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[ CAS No. 135050-44-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 135050-44-1
Chemical Structure| 135050-44-1
Chemical Structure| 135050-44-1
Structure of 135050-44-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 135050-44-1 ]

CAS No. :135050-44-1 MDL No. :MFCD00051845
Formula : C6H5ClIN Boiling Point : -
Linear Structure Formula :- InChI Key :ONZHMGRKWJMTDE-UHFFFAOYSA-N
M.W : 253.47 Pubchem ID :282926
Synonyms :

Calculated chemistry of [ 135050-44-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 48.57
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.77
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.49
Solubility : 0.0816 mg/ml ; 0.000322 mol/l
Class : Soluble
Log S (Ali) : -2.71
Solubility : 0.491 mg/ml ; 0.00194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.61
Solubility : 0.0624 mg/ml ; 0.000246 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.85

Safety of [ 135050-44-1 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P301+P310-P305+P351+P338 UN#:2811
Hazard Statements:H301-H312+H332-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 135050-44-1 ]

* 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 [ 135050-44-1 ]
  • Downstream synthetic route of [ 135050-44-1 ]

[ 135050-44-1 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 135050-44-1 ]
  • [ 5345-54-0 ]
Reference: [1] Synthesis, 1998, # 11, p. 1599 - 1603
  • 2
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 3
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 4
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 5
  • [ 41252-96-4 ]
  • [ 135050-44-1 ]
Reference: [1] Science, 2013, vol. 342, # 6162, p. 1073 - 1076
[2] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[3] Green Chemistry, 2015, vol. 17, # 2, p. 898 - 902
[4] ChemCatChem, 2017, vol. 9, # 6, p. 1128 - 1134
  • 6
  • [ 108-42-9 ]
  • [ 135050-44-1 ]
Reference: [1] Organic Letters, 2001, vol. 3, # 7, p. 991 - 992
[2] Journal of Organic Chemistry, 2002, vol. 67, # 24, p. 8622 - 8624
[3] RSC Advances, 2014, vol. 4, # 12, p. 6267 - 6274
[4] Organic Preparations and Procedures International, 2002, vol. 34, # 6, p. 647 - 651
[5] Asian Journal of Chemistry, 2011, vol. 23, # 1, p. 41 - 43
[6] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[7] Tetrahedron, 1994, vol. 50, # 17, p. 5139 - 5146
[8] Molecules, 2002, vol. 7, # 12, p. 867 - 870
[9] Organic Letters, 2006, vol. 8, # 10, p. 2043 - 2045
[10] Journal of the American Chemical Society, 1918, vol. 40, p. 932
[11] Molecules, 2004, vol. 9, # 7, p. 617 - 621
[12] Tetrahedron Letters, 2007, vol. 48, # 35, p. 6124 - 6128
  • 7
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 8
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 9
  • [ 108-42-9 ]
  • [ 6828-35-9 ]
  • [ 135050-44-1 ]
Reference: [1] Synlett, 2012, # 2, p. 208 - 214
  • 10
  • [ 135050-44-1 ]
  • [ 141738-80-9 ]
YieldReaction ConditionsOperation in experiment
71%
Stage #1: With hydrogenchloride In water at 0℃; for 0.0833333 h; Schlenk technique
Stage #2: With tert.-butylnitrite In water at -196 - 20℃; Schlenk technique; Inert atmosphere
Stage #3: at -78 - 20℃; for 5 h; Schlenk technique; Inert atmosphere
General procedure: An oven-dried Schlenk tube (A) equipped with a magnetic stir bar was charged with AgF (132.2 mg, 1.05 mmol, 3.5 equiv), sealed with a septum, and degassed by alternating vacuum evacuation and nitrogen backfill (three times) before freshly distilled EtCN (3 mL)was added. To the resulting suspension, which was precooled to –78 °C (dry ice–acetone bath), was added TMSCF3 (149.3 mg, 1.05 mmol, 3.5 equiv) by microsyringe. The mixture was allowed towarm to r.t. and stirring was continued for an additional 15 min. In due course, AgF solid dissolved and a gray, dark solution of [Ag-CF3] formed. Another Schlenk tube (B) equipped with a magnetic stir bar was charged with the aniline (ArNH2; 0.30 mmol, 1.0 equiv) in freshly distilled EtCN (1.5 mL). To the resulting solution, which was precooled to 0 °C (ice bath), aq HCl (12 M; 50.0 μL, 0.60mmol, 2.0 equiv) was added; precipitate formed immediately. After 5 min stirring, t-BuONO (37.7 mg, 0.33 mmol, 1.1 equiv) was added by microsyringe, and the mixture was allowed to stir at 0 °C for 15 min. The resulting suspension in Schlenk tube (B) was degassed by alternating vacuum evacuation at –196 °C (liquid nitrogen), then the solution was allowed to warm to r.t. under a nitrogen atmosphere (three times), and finally cooled to –78 °C (dry ice–acetone bath). The gray, dark solution of [AgCF3] in Schlenk tube (A), which was precooled to –78 °C (dry ice–acetone bath), was added to Schlenk tube (B) (ArN2+Cl–) by syringe at –78 °C (dry ice–acetone bath) over a period of 1 h. After the addition was complete, the reaction mixture was stirred for 3 h at –78 °C (dry ice–acetone bath), allowed to warm to r.t., and stirring was continued for an additional 1 h. An off-white precipitate was observed, and the reaction mixture was diluted with EtOAc (3 mL) and filtered through a short silica gel column. The solvent was removed under reduced pressure with a rotatory evaporator, and the crude residue was purified by silica gel column chromatography to give the desired trifluoromethylation product 3. The yields of products 3a, 3f, 3g, 3l, 3o, 3r, 3x, and 3zb are based on the 19F NMR spectra with 4-F3COC6H4OMe as internal standard. Analytical data for the representative product ethyl 4-(trifluoromethyl)benzoate (3i) are provided below. Data for other products can be found in the literature.
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 28, p. 10330 - 10333
[2] Synthesis (Germany), 2014, vol. 46, # 16, p. 2143 - 2148
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