivatives, solubility, and interfacial properties of 2-methyl-2-polyfluoroalkenyloxymethyl-1,3-propanediols: potential building blocks for syntheses of amphiphatic macromolecules PubMed: Diastereoselection during 1,2-Addition of the Allylindium Reagent to alpha-Thia and alpha-Amino Aldehydes in Aqueous and Organic Solvents PubMed: Unique structural properties of 2,4,6-tri-tert-butylanilide: isomerization and switching between separable amide rotamers through the reaction of anilide enolates PubMed: Total synthesis of a cuticular hydrocarbon from the cane beetle Antitrogus parvulus: confirmation of the relative stereochemistry PubMed: Motilides, macrolides with gastrointestinal motor stimulating activity. II. 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