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[ CAS No. 141743-49-9 ] {[proInfo.proName]}

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Chemical Structure| 141743-49-9
Chemical Structure| 141743-49-9
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Product Details of [ 141743-49-9 ]

CAS No. :141743-49-9 MDL No. :MFCD07774189
Formula : C6H4F2IN Boiling Point : -
Linear Structure Formula :- InChI Key :HCUZNQLIMDDCHF-UHFFFAOYSA-N
M.W : 255.00 Pubchem ID :278943
Synonyms :

Calculated chemistry of [ 141743-49-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.48
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 3.26
Log Po/w (SILICOS-IT) : 2.95
Consensus Log Po/w : 2.62

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.168 mg/ml ; 0.000658 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 1.38 mg/ml ; 0.00541 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.55
Solubility : 0.0717 mg/ml ; 0.000281 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.04

Safety of [ 141743-49-9 ]

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 [ 141743-49-9 ]

* 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 [ 141743-49-9 ]
  • Downstream synthetic route of [ 141743-49-9 ]

[ 141743-49-9 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 5509-65-9 ]
  • [ 141743-49-9 ]
YieldReaction ConditionsOperation in experiment
95% With Iodine monochloride In acetic acid at 20℃; for 0.25 h; 2, 6-Difluorobenzenamine (3. 0g, 22.56 mmoles) was dissolved in acetic acid (10 ml). Iodine monochloride (3.581g, 22.56 mmoles) was added to the solution. The mixture was stirred for 15 minutes at room temperature. After evaporation of the solvent, the residue was treated with an aqueous solution of sodium carbonate. The aqueous solution was extracted with dichloromethane. The organic extract was dried over MgS04 and was evaporated. Yield: 95percent of intermediate 33.
95%
Stage #1: With Iodine monochloride; acetic acid In water at 20℃; for 0.25 h;
Stage #2: With sodium carbonate In water
Example A1; a) Preparation of intermediate 1; 2,6-difluorobenzeneamine (3.0g, 22.56 mmoles) was dissolved in acetic acid (10 ml).Iodine monochloride (3.58lg, 22.56 mmoles) was added to the solution. The mixturewas stirred for 15 minutes at room temperature. After evaporation of the solvent, theresidue was treated with an aqueous solution of sodium carbonate. The aqueoussolution was extracted with dichloromethane. The organic extract was dried overMgSCU and was evaporated. Yield : 95percent of intermediate 1.
51% With silver(I) nitrite; iodine In dichloromethane at 0 - 20℃; for 1 h; Step 1: 4-Amino-3,5-difluoro-benzonitrile; To a suspension of iodine (5.59g, 22.0mmol) and AgNO2 (6.85g, 22.0mmol) in EPO <DP n="79"/>methylene chloride was added a solution of 2,6-difluoroaniline (2.58g, 20.0mmol) in methylene chloride at O0C, and the mixture was stirred for 30min at O0C and 30min at ambient temperature. The reaction was quenched with Na2S2O3. The reaction solution was extracted with methylenechloride, washed with water and brine, dried over anhyd. MgSO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (hexane/ethylacetate = 15/1) to yield a yellow solid (2.57mg, 51percent).
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 51, p. 20597 - 20600
[2] Patent: WO2004/74266, 2004, A1, . Location in patent: Page 54
[3] Patent: WO2006/15985, 2006, A1, . Location in patent: Page/Page column 54
[4] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7370 - 7382
[5] European Journal of Organic Chemistry, 2010, # 16, p. 3049 - 3067
[6] Patent: WO2006/98554, 2006, A1, . Location in patent: Page/Page column 77
[7] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3349 - 3353[8] Angew. Chem., 2017, vol. 129, p. 3397 - 3401,5
[9] Patent: US5314640, 1994, A,
[10] Patent: US5356558, 1994, A,
  • 2
  • [ 141743-49-9 ]
  • [ 544-92-3 ]
  • [ 110301-23-0 ]
YieldReaction ConditionsOperation in experiment
66% for 2 h; Heating / reflux A mixture of the solid and CuCN in DMF was heated with reflux for 2 days and then filtered through celite. The filtrate was dissolved in methylene chloride and water, and the aqueous phase was extracted with methylene chloride. The combined organic layer was washed with brine, dried over anhyd. MgSO4, filtered, and concentrated under reduced pressure. The crude residue was column-chromatographed (hexane/ethylacetate = 4/1) to yield a yellow solid (1.03g, 66percent).1HNMR (300MHz, CDC13): 7.15 (dd, 2H, J= 2.4 and 6.0 Hz), 4.28 (bs, 2H).
Reference: [1] Patent: WO2006/98554, 2006, A1, . Location in patent: Page/Page column 78
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