| Identification | More | [Name]
(3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE | [CAS]
3607-17-8 | [Synonyms]
(3-BROMOPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE
BROMOPROPYLTRIPHENYLPHOSPHONIUM BROMIDE
BTB
bromo(3-bromopropyl)triphenylphosphorane
bromo(3-bromopropyl)triphenylphosphorus
3-(bromopropyl)triphenylphosphonium
(3-Bromopropyl)triphenylphosphonium bromide, 98 % | [EINECS(EC#)]
222-770-9 | [Molecular Formula]
C21H21Br2P | [MDL Number]
MFCD00011866 | [Molecular Weight]
464.17 | [MOL File]
3607-17-8.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO OFF-WHITE CRYSTALLINE POWDER | [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 Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29319090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO OFF-WHITE CRYSTALLINE POWDER | [Uses]
(3-Bromopropyl)triphenylphosphonium Bromide is used in rearrangement reactions of cyclic organic molecules and in organic synthesis. | [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
| [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 |
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