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Product Details of (4-Carboxybut-1-yl)(triphenyl)phosphonium bromide

CAS No. :17814-85-6
Formula : C23H24BrO2P
M.W : 443.31
SMILES Code : O=C(CCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)O.[Br-]
MDL No. :MFCD00011906
InChI Key :MLOSJPZSZWUDSK-UHFFFAOYSA-N
Pubchem ID :161236

Safety of (4-Carboxybut-1-yl)(triphenyl)phosphonium bromide

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of (4-Carboxybut-1-yl)(triphenyl)phosphonium bromide

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 17814-85-6 ]

[ 17814-85-6 ] Synthesis Path-Downstream   1~3

  • 2
  • [ 51388-75-1 ]
  • [ 17814-85-6 ]
  • [ 551-11-1 ]
YieldReaction ConditionsOperation in experiment
152 mg 4-Carboxybutyl)(triphenyl)phosphonium bromide 29 (de los Angeles Rey, M. et al., J. Org. Chem. 64, 3196-3206 (1999) Note: Material prepared as described in this reference, but using toluene in place of benzene and pentane in place of hexane during the washing of the product) (2.00 g, 4.52 mmol), which corresponds to compound (VIII) described above, was added to a flame dried schlenk flask, under N2, and anhydrous THF (16.0 ml) added. The resulting suspension was cooled to 0 C. KOt-Bu (1.01 g, 9.03 mmol) was added in one portion and the resulting orange mixture stirred at 0 C for 40 min. A solution of crude triol 28 (203 mg, 0.75 mmol) in anhydrous THF (4.0 ml) was added dropwise via syringe. After complete addition the mixture was stirred at r.t. for 1 h. The reaction was quenched with H20 (25 ml) and washed with Et20 (2 x 25 ml) to remove triphenylphosphine oxide. The aqueous phase was made acidic with 1 M HCI (~10 ml) and extracted with CH2CI2 (5 x 25 ml). The combined organic phases were dried (MgS04), filtered, and concentrated to give the crude material. This was triturated with EtOAc/heptane and the solids filtered and washed with EtOAc (4 x 5 ml). The filtrate was concentrated under vacuum and purified by column chromatography on silica, eluting with EtOAc/petrol/AcOH (60:35:5) to give PGF2a. This was dissolved in CH2CI2 and washed with H20 (5 ml). The organic phase was then dried (MgS04), filtered, and concentrated to give PGF2a (152 mg, 57% over 2 steps) as a clear, colourless oil. The H NMR data was consistent with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)). The 13C NMR data was in excellent agreement with that reported by Parve (Parve, O. et al., Bioorg. Med. Chem. Lett. 9, 1853-1858 (1999)). The IR and optical rotation data are in agreement with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)) and Corey (Corey, E. et ai, J. Am. Chem. Soc. 92, 397-398 (1970)). Rf = 0.24 (EtOAc:40/60 petroleum ether:AcOH, 60:35:5) vmax (neatVcm-1 3339, 2961, 2930, 2857, 2490, 1705, 1457, 1380, 1245, 1118, 1086, 1047, 970, 910, 878, 731 *H NMR (400 MHz; CDCfe) deltaEta = 0.89 (3 H, t, J = 6.8 Hz, CH3), 1.24-1.41 (6 H, m, 3 x CH2), 1.43-1.54 (2 H, m,), 1.54-1.63 (1 H, m), 1.63-1.73 (2 H, m), 1.76 (1 H, m), 2.07-2.28 (5 H, m), 2.28-2.39 (3 H, m), 3.96 (1 H, m, CAOH), 4.11 (1 H, q, J = 6.8 Hz, CAOH), 4.18 (1 H, m, CAOH), 4.35-5.20 (1 H, br. s, C02H), 5.32-5.41 (1 H, m, =CH), 5.41-5.50 (1 H, m, =CH), 5.50 (1 H, dd, J = 15.4, 8.4 Hz, =CH), 5.58 (1 H, dd, J = 15.4, 6.6 Hz, =CH) 13C NMR (125 MHz; CDCI3) 5C = 14.0 (CH3), 22.6 (CH2), 24.5 (CH2), 25.2 (CH2), 25.2 (CH2), 26.3 (CH2), 31.7 (CH2), 33.1 (CH2), 36.9 (CH2), 42.7 (CH2), 50.0 (CH), 55.2 (CH), 72.3 (ACOH), 73.2 (ACOH), 77.4 (ACOH), 129.2 (=CH), 129.5 (=CH), 132.8 (=CH), 135.1 (=CH), 177.5 (C=0) HRMS (ESI) calcd for Q^OsNa [MNa+] 377.2298, found 377.2303 [a]D22 -23.5 (c. 1.0, THF) (lit.,49 [a]D20 -24.9 (c. 0.57, THF)) (lit.,51 [a]D25 -23.8 (synthetic material) (c. 1.0, THF)) (lit.,51 [a]D25 -23.5 (natural material) (c. 1.0, THF))
152 mg 5F. (Z)-7-(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E,3S)-3-hydroxy-1-octenyl]cyclopentyl-5-heptenoic acid, PGF2alpha (1) (4-Carboxybutyl)(triphenyl)phosphonium bromide 29 (de los Angeles Rey, M. et al., J. Org. Chem. 64, 3196-3206 (1999) Note: Material prepared as described in this reference, but using toluene in place of benzene and pentane in place of hexane during the washing of the product) (2.00 g, 4.52 mmol), which corresponds to compound (VIII) described above, was added to a flame dried schlenk flask, under N2, and anhydrous THF (16.0 ml) added. The resulting suspension was cooled to 0 C. KOt-Bu (1.01 g, 9.03 mmol) was added in one portion and the resulting orange mixture stirred at 0 C. for 40 min. A solution of crude triol 28 (203 mg, 0.75 mmol) in anhydrous THF (4.0 ml) was added dropwise via syringe. After complete addition the mixture was stirred at r.t. for 1 h. The reaction was quenched with H2O (25 ml) and washed with Et2O (2*25 ml) to remove triphenylphosphine oxide. The aqueous phase was made acidic with 1 M HCl (?10 ml) and extracted with CH2Cl2 (5*25 ml). The combined organic phases were dried (MgSO4), filtered, and concentrated to give the crude material. This was triturated with EtOAc/heptane and the solids filtered and washed with EtOAc (4*5 ml). The filtrate was concentrated under vacuum and purified by column chromatography on silica, eluting with EtOAc/petrol/AcOH (60:35:5) to give PGF2alpha. This was dissolved in CH2Cl2 and washed with H2O (5 ml). The organic phase was then dried (MgSO4), filtered, and concentrated to give PGF2alpha (152 mg, 57% over 2 steps) as a clear, colourless oil. The 1H NMR data was consistent with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)). The 13C NMR data was in excellent agreement with that reported by Parve (Parve, O. et al., Bioorg. Med. Chem. Lett. 9, 1853-1858 (1999)). The IR and optical rotation data are in agreement with that reported by Mulzer (Sheddan, N. A. et al., Org. Lett. 8, 3101-3104 (2006)) and Corey (Corey, E. et al., J. Am. Chem. Soc. 92, 397-398 (1970)). Rf=0.24 (EtOAc:40/60 petroleum ether:AcOH, 60:35:5) numax (neat)/cm-1 3339, 2961, 2930, 2857, 2490, 1705, 1457, 1380, 1245, 1118, 1086, 1047, 970, 910, 878, 731 1H NMR (400 MHz; CDCl3) deltaH=0.89 (3H, t, J=6.8 Hz, CH3), 1.24-1.41 (6H, m, 3*CH2), 1.43-1.54 (2H, m,), 1.54-1.63 (1H, m), 1.63-1.73 (2H, m), 1.76 (1H, m), 2.07-2.28 (5H, m), 2.28-2.39 (3H, m), 3.96 (1H, m, CHOH), 4.11 (1H, q, J=6.8 Hz, CHOH), 4.18 (1H, m, CHOH), 4.35-5.20 (1H, br. s, CO2H), 5.32-5.41 (1H, m, =CH), 5.41-5.50 (1H, m, =CH), 5.50 (1H, dd, J=15.4, 8.4 Hz, =CH), 5.58 (1H, dd, J=15.4, 6.6 Hz, =CH) 13C NMR (125 MHz; CDCl3) deltaC=14.0 (CH3), 22.6 (CH2), 24.5 (CH2), 25.2 (CH2), 25.2 (CH2), 26.3 (CH2), 31.7 (CH2), 33.1 (CH2), 36.9 (CH2), 42.7 (CH2), 50.0 (CH), 55.2 (CH), 72.3 (HCOH), 73.2 (HCOH), 77.4 (HCOH), 129.2 (=CH), 129.5 (=CH), 132.8 (=CH), 135.1 (=CH), 177.5 (C=O) HRMS (ESI) calcd for C20H34O5Na [MNa+] 377.2298. found 377.2303. [alpha]D22 -23.5 (c. 1.0, THF) (lit., 49[alpha]D20 -24.9 (c. 0.57, THF)) (lit., 51[alpha]D25 -23.8 (synthetic material) (c. 1.0, THF)) (lit., 51[alpha]D25 -23.5 (natural material) (c. 1.0, THF))
  • 3
  • [ 107-75-5 ]
  • [ 17814-85-6 ]
  • (Z)-12-hydroxy-8,12-dimethyltridec-5-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% General procedure: Under an atmosphere of argon, the carboxyalkyl triphenyl phosphonium bromide (2.0 equiv) is dissolved in anhydrous THF (0.6 M) The suspension is cooled to 0 C and KOt-Bu (powder or 1 M in THF; 4.0 equiv) is added dropwise. After 30 min of stirring at room temperature, a solution of the aldehyde (1.0 equiv) in anhydrous THF (2 M) is added dropwise at 0 C. The reaction is stirred at room temperature and after the aldehyde is consumed, the mixture is quenched with 1 M aq. HCl solution (20 mL), extracted with Et2O (3 30 mL) and washed with H2O (2 60 mL). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, filtered and the solvent is removed under reduced pressure. The residue is purified on silica gel to yield the title compound.
 

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