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[ CAS No. 36653-82-4 ]

{[proInfo.proName]} (Synonyms:cetyl alcohol;Hexadecan-1-ol;palmityl alcohol) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 36653-82-4
Chemical Structure| 36653-82-4
Structure of 36653-82-4 * Storage: {[proInfo.prStorage]}

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Product Details of [ 36653-82-4 ]

CAS No. :36653-82-4 MDL No. :MFCD00004760
Formula : C16H34O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :242.44 g/mol Pubchem ID :2682
Synonyms :

Safety of [ 36653-82-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 36653-82-4 ]

  • Upstream synthesis route of [ 36653-82-4 ]
  • Downstream synthetic route of [ 36653-82-4 ]

[ 36653-82-4 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 36653-82-4 ]
  • [ 112-82-3 ]
YieldReaction ConditionsOperation in experiment
99% With ethyl 2,2-dibromoacetoacetate; triphenylphosphine In dichloromethane at 20℃; for 0.25 h; General procedure: Ethyl α,α-dibromoacetoacetate 2a (0.41 mmol, 1.2 equiv), alcohols 1a-1s (0.34 mmol, 1.0 equiv) and Ph3P (0.68 mmol, 2.0 equiv) were added under ambient temperature to 3 mL of DCE in air. After stirred at room temperature for appropriate time (monitored by TLC), the reaction was quenched by addition of H2O (3 mL) and then extracted with ethyl acetate (3×3 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography on silica gel with petroleum ether or mixture of petroleum ether and ethyl acetate as eluent to afford the corresponding products 3a-3s.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 1, p. 90 - 93
[2] Chemistry and Physics of Lipids, 1993, vol. 66, # 3, p. 161 - 170
[3] JAOCS, Journal of the American Oil Chemists' Society, 1996, vol. 73, # 7, p. 847 - 850
[4] Journal of the American Pharmaceutical Association (1912-1977), vol. 38, p. 288[5] Chem.Abstr., 1949, p. 8610
[6] Bulletin de la Societe Chimique de France, 1939, vol. <5> 6, p. 1670,1674
[7] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1943, vol. 279, p. 76,83
[8] Journal of the American Chemical Society, 1947, vol. 69, p. 236
[9] Chemische Berichte, 1943, vol. 76, p. 591
[10] Journal of the Chemical Society, 1948, p. 642[11] Journal of the Chemical Society, 1934, p. 339
[12] Pr.S.Dakota Acad., 1939, vol. 19, p. 124[13] Chem.Abstr., 1940, p. 2784
[14] Helvetica Chimica Acta, 1937, vol. 20, p. 1466,1467
[15] Chemische Berichte, 1936, vol. 69, p. 1766,1769,1784
[16] Chemische Berichte, 1934, vol. 67, p. 1122
[17] Gazzetta Chimica Italiana, 1950, vol. 80, p. 180,183
[18] Journal of the American Chemical Society, 1916, vol. 38, p. 1076
[19] Tetrahedron Letters, 1978, p. 4483 - 4486
[20] Journal fuer Praktische Chemie (Leipzig), 1960, vol. 10, p. 265 - 289
[21] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 712 - 718
[22] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 16, p. 2663 - 2665
[23] Advanced Synthesis and Catalysis, 2016, vol. 358, # 21, p. 3394 - 3413
  • 2
  • [ 36653-82-4 ]
  • [ 2197-63-9 ]
YieldReaction ConditionsOperation in experiment
11% at 80℃; Production Example 5; Synthesis of Dicetylphosphate; To a mixture of cetyl alcohol (19.50 g, 80.4 mmol) and benzene (100 ml), phosphorus oxychloride (2.5 ml, 26.8 mmol) was added dropwise at 80° C. (solvent reflux temperature) and further stirred for 12 hours. The solvent of the reaction solution was evaporated under a reduced pressure. To the obtained residue, benzene (50 ml) was added and cooled overnight. The precipitate generated was filtrated to obtain the titled compound (white powder, 1.64 g, 3.0 mmol, yield: 11percent).1H-NMR (ppm) δ: 0.87-0.89 (t, 6H), 1.25-1.37 (br, s, 52H), 1.65-1.72 (m, 4H), 4.00-4.06 (m4H), 7.05 (br, s, 1H)13C-NMR (ppm) δ: 14.11, 22.69, 25.44, 29.18, 29.36, 29.54, 29.61, 29.66, 29.67, 29.70, 29.71, 30.16, 30.21, 31.93, 67.69, 67.7331P-NMR (ppm) δ: 2.15SIMS mass analysis:Actual measurement value; 547.85Theoretical value; 547.83, relative to (C32H68O4P)+
Reference: [1] Patent: US2010/94020, 2010, A1, . Location in patent: Page/Page column 18
[2] Bulletin of the Chemical Society of Japan, 1978, vol. 51, p. 1877 - 1879
[3] Chemical and Pharmaceutical Bulletin, 1995, vol. 43, # 10, p. 1751 - 1754
[4] Bioconjugate Chemistry, 2010, vol. 21, # 5, p. 844 - 852
  • 3
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  • [ 4697-37-4 ]
  • [ 2197-63-9 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 298
  • 4
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  • [ 770-12-7 ]
  • [ 2197-63-9 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 1584,1585
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  • [ 4697-37-4 ]
  • [ 1623-14-9 ]
  • [ 598-02-7 ]
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  • [ 2197-63-9 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 298
  • 6
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  • [ 540-10-3 ]
YieldReaction ConditionsOperation in experiment
99% With sodium bromate; sulfuric acid; sodium bromide In water at 20℃; for 24 h; General procedure: A total of 1.0 g of 1-octanol (7.69 mmol) was taken in a 50-mL round-bottomed flask, to it NaBr 0.523 g (0.66 eq.), NaBrO 3 0.383 g (0.33 eq.), and 10 mL of H 2 O [comprises the bromide and bromate in 2:1 molar ratio] were added[6f]. The reaction mixture was stirred vigorously to dissolve the contents completely. To the above reaction mixture, the aqueous H 2 SO 4 solution (0.5 eq.) was added slowly under stirring over a period of 2.5 h at room temperature (prepared by adding 0.21 mL of 98percent H 2 SO 4 to 1 mL of water). The reaction mixture was allowed to stir for up to 24 h. After the completion of reaction, the product was extracted with CH 2 Cl 2 (3 15 mL), the organic layer was dried with Na 2 SO 4 and removal of the solvent obtained octyloctanoate in 98percent yield (0.953 g) as colorless liquid. The product was confirmed by GC–MS as well as by NMR.
Reference: [1] Synthetic Communications, 2018, vol. 48, # 13, p. 1663 - 1670
  • 7
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  • [ 57-10-3 ]
  • [ 540-10-3 ]
YieldReaction ConditionsOperation in experiment
98.3 %Chromat. With tungsten oxide impregnated Zr incorporated mesoporous silica SBA-15 In 1,3,5-trimethyl-benzene at 162℃; for 6 h; Inert atmosphere; Dean-Stark Cetyl alcohol (CA) and palmitic acid (PA) esterification reactions were performed under N2 atmosphere in a four necked round bot-tom flask (250 ml) equipped with a Teflon coated magnetic stirring bar with a stirring rate of 520 rpm and a Dean Stark apparatus surmounted with a reflux condenser. In a typical experiment, 160 mgof catalyst was added into 25 ml of mesitylene and heated up to reaction temperature of 162 C. An equimolar solution of palmitic acid and cetyl alcohol (6 mmol) in 15 ml of mesitylene at room temperature was added into the reactor. All the reactions were carried out for a reaction time of 6 h. In a preliminary set of experiments (Table 1) it was found that the reaction was not controlled by external diffusion at 520 rpm. Samples taken at regular intervals were analyzed by Agilent 6890 gas chromatography using Ultra 1(25 m × 0.3 mm) capillary column equipped with FID. The injector temperature was 280C and the detector temperature was 320 C.The GC oven temperature was changed from 50C at 12C/min to 300C where it was kept for 35 min. Helium was used as the car-rier gas at a flow rate of 37.3 ml/min The split ratio was 24.9:1. Conversion of cetyl alcohol (CA), yield of cetyl palmitate (CP) and the selectivity to CP were defined as below. Conversion(percent)= (CAin −CAout )CAin×100 Yield(percent)= CPoutCAin×100 Selectivity to CP(percent) = CPout(CAin −CAout )×100
Reference: [1] Synthesis, 2005, # 12, p. 1939 - 1944
[2] Chemistry Letters, 2005, vol. 34, # 11, p. 1502 - 1503
[3] Tetrahedron Letters, 2007, vol. 48, # 39, p. 6962 - 6965
[4] Agricultural and Biological Chemistry, 1988, vol. 52, # 11, p. 2933 - 2936
[5] Synthetic Communications, 1986, vol. 16, p. 1423 - 1430
[6] Biochemische Zeitschrift, 1931, vol. 241, p. 467
[7] Biochemische Zeitschrift, 1933, vol. 259, p. 424
[8] Biochemische Zeitschrift, 1933, vol. 259, p. 424
[9] Journal of the American Pharmaceutical Association (1912-1977), 1944, vol. 33, p. 107[10] Chem.Abstr., 1944, p. 2765
[11] Agricultural and Biological Chemistry, 1988, vol. 52, # 10, p. 2631 - 2632
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[13] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[14] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[15] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 3-4
[16] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[17] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[18] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[19] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[20] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[21] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
[22] Patent: US2005/240040, 2005, A1, . Location in patent: Page/Page column 4
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[26] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 8-9
[27] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[28] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 21-22
[29] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 13
[30] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 13
[31] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 19-20
[32] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[33] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[34] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[35] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[36] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[37] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[38] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[39] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[40] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[41] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[42] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[43] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[44] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[45] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[46] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[47] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[48] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10
[49] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 7
[50] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 16-17
[51] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 16-17
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[58] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
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[65] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[66] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[67] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
[68] Patent: WO2006/64685, 2006, A1, . Location in patent: Page/Page column 10-11
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[74] Applied Catalysis A: General, 2016, vol. 522, p. 194 - 200
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Reference: [1] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 1
[2] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 1-2
[3] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
[4] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
[5] Patent: US2005/33070, 2005, A1, . Location in patent: Page/Page column 2
  • 9
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  • [ 112-67-4 ]
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Reference: [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1922, vol. 119, p. 282
[2] Bulletin de la Societe Chimique de France, 1947, p. 322
[3] Journal of the American Chemical Society, 1951, vol. 73, p. 5406,5407
[4] J. Appl. Chem. USSR (Engl. Transl.), 1968, vol. 41, p. 2371 - 2376[5] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1968, vol. 41, p. 2517 - 2523
  • 10
  • [ 112-39-0 ]
  • [ 629-62-9 ]
  • [ 34557-54-5 ]
  • [ 544-76-3 ]
  • [ 14852-31-4 ]
  • [ 36653-82-4 ]
  • [ 629-80-1 ]
  • [ 540-10-3 ]
  • [ 201230-82-2 ]
  • [ 57-10-3 ]
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  • [ 629-80-1 ]
  • [ 540-10-3 ]
  • [ 124-38-9 ]
  • [ 201230-82-2 ]
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Reference: [1] RSC Advances, 2016, vol. 6, # 36, p. 30372 - 30383
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Reference: [1] Synthesis, 1990, # 9, p. 853 - 854
[2] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4732 - 4741
  • 13
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4732 - 4741
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Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 15, p. 4732 - 4741
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Reference: [1] Applied Catalysis A: General, 2016, vol. 526, p. 183 - 190
  • 16
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  • [ 23377-40-4 ]
Reference: [1] Patent: US2012/58976, 2012, A1,
[2] ChemMedChem, 2013, vol. 8, # 3, p. 511 - 520
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  • [ 58066-85-6 ]
Reference: [1] Patent: US2007/264206, 2007, A1, . Location in patent: Page/Page column 8
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Reference: [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 8, p. 1558 - 1564
[2] Chemistry and Physics of Lipids, 2001, vol. 109, # 2, p. 203 - 207
[3] Die Pharmazie, 1982, vol. 37, # 10, p. 706 - 708
[4] Pharmaceutica Acta Helvetiae, 1958, vol. 33, p. 349,350
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  • [ 55357-38-5 ]
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  • [ 122-18-9 ]
Reference: [1] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 11, p. 784 - 787[2] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 11, p. 1344 - 1348
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  • [ 282526-98-1 ]
Reference: [1] Patent: CN105439974, 2016, A,
[2] Patent: WO2018/11676, 2018, A1,
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