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[ CAS No. 2338-75-2 ] {[proInfo.proName]}

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Chemical Structure| 2338-75-2
Chemical Structure| 2338-75-2
Structure of 2338-75-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2338-75-2 ]

CAS No. :2338-75-2 MDL No. :MFCD00001921
Formula : C9H6F3N Boiling Point : -
Linear Structure Formula :- InChI Key :QNKOCFJZJWOXDE-UHFFFAOYSA-N
M.W : 185.15 Pubchem ID :75359
Synonyms :

Calculated chemistry of [ 2338-75-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 40.97
TPSA : 23.79 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) : -5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.19
Log Po/w (WLOGP) : 3.92
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.58
Solubility : 0.49 mg/ml ; 0.00265 mol/l
Class : Soluble
Log S (Ali) : -2.32
Solubility : 0.879 mg/ml ; 0.00475 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0311 mg/ml ; 0.000168 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 2338-75-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2338-75-2 ]

* 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 [ 2338-75-2 ]
  • Downstream synthetic route of [ 2338-75-2 ]

[ 2338-75-2 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 18293-53-3 ]
  • [ 402-43-7 ]
  • [ 2338-75-2 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 45, p. 15824 - 15832
  • 2
  • [ 128796-39-4 ]
  • [ 107-14-2 ]
  • [ 2338-75-2 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
  • 3
  • [ 402-49-3 ]
  • [ 2338-75-2 ]
Reference: [1] Patent: US5502054, 1996, A,
[2] Patent: US5622954, 1997, A,
  • 4
  • [ 2942-58-7 ]
  • [ 2338-75-2 ]
Reference: [1] Chemistry Letters, 2004, vol. 33, # 9, p. 1192 - 1193
[2] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 7, p. 1106 - 1117
  • 5
  • [ 7677-24-9 ]
  • [ 455-24-3 ]
  • [ 2338-75-2 ]
Reference: [1] Synthesis (Germany), 2013, vol. 45, # 23, p. 3233 - 3238
  • 6
  • [ 128796-39-4 ]
  • [ 6011-14-9 ]
  • [ 2338-75-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 7
  • [ 349-95-1 ]
  • [ 2338-75-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 7, p. 1106 - 1117
[2] Chemistry Letters, 2004, vol. 33, # 9, p. 1192 - 1193
[3] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252
[4] Journal of pharmaceutical sciences, 1973, vol. 62, # 6, p. 910 - 913
[5] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253
[6] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[7] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
  • 8
  • [ 928664-98-6 ]
  • [ 402-43-7 ]
  • [ 2338-75-2 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6948 - 6951
  • 9
  • [ 1071-36-9 ]
  • [ 98-56-6 ]
  • [ 2338-75-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 19, p. 4470 - 4474
  • 10
  • [ 143-33-9 ]
  • [ 402-49-3 ]
  • [ 2338-75-2 ]
Reference: [1] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[2] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252
  • 11
  • [ 455-24-3 ]
  • [ 2338-75-2 ]
Reference: [1] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[2] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
  • 12
  • [ 583-02-8 ]
  • [ 2338-75-2 ]
Reference: [1] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
  • 13
  • [ 329-15-7 ]
  • [ 2338-75-2 ]
Reference: [1] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
  • 14
  • [ 402-51-7 ]
  • [ 2338-75-2 ]
Reference: [1] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253
  • 15
  • [ 151-50-8 ]
  • [ 402-49-3 ]
  • [ 2338-75-2 ]
Reference: [1] Arzneimittel Forschung, 1965, vol. 15, p. 1251 - 1253
  • 16
  • [ 143-33-9 ]
  • [ 939-99-1 ]
  • [ 2338-75-2 ]
Reference: [1] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
[2] Journal of pharmaceutical sciences, 1973, vol. 62, # 6, p. 910 - 913
  • 17
  • [ 2338-75-2 ]
  • [ 1891-90-3 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 30, p. 18588 - 18591
  • 18
  • [ 2338-75-2 ]
  • [ 32857-62-8 ]
Reference: [1] Journal of pharmaceutical sciences, 1973, vol. 62, # 6, p. 910 - 913
[2] Journal of pharmaceutical sciences, 1973, vol. 62, # 6, p. 910 - 913
  • 19
  • [ 2338-75-2 ]
  • [ 775-00-8 ]
YieldReaction ConditionsOperation in experiment
97.89% With ammonia; hydrogen In methanol (4-Trifluoromethyl-phenyl)-acetonitrile (2g, 10.81mmol) in methanolic ammonia (50mL) was added to Raney nickel (400mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10percent methanol in CHC13). The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2g of the product (97.89percent yield).LCMS purity: 98.73percent, m/z = 190.0 (M+l)
97.89% With ammonia; hydrogen In methanol Step 1:
Preparation of Intermediate 2-(4-Trifluoromethyl-phenyl)-ethylamine (I-16a)
(4-Trifluoromethyl-phenyl)-acetonitrile (2 g, 10.81 mmol) in methanolic ammonia (50 mL) was added to Raney nickel (400 mg) in methanol taken in a parr hydrogenator.
The flask was stirred at 50 PSI overnight.
The reaction was monitored by TLC (10percent methanol in CHCl3).
The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2 g of the product (97.89percent yield).
LCMS purity: 98.73percent, m/z=190.0 (M+1)
95% With ammonia; hydrogen In methanol To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2 N NH3/MeOH (400 mL) was added Raney Ni (-4. 0 g). The reaction mixture was placed in a Parr Apparatus and hydrogentated under 50 lb pressure of H2 overnight. The solution was filtered through celite and concentrated IN VACUO to yield the desired amine (38 g, 95percent). ESI-MS calc. For CGHIOF3N : 189; Found: 190 (M+H)
95% With ammonia; hydrogen In methanol To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (~4. 0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9HlOF3N : 189; Found: 190 (M+H).
95% With ammonia In methanol INTERMEDIATE 13; To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (-4. 0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated iM vacuo to yield the desired amine (38 g, 95percent).
95% With ammonia In methanol To a solution of 4-trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni (4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+M).
95% With ammonia; hydrogen In methanol EXAMPLES INTERMEDIATE 1 Step A; To a solution of 4- trifluoromethyl phenylacetonitrile (40 g, 220 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni ((at)4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 1b pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+H).
95% With ammonia In methanol To a solution of 4- trifluoromethyl phenylacetonitrile (40 g, 215 mmol) in 2N NH3/MeOH (400 mL) was added Raney Ni ((at)4.0 g). The reaction mixture was placed in a par-shaker and shook under 50 Lb pressure overnight. The solution was filtered through celite and concentrated in vacuo to yield the desired amine (38 g, 95percent). ESI-MS calc. For C9H10F3N: 189; Found: 190 (M+H).

Reference: [1] Patent: WO2012/35078, 2012, A1, . Location in patent: Page/Page column 67
[2] Patent: US2014/45872, 2014, A1, . Location in patent: Paragraph 0403
[3] Patent: WO2004/82682, 2004, A1, . Location in patent: Page 44-45
[4] Patent: WO2003/93231, 2003, A2, . Location in patent: Page/Page column 48
[5] Patent: WO2005/80371, 2005, A1, . Location in patent: Page/Page column 49
[6] Patent: US2007/117797, 2007, A1, . Location in patent: Page/Page column 21
[7] Patent: WO2005/120505, 2005, A2, . Location in patent: Page/Page column 27-28
[8] Patent: WO2005/110409, 2005, A2, . Location in patent: Page/Page column 36
[9] Organic Letters, 2014, vol. 16, # 4, p. 1092 - 1095
[10] Journal of Organic Chemistry, 1981, vol. 46, # 21, p. 4247 - 4252
[11] Canadian Journal of Chemistry, 1970, vol. 48, p. 125 - 132
[12] Patent: US2008/81803, 2008, A1, . Location in patent: Page/Page column 24
[13] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 15, p. 7415 - 7423
[14] Patent: US2005/267146, 2005, A1, . Location in patent: Page/Page column 18
[15] Chemistry - A European Journal, 2014, vol. 20, # 28, p. 8682 - 8690
[16] Patent: WO2005/110409, 2005, A2, . Location in patent: Page/Page column 41
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