Benzyltriphenylphosphonium bromide
Preparation- Product Name
- Benzyltriphenylphosphonium bromide
- CAS No.
- 1449-46-3
- Chemical Name
- Benzyltriphenylphosphonium bromide
- Synonyms
- TZP;SKL082;NSC 54813;CAS1449-46-3;Benzyltriphen;Benzyl triphenyl pho;Benzyl threephosphoniuM broMide;Benzyltriphenylphosphine bromide;Benzyltriphenylphosphanium bromid;Bromo(benzyl)triphenylphosphorane
- CBNumber
- CB4319243
- Molecular Formula
- C25H22BrP
- Formula Weight
- 433.32
- MOL File
- 1449-46-3.mol
Benzyltriphenylphosphonium bromide Property
- Melting point:
- 295-298 °C(lit.)
- storage temp.
- Inert atmosphere,Room Temperature
- form
- solid
- color
- White to Almost white
- Water Solubility
- Soluble in water.
- Sensitive
- Hygroscopic
- BRN
- 3599867
- InChI
- InChI=1S/C25H22P.BrH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1
- InChIKey
- WTEPWWCRWNCUNA-UHFFFAOYSA-M
- SMILES
- [P+](CC1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1=CC=CC=C1.[Br-]
- CAS DataBase Reference
- 1449-46-3(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36/37/39
- WGK Germany
- 3
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 29319090
- Storage Class
- 11 - Combustible Solids
- Hazard Classifications
- Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 430056
- Product name
- Benzyltriphenylphosphonium bromide
- Purity
- 96%
- Packaging
- 50g
- Price
- $112
- Updated
- 2025/07/31
- Product number
- 430056
- Product name
- Benzyltriphenylphosphonium bromide
- Purity
- 96%
- Packaging
- 250g
- Price
- $328
- Updated
- 2025/07/31
- Product number
- B2025
- Product name
- Benzyltriphenylphosphonium Bromide
- Purity
- >98.0%(HPLC)(T)
- Packaging
- 25g
- Price
- $36
- Updated
- 2025/07/31
- Product number
- B316170
- Product name
- Benzyltriphenylphosphonium bromide
- Packaging
- 10g
- Price
- $65
- Updated
- 2021/12/16
- Product number
- AK164415
- Product name
- Benzyltriphenylphosphonium bromide
- Purity
- 95%
- Packaging
- 1kg
- Price
- $91
- Updated
- 2021/12/16
Benzyltriphenylphosphonium bromide Chemical Properties,Usage,Production
Preparation
Benzyl triphenylphosphonium bromide is prepared by the following steps:To a solution of Ph3P (22 g, 0.084 mol) in toluene, BnBr (10 ml, 0.084 mol) was added dropwise with ice-cooling and stirred at room temperature for 2 hours. A solid was formed, which was filtered and washed with toluene and then dry pet ether to remove unreacted Ph3P. The salt was dried under vacuum (35 g, 96% yield).
Chemical Properties
WHITE CRYSTALLINE POWDER
Uses
Benzyltriphenylphosphonium bromide is used as a reactant for stereoselective azidolysis of vinyl epoxides, enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine, biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A, enantioselective synthesis of syn-diarylheptanoids from D-glucose, preparation of β-amyloid plaque ligands and decarboxylative cyclopropanation. It react with 4-methyl-oxetan-2-one to produce 4-hydroxy-1-phenyl-1-(triphenyl-l5-phosphanylidene)-pentan-2-one.
reaction suitability
reaction type: C-C Bond Formation
Synthesis
100-39-0
603-35-0
1449-46-3
The general procedure for the synthesis of triphenylbenzylphosphonium bromide from benzylbromide and triphenylphosphine was as follows: triphenylphosphine (7.868 g, 1.0 eq.) and benzylbromide (3.73 mL, 1.04 eq.) were dissolved in dimethylformamide (DMF) (30 mL) and the mixture was transferred to a 100 mL round bottom flask equipped with a reflux condenser. The reaction mixture was heated to reflux and kept for 1 hr and subsequently cooled to room temperature. The precipitated white crystalline solid was collected by filtration, washed with ether (100 mL) and finally dried under vacuum at 60 °C for 5 h to afford the product triphenylbenzylphosphonium bromide (12.676 g, 98% yield).
References
[1] Synthetic Communications, 2001, vol. 31, # 21, p. 3377 - 3382
[2] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3529 - 3536
[3] Canadian Journal of Chemistry, 2004, vol. 82, # 9, p. 1365 - 1371
[4] Patent: WO2004/52823, 2004, A1. Location in patent: Page 8
[5] Organic Letters, 2013, vol. 15, # 22, p. 5650 - 5653
Benzyltriphenylphosphonium bromide Preparation Products And Raw materials
Raw materials
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View Lastest Price from Benzyltriphenylphosphonium bromide manufacturers
- Product
- Benzyltriphenylphosphonium bromide 1449-46-3
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 30tons/month
- Release date
- 2023-02-23
- Product
- Benzyltriphenylphosphonium bromide 1449-46-3
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-28
- Product
- Benzyltriphenylphosphonium bromide 1449-46-3
- Price
- US $79.00-38.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-12-12