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[ CAS No. 13420-63-8 ] {[proInfo.proName]}

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Chemical Structure| 13420-63-8
Chemical Structure| 13420-63-8
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Product Details of [ 13420-63-8 ]

CAS No. :13420-63-8 MDL No. :MFCD06808823
Formula : C7H4ClIO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KNWHWEKCHWFXFZ-UHFFFAOYSA-N
M.W : 282.46 Pubchem ID :13399374
Synonyms :

Calculated chemistry of [ 13420-63-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.13
TPSA : 37.3 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) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 2.64
Log Po/w (MLOGP) : 3.09
Log Po/w (SILICOS-IT) : 2.83
Consensus Log Po/w : 2.54

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.57
Solubility : 0.0766 mg/ml ; 0.000271 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.262 mg/ml ; 0.000928 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.131 mg/ml ; 0.000465 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.78

Safety of [ 13420-63-8 ]

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

Application In Synthesis of [ 13420-63-8 ]

* 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 [ 13420-63-8 ]
  • Downstream synthetic route of [ 13420-63-8 ]

[ 13420-63-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 118-91-2 ]
  • [ 13420-63-8 ]
YieldReaction ConditionsOperation in experiment
91% With [bis(acetoxy)iodo]benzene; iodine; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24 h; Sealed tube General procedure: In a flame-dried 100 mL round-bottom flask, benzoic acid starting material (16.4 mmol, 1.0 equiv.), palladium acetate (0.05 equiv.), iodobenzene diacetate (1.5 equiv.), and iodine (1.5 equiv.) were dissolved in anhydrous DMF (40 mL) under atmospheric air. The flask was then sealed with a septum and the reaction mixture was stirred at 100 °C for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and then washed with 0.5 N HCl (420 mL). The organic phase was washed with brine, dried over Na2SO4, and concentrated in a rotary evaporator. The residue was purified by column chromatography on silica gel (3 : 1 hexane/EtOAc) to give the desired iodinated product.
Reference: [1] ACS Catalysis, 2018, vol. 8, # 2, p. 920 - 925
[2] Australian Journal of Chemistry, 2015, vol. 68, # 6, p. 912 - 918
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 28, p. 5215 - 5219
[4] Synthetic Communications, 2005, vol. 35, # 6, p. 799 - 806
  • 2
  • [ 2148-56-3 ]
  • [ 13420-63-8 ]
YieldReaction ConditionsOperation in experiment
73% With hydrogenchloride; potassium iodide; sulfuric acid; sodium nitrite In water Reference Example 2-21
2-Chloro-6-iodobenzoic acid
The title compound was prepared according to the method described in Collection Czechoslov. Chem. Commn., vol.40, p.719 (1975).
To an ice-cold mixture of 2-amino-6-chlorobenzoic acid (10.0 g, 58.3 mmol) and conc. hydrochloric acid (50 mL), was added dropwise a solution of sodium nitrite (4.42 g, 64.1 mmol) in water (10 mL).
Furthermore, a solution of potassium iodide (14.5 g, 87.5 mmol) and conc. sulfuric acid (4 mL) in water (30 mL) was added thereto at the same temperature, and the mixture was heated to 100° C. and stirred for 2 hours.
The reaction mixture was allowed to cool to room temperature, poured into an aqueous sodium thiosulfate solution, and organic matter was extracted with ethyl acetate.
The extract was washed with saturated brine and water and dried over anhydrous sulfuric acid, and the solvent was evaporated under reduced pressure.
The resulting crude crystals were collected by filtration, washed with hexane/diethylether, and air dried to give the title compound (12.1 g, 73percent yield).
NMR (CDCl3) δ: 7.20 (1H, dd, J=2.6 Hz, 8.8 Hz), 7.97 (1H, d, J=8.8 Hz), 7.99 (1H, d, J=2.6 Hz), hidden (1H).
2 g With hydrogenchloride; sulfuric acid; potassium iodide; sodium nitrite In water at 0℃; for 2 h; Reflux To the cold solution of 2-amino-6-chlorobenzoic acid (2.0 g, 11.6 mmol) in cone. HC1 (10 mL) was added aq. solution of sodium nitrite (0.8 g, 11.6 mmol) at 0 C followed by addition of solution of potassium iodide (2.88 g, 17.4 mmol) in water and cone, sulphuric acid (1 mL). The reaction mixture was refluxed for 2 h. The reaction mass was washed with sodium metabisulphate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 2.0 g of desired product.1H NMR (300 MHz, DMSO d6): δ 7.08 (t, J=7.8 Hz, 1H), 7.42 (d, J- 8.4 Hz, 1H), 7.76 (d, J = 7.8 Hz, 1H), 8.37 (br s, 1H); MS (m/z): 280.59 (M)-
Reference: [1] Patent: US2003/187014, 2003, A1,
[2] Patent: WO2013/186692, 2013, A1, . Location in patent: Page/Page column 89; 90
[3] Organic Letters, 2018, vol. 20, # 2, p. 345 - 348
  • 3
  • [ 100960-33-6 ]
  • [ 13420-63-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1968, vol. 33, # 6, p. 1852 - 1872
  • 4
  • [ 13420-63-8 ]
  • [ 51738-07-9 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 2, p. 345 - 348
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