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Chemical Structure| 104-87-0
Chemical Structure| 104-87-0
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Product Details of [ 104-87-0 ]

CAS No. :104-87-0 MDL No. :MFCD00006954
Formula : C8H8O Boiling Point : -
Linear Structure Formula :- InChI Key :FXLOVSHXALFLKQ-UHFFFAOYSA-N
M.W :120.15 Pubchem ID :7725
Synonyms :
p-Tolualdehyde

Calculated chemistry of [ 104-87-0 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.8
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 2.14
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.524 mg/ml ; 0.00436 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 0.89 mg/ml ; 0.00741 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.249 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 104-87-0 ]

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

Application In Synthesis of [ 104-87-0 ]

* 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 [ 104-87-0 ]
  • Downstream synthetic route of [ 104-87-0 ]

[ 104-87-0 ] Synthesis Path-Upstream   1~58

  • 1
  • [ 104-87-0 ]
  • [ 22483-09-6 ]
  • [ 42398-73-2 ]
YieldReaction ConditionsOperation in experiment
66%
Stage #1: at 90℃;
Stage #2: With chloroformic acid ethyl ester; triethyl phosphite In chloroform at 0 - 20℃; for 24 h;
Stage #3: With titanium tetrachloride In chloroform at 0 - 20℃; Reflux
Para-tolualdehyde (53 mL, 0.486 mol) was stirred in a solvent of chloroform (900 mL). Aminoacetaldehyde dimethyl acetal (59.3 mL, 0.486 mol) was slowly added thereto, followed by stirring at 90° C. until about one-half of the reaction solution was evaporated. The reaction solution was cooled to room temperature, and the resulting yellow reaction solution was dissolved in chloroform (400 mL), followed by cooling the solution to 0° C. or below. Ethyl chloroformate (48 mL, 0.486 mol) and triethylphosphite (104 mL, 0.583 mol) were slowly added to the reaction solution. The reaction solution was stirred for 24 hours at room temperature. The reaction solution was cooled to 0° C. or below, slowly added with titanium tetrachloride (213.6 mL, 1.94 mol), and refluxed for 12 hours or more. The reaction solution was cooled to room temperature, and stirred for 12 hours or more. The reaction mixture was poured to an ice water to separate the organic layer and the aqueous layer, and the aqueous layer was washed with dichloromethane. A saturated sodium tartrate solution was added to the aqueous layer, adjusted to pH 9 by adding ammonia water, and subjected to extraction with dichloromethane. The obtained organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.3 g, 66percent). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.23 (s, 1H), 8.45 (d, 1H), 8.02 (d, 1H), 7.72 (d, 2H), 7.54 (d, 1H), 2.49 (s, 3H)
66%
Stage #1: at 90℃;
Stage #2: With chloroformic acid ethyl ester; triethyl phosphite In chloroform at 0 - 20℃; for 24 h;
Stage #3: With titanium tetrachloride In chloroform at 0℃; for 12 h; Reflux
p-Tolualdehyde (53 mL, 0.486 mol) was stirred in a solvent of chloroform (900 mL), slowly added with aminoacetaldehyde dimethyl acetal (59.3 mL, 0.486 mol), and stirred at 90°C until about a half of the reaction solution had evaporated.
The reaction solution was cooled to room temperature, and the yellow reaction solution was dissolved in chloroform (400 mL), followed by cooling to 0°C or lower.
The reaction solution was slowly added with ethyl chloroformate (48 mL, 0.486 mol) and triethyl phosphite (104 mL, 0.583 mol), followed by stirring for 24 hours at room temperature.
The reaction solution was cooled to 0°C or lower, slowly added with titanium tetrachloride (213.6 mL, 1.94 mol), and refluxed for 12 hours or more.
The temperature of the reaction solution was adjusted to room temperature and stirred for over 12 hours.
The reaction mixture was poured over an ice water to separate the organic layer and the aqueous layer, and the aqueous layer was washed with dichloromethane.
The aqueous layer was poured into a saturated potassium sodium tartrate solution, and adjusted to have a pH value of 9 by adding an aqueous ammonia solution, and then extracted with dichloromethane.
The combined organic layer thus obtained was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (46.3 g, 66 percent).
1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.23(s, 1H), 8.45(d, 1H), 8.02(d, 1H), 7.72(d, 2H), 7.54(d, 1H), 2.49(s, 3H)
66%
Stage #1: at 90℃;
Stage #2: With chloroformic acid ethyl ester; triethyl phosphite In chloroform at 0 - 20℃; for 24 h;
Stage #3: With titanium tetrachloride In chloroform at 0℃; Reflux
p-Tolualdehyde (53 mL, 0.486 mol) was stirred in a solvent of chloroform (900 mL), slowly added with aminoacetaldehyde dimethyl acetal (59.3 mL, 0.486 mol), and stirred at 90° C. until about a half of the reaction solution had evaporated.
The reaction solution was cooled to room temperature, and the yellow reaction solution was dissolved in chloroform (400 mL), followed by cooling to 0° C. or lower.
The reaction solution was slowly added with ethyl chloroformate (48 mL, 0.486 mol) and triethyl phosphite (104 mL, 0.583 mol), followed by stirring for 24 hours at room temperature.
The reaction solution was cooled to 0° C. or lower, slowly added with titanium tetrachloride (213.6 mL, 1.94 mol), and refluxed for 12 hours or more.
The temperature of the reaction solution was adjusted to room temperature and stirred for over 12 hours.
The reaction mixture was poured over an ice water to separate the organic layer and the aqueous layer, and the aqueous layer was washed with dichloromethane.
The aqueous layer was poured into a saturated potassium sodium tartrate solution, and adjusted to have a pH value of 9 by adding an aqueous ammonia solution, and then extracted with dichloromethane.
The combined organic layer thus obtained was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (46.3 g, 66percent).
1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.23 (s, 1H), 8.45 (d, 1H), 8.02 (d, 1H), 7.72 (d, 2H), 7.54 (d, 1H), 2.49 (s, 3H)
Reference: [1] Patent: US2014/371219, 2014, A1, . Location in patent: Paragraph 0216; 0217
[2] Patent: EP2876107, 2015, A1, . Location in patent: Paragraph 0072
[3] Patent: US2015/191450, 2015, A1, . Location in patent: Paragraph 0143; 0144
  • 2
  • [ 541-41-3 ]
  • [ 104-87-0 ]
  • [ 22483-09-6 ]
  • [ 42398-73-2 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: at 22 - 65℃;
Stage #2: With triethyl phosphite In chloroform at -3 - 20℃; for 23 h;
Stage #3: With titanium tetrachloride In chloroform at 52℃; for 10.5 h;
Aminoacetaldehyde dimethyl acetal (8.83 mL, 81.1 mmol) was added over 1 min to a stirred solution of p-tolualdehyde (9.88 mL, 81.1 mmol) in chloroform (150 mL) at 22 0C. An exotherm was noted. The reaction was heated to reflux (65 0C) and half the solvent was removed (azeotropically to remove water). The heat was removed and the yellow solution was cooled to r.t. NMR showed the imine was formed smoothly, however, a trace of aldehyde was observed. The yellow solution was diluted with chloroform to bring the volume back to -100 mL, cooled to -3 0C and ethyl chloroformate (7.99 mL, 81.1 mmol) was added dropwise over 5 min followed by triethyl phosphite (17.4 mL, 97.3 mmol) over 10 minutes. The clear yellow solution was then allowed to warm to RT. A reflux condenser added to reaction vessel. After 23 h, titanium tetrachloride (35.6 mL, 324 mmol) was added very slowly (strong exotherm and white fumes observed) and the reaction began to gently reflux (50 °C). Color changed from yellow to dark red to dark brown. Once addition was complete, the dark brown solution was heated to reflux (52 0C) for 10.5 h. After allowing to cool to RT overnight, the dark brown solution was poured onto ice (filled a 2 L beaker with approximately 1 L of ice), the organic layer was separated off, and the aqueous layer was washed with DCM (2 x 100 mL). The aqueous layer (now orange in color) was poured into a solution of potassium sodium tartrate tetrahydrate (183 g, 648 mmol) in water (300 mL), basified to pH 9 with 28-30 percent ammonium hydroxide (a white ppt crashed out) and then extracted with DCM (3 x 200 mL). The organic layer was separated, dried over sodium sulfate, filtered and the solvent was evaporated in vacuo to yield 6-methylisoquinoline (9.02 g, 78percent yield) as a light tan amorphous solid. Found MS (ESI, pos. ion) m/z: 144.1 [M+H]+
Reference: [1] Patent: WO2008/153947, 2008, A2, . Location in patent: Page/Page column 53
  • 3
  • [ 104-87-0 ]
  • [ 645-36-3 ]
  • [ 42398-73-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 1, p. 180 - 186
[2] Monatshefte fuer Chemie, 1897, vol. 18, p. 5[3] Monatshefte fuer Chemie, 1894, vol. 15, p. 304
  • 4
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  • [ 42398-73-2 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 19, p. 3344 - 3346
[2] Patent: WO2013/100632, 2013, A1,
  • 5
  • [ 104-87-0 ]
  • [ 543-24-8 ]
  • [ 93634-54-9 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 52, p. 12296 - 12306
[2] Nucleosides and Nucleotides, 1993, vol. 12, # 9, p. 925 - 940
[3] European Journal of Organic Chemistry, 2013, # 29, p. 6611 - 6618
[4] Organic and Biomolecular Chemistry, 2004, vol. 2, # 18, p. 2684 - 2691
[5] Amino Acids, 2010, vol. 38, # 3, p. 701 - 709
[6] Monatshefte fur Chemie, 2006, vol. 137, # 2, p. 163 - 168
[7] Bulletin of the Chemical Society of Japan, 1957, vol. 30, p. 698
[8] Bollettino Chimico Farmaceutico, 1996, vol. 135, # 8, p. 465 - 467
[9] Tetrahedron, 2000, vol. 56, # 19, p. 2941 - 2951
[10] Heterocycles, 2000, vol. 53, # 10, p. 2261 - 2274
[11] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5317 - 5322
[12] Tetrahedron, 2004, vol. 60, # 42, p. 9517 - 9524
[13] Journal of Medicinal Chemistry, 1996, vol. 39, # 14, p. 2773 - 2780
[14] Journal of the American Chemical Society, 2008, vol. 130, # 43, p. 14096 - 14098
[15] Tetrahedron, 2013, vol. 69, # 46, p. 9766 - 9771
[16] Advanced Synthesis and Catalysis, 2018, vol. 360, # 4, p. 738 - 743
  • 6
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  • [ 93634-54-9 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 15, p. 3586 - 3589
  • 7
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  • [ 79-19-6 ]
  • [ 26907-54-0 ]
YieldReaction ConditionsOperation in experiment
80% With tert.-butylhydroperoxide In ethanol; water at 20℃; for 4 h; Green chemistry General procedure: A mixture of aldehydes (1 mmol), thiosemicarbazide (1 mmol) in ethanol (10 mL) and tert-butyl hydroperoxide (TBHP, 70percent aqueous solution) (1 mmol) was stirred at room temperature for 4h. The progress of the reaction was monitored by TLC using hexane/ EtOAc as the mobile phase. After the completion of the reaction, ethanol was evaporated under vacuum to obtain a solid residue. To this solid residue, ethyl acetate (10 ml) and water (10 ml) were added followed by saturated sodium bicarbonate solution (10 mL). Separated organic layer was dried over anhydrous sodium sulfate and evaporated under vacuum to obtain the product, which was further purified using silica gel column chromatography (hexane/ethyl acetate).
Reference: [1] Synthetic Communications, 2018, vol. 48, # 3, p. 285 - 290
  • 8
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  • [ 26907-54-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 19, p. 5735 - 5738
[2] Asian Journal of Chemistry, 2011, vol. 23, # 3, p. 1305 - 1308
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2014, vol. 29, # 5, p. 611 - 618
[4] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1018 - 1024
[5] European Journal of Medicinal Chemistry, 2016, vol. 124, p. 237 - 247
[6] Medicinal Chemistry Research, 2017, vol. 26, # 4, p. 819 - 829
[7] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1872 - 1879
[8] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491
  • 9
  • [ 104-87-0 ]
  • [ 107-13-1 ]
  • [ 3528-45-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 6, p. 1133 - 1136
  • 10
  • [ 104-87-0 ]
  • [ 459-57-4 ]
  • [ 3476-86-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1984, # 4, p. 615 - 620
  • 11
  • [ 104-87-0 ]
  • [ 36276-24-1 ]
YieldReaction ConditionsOperation in experiment
60.36%
Stage #1: With aluminum (III) chloride In dichloromethane at 0 - 40℃; for 0.5 h;
Stage #2: With bromine In dichloromethane at 0 - 20℃;
To a stirred solution of 4-methylbenzaldehyde (20.0 g, 166.5 mmol) in DCM (150 mL)at 0 00 AId3 (26.5 g, 198.7 mmol) was added portion wise. It was then heated at 4000 for 30 mm. , Br2 (31.9 g, 199.6 mmol) in DCM (50 mL) was then added to thereaction mixture drop wise at 0 00 and stirred at room temperature over night. The reaction mixture was diluted with ice water and extracted with DCM. The organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated under vacuo. The crude product was purified by columnchromatography to yield the title compound (20 g, 60.36percent) as yellow oil.
Reference: [1] Dalton Transactions, 2004, # 2, p. 319 - 326
[2] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 77
[3] Journal of Organic Chemistry, 1958, vol. 23, p. 1412,1217
[4] Org. Synth. Coll. Vol., 1973, vol. V, p. 117,120
  • 12
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YieldReaction ConditionsOperation in experiment
60.36%
Stage #1: With aluminum (III) chloride In dichloromethane at 0 - 40℃; for 0.5 h;
Stage #2: With (3-bromo-4-methyl-phenyl)-methanol In dichloromethane at 0 - 20℃;
To a stirred solution of 4-methylbenzaldehyde (20.0 g, 166.5 mmcl) in DCM (150 mL)at 000 AICI3 (26.5 g, 198.7 mmol) was added portion wise. It was heated at 40°C for30 mm, then Br2 (31.9 g, 199.6 mmol) in DCM (50 mL) was added drop wise at 000 and stirred at room temperature over night. The reaction mixture was diluted with ice water and extracted with DCM. The organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated under vacuo. The crudeproduct was purified by column chromatography to yield the title compound (20 g,60.36percent) as yellow oil.
Reference: [1] Patent: WO2014/202528, 2014, A1, . Location in patent: Page/Page column 63
  • 13
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  • [ 31680-07-6 ]
Reference: [1] Liebigs Annalen der Chemie, 1985, vol. 1985, # 7, p. 1413 - 1421
[2] Journal of the American Chemical Society, 2003, vol. 125, # 14, p. 4068 - 4069
[3] Journal of the American Chemical Society, 1936, vol. 58, p. 2050,2054
[4] Chemische Berichte, 1899, vol. 32, p. 1287
[5] Justus Liebigs Annalen der Chemie, 1906, vol. 347, p. 353
[6] Chemische Berichte, 1899, vol. 32, p. 1287
  • 14
  • [ 106-42-3 ]
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Reference: [1] Annales de Chimie (Cachan, France), 1936, vol. <11> 5, p. 5,42
  • 15
  • [ 106-42-3 ]
  • [ 7664-93-9 ]
  • [ 7697-37-2 ]
  • [ 31680-07-6 ]
  • [ 104-87-0 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1934, vol. 198, p. 2105[2] Annales de Chimie (Cachan, France), 1936, vol. <11> 5, p. 1,43
  • 16
  • [ 134890-52-1 ]
  • [ 1187-46-8 ]
  • [ 104-87-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 1031 - 1034
  • 17
  • [ 104-87-0 ]
  • [ 6232-88-8 ]
  • [ 99-94-5 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
  • 18
  • [ 104-87-0 ]
  • [ 5162-82-3 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 31, p. 3131 - 3134
[2] Tetrahedron Letters, 1982, vol. 23, # 31, p. 3131 - 3134
  • 19
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  • [ 446-65-1 ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride; tetrabutyl ammonium fluoride In tetrahydrofuran 6.9.
Synthesis of (2S)-2-Amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-p-tolylethoxy)pyrimidin-4-yl)phenyl)propanoic acid
Tetrabutylammonium fluoride (0.1 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-methyl-benzaldehyde (1.2 g, 10 mmol) and TMSCF3 (1.8 ml, 12 mmol) in 10 ml THF at 0° C.
The formed mixture was warmed up to room temperature and stirred for 4 hours.
The reaction mixture was then treated with 12 ml of 1N HCl and stirred overnight.
The product was extracted with ethyl acetate (3*20 ml).
The organic layer was separated and dried over sodium sulfate.
The organic solvent was evaporated to give 1.6 g of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol, yield 86percent.
86% With hydrogenchloride; tetrabutyl ammonium fluoride In tetrahydrofuran 6.7.
Synthesis of (2S)-2-Amino-3-(4-(2-amino-6-(2,2,2-trifluoro-1-p-tolylethoxy)pyrimidin-4-yl)phenyl)propanoic acid
Tetrabutylammonium fluoride (0.1 ml; 1.0 M solution in tetrahydrofuran) was added to a solution of 4-methyl-benzaldehyde (1.2 g, 10 mmol) and TMSCF3 (1.8 ml, 12 mmol) in 10 ml THF at 0° C.
The formed mixture was warmed up to room temperature and stirred for 4 hours.
The reaction mixture was then treated with 12 ml of 1N HCl and stirred overnight.
The product was extracted with ethyl acetate (3*20 ml).
The organic layer was separated and dried over sodium sulfate.
The organic solvent was evaporated to give 1.6 g of 1-(4-methylphenyl)-2,2,2-trifluoro-ethanol, yield 86percent.
5.5 g With tetrabutyl ammonium fluoride; (trifluoromethyl)trimethylsilane In tetrahydrofuran at 0℃; for 4 h; A catalytic amount of lM-tetrabutylammonium fluoride in THF (0.5 mL) was addedto a solution oftrimethyl(trit1uoromethyl)silane (9.0 mL, 1.2 equiv.) and 4-rnethylbenzaldehyde 144a (6.0 g, l equiv.) in THF (50 rnL) at 0°C ·with stirring Cooling bath15 \vas removed and the reaction was continued for 4 hr. The thin layer chromatography inhexane:ethylacetate (l9:l:v/v) showed the completion ofthe reaction. A lN HCl aqueoussolution (60 mL) was added to the reaction mixture, and the reaction was continued for 16 hr.The mixture was diluted with ethyl acetate and washed with brine, dried over sodium sulfate,filtered and concentrated in vacuo to give the 2,2,2-trit1uoro-l-p-tolylethanol144b (5.5 g)20 which was used as such in the next step; 1-1 NMR (400 MHz, DMSO-d6): o 7.37 (d, J '" 7.9Hz, 2H), 7.21 d, J '" 8.2 Hz, 2H), 6.74 (d, J '" 5.6 Hz, lH), 5.18-4.99 (m, H-r), 2.31 (s, 3H)
Reference: [1] Patent: US2009/5381, 2009, A1,
[2] Patent: US2009/5382, 2009, A1,
[3] Patent: US2009/29993, 2009, A1,
[4] Journal of Organic Chemistry, 2013, vol. 78, # 2, p. 711 - 716
[5] Patent: WO2018/39386, 2018, A1, . Location in patent: Page/Page column 288
[6] Organic and Biomolecular Chemistry, 2018, vol. 16, # 25, p. 4715 - 4719
  • 20
  • [ 104-87-0 ]
  • [ 81290-20-2 ]
  • [ 446-65-1 ]
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 33, p. 4483 - 4486
[2] Journal of Organic Chemistry, 2012, vol. 77, # 18, p. 8131 - 8141
[3] RSC Advances, 2016, vol. 6, # 86, p. 82716 - 82720
[4] Tetrahedron, 2009, vol. 65, # 11, p. 2232 - 2238
[5] Organic Letters, 2014, vol. 16, # 22, p. 6004 - 6007
[6] Chemical Communications, 2015, vol. 51, # 4, p. 658 - 660
[7] Chemical Communications, 2018, vol. 54, # 78, p. 11017 - 11020
  • 21
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Reference: [1] Chemical Communications, 1998, # 12, p. 1251 - 1252
[2] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1446 - 1450
  • 22
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  • [ 3097-21-0 ]
  • [ 446-65-1 ]
YieldReaction ConditionsOperation in experiment
6 %Chromat. With potassium carbonate In N,N-dimethyl-formamide at 10 - 35℃; for 15 h; To a 10 mL eggplant-shaped flask equipped with a magnetic stirrer, 0.06 g (0.5 mmol) of 4-methylbenzaldehyde, 0.28 g (2 mmol) of potassium carbonate and 1 mL of DMF were added.
While the mixture was stirred at room temperature, 0.33 g (1 mmol) of 1,3-dimethyl-2-trifluoromethylbenzimidazolium methyl sulfate was added thereto.
The mixture was stirred at room temperature for 15 hours.
The formation of 1-(4-methylphenyl)-2,2,2-trifluoroethanol (parent ion; 190) was confirmed by GC-MS analysis on the reaction mixture. As a result of GC analysis (area percentage) on the reaction mixture, the components in the reaction mixture excluding the solvents and the like were as follows: 6percent of 1-(4-methylphenyl)-2,2,2-trifluoroethanol (target compound), 31percent of 4-methylbenzaldehyde (starting compound) and 63percent of 2,3-dihydro-1,3-dimethylbenzimidazole-2-one (compound derived from the fluoroalkylating agent). The yield of 1-(4-methylphenyl)-2,2,2-trifluoroethanol (target compound) was 16percent in terms of GC area percentage.
Reference: [1] Patent: US2017/197920, 2017, A1, . Location in patent: Paragraph 1333-1334
  • 23
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  • [ 104-87-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 7, p. 1951 - 1957
[2] Chemistry Letters, 1984, p. 517 - 520
  • 24
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Reference: [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 6, p. 937 - 940
[2] Tetrahedron Letters, 2005, vol. 46, # 18, p. 3161 - 3164
  • 25
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  • [ 445476-82-4 ]
  • [ 446-65-1 ]
Reference: [1] Synlett, 2002, # 4, p. 646 - 648
[2] Journal of Fluorine Chemistry, 2005, vol. 126, # 4, p. 491 - 498
  • 26
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3300 - 3305
  • 27
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  • [ 104-87-0 ]
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  • 28
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  • 29
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  • [ 104-87-0 ]
Reference: [1] Journal of Physical Chemistry, 1981, vol. 85, # 19, p. 2740 - 2746
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  • [ 123-08-0 ]
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  • [ 3179-08-6 ]
Reference: [1] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[2] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 4; 15; 16; 18 Sheet 73/106
[3] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[4] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[5] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[6] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[7] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[8] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[9] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 4; 15; 16; 18; Sheet 77/106
[10] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[11] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[12] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 4; 15; 16; 18; Sheet 75/106
[13] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[14] Patent: US2009/43134, 2009, A1, . Location in patent: Page/Page column 15; 16
[15] Chemistry - A European Journal, 2009, vol. 15, # 29, p. 7052 - 7062
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[2] Chemische Berichte, 1961, vol. 94, p. 907 - 914
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[2] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7219 - 7222
[4] Patent: WO2009/109998, 2009, A1,
[5] Patent: WO2009/109999, 2009, A1,
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[2] Journal of the American Chemical Society, 1955, vol. 77, p. 3798,3800
[3] Patent: US2862967, 1955, ,
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 17, p. 2829 - 2837
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[2] Journal of the Chemical Society, Chemical Communications, 1985, # 2, p. 64 - 65
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  • [ 104-87-0 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 90 - 103
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  • [ 141-82-2 ]
  • [ 104-87-0 ]
  • [ 68208-18-4 ]
YieldReaction ConditionsOperation in experiment
68.9% With ammonium acetate In ethanol at 80 - 90℃; for 7.5 h; To 250 mL of ethanol were added 50.0 g (0.42 mol) of 4-tolylaldehyde, 47.6 g (0.46 mol) of malonic acid and 64.2 g (0.83 mol) of ammonium acetate, and the mixture was reacted while stirring under reflux (80 to 90°C) for 7.5 hours. The obtained reaction mixture was stirred at 0 to 5°C for 30 minutes and then filtered to give 51.4 g of 3-amino-3-(4-tolyl)propionic acid (racemic mixtures) (isolation yield based on 4-tolylaldehyde: 68.9percent) as white powder. Incidentally, physical properties of the 3-amino-3-(4-tolyl)propionic acid (racemic mixtures) were as follows. 1H-NMR (δ (ppm), D2O+DCl) : 2.30 (s, 3H), 3.04 (dd, 1H, J=17.1, 6.8Hz), 3.20 (dd, 1H, J=17.1, 7.3Hz), 4.74 (dd, 1H, J=7.3, 6.8Hz), 7.29 (d, 2H, 8.3Hz), 7.36 (d, 2H, 8.3Hz) 13C-NMR (δ (ppm), D2O+DCl): 23.4, 40.7, 54.4, 130.0, 133.0, 135.0, 143.1, 176.3 MS (EI) m/z: 179 (M+) MS (CI, i-C4H10) m/z: 180 (MH+) Elemental analysis; Calcd: C,67.02percent; H,7.31percent; N,7.82percent Found: C,67.05percent; H,7.40percent; N,7.66percent
67% With ammonium acetate In butan-1-olReflux General procedure: A mixture of appropriate aldehyde 2.40 g (1-15), 2.44 g ofmalonic acid and 3.54 g of ammonium acetate (1:1.1:2.3), in 200mLof the 1-butanol was refluxed for 1.5-2 h until the evolution of CO2ceased. The precipitate formed was filtered and washed withboiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and100mL of water. Precipitates were dried at 80-100 °C for 8-10 h.Purity of product was checked by TLC, and yield obtained about65-80percent in each reaction.
Reference: [1] Patent: EP1621529, 2006, A1, . Location in patent: Page/Page column 27-28
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[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 395 - 406
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[5] Bulletin de la Societe Chimique de France, 1987, # 6, p. 1079 - 1083
[6] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 6, p. 1356 - 1365
[7] Patent: US4598077, 1986, A,
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[2] Russian Chemical Bulletin, 2004, vol. 53, # 9, p. 1846 - 1858
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Reference: [1] Patent: WO2014/202580, 2014, A1,
[2] Patent: WO2014/202528, 2014, A1,
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Reference: [1] Organic Process Research and Development, 2008, vol. 12, # 2, p. 339 - 344
  • 50
  • [ 2942-13-4 ]
  • [ 104-87-0 ]
  • [ 101078-51-7 ]
YieldReaction ConditionsOperation in experiment
51% With tert.-butylhydroperoxide; copper dichloride In water at 80℃; for 24.5 h; Inert atmosphere; Schlenk technique General procedure: A 25 mL reaction vessel was charged with benzothiazole 1 (1.86 mmol, 1.1 equiv), aldehyde 2 (1.69 mmol), CuCl2 (0.51mmol, 0.3 equiv), and tert-butylhydroperoxide (2.36 mmol, 1.4 equiv, 70percent aqueous solution) under nitrogen. The reactionmixture was stirred in an ice bath for 30 min, and then stirred at 80°C for 24 h. After cooling to room temperature, the mixture was purified by column chromatography using silica gel (petroleum ether/ethyl acetate) to afford the products 3.
Reference: [1] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 7086 - 7091
[2] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1806 - 1809
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[2] Patent: WO2014/202528, 2014, A1,
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