(3-Methyl-2-butenyl)triphenyl-phosphonium Bromide

Base Information

• Chemical Name: (3-Methyl-2-butenyl)triphenyl-phosphonium Bromide
• CAS No.: 1530-34-3
• Molecular Formula: C23H24 P . Br
• Molecular Weight: 411.321
• Hs Code.: 2931900090
• European Community (EC) Number: 216-224-9
• NSC Number: 219242
• DSSTox Substance ID: DTXSID30934647
• Mol file: 1530-34-3.mol

Synonyms:1530-34-3;(3-Methyl-2-butenyl)triphenyl-phosphonium Bromide;(3,3-DIMETHYLALLYL)TRIPHENYLPHOSPHONIUM BROMIDE;(3-Methylbut-2-enyl)triphenylphosphonium bromide;EINECS 216-224-9;3-methylbut-2-enyl(triphenyl)phosphanium;bromide;C23H24P.Br;SCHEMBL2445872;C23-H24-P.Br;DTXSID30934647;FTMCNCGWNJMMQS-UHFFFAOYSA-M;BAA53034;MFCD00051864;NSC219242;AKOS025294581;CS-W011676;NSC 219242;NSC-219242;FT-0614075;3,3-dimethylallyl triphenylphosphonium bromide;3,3-dimethylallyl-triphenylphosphonium bromide;3,3-dimethylallyl-triphenyl-phosphonium bromide;F17172;(3-Methyl-2-butenyl)triphenyl-phosphoniumBromide;EN300-7457095;A883853;3,3-DIMETHYLALLYLTRIPHENYLPHOSPHONIUM BROMIDE;(3-Methylbut-2-en-1-yl)(triphenyl)phosphanium bromide;(3-METHYLBUT-2-EN-1-YL)TRIPHENYLPHOSPHANIUM BROMIDE;(3,3-Dimethylallyl)triphenylphosphonium bromide;(3-Methyl-2-butenyl)triphenylphosphonium bromide~Prenyltriphenylphosphonium bromide

Chemical Property of (3-Methyl-2-butenyl)triphenyl-phosphonium Bromide

Chemical Property:

• Melting Point: 237-239°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 13.59000
• Density: g/cm³
• LogP: 1.95070
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Chloroform, Dichloromethane, Methanol, Water
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 410.07990
• Heavy Atom Count: 25
• Complexity: 343

Purity/Quality:

97% ^*data from raw suppliers

(3-Methyl-2-butenyl)triphenyl-phosphoniumBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C.[Br-]
• General Description: (3,3-Dimethylallyl)triphenylphosphonium bromide (also known as (3-methyl-2-butenyl)triphenylphosphonium bromide) is a Wittig reagent used in organic synthesis to introduce a 3-methyl-2-butenyl (prenyl) group into target molecules. In the context of the provided literature, it serves as a key intermediate in the total synthesis of isosolanone, where it participates in a Wittig olefination reaction with a ketonic nitrile to form a dienenitrile precursor. This demonstrates its utility in constructing carbon-carbon double bonds in complex organic frameworks, particularly in natural product synthesis. **Return:** (3,3-Dimethylallyl)triphenylphosphonium bromide is a phosphonium salt employed as a Wittig reagent for the introduction of a 3-methyl-2-butenyl group in organic synthesis, notably utilized in the construction of diene intermediates during the synthesis of natural products such as isosolanone.

Technology Process of (3-Methyl-2-butenyl)triphenyl-phosphonium Bromide

There total 8 articles about (3-Methyl-2-butenyl)triphenyl-phosphonium 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:

Reference yield: 100.0%

triphenylphosphine (603-35-0) + prenyl bromide (870-63-3) → (3-methylbut-2-enyl)triphenylphosphonium bromide (1530-34-3)

Guidance literature:

In toluene; at 110 ℃; Inert atmosphere;

DOI:10.1002/ejoc.200900841

Reference yield:

3-methylbut-2-enyl acetate (1191-16-8) + triphenylphosphine (603-35-0) → (3-methylbut-2-enyl)triphenylphosphonium bromide (1530-34-3)

Guidance literature:

With sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; for 2h; Heating;

DOI:10.1246/bcsj.57.3013

Reference yield:

isoprene (78-79-5,9003-31-0) → (3-methylbut-2-enyl)triphenylphosphonium bromide (1530-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 g / hydrobromic acid / 8 h / 0 °C

2: 27.2 g / benzene / Ambient temperature

With hydrogen bromide; In benzene;

DOI:10.1248/cpb.29.2182

upstream raw materials:

triphenylphosphine hydrobromide

3-methyl-2-buten-1-ol

5,5-Dimethyl-2-pyrazolin-3-yltriphenylphosphoniumbromid

triphenylphosphine

Downstream raw materials:

4-methyldaphnetin

2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene

(Z)-7-methylocta-4,6-dien-1-yl (4-methoxybenzyl) ether