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[ CAS No. 106-02-5 ] {[proInfo.proName]}

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Chemical Structure| 106-02-5
Chemical Structure| 106-02-5
Structure of 106-02-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 106-02-5 ]

CAS No. :106-02-5 MDL No. :MFCD00039667
Formula : C15H28O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FKUPPRZPSYCDRS-UHFFFAOYSA-N
M.W : 240.38 Pubchem ID :235414
Synonyms :
15-Pentadecanolactone

Safety of [ 106-02-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106-02-5 ]

* 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.

  • Upstream synthesis route of [ 106-02-5 ]
  • Downstream synthetic route of [ 106-02-5 ]

[ 106-02-5 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 89611-22-3 ]
  • [ 106-02-5 ]
  • [ 2044-64-6 ]
Reference: [1] Tetrahedron Letters, 1984, vol. 25, # 3, p. 273 - 276
  • 2
  • [ 106-02-5 ]
  • [ 56523-59-2 ]
YieldReaction ConditionsOperation in experiment
91% at 60℃; for 16 h; Autoclave; Inert atmosphere Example B-2
Preparation of 15-bromopentadecanoic acid
15-Pentadecanolide of 14.3 g (59.5 mmol), and 32percent hydrogen bromide/acetic acid solution of 24.8 g (98.0 mmol, 1.6 eq) were added to 100 mL of autoclave protected with Teflon (registered trade name).
After purging with nitrogen and sealing, the autoclave was placed in an oil bath at 60°C and stirring was carried out for 16 hours.
For the stirring, a magnetic stirrer was used.
After cooling, 14 mL of water was added, and by using 200 mL of hot hexane the mixture was transferred to a separatory funnel.
After washing with ion exchange water, it was dried over the magnesium sulfate.
After filtration, 17.4 g of the target compound was obtained by crystallization using n-hexane (yield 91percent).
Reference: [1] Australian Journal of Chemistry, 1998, vol. 51, # 7, p. 581 - 586
[2] Patent: EP2143705, 2010, A1, . Location in patent: Page/Page column 17
[3] Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4617 - 4618
[4] Angewandte Chemie - International Edition, 2005, vol. 44, # 30, p. 4731 - 4735
[5] Journal of the American Chemical Society, 2006, vol. 128, # 40, p. 13040 - 13041
[6] Chemical Communications, 2017, vol. 53, # 11, p. 1813 - 1816
  • 3
  • [ 106-02-5 ]
  • [ 64-19-7 ]
  • [ 56523-59-2 ]
  • [ 69186-31-8 ]
YieldReaction ConditionsOperation in experiment
47 %Chromat. at 60 - 100℃; for 46 h; Inert atmosphere Example B-3
Preparation of 15-bromopentadecanoic acid (open system)
To a two-necked 50 mL of flask equipped with a refluxing condenser tube and a magnetic stirrer, 15-pentadecanolide of 1. 0 g (4.2 mmol), and 32percent hydrogen bromide/acetic acid solution of 3.3g (13.1 mmol, 3.1 eq) were added.
The flask was placed in an oil bath at 60°C and stirring was carried out for 16 hours under nitrogen atmosphere.
Sampling analysis based on GC indicated that area percentage consisted of the target compound 15-bromopentadecanoic acid 10percent, the starting material 15-pentadecanolide 89percent and byproduct 15-acetoxypentadecanoic acid 1percent.
Further, after heating and stirring in an oil bath at 80°C for 8 hours, the area percentage consisted of the target compound 31percent, the starting material 65percent and byproduct 4percent.
Further, after heating and stirring in an oil bath at 100°C for 20 hours, the area percentage consisted of the target compound 42percent, the starting material 52percent, and by product 6percent.
Still further, after 32percent hydrogen bromide/acetic acid solution 3 g (11.9 mmol, 2.8 eq) were added and then the resultant was heated and stirred in an oil bath at 100°C for 2 hours, the area percentage consisted of the target compound 47percent, the starting material 47percent, and byproduct 6percent.
Reference: [1] Patent: EP2143705, 2010, A1, . Location in patent: Page/Page column 17
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