56404-21-8|1-Iodo-2,4-dimethyl-3-nitrobenzene| Ambeed

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Quality Control of [ 56404-21-8 ] Purity: 97% SDS Specification

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Product Details of [ 56404-21-8 ]

CAS No. :	56404-21-8
Formula :	C₈H₈INO₂
M.W :	277.06
SMILES Code :	CC1=C(C(C)=C(I)C=C1)[N+]([O-])=O
MDL No. :	MFCD02709656
InChI Key :	BIACWLGCCVBYNE-UHFFFAOYSA-N
Pubchem ID :	2324887

Safety of [ 56404-21-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 56404-21-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	57.91
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	45.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.11
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	3.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.82
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.	2.42
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	1.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.4

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.83
Solubility	0.0406 mg/ml ; 0.000147 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.	-3.76
Solubility	0.048 mg/ml ; 0.000173 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	-3.5
Solubility	0.0876 mg/ml ; 0.000316 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	Yes
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	Yes
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.	-5.77 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	3.0 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<0.0
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)	2.22

Application In Synthesis of [ 56404-21-8 ]

* 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.

Downstream synthetic route of [ 56404-21-8 ]

[ 56404-21-8 ] Synthesis Path-Downstream 1~35

1
[ 56404-21-8 ]
[ 135630-62-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

2
[ 81-20-9 ]
[ 56404-21-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	With iodine; periodic acid; In sulfuric acid; acetic acid; at 90℃; for 168.0h;	Scheme 4, step A: To 1,3-dimethyl-2-nitro-benzene (68.5 g, 453.2 mmol) isadded sulfuric acid (27.2 mL, 510 mmol), acetic acid (543.8 mL, 9.49 mol), iodine (46 g,181.3 mmol) and HI04 (91.9 g, 403.3 mmol). The reaction is heated to 90C for 7 days.The reaction mixture is cooled to ambient temperature and water ( 500 mL) is added. Theresulting solid is collected by filtration and washed with cold water. The solid is dried under reduced pressure at 45C overnight to afford the title compound as a yellow solid (119 g, 95 %). 1H NMR (300.16 MHz, CDCh): o 7.80 (d, J= 8.2 Hz, 1H), 6.85 (d, J= 8.2Hz, 1H), 2.37 (s, 3H), 2.23 (s, 3H).
95%	With sulfuric acid; iodine; acetic acid; periodic acid; at 90℃; for 168.0h;	To l,3-dimethyl-2-nitro-benzene (68.5 g, 453.2 mmol) is added sulfuric acid (27.2 mL, 510 mmol), acetic acid (543.8 mL, 9.49 mol), iodine (46 g, 181.3 mmol) and HI04 (91.9 g, 403.3 mmol). The reaction is heated to 90 C for 7 days. The reaction mixture is cooled to ambient temperature, and water (500 mL) is added. The resulting solid is collected by filtration and washed with cold water. The solid is dried under reduced pressure at 45 C overnight to afford l-iodo-2,4-dimethyl-3-nitro-benzene as a yellow solid (119 g, 95 %). 1H NMR (300.16 MHz, CDC13): delta 7.80 (d, J= 8.2 Hz, 1H), 6.85 (d, J= 8.2 Hz, 1H), 2.37 (s, 3H), 2.23 (s, 3H).
79%	With iodine; periodic acid; In sulfuric acid; acetic acid; at 90℃; for 96.0h;	To a mixture of 2,6-dimethylnitrobenzene (15 Ig, l .Omol), acetic acid (1200ml), and cone. H2SO4 (60ml) was added iodine (102g, 0.4mol) and periodic acid dehydrate (205g, 0.9mol). The resulting solution was heated at 90 0C for 4 days. After cooling to room temperature, the reaction mixture was diluted with water (2000ml). The yellow crystals were filtered and washed with water to give 220 g of pure product (79%). 1H-NMR delta (DMSO-d6, 300MHz): 7.95 (d, J=7.8Hz, IH), 7.08 (d, J=7.8Hz, IH), 2.27 (s, 3H), 2.16 (s, 3H).

42%

With sulfuric acid; iodine; acetic acid; periodic acid; at 90℃; for 72.0h;

Example 40: 3-(7-Methyl-1 H-indazol-4-yl)-7-(6-((1 S,4S)-5-methyl-2,5- diazabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)-2-(pyridin-4-yl)pyrazolo[1 ,5-a]pyrimidine; <n="67"/> Step 1 : A mixture of nitro-m-xylene (3.02 g, 20.0 mmol), iodine (2.04 g, 8.0 mmol), periodic acid (4.1 g, 18.0 mmol), and concentrated sulfuric acid (1.2 ml.) in acetic acid (2.4 ml.) was heated at 90 C for 3 days. The reaction was then cooled, poured in to water and extracted with dichloromethane. The combined organics were cooled and washed with a cold solution of 2N sodium hydroxide, and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with hexanes and the solid was collected by filtration, washed with hexanes and dried to yield 2.3 g (42%) of 1-iodo-2,4- dimethyl-3-nitrobenzene as a white solid. MS: 278.1 [M+H]+

References: [1]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 1445 - 1450.
[2]Patent: WO2014/4230,2014,A1 .Location in patent: Page/Page column 16; 17.
[3]Patent: WO2015/94912,2015,A1 .Location in patent: Page/Page column 9.
[4]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 105 - 109.
[5]Patent: WO2008/66900,2008,A1 .Location in patent: Page/Page column 91.
[6]Patent: WO2009/108838,2009,A1 .Location in patent: Page/Page column 64-65.
[7]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

3
C₁₂H₉F₆O₄Tl [ No CAS ]
[ 56404-21-8 ]

References: [1]Journal of Organic Chemistry,1975,vol. 40,p. 3441 - 3443.

4
[ 56404-21-8 ]
3-iodo-2,6-dimethylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron; ammonium chloride; In ethanol; water;Reflux;	Step 2: To a hot suspension of iron powder (2.3 g, 8.3 mmol), ammonium chloride (2.16 g, 38.7 mmol) and water (18 ml.) in ethanol (50 ml.) was added 1-iodo-2,4- dimethyl-3-nitrobenzene in portions over a period of 10 minutes. The resulting mixture was heated at reflux for 1 hour, and filtered hot through a pad of Celite. The Celite was washed with ethanol and ethyl acetate and the filtrate was concentrated in vacuo. The residue was extracted with dichloromethane, the organics were dried over anhydrous sodium sulfate and filtered and the filtrate was evaporated to yield 2.Og (98%) of 3-iodo-2,6-dimethyl- phenylamine as a white solid. MS: 248.1 [M+H]+

References: [1]Patent: WO2009/108838,2009,A1 .Location in patent: Page/Page column 65.
[2]Chemical and Pharmaceutical Bulletin,2004,vol. 52,p. 1445 - 1450.

5
[ 56404-21-8 ]
[ 135630-63-6 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

6
[ 56404-21-8 ]
[ 135630-64-7 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

7
[ 56404-21-8 ]
[ 135630-65-8 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

8
[ 56404-21-8 ]
[ 135630-67-0 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

9
[ 56404-21-8 ]
[ 135650-60-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

10
[ 56404-21-8 ]
[ 135630-68-1 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

11
[ 56404-21-8 ]
[ 135630-66-9 ]

References: [1]Chemical and Pharmaceutical Bulletin,1991,vol. 39,p. 1085 - 1087.

12
[ 539-74-2 ]
[ 56404-21-8 ]
[ 1030025-85-4 ]

Yield	Reaction Conditions	Operation in experiment
		This compound was synthesized using the procedure described in example 2, step B, from 5-iodo-l,3-dimethyl-2-nitrobenzene (see example 2) and ethyl 3-bromopropanoate

References: [1]Patent: WO2008/66900,2008,A1 .Location in patent: Page/Page column 99.

13
[ 2969-81-5 ]
[ 56404-21-8 ]
[ 1030025-77-4 ]

Yield	Reaction Conditions	Operation in experiment
68%		A three-necked flask equipped with a thermometer, a gas inlet, and a magnetic stirring bar was charged under argon with MnBr2 (320mg, 1.5mmol) in DMPU (25ml). CuCl (85mg, lmmol), ethyl 4-bromobutyrate (5.85g, 30mmol) and Et2Zn (2.7ml, 27mmol) were successively added. The reaction mixture turned dark red and was stirred for 4 h at 25 0C. After cooling to -30 0C, a solution of Cl2Pd(dppf) (0.925g, lOmmol) and <strong>[56404-21-8]2,4-dimethyl-3-nitroiodobenzene</strong> (6.93g, 25mmol) in anhydrous THF (25ml) was slowly added. The reaction mixture was warmed to 25 C for 30 min and was then stirred at 65 C overnight and quenched with an aqueous 2N HCl solution (100ml). This mixture was extracted with CH2Cl2 three times, and the organic layer was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure, and the crude residue obtained was purified by Biotage (hexane/EtOAc, 0-30%, 40min) to give 4.5g of yellow oily products (68 %). 1H-NMR delta (CDCl3, 300MHz): 7.13 (d, J=7.8Hz, IH), 7.03 (d, J=7.8Hz, IH), 4.12 (q, J=7.2Hz, 2H), 2.64 (t, J=7.8Hz, 2H), 2.34 (t, J=7.8Hz, 2H), 2.23 (s, 3H), 2.20 (s, 3H), 1.86 (m, J=7.8Hz, 2H), 1.24 (t, J=7.8Hz, 3H).

References: [1]Patent: WO2008/66900,2008,A1 .Location in patent: Page/Page column 91-92.

14
[ 3054-95-3 ]
[ 56404-21-8 ]
[ 1030025-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tributyl-amine; tetrabutyl-ammonium chloride;palladium diacetate; In N,N-dimethyl-formamide; at 90℃; for 2.0h;Product distribution / selectivity;	To a solution of <strong>[56404-21-8]2,4-dimethyl-3-nitroiodobenzene</strong> (14Og, 0.51mol), acrolein diethylactal (229ml, 1.5mol), W-Bu4NCl (139g, 0.5mol), «-Bu3N (238ml, l .Omol) in 2000ml of DMF, Pd(OAc)2 (3.4g, 0.015mol) was added. The mixture was warmed at 90 0C and stirred for 2 hours. After cooling, the reaction mixture was diluted with 2N HCl and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was used for next step without further purification. An analytically pure sample was obtained by chromatography (ISCO, hexane/ethyl acetate, 0-30%, 40 min). 1H- NMR delta (DMSO-d6, 300MHz): 7.27 (d, J=7.8Hz, IH), 7.16 (d, J=7.8Hz, IH), 4.03 (q, J=7.2Hz, 2H), 2.87 (t, J=7.8Hz, 2H), 2.57 (t, J=7.8Hz, 2H), 2.16 (s, 3H), 2.13 (s, 3H), 1.14 (t, J=7.2Hz, 3H).

References: [1]Patent: WO2008/66900,2008,A1 .Location in patent: Page/Page column 98-99.

15
[ 67-56-1 ]
[ 201230-82-2 ]
[ 56404-21-8 ]
[ 24805-54-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With palladium diacetate; triethylamine; 1,4-di(diphenylphosphino)-butane; In acetonitrile; at 100℃; under 4137.41 Torr; for 2.0h;Autoclave; Sealed tube;	Scheme 4, Step B: To a 2 L Parr autoclave with mechanical stirring is added <strong>[56404-21-8]1-iodo-2,4-dimethyl-3-nitro-benzene</strong> (70 g, 252.7 mmol), Pd(OAc)2 (2.8 g, 12.6 mmol),1 ,4-bis( diphenylphosphino )butane ( 6.5 g, 15.2 mmol), acetonitrile ( 462 mL ),triethylamine (88.2 mL), and methanol (280 mL). The Parr autoclave is sealed, purgedand pressurized with CO to 551.6 kPa (80 psig). The mixture is heated to 100C for 2hours. The mixture is cooled to ambient temperature and then vented. The mixture isthen concentrated to dryness under reduced pressure. Ethyl acetate (300 mL) and water(300 mL) are added. The layers are separated and the aqueous layer discarded. The organic layer is dried over MgS04, filtered, and concentrated to dryness to afford the title20compound as a red oil which crystallizes upon standing (52 g, 98 %). 1 H NMR (300.13MHz, CDCl3): o 7.89 (d, J= 8.2 Hz, 1H), 7.19 (d, J= 8.2 Hz, 1H), 3.91 (s, 3H), 2.49 (s,3H), 2.33 (s, 3H).
98%	With palladium diacetate; triethylamine; 1,4-di(diphenylphosphino)-butane; In acetonitrile; at 100℃; under 4137.41 Torr; for 2.0h;Autoclave;	To a 2 L Parr autoclave with mechanical stirring is added 1- iodo-2,4-dimethyl-3-nitro-benzene (70 g, 252.7 mmol), Pd(OAc)2 (2.8 g, 12.6 mmol), l,4-bis(diphenylphosphino)butane (6.5 g, 15.2 mmol), acetonitrile (462 mL), triethylamine (88.2 mL), and MeOH (280 mL). The Parr autoclave is sealed, purged, and pressurized with CO to 551.6 kPa (80 psig). The mixture is heated to 100 C for 2 hours. The mixture is cooled to ambient temperature and then vented. The mixture is then concentrated to dryness under reduced pressure. EtOAc (300 mL) and water (300 mL) are added. The layers are separated, and the aqueous layer discarded. The organic layer is dried over MgS04, filtered, and concentrated to dryness to afford methyl 2,4-dimethyl- 3-nitro-benzoate as a red oil that crystallizes upon standing (52 g, 98 %). 1H NMR (300.13 MHz, CDC13): delta 7.89 (d, J= 8.2 Hz, 1H), 7.19 (d, J= 8.2 Hz, 1H), 3.91 (s, 3H), 2.49 (s, 3H), 2.33 (s, 3H).

References: [1]Patent: WO2014/4230,2014,A1 .Location in patent: Page/Page column 17.
[2]Patent: WO2015/94912,2015,A1 .Location in patent: Page/Page column 9.
[3]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 105 - 109.

16
[ 56404-21-8 ]
[ 24812-89-3 ]

References: [1]Patent: WO2014/4230,2014,A1 .
[2]Patent: WO2015/94912,2015,A1 .

17
[ 56404-21-8 ]
[ 1529760-82-4 ]

References: [1]Patent: WO2014/4230,2014,A1 .
[2]Patent: WO2015/94912,2015,A1 .

18
[ 56404-21-8 ]
[ 1529760-83-5 ]