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| | (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide Basic information |
| Product Name: | (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide | | Synonyms: | [2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-triphenylphosphonium bromide;tert-Butoxycarbonylmethyltriphenylphosphoniumbrom;(tert-Butoxycarbonylmethyl)tripheenyphosphonium bromide;(TERT-BUTOXYCARBONYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE;carbo-tert-butoxymethyl triphenylphosphonium bromide;(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide;(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide, 98 %;carbo-tert-butoxymethyl triphenylphosp | | CAS: | 59159-39-6 | | MF: | C24H26BrO2P | | MW: | 457.34 | | EINECS: | | | Product Categories: | C-C Bond Formation;Olefination;Wittig Reagents | | Mol File: | 59159-39-6.mol |  |
| | (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide Chemical Properties |
| Melting point | 178 °C (dec.)(lit.) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | soluble in Methanol | | form | powder to crystal | | color | White to Almost white | | BRN | 4631405 | | InChI | 1S/C24H26O2P.BrH/c1-24(2,3)26-23(25)19-27(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,19H2,1-3H3;1H/q+1;/p-1 | | InChIKey | ZGLFRTJDWWKIAK-UHFFFAOYSA-M | | SMILES | [Br-].CC(C)(C)OC(=O)C[P+](c1ccccc1)(c2ccccc2)c3ccccc3 | | CAS DataBase Reference | 59159-39-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | HS Code | 29319019 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide Usage And Synthesis |
| Uses | Reactant for:
- Rhodium-catalyzed asymmetric hydrogenation reactions
- Wittig reaction
- Wittig methylenation
- Preparation of N-(phenylmethyl)-cis-pyrrolidinediacetic acid esters via double aza-Michael addition reaction
- Stereoselective preparation of of α-fluoro-α,β-unsaturated esters via deprotonation, followed by fluorination and stereoselective Wittig olefination with aldehydes
- Wittig chain extension reactions
| | reaction suitability | reaction type: C-C Bond Formation | | Synthesis | Example 3: The general procedure for the synthesis of (tert-butoxycarbonylmethyl)triphenylphosphonium bromide from tert-butyl bromoacetate and triphenylphosphine is as follows: In another embodiment, the functionalized lactone comprises a carboxylate protecting group as shown in Fig. 1. 10. Ylide synthesis was carried out using the following reagents and conditions: (a) triphenylphosphine (PPh3), benzene (C6H6), reaction time 12 h at room temperature (rt); (b) 20% aqueous sodium hydroxide solution (NaOH, aq), reaction time 5 h at room temperature. | | References | [1] Patent: US2007/265243, 2007, A1. Location in patent: Page/Page column 4
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 199 - 209
[3] Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 5, p. 1188 - 1208
[4] Patent: US2007/43088, 2007, A1. Location in patent: Page/Page column 5
[5] Organic Process Research and Development, 2009, vol. 13, # 4, p. 710 - 715 |
| | (tert-Butoxycarbonylmethyl)triphenylphosphanium bromide Preparation Products And Raw materials |
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