| Identification | Back Directory | [Name]
Benzyl (triphenylphosphoranylidene)acetate | [CAS]
15097-38-8 | [Synonyms]
LABOTEST-BB LT00452383
BENZYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE
Benzyl 2-(triphenylphosphoranylidene)acetate
Benzyl(triphenylphosphoranylidene)acetate 97%
(BenzyloxycarbonylMethylene)triphenylphosphorane
Benzyl (triphenylphosphoranylidene)acetate, 97 %
2-(Triphenylphosphoranylidene)acetic acid phenylmethyl ester
Acetic acid,2-(triphenylphosphoranylidene)-, phenylMethyl ester | [Molecular Formula]
C27H23O2P | [MDL Number]
MFCD00191787 | [MOL File]
15097-38-8.mol | [Molecular Weight]
410.44 |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [Melting point ]
120-122 °C(lit.)
| [Boiling point ]
571.1±43.0 °C(Predicted) | [density ]
1.19±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [form ]
Powder | [color ]
White to off-white | [InChI]
InChI=1S/C27H23O2P/c28-27(29-21-23-13-5-1-6-14-23)22-30(24-15-7-2-8-16-24,25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20,22H,21H2 | [InChIKey]
INKMLGJBBDRIQR-UHFFFAOYSA-N | [SMILES]
C(OCC1=CC=CC=C1)(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
white to off-white powder | [Uses]
Reactant for:
- Tributylphosphine-mediated vinylogous Wittig reactions
- Synthesis of 1,2-dioxanes for antitrypanosomal activity
- Organocatalytic Michael-type reactions / Wittig reactions of phosphorus ylides and unsaturated ketones
- Stereoselective phosphine-catalyzed cycloaddition to form spirocyclopenteneoxindoles
- Enantioselective synthesis of pantothenic acid
- Preparation of phosphorus ylides from phosphoranes and acetic anhydride
| [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
The general procedure for the synthesis of (benzyloxycarbonylmethylene)triphenylphosphonium bromide from benzyloxycarbonylmethylene)triphenylphosphonium bromide was as follows: (2-(benzyloxy)-2-oxoethyl)triphenylphosphonium bromide (2.00 g, 4.07 mmol) and NaOH (0.081 g, 2.035 mmol) were dissolved in CH2Cl2 (20 mL), and the reaction was stirred for 1 hr at 25 °C . After completion of the reaction, the reaction mixture was diluted with CH2Cl2 (50 mL) and washed with deionized water (30 mL). The organic layer was separated and concentrated to afford benzyl 2-(triphenylphosphoranylidene)acetate (1.5 g, 3.25 mmol, 80% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.60-7.65 (m, 6H), 7.51-7.54 (m, 4H), 7.42-7.46 (m, 6H), 7.20 (s, 4H), 5.00 (s, 2H), 2.96 (s, 1H); LC-MS(ESI) m/z 411.1 (M + H) +. | [References]
[1] Heterocycles, 2007, vol. 73, # C, p. 751 - 768
[2] Patent: US2018/99931, 2018, A1. Location in patent: Paragraph 2180
[3] Organic Letters, 2005, vol. 7, # 19, p. 4289 - 4291
[4] Patent: WO2006/17542, 2006, A1. Location in patent: Page/Page column 42-43
[5] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 12926 - 12928 |
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