2296-23-3|4-Hydroxy-3-iodobenzonitrile| Ambeed

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Quality Control of [ 2296-23-3 ] Purity: 97% SDS Specification

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Product Details of [ 2296-23-3 ]

CAS No. :	2296-23-3
Formula :	C₇H₄INO
M.W :	245.02
SMILES Code :	N#CC1=CC=C(O)C(I)=C1
MDL No. :	MFCD11054826
InChI Key :	XAONDNGLTPLRKO-UHFFFAOYSA-N
Pubchem ID :	10955815

Safety of [ 2296-23-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 2296-23-3 ] Show Less

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	45.9
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	44.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.69
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.94
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.71
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.9

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.03
Solubility	0.231 mg/ml ; 0.000943 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.49
Solubility	0.795 mg/ml ; 0.00325 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.87
Solubility	0.334 mg/ml ; 0.00136 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.42 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.9

Application In Synthesis of [ 2296-23-3 ]

* 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.

Downstream synthetic route of [ 2296-23-3 ]

[ 2296-23-3 ] Synthesis Path-Downstream 1~35

1
[ 767-00-0 ]
[ 2296-23-3 ]
[ 1689-83-4 ]

References: [1]Journal of the Chemical Society,1949,p. 642,645.

2
[ 767-00-0 ]
[ 2296-23-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With ammonium hydroxide; iodine; potassium iodide; In water; at 20℃; for 16h;Inert atmosphere;	To a solution of 4-hydroxy-benzonitrile (5 g, CAS: 767-00-0) in NH4OH (225 mL) was added a solution of KI (34.14 g, CAS: 7681-11-0) and ?2(10.65 g, CAS: 7553-56-2) in H20 (50 mL). The reaction mixture was stirred at rt for 16 hours. The reaction mixture was filtered andthe filtrate was evaporated. The residue was dissolved in DCM (250 mL) and was washed with H20 (2x150 mL), saturated aqueous Na5203 solution (100 mL) and brine (100 mL). The organic layer was dried over anhydrous Na2504, filtered and concentrated under reduced pressure to give the title compound (8.44 g, 82%) that was used in the next step without further purification. LC-MS: (ESI): mlz = 244.0 [M-H]
80%	With ammonium hydroxide; iodine; potassium iodide; In water; for 6h;	To a solution of A- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of I2 (1.06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H2O (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H2O (3 ml). The precipitate formed was filtered off, washed with cold H2O (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1H-NMR (CDCI3) 7.96 (d, 1 H, 1 .9 Hz); 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz); 7.03 (d, 1 H, J = 8.5 Hz); 6.03 (s, 1 H);
80%	With ammonia; iodine; potassium iodide; In water; for 6h;	To a solution of 4- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of I2 (1.06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H2O (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H2O (3 ml). The precipitate formed was filtered off, washed with cold H2O (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1 H-NMR (CDCI3 ) 6.03 (s, 1 H); 7.03 (d, 1 H, J = 8.5 Hz); 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz); 7.96 (d, 1 H, 1 .9 Hz).

80%	With ammonium hydroxide; iodine; potassium iodide; In water; for 6h;	To a solution of 4- hydroxybenzonitrile (0.5 g; 4.18 mmol) in 25% NH4OH (22 ml) a solution of l2 (1 .06 g; 4.18 mmol) and Kl (3.41 g; 20.54 mmol) in H20 (5 ml) was added at once with stirring. The stirring was continued for 6 h, during which time the mixture turn from black into colourless. The precipitate formed was filtered off and filtrate was evaporated to dryness under reduced pressure. The residue was treated with H20 (3 ml). The precipitate formed was filtered off, washed with cold H20 (3 x 2 ml), and dried in vacuo to give the title compound (0.82 g; 80%), as colourless solid. 1 H-NMR (CDCI3) 7.96 (d, 1 H, 1 .9 Hz) ; 7. 53 (dd, 1 H, J = 1 .9 Hz, 8.5 Hz) ; 7.03 (d, 1 H, J = 8.5 Hz); 6.03 (s, 1 H) ;
	With ammonia; iodine; In methanol; water; at 20℃; for 2h;	A. 3-Iodo-4-hydroxybenzonitrile 11.9 g (0.1 mol) of 4-hydroxybenzonitrile are dissolved in 250 ml of methanol and 250 ml of 20% aqueous ammonia are added. A solution of 31.75 g of iodine in 250 ml of methanol is then added dropwise, with care, due to the explosive nature of the reaction. After addition, the mixture is stirred for 2 hours at ambient temperature. The methanol is evaporated off, dilution is carried out in water and acidification with a hydrochloric acid solution is performed until pH=2 to 3 is obtained. Extraction with ethyl acetate and washing with water, a sodium thiosulfate solution and a saturated sodium chloride solution are subsequently carried out. In this way, 24.73 g of desired compound are obtained. M.p.: 144-146 C. The compound below was prepared using the same process as above:

References: [1]Journal of the Brazilian Chemical Society,2010,vol. 21,p. 3 - 6.
[2]Patent: WO2017/37146,2017,A1 .Location in patent: Page/Page column 186.
[3]Patent: WO2010/43000,2010,A1 .Location in patent: Page/Page column 45-46.
[4]Patent: WO2010/42998,2010,A1 .Location in patent: Page/Page column 103; 104.
[5]Asian Journal of Chemistry,2011,vol. 23,p. 41 - 43.
[6]Patent: WO2014/63199,2014,A1 .Location in patent: Page/Page column 24.
[7]Organic Letters,2017,vol. 19,p. 3576 - 3579.
[8]Tetrahedron,2005,vol. 61,p. 11657 - 11663.
[9]Chemical Communications,2004,p. 2288 - 2289.
[10]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2011,vol. 41,p. 258 - 261.
[11]Organic Letters,2002,vol. 4,p. 4727 - 4729.
[12]Journal of Medicinal Chemistry,2001,vol. 44,p. 2753 - 2771.
[13]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6043 - 6048.
[14]Tetrahedron Letters,1982,vol. 23,p. 1439 - 1442.
[15]Journal of Medicinal Chemistry,2005,vol. 48,p. 6482 - 6490.
[16]Organic Letters,2009,vol. 11,p. 5350 - 5353.
[17]Patent: US2004/10011,2004,A1 .Location in patent: Page/Page column 25.
[18]Journal of Medicinal Chemistry,2009,vol. 52,p. 5763 - 5767.
[19]Bioorganic and medicinal chemistry letters,2020.

3
[ 2296-23-3 ]
[ 74-88-4 ]
[ 82504-06-1 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 1439 - 1442.

4
[ 1689-83-4 ]
[ 2296-23-3 ]
[ 767-00-0 ]

References: [1]Journal of Organic Chemistry,1998,vol. 63,p. 3911 - 3917.
[2]Journal of Organic Chemistry,1998,vol. 63,p. 3911 - 3917.

Yield	Reaction Conditions	Operation in experiment
67%		Example 87A 4-hydroxy-3-iodobenzonitrile In a 2000 mL round-bottom flask containing 10.0 g (84 mmol) of 4-cyanophenol, 450 mL conc. animonium hydroxide was added and contents were allowed to stir at 25 C. for 15 min. Next, a solution of 67.9 g (409 mmol) potassium iodide and 21.3 g (84 mmol) iodine chips, dissolved in 100 mL water, was quickly added. The reaction mixture was allowed to stir at 25 C. for 18 h at which time contents were filtered. The filtrate was concentrated under reduced pressure and redissolved in 500 mL dichloromethane. The organic layer was then washed twice with 250 mL water, dried, and concentrated under reduced pressure to provide the title compound as a light yellow solid (14.3 g, 67% yield). 1H-NMR (300 MHz, CDCl3) delta 7.03 (d, 1H), 7.66 (dd, 1H), 7.98 (s, 1H); MS DCI m/e, 263 (M+NH4)+.

7
[ 2296-23-3 ]
[ 360791-76-0 ]
[ 360791-77-1 ]

References: [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 2753 - 2771.

8
[ 2296-23-3 ]
[ 536-74-3 ]
[ 79008-77-8 ]

References: [1]Organic Letters,2002,vol. 4,p. 4727 - 4729.

9
[ 2296-23-3 ]
[ 10365-98-7 ]
[ 450842-38-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5057 - 5062.

10
[ 2296-23-3 ]
[ 90555-66-1 ]
[ 565203-86-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5057 - 5062.

11
[ 2296-23-3 ]
[ 82203-84-7 ]
2-(4-chloro-phenyl)-3-trifluoromethyl-benzofuran-5-carbonitrile [ No CAS ]

References: [1]Tetrahedron,2004,vol. 60,p. 11695 - 11700.

12
[ 2296-23-3 ]
[ 460747-73-3 ]
[ 460747-72-2 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 6482 - 6490.

13
[ 2296-23-3 ]
[ 98-60-2 ]
4-cyano-2-iodophenyl 4-chlorobenzenesulfonate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 4364 - 4366.

14
[ 2296-23-3 ]
[ 100-52-7 ]
4-hydroxy-3-(hydroxy-phenyl-methyl)-benzonitrile [ No CAS ]

References: [1]Chemical Communications,2004,p. 2288 - 2289.

15
[ 2296-23-3 ]
[ 927-74-2 ]
[ 919088-04-3 ]