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| | Butyltriphenylphosphonium bromide Basic information |
| | Butyltriphenylphosphonium bromide Chemical Properties |
| Melting point | 240-243 °C(lit.) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform, Methanol | | form | Crystalline Powder | | color | White | | Water Solubility | soluble | | Sensitive | Hygroscopic | | BRN | 3580224 | | InChI | InChI=1S/C22H24P.BrH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1 | | InChIKey | IKWKJIWDLVYZIY-UHFFFAOYSA-M | | SMILES | [P+](CCCC)(C1C=CC=CC=1)(C1C=CC=CC=1)C1=CC=CC=C1.[Br-] | | CAS DataBase Reference | 1779-51-7(CAS DataBase Reference) | | EPA Substance Registry System | Phosphonium, butyltriphenyl-, bromide (1779-51-7) |
| Hazard Codes | Xn | | Risk Statements | 21/22-36/37/38 | | Safety Statements | 36/37-36/37/39-26 | | RIDADR | 3464 | | WGK Germany | 3 | | RTECS | TA1855200 | | TSCA | TSCA listed | | HazardClass | 6.1 | | PackingGroup | III | | HS Code | 29319090 | | Storage Class | 13 - Non Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | Butyltriphenylphosphonium bromide Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | suzuki reaction | | Uses | PTC catalyst | | Uses | Reactant for:
Free radical 5-exo-dig cyclization
Intramolecular hydroacylalkoxylation
Wittig reactions for stereoselective synthesis of alkenes
Dimerization of α-olefins
Alkylidenation of hydrazides for synthesis of indoles
Tandem cyclization and 1,2-thiolate shift of nitrogen ylides | | Uses | n-Butyltriphenylphosphonium Bromide is used in the synthesis of inhibitors of tubulin polymerization thus expressing antimitotic and antitubulin properties. Also used in the synthesis of 3-phenylpropanoic acids as peroxisome proliferator-activated receptor dual agonists affecting the mitochondrial carnitine system. | | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | Under nitrogen protection, 280 g of bromobutane and 696 g of triphenylphosphine were added to a 2 L four-neck flask dissolved in 500 mL of xylene. The reaction mixture was heated to reflux temperature with continuous stirring for 6 hours. After completion of the reaction, the system was cooled to room temperature, the precipitated white crystals were collected by filtration and washed with xylene. After drying, 797 g of butyltriphenylphosphonium bromide was obtained as a white solid in 97.7% yield. | | References | [1] Patent: JP6136589, 2017, B2. Location in patent: Paragraph 0102-0104
[2] Acta Chimica Hungarica, 1987, vol. 124, # 5, p. 737 - 748
[3] Journal of Fluorine Chemistry, 2002, vol. 113, # 2, p. 177 - 183
[4] Pharmazie, 1999, vol. 54, # 1, p. 26 - 30
[5] Synthetic Communications, 1981, vol. 11, # 2, p. 125 - 132 |
| | Butyltriphenylphosphonium bromide Preparation Products And Raw materials |
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