1530-34-3

Usage

Uses

Used in Organic Synthesis:
(3,3-DIMETHYLALLYL)TRIPHENYLPHOSPHONIUM BROMIDE is used as a reagent in the field of organic synthesis for its ability to participate in various chemical reactions, such as substitution, addition, and elimination reactions. Its unique structure allows it to act as a versatile building block for the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (3,3-DIMETHYLALLYL)TRIPHENYLPHOSPHONIUM BROMIDE is used as an intermediate in the synthesis of various pharmaceutical compounds. Its reactivity and stability make it a valuable component in the development of new drugs and therapeutic agents.
Used in Chemical Research:
(3,3-DIMETHYLALLYL)TRIPHENYLPHOSPHONIUM BROMIDE is also used as a research tool in chemical laboratories. Its unique properties and reactivity make it an interesting subject for studying various aspects of chemistry, such as reaction mechanisms, stereochemistry, and the development of new synthetic methods.
Used in Material Science:
In the field of material science, (3,3-DIMETHYLALLYL)TRIPHENYLPHOSPHONIUM BROMIDE can be used as a component in the development of new materials with specific properties, such as conductivity, magnetism, or optical properties. Its unique structure and reactivity can contribute to the creation of novel materials with potential applications in various industries.

InChI:InChI=1/C23H24P.BrH/c1-20(2)18-19-24(21-12-6-3-7-13-21,22-14-8-4-9-15-22)23-16-10-5-11-17-23;/h3-18H,19H2,1-2H3;1H/q+1;/p-1

Upstream product

• 603-35-0 triphenylphosphine 
• 870-63-3 prenyl bromide 
• 67883-17-4 1-bromo-3-methyl-3-trimethyl-silyloxybutane 
• 6399-81-1 triphenylphosphine hydrobromide 
• 78-79-5 isoprene 
• 32251-63-1 5,5-Dimethyl-2-pyrazolin-3-yltriphenylphosphoniumbromid 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 556-82-1 3-methyl-2-buten-1-ol 

Downstream Products

• 39491-73-1 (E)-(4-methylpenta-1,3-dien-1-yl)benzene 
• 39491-72-0 (Z)-(4-methylpenta-1,3-dien-1-yl)benzene 
• 88001-22-3 ((Z)-4-Methyl-penta-1,3-dienyl)-cyclohexane 
• 88001-21-2 ((E)-4-Methyl-penta-1,3-dienyl)-cyclohexane 
• 2107-77-9 4-methyldaphnetin 
• 31188-53-1 Triphenyl-3,3-dimethyl-allylidenphosphoran 
• 1012069-35-0 2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene 
• 188905-91-1 (Z)-7-methylocta-4,6-dien-1-yl (4-methoxybenzyl) ether 
• 188905-90-0 (E)-7-methylocta-4,6-dien-1-yl (4-methoxybenzyl) ether 
• 1133909-76-8 (Z)-1,1-diphenyl-2-(4-methylpenta-1,3-dienyl)cyclopropane 

Relevant academic research and scientific papers

Novel methodology for the preparation of five-, seven-, and nine-membered fused rings on C60

The photocycloaddition of dienyl cyclopropanes to C60 gives a new synthetic approach to yield stereospecifically five-, seven-, and nine-membered [60]fullerene adducts. Our results suggest the formation of a biradical intermediate between the dienyl substrate and C60. An electron transfer between the triplet excited state of C60 and the dienyl substrate precedes the formation of the intermediate.

A total synthesis of isosolanone

Nitroaldol reaction of acetone with nitromethane in the presence of base to give a nitroalcohol 3, followed by acetylation, and subsequent reduction of the resultant acetate 4 with NaBH4 gave 2-methyl-1 nitropropane 5. Michael reaction of 5 in base with acrylonitrile to give nitronitrile 6, and Nef conversion of the nitro group resulted in the corresponding ketonic nitrile 7. Wittig olefination of the ketonic nitrile with 3-methyl-2-butenyl triphenylphosphonium bromide 8 gave dienenitrile 9, which upon treatment with MeLi, followed by acidic work up, provided isosolanone 2.

Photocycloaddition of biscyclopropyl alkenes to C60: An unprecedented approach toward cis-1 tricyclic-fused fullerenes

A novel, simple, and entirely regioselective tandem cycloaddition of biscyclopropyl-substituted alkenes to [60]fullerene has been revealed. This reaction affords cis-1 tricyclic-fused organofullerenes bearing the hitherto elusive 5-4-5 fused tricyclic ring system.

Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.

Concerning the reactivity of ptad with isomeric dienes: The mechanism of the Diels-Alder cycloaddition

Cyclopropyl substituted dienes are employed as mechanistic probes in the triazolinedione Diels-Alder (DA) reaction. In aprotic and protic solvents, apart from the DA adducts that bear an intact cyclopropyl group, complicated and rearranged products are also obtained. These results provide solid evidence for the involvement of an open intermediate with a lifetime greater than 2 x 10 -12 s.

Biradical intermediate in the [2 + 2] photocycloaddition of dienes and alkenes to [60]fullerene

The photocycloaddition of vinylcyclopropanes to C60 yields stereospecifically a five-membered [60]fullerene adduct. These results suggest a biradical intermediate of the [2 + 2] photocycloaddition between dienes or arylalkenes and C60. An electron transfer between the triplet excited state of C60 and the unsaturated substrates precedes the formation of the intermediate. Copyright

Didehydrogeranylgeranyl (ΔΔGG): A fluorescent probe for protein prenylation

The first intrinsically fluorescent analog of geranylgeraniol, (2E,6E,8E,10E,12E,14E)-geranylgeraniol (all-trans-ΔΔGGOH·1) has been synthesized stereoselectively and shown to substitute for the geranylgeranyl (GG) moiety in prenyl transferase reactions and in protein-ligand binding assays. All-trans-ΔΔGGOH 1 showed blue fluorescence in methanol, with λex = 310 nm and λem = 410 nm (ε310 = 2.4 × 104 M-1 cm-1), but was only weakly fluorescent in aqueous solution. The prenyl transferase efficiency for ΔΔGGPP 2 as a substrate for yeast protein geranylgeranyl transferase (PGGTase-I) was 60% relative to that for GGPP. The binding of ΔΔGG-AcCysMe 3 to the recombinant Rho GTPase dissociation inhibitor (RhoGDI) had a KD of 15.1 ± 1.2 μM, 6-fold lower than the affinity of GG-AcCysMe. Thus, the ΔΔGG moiety is a novel fluorophore suitable for studying the interaction and subcellular localization of prenylated small GTPase proteins in signaling complexes. Copyright

A mild and selective deprotection of p-methoxybenzyl (PMB) ether by magnesium bromide diethyl etherate-methyl sulfide

The magnesium bromide diethyl etherate (MgBr2 · OEt2)-methyl sulfide (Me2S) system is useful for the mild and chemo-selective deprotection of p-methoxybenzyl (PMB) ether in the presence of 1,3-diene, t-butyldimethylsilyl (TBDMS) ether, benzoate, benzyl ether and acetonide.

A New Photochemical Synthesis of Cyclopropanecarboxylic Acids Present in Pyrethroids by the Aza-di-?-methane Rearrangement

A novel synthetic route to chrysanthemic acid, 2-cyclopentylidenmethyl-3,3-dimethylcyclopropanecarboxylic acid, fluorenespiro-2,2-dimethylcyclopropanecarboxylic acid and indenespiro-2,2-dimethylcyclpropanecarboxylic acid, all of them present in pyrethroids of known insecticidal activity, is described.The key step in the synthesis is the aza-di-?-methane rearrangement of some 1-aza-1,4,6-trienes and some 1-aza-1,4-dienes, using triplet sensitization.