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Chemical Structure| 2136-75-6

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Product Details of 2-(Triphenylphosphoranylidene)acetaldehyde

CAS No. :2136-75-6
Formula : C20H17OP
M.W : 304.32
SMILES Code : C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :MFCD00006994
InChI Key :CQCAYWAIRTVXIY-UHFFFAOYSA-N
Pubchem ID :75051

Safety of 2-(Triphenylphosphoranylidene)acetaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P302+P352-P305+P351+P338

Application In Synthesis of 2-(Triphenylphosphoranylidene)acetaldehyde

* 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 [ 2136-75-6 ]

[ 2136-75-6 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 7310-97-6 ]
  • [ 2136-75-6 ]
  • [ 142397-45-3 ]
  • 2
  • [ 118289-17-1 ]
  • [ 2136-75-6 ]
  • 3-[4-(2-bromopyridinyl)]-2-propenal [ No CAS ]
  • 3
  • [ 2136-75-6 ]
  • [ 109466-87-7 ]
  • (E)-3-[2-nitro-4-(trifluoromethyl)phenyl]acrylaldehyde [ No CAS ]
  • 4
  • [ 2136-75-6 ]
  • [ 21204-67-1 ]
  • [ 13937-08-1 ]
  • methyl (triphenylphosphoranylidine) acetate [ No CAS ]
  • 5
  • [ 2136-75-6 ]
  • [ 1439-36-7 ]
  • [ 13937-08-1 ]
  • [ 66085-96-9 ]
  • 6
  • [ 16583-06-5 ]
  • [ 2136-75-6 ]
  • (E)-2,3,4,5-tetrafluorocinnamaldehyde [ No CAS ]
  • (E,E)-5-(2,3,4,5-tetrafluorophenyl)penta-2,4-dienal [ No CAS ]
  • 7
  • [ 62254-74-4 ]
  • [ 2136-75-6 ]
  • C7H7NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 25℃; General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4 days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature.
  • 8
  • [ 3012-80-4 ]
  • [ 2136-75-6 ]
  • [ 545424-53-1 ]
YieldReaction ConditionsOperation in experiment
46% In N,N-dimethyl-formamide; at 25℃; General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature.
  • 9
  • [ 19955-99-8 ]
  • [ 2136-75-6 ]
  • 3-(3-vinylphenyl)acrolein [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% In toluene; for 17h;Reflux; Into a 1L dry single-mouth flask, add <strong>[19955-99-8]3-vinylbenzaldehyde</strong> (13.2g, 0.10 mol), (formylmethylene)triphenylphosphine (33.5g, 0.11mmol) and toluene (200 ml). Reflux the reaction system for 17 hours then concentrated. The crude product is purified by column chromatography (eluant: petroleum ether/ethyl acetate of the volume ratio: 100/1 to 80/20) to obtain a yellow solid (9.6g, yield: 60%)
  • 10
  • [ 5779-93-1 ]
  • [ 2136-75-6 ]
  • (E)-3-(2,3-dimethylphenyl)acrylaldehyde [ No CAS ]
  • 11
  • [ 18362-30-6 ]
  • [ 2136-75-6 ]
  • (E)-3-(2-chloro-6-hydroxyphenyl)acrylaldehyde [ No CAS ]
  • 12
  • [ 2136-75-6 ]
  • [ 148625-35-8 ]
  • C11H9NO5 [ No CAS ]
  • 13
  • [ 2136-75-6 ]
  • [ 109466-87-7 ]
  • C10H6F3NO3 [ No CAS ]
  • 14
  • [ 89-98-5 ]
  • [ 2136-75-6 ]
  • [ 1794-45-2 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; A suspension of 2-chlorobenzaldehyde (200 mg, 1.428 mmol) in dichloromethane was degassed with ISh for 15 minutes at room temperature, following which 2-(triphenyl- 5- phosphanylidene)acetaldehyde (433 mg, 1.428 mmol) was added and the resulting reaction mixture stirred overnight. The crude reaction mixture was concentrated in vacuo and passed through a silica plug using 2% ethyl acetate in hexane as an eluent.
  • 15
  • [ 61018-49-3 ]
  • [ 2136-75-6 ]
  • (E)-3-(5-methyl-1,3,4-thiadiazol-2-yl)prop-2-enal [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile; at 20℃; for 24h; 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H).
In acetonitrile; at 20℃; for 24h; 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H).
 

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