132131-24-9|2-Amino-5-iodobenzonitrile| Ambeed

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Quality Control of [ 132131-24-9 ] Purity: 95% SDS Specification

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Product Details of [ 132131-24-9 ]

CAS No. :	132131-24-9
Formula :	C₇H₅IN₂
M.W :	244.03
SMILES Code :	NC1=C(C=C(I)C=C1)C#N
MDL No. :	MFCD07787432
InChI Key :	PRIOKVMBFXTMRV-UHFFFAOYSA-N
Pubchem ID :	9964803

Safety of [ 132131-24-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 132131-24-9 ] 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	1.0
Num. H-bond donors	1.0
Molar Refractivity	48.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	49.81 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.61
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	2.16
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.75
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	2.05
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.16
Solubility	0.17 mg/ml ; 0.000695 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.	-2.84
Solubility	0.354 mg/ml ; 0.00145 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	-3.08
Solubility	0.203 mg/ml ; 0.00083 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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.25 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	2.0 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)	1.82

Application In Synthesis of [ 132131-24-9 ]

* 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.

Downstream synthetic route of [ 132131-24-9 ]

[ 132131-24-9 ] Synthesis Path-Downstream 1~35

1
[ 29671-92-9 ]
[ 132131-24-9 ]
[ 132131-20-5 ]

References: [1]European Journal of Medicinal Chemistry,1992,vol. 27,p. 7 - 18.

2
[ 1885-29-6 ]
[ 132131-24-9 ]

Yield	Reaction Conditions	Operation in experiment
92.6%	With ammonium iodide; dihydrogen peroxide; acetic acid; at 20℃; for 12h;	General procedure: Followed previous procedures: 1 a mixture of 2-aminobenzonitrile (0.02 mol) and ammonium iodide (0.02 mol) were dissolved in acetic acid (50 mL), and then 30% aqueous hydrogen peroxide solution (0.13 mol) was slowly added at room temperature and stirred for 12 h. After reaction completion, the reaction solution was treated with aqueous sodium thiosulfate solution 40 mL (0.03 mol) and basified to about pH~8 by the addition of 20% sodium hydroxide. The reaction mixture was stirred at room temperature for 0.5 h. The desired product, which was partially precipitated during this step, was isolated by vacuum filtration to afford A as silvery white flake solid (yield 92.6%).
84.9%	With Iodine monochloride; acetic acid; at 20℃; for 3h;	The 2.0g (16.9mmol) 2- aminobenzonitrile (Compound of Formula II) was dissolved in 20mL glacial acetic acid; was slowly added dropwise 2.8g (17.2 mmol) 10mL glacial acetic acid solution of iodine monochloride dropwise was completed, the reaction mixture was stirred 3H at room temperature; the reaction mixture was poured into 150mL ice water, Suction filtered, the filter cake was washed with water, dried with cyclohexane - toluene: Recrystallization (9 1, v / v), to give 2-amino-5-iodobenzonitrile (formula III Compound) (3.5g, molar yield of 84.9%, HPLC purity 98.7%),
48%	With ammonium iodide; dihydrogen peroxide; acetic acid; In water; at 20℃; for 12h;	[612] Preparation 52: Synthesis of 2-amino-5-iodo-benzonitrile [613] [614] 2-Amino-benzonitrile (10g, 0.085mol) and ammonium iodide (13.5g, 0.094mol) were dissolved in acetic acid (200mL). 30% aqueous hydrogen peroxide solution (5.3mL, 0.094mL) was slowly added at room temperature and stirred for 12 h. After completion of the reaction, the reaction solution was filtered through celite. The filtrate was treated with aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and filtered. The solid obtained using dichloromethane (10mL) and hexane (200mL) was filtered and dried under nitrogen gas to give the title compound (10g, Yield 48%). [615] NMR: 1H-NMR(CDCl3) delta 7.64 (1H, d), 7.56 (1H, dd), 6.35 (1H, d), 4.44 (2H, br s) [616] Mass(EI) 245 (M++1) [617]

	With Iodine monochloride; acetic acid; at 25 - 35℃;	Example-2; Preparation of N{3-chloro-4-[(3-fluorobenzyloxy]phenyl}-6-[5-([2-methanesulphonyl) ethyl]amino}methyl)-2-furyl]-4-quinazoIinamine. (or) Lapatinib base (1)(i) Preparation of 2-amino-5-iodobenzonitrile (7)Into a one liter four necked round bottomed flask, acetic acid (200 mL), 2-aminobenzonitrile(30.0 g) were charged. To this reaction mass, iodinemonochloride (44 g) in acetic acid (200 mL) solution was added drop-wise at 25-35C. The reaction mass was maintained at 25-350C for about 3 hrs. The completion of the reaction was monitored by TLC. The reaction mass was poured into ice cold water, stirred for 1 hour and filtered and dried under vacuum to get55.0 g of brick-red coloured powder.Purity: 97.1% by HPLC To enhance the purity of the product the following recrystallization process was adopted.Purification:Into a two liter four necked round bottomed flask, 275 mL of toluene and 55 g of crude 2- aminobenzonitrile as obtained above were charged. The mass was stirred for 30 min and clarified with activated carbon (5g) and filtered. To the filtrate 825 mL of hexane was added and stirred for 1 hr. at 25-30 C to crystallize out the product. The product was filtered and dried under vacuum at 30-40 C to get 46.5 g of 2-amino-5-iodobenzonitrile as a pinkish coloured crystalline powder.Melting -range: 85 to 87 CPurity : 99.89% by HPLC
	With Iodine monochloride; acetic acid; at 25 - 35℃; for 3h;	Example-1 Preparation of N {3-chloro-4-[(3-fluorobenzyloxy] phenyl}-6-[5-([2- methanesulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazoIinamine. (or) Lapatinib base (1)(i) Preparation of 2-amino-S-iodobenzonitrile (7)Into a one liter four necked round bottomed flask, acetic acid (200 mL), 2- aminobenzonitrile (30.0 g) were charged. To this reaction mass, iodinemonochloride (44 g) in acetic acid (200 mL) solution was added drop-wise at 25-35C. The reaction mass was maintained at 25-35C for about 3 hrs. The completion of the reaction was monitored by TLC. The reaction mass was poured into ice cold water, stirred for 1 hour and filtered and dried under vacuum to get 55.0 g of brick -red coloured powder. Purity: 97.1% by HPLCTo enhance the purity of the product the following recrystall ization process was adopted.

References: [1]Acta Crystallographica, Section C: Crystal Structure Communications,2007,vol. 63,p. o408-o410.
[2]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1584 - 1587.
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4309 - 4313.
[4]Journal of Enzyme Inhibition and Medicinal Chemistry,2019,vol. 34,p. 1668 - 1677.
[5]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2637 - 2649.
[6]Patent: CN103896889,2016,B .Location in patent: Paragraph 0041-0043.
[7]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. 959 - 964.
[8]European Journal of Medicinal Chemistry,1992,vol. 27,p. 7 - 18.
[9]Journal of Organic Chemistry,2001,vol. 66,p. 7522 - 7526.
[10]Patent: WO2011/43568,2011,A2 .Location in patent: Page/Page column 46.
[11]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S539-S540.
[12]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 40,p. 83 - 84.
[13]Tetrahedron Letters,2007,vol. 48,p. 6124 - 6128.
[14]Patent: WO2010/61400,2010,A1 .Location in patent: Page/Page column 14.
[15]Patent: WO2011/39759,2011,A1 .Location in patent: Page/Page column 13.

3
[ 108-94-1 ]
[ 132131-24-9 ]
[ 252357-65-6 ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. 959 - 964.
[2]Journal of labelled compounds and radiopharmaceuticals,1997,vol. 40,p. 83 - 84.
[3]Journal of labelled compounds and radiopharmaceuticals,1999,vol. 42,p. S539-S540.

4
[ 132131-24-9 ]
[ 107-15-3 ]
[ 351425-99-5 ]

References: [1]Arzneimittel-Forschung/Drug Research,2001,vol. 51,p. 284 - 292.

5
[ 62673-31-8 ]
[ 132131-24-9 ]
[ 66682-68-6 ]