| Identification | More | [Name]
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide | [CAS]
59159-39-6 | [Synonyms]
(TERT-BUTOXYCARBONYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
tert-Butoxycarbonylmethyltriphenylphosphoniumbrom
(tert-Butoxycarbonylmethyl)tripheenyphosphonium bromide
carbo-tert-butoxymethyl triphenylphosphonium bromide
(tert-Butoxycarbonylmethyl)triphenylphosphanium bromide
(tert-Butoxycarbonylmethyl)triphenylphosphonium bromide, 98 % | [Molecular Formula]
C24H26BrO2P | [MDL Number]
MFCD00075527 | [Molecular Weight]
457.34 | [MOL File]
59159-39-6.mol |
| Chemical Properties | Back Directory | [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) |
| Safety Data | Back Directory | [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 ]
29319019 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [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 |
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