(3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE Chemical Properties

Melting point:

228-230 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

form 

solid

color 

White

Sensitive 

Hygroscopic

BRN 

6422974

InChI

InChI=1S/C21H21BrP.BrH/c22-17-10-18-23(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H/q+1;/p-1

InChIKey

ZAHUZZUGJRPGKW-UHFFFAOYSA-M

SMILES

[P+](CCCBr)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br-]

CAS DataBase Reference

3607-17-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-21/22

Safety Statements 

26-37/39-36/37

WGK Germany 

3

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE Usage And Synthesis

Chemical Properties

WHITE TO OFF-WHITE CRYSTALLINE POWDER

Uses

Reactant involved in:

• Synthesis of functionalized polyurethanes using cationic ring-opening polymerization and click chemistry
• Semipinacol rearrangement and direct arylation
• Olefination of benzaldehydes
• C-H activation / cycloisomerization
• Intramolecular dehydrobromination
• Cycloisomerizations of bromodienes and enynes

Uses

(3-Bromopropyl)triphenylphosphonium Bromide is used in rearrangement reactions of cyclic organic molecules and in organic synthesis.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

The general procedure for the synthesis of (3-bromopropyl)triphenylphosphonium bromide from triphenylphosphine and 1,3-dibromopropane was as follows: Triphenylphosphine (511 g, 1.85 mol, purity 95.0%) and toluene (800 g) were added to a reactor equipped with a stirrer, and stirred until completely dissolved. Under the condition of temperature lower than 5℃, 1,3-dibromopropane (371g, 1.82mol, purity 99.0%) was added slowly dropwise, and the dropwise addition time was controlled within 1 hour. After the dropwise addition, the reaction mixture was heated to reflux and the reflux reaction was maintained for 17 hours. After completion of the reaction, the mixture was cooled to room temperature to obtain the suspension. The suspension was filtered at 20 °C and the solid product was collected. The solid product was washed with toluene (2 x 800 g) and then dried under vacuum at 60 °C for 21 h. White crystalline 3-bromopropyltriphenylphosphonium bromide (Olo-IM3) was obtained in a yield of 757 g (1.63 mol) in 89.6% yield.

References

[1] Chemical Communications, 2014, vol. 50, # 45, p. 5993 - 5996
[2] Tetrahedron Letters, 2003, vol. 44, # 24, p. 4547 - 4550
[3] Patent: US2007/232814, 2007, A1. Location in patent: Page/Page column 24
[4] Tetrahedron Letters, 1985, vol. 26, # 47, p. 5747 - 5748
[5] Tetrahedron, 1981, vol. 37, # 16, p. 2855 - 2860

(3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE(3607-17-8)Related Product Information

• 3-((Dimethylamino)propyl)triphenylphosphonium bromide
• (3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE
• ISOPROPYLTRIPHENYLPHOSPHONIUM IODIDE
• (CYANOMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
• (4-BROMOBENZYL)TRIPHENYLPHOSPHONIUM BROMIDE
• CYANOMETHYLTRI-N-BUTYLPHOSPHONIUM CHLORIDE
• Phosphonium, (2-methoxyethyl)triphenyl-, bromide
• IODOMETHYL-TRIPHENYL-PHOSPHONIUM IODIDE
• (CYANOMETHYL)TRIPHENYLPHOSPHONIUM CHLORIDE
• Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate
• Methyltriphenylphosphonium bromide
• (3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE
• Triphenyl(propyl)phosphonium bromide
• Triphenylphosphine hydrobromide
• Ethyltriphenylphosphonium bromide
• DIPHENYL-N-PROPYLPHOSPHINE
• TETRAMETHYLPHOSPHONIUM BROMIDE
• (3-BROMOBUTYL)TRIPHENYLPHOSPHONIUM BROMIDE