126717-59-7|3-Bromo-6-methoxy-2-picoline| Ambeed

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Quality Control of [ 126717-59-7 ] Purity: 98% SDS Specification

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Product Details of [ 126717-59-7 ]

CAS No. :	126717-59-7
Formula :	C₇H₈BrNO
M.W :	202.05
SMILES Code :	BrC1=CC=C(N=C1C)OC
MDL No. :	MFCD03094943
InChI Key :	VWNXCCTWVAQAPL-UHFFFAOYSA-N
Pubchem ID :	10798146

Safety of [ 126717-59-7 ]

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

Computational Chemistry of [ 126717-59-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.29
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.39
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.39
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	2.25
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.16
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.	1.65
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	2.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.18

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.89
Solubility	0.261 mg/ml ; 0.00129 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.	-2.35
Solubility	0.901 mg/ml ; 0.00446 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	-3.4
Solubility	0.081 mg/ml ; 0.000401 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.	-5.93 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	0.0 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)	1.77

Application In Synthesis of [ 126717-59-7 ]

* 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 [ 126717-59-7 ]

[ 126717-59-7 ] Synthesis Path-Downstream 1~35

1
[ 63071-03-4 ]
[ 126717-59-7 ]
3-bromo-2-methoxy-6-methylpyridine [ No CAS ]

References: [1]Dalton Transactions,2014,vol. 43,p. 5667 - 5679.
[2]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

2
[ 63071-03-4 ]
[ 126717-59-7 ]
3,5-dibromo-2-methoxy-6-methylpyridine [ No CAS ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

3
[ 930-68-7 ]
[ 126717-59-7 ]
[ 156094-75-6 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 553 - 556.
[2]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

4
[ 930-68-7 ]
[ 126717-59-7 ]
1-(3-Bromo-6-methoxy-pyridin-2-ylmethyl)-cyclohex-2-enol [ No CAS ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.
[2]Heterocycles,2009,vol. 79,p. 791 - 804.

5
[ 5323-87-5 ]
[ 126717-59-7 ]
[ 156094-70-1 ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

6
[ 126717-59-7 ]
[ 63755-30-6 ]
[ 91618-17-6 ]

References: [1]Heterocycles,1990,vol. 31,p. 523 - 527.

7
[ 126717-59-7 ]
[ 132606-40-7 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2971 - 2977.

8
[ 126717-59-7 ]
[ 156094-64-3 ]
3-bromo-2-(dibromomethyl)-6-methoxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); acetic acid; In tetrahydrofuran; for 12h;Reflux;	The compound <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> (15 g, 0.076 mol), N-bromosuccinimide (40 g, 0.22 mol),Tetrahydrofuran (100 mL), acetic acid (7.5 mL),Azobisisobutyronitrile (0.45 g, 2.7 mmol) was added to a 500 ml single-mouth flask equipped with a reflux apparatus, and the reaction system was heated to reflux for 12 hours.Cool to room temperature and add ethyl acetate (150 mL).Adjust the pH to about 8 with a saturated aqueous solution of sodium bicarbonate (40 mL).The organic phase was washed with saturated brine (30 mL) and dried over anhydrous sodium sulfate.Dry to give a clear oily mixture of compound 3-bromo-2-(dibromomethyl)-6-methoxypyridine and 3-bromo-2-(bromomethyl)-6-methoxypyridine (26 g ),Used directly in the next step.

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.
[2]Patent: CN104151240,2017,B .Location in patent: Paragraph 0027; 0029; 0031; 0033.

9
[ 126717-59-7 ]
[ 108-94-1 ]
1-(6-Methoxy-2-methyl-pyridin-3-yl)-cyclohexanol [ No CAS ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

10
[ 126717-59-7 ]
[ 106-95-6 ]
[ 156094-74-5 ]

References: [1]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.
[2]Synthetic Communications,1997,vol. 27,p. 61 - 68.

11
[ 126717-59-7 ]
[ 68-12-2 ]
[ 156094-77-8 ]

Yield	Reaction Conditions	Operation in experiment
92%		A solution of 2-methoxy-5-bromo-6-picoline (73 wt % solution in toluene,3.17 kg, 11.45 moles) in THF (18.3 L) was cooled to -60 C and treated with 2.5 N n-butyllithium in hexanes (4.87 L, 12.2 mol, 1.06 eq). After 0.5 h, dimethylformamide (1.76 L, 22.8 mol, 2.0 eq) was charged at <-50 C. After warming to ambient temperature, an aqueous solution of ammonium chloride (1.6 kg/16.2 L water) was charged and the layers separated. The aqueous phase was re-extracted with methyl ^-butylether (3.3 L) and the combined organic extracts were washed with saturated brine (2.5 L). There was a total of 22.4 kg of organic solution (7.08 wt %) corresponding to a 92% solution yield.

References: [1]Heterocycles,2009,vol. 79,p. 791 - 804.
[2]Patent: WO2005/51954,2005,A2 .Location in patent: Page/Page column 40.
[3]Tetrahedron Letters,2006,vol. 47,p. 553 - 556.
[4]Synthetic Communications,1994,vol. 24,p. 1367 - 1379.

12
[ 54923-31-8 ]
[ 74-88-4 ]
[ 126717-59-7 ]

Yield	Reaction Conditions	Operation in experiment
63%		Example 3 3-(2,5-Dimethyl-6-oxo-1 6-dihydropyridin-3-(at)l)benzonitrile Step 1: 3-Bromo-6-methoxy-2-methylpyridine: A mixture of 5-bromo-6-methyl-1H-pyridin- 2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2- methylpyridine (3.7 g, 63% yield) as an oil. LC/MS RT 3.76 min; MS m/e = 202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (lH, d), 3.89 (3H, s), 2.57 (3H, s).

References: [1]Heterocycles,1990,vol. 31,p. 819 - 824.
[2]Patent: WO2005/97750,2005,A1 .Location in patent: Page/Page column 71.

13
[ 63071-03-4 ]
[ 126717-59-7 ]

Yield	Reaction Conditions	Operation in experiment
76%		Step B. 3-Bromo-6-methoxy-2-methyl-pyridine. A mixture of 2-methoxy-6-methyl-pyridine (15.2 g, 123 mmol) and 1,3-dibromo-5,5-dimethyl hydantoin (35.3 g, 123 mmol) in THF (1 L) was stirred at rt for 48 h in the dark. The mixture was treated with 10% aq. Na2S2O3 (100 mL) and stirred for 1 h. The mixture was extracted with Et2O. The organic layer was washed with H2O (2*), dried (MgSO4), and concentrated. The residue was purified (SiO2; 0-5% EtOAc/hexanes) to give the title compound (18.7 g, 76%). MS (ESI): mass calcd. for C7H8BrNO, 200.98; m/z found, 202.2 [M+H]+. 1H NMR (CDCl3): 7.60 (d, J=8.6, 1H), 8.45 (d, J=8.7, 1H), 3.90 (s, 3H), 2.54 (s, 3H).
	With potassium hydroxide; tetraethylammonium chloride; bromine; potassium bromide; In water; at 0 - 20℃; for 17.6667h;	(2) Synthesis of 3-bromo-6-methoxy-2-methylpyridine 15.3g of 2-methoxy-6-methylpyridine was dissolved in 100ml of potassium bromide aqueous solution, prepared that 50.1g of potassium bromide was dissolved in 200ml of water, 11.9g of potassium hydroxide and 40g of tetraethylammonium chloride were added. The solution of 7.6ml of bromine in 100ml of potassium bromide aqueous solution was added in on ice-cooling to the reaction liquid using a dropping funnel for 40 minutes. After completion of dropping, an ice bath was removed, which was stirred for 17 hours at room temperature. Sodium sulfite aqueous solution and ethyl acetate were added to reaction liquid, and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure to give 19.6g of the title compound. 1H-NMR(CDCl3) delta (ppm): 2.56 (s,3H), 3.89 (s, 3H), 6.45 (d, 1H, J=8.0Hz), 7.60(d, 1H, J=8.0Hz).
	With bromine; In disodium hydrogen phosphate;	(18-1) 2-Methoxy-6-methylpyridine (10 mL, 81 mmol) was suspended in a 0.15 mol//L disodium hydrogen phosphate aqueous solution (160 mL). Thereafter, a solution prepared by suspending bromine (4.15 mL, 81 mmol) in a 0.15 mol//L disodium hydrogen phosphate aqueous solution (160 mL) was added dropwise to the suspension at room temperature over 1 hour. The reaction solution was stirred at the same temperature as described above overnight. Thereafter, the reaction solution was extracted with methylene chloride (300 mL) three times. Organic layers were gathered. The resultant was dried over anhydrous magnesium sulfate and was then filtrated, followed by vacuum concentration. The obtained residue was distilled away under reduced pressure (91 C.-96 C./16 mmHg), so as to obtain 9.47 g of 3-bromo-6-methoxy-2-methyl-pyridine.

References: [1]Tetrahedron,2000,vol. 56,p. 3181 - 3187.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 11187 - 11194.
[3]Synthetic Communications,1997,vol. 27,p. 61 - 68.
[4]Tetrahedron Letters,1997,vol. 38,p. 4415 - 4416.
[5]Journal of the Chemical Society. Perkin transactions I,1998,p. 3151 - 3155.
[6]Patent: US2006/287292,2006,A1 .Location in patent: Page/Page column 28.
[7]Patent: EP1847535,2007,A1 .Location in patent: Page/Page column 123-124.
[8]Patent: US2011/294857,2011,A1 .
[9]Science China Chemistry,2012,vol. 55,p. 1097 - 1100.

14
[ 35357-34-7 ]
[ 126717-59-7 ]
[ 13427-53-7 ]
10-(6-Methoxy-2-methyl-pyridin-3-yl)-1,4-dioxa-spiro[4.5]dec-6-en-8-one [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 3151 - 3155.

15
[ 935-50-2 ]
[ 126717-59-7 ]
[ 150-76-5 ]
4,4-Dimethoxy-5-(6-methoxy-2-methyl-pyridin-3-yl)-cyclohex-2-enone [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 3151 - 3155.

16
[ 126717-59-7 ]
[ 119414-47-0 ]
(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(6-methoxy-2-methyl-pyridin-3-yl)-cyclohexanone [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1998,p. 3151 - 3155.

17
[ 126717-59-7 ]
[ 269058-50-6 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 5 - 50℃; for 19h;	Step C. 3-Bromo-6-methoxy-2-methyl-pyridine N-oxide. A 5 C. solution of <strong>[126717-59-7]3-bromo-6-methoxy-2-methyl-pyridine</strong> (20.8 g, 103 mmol) in CHCl3 (550 mL) was treated with mCPBA (60%; 44.4 g, 154 mmol) slowly in portions over 1 h. The mixture was allowed to warm to rt, and then was heated at 50 C. for 18 h. The mixture was cooled to rt, treated with 5% aq. Na2CO3 (300 mL), and stirred for 1 h. The mixture was diluted with DCM and washed with H2O (3*). The organic layer was separated, dried (MgSO4), and concentrated to a light yellow oil (26.9 g). The oil was purified (SiO2; 0-5% 2 M NH3 in MeOH/DCM) to give the title compound (15.7 g, 70%). MS (ESI): mass calcd. for C7H8BrNO2, 216.97; m/z found, 218.2 [M+H]+. 1H NMR (CDCl3): 7.44 (d, J=8.9, 1H), 6.68 (d, J=9.0, 1H), 4.05 (s, 3H), 2.74 (s, 3H).
52%	With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 - 20℃; for 48h;	To a solution of <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> (5 g, 24.75 mmol) in chloroform (100 mL) was added mCPBA (8.52 g, 49.37 mmol) in portions at 0 C. The resulting mixture was stirred at room temperature for 2 d. The reaction mixture was then diluted with sat. NaHCO3 solution (200 mL) and was extracted with dichloromethane (250 mL*2). The combined organic phase was washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with methanol in dichloromethane (1% to 5% gradient) to yield <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> 1-oxide as yellow solid (2.8 g, 52%). MS: m/z=217.9 [M+H]+.

References: [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 2865 - 2876.
[2]Patent: US2006/287292,2006,A1 .Location in patent: Page/Page column 28-29.
[3]Tetrahedron Letters,2000,vol. 41,p. 2007 - 2009.
[4]Patent: US2016/75711,2016,A1 .Location in patent: Paragraph 0570-0571.

18
[ 126717-59-7 ]
[ 870-63-3 ]
[ 283612-39-5 ]

References: [1]Tetrahedron,2000,vol. 56,p. 3181 - 3187.

19
[ 126717-59-7 ]
[ 219735-84-9 ]
[ 503184-36-9 ]

References: [1]Bioorganic and medicinal chemistry letters,2003,vol. 13,p. 289 - 291.

20
[ 126717-59-7 ]
[ 156094-64-3 ]

Yield	Reaction Conditions	Operation in experiment
15.5 g		The compound <strong>[126717-59-7]3-bromo-6-methoxy-2-methylpyridine</strong> (15 g, 0.076 mol), N-bromosuccinimide (40 g, 0.22 mol),Tetrahydrofuran (100 mL), acetic acid (7.5 mL),Azobisisobutyronitrile (0.45 g, 2.7 mmol) was added to a 500 ml single-mouth flask equipped with a reflux apparatus, and the reaction system was heated to reflux for 12 hours.Cool to room temperature and add ethyl acetate (150 mL).Adjust the pH to about 8 with a saturated aqueous solution of sodium bicarbonate (40 mL).The organic phase was washed with saturated brine (30 mL) and dried over anhydrous sodium sulfate.Dry to give a clear oily mixture of compound 3-bromo-2-(dibromomethyl)-6-methoxypyridine and 3-bromo-2-(bromomethyl)-6-methoxypyridine (26 g ),Used directly in the next step.3-Bromo-2-(dibromomethyl)-6-methoxypyridine in sequence at room temperaturea mixture with 3-bromo-2-(bromomethyl)-6-methoxypyridine (26 g),Anhydrous tetrahydrofuran (100 mL), N,N-diisopropylethylamine(25.8 mL, 0.19 moL), added to a 500 ml three-neck bottle,Nitrogen protection, cooling to 0 C, diethyl phosphite(18.6 mL, 0.14 mol) was added dropwise to the reaction system.After completion, the reaction solution was stirred at normal temperature for 12 hours.Ethyl acetate (200 mL) was added to the reaction system.Wash twice with saturated brine (20 mL) and dry over anhydrous sodium sulfate.Spin dry, pass through the column (petroleum ether (v) / ethyl acetate (v) = 50:1)3-bromo-2-(bromomethyl)-6-methoxypyridine (15.5 g, two-step yield: 77%)Transparent oil.

References: [1]Organic Letters,2010,vol. 12,p. 2551 - 2553.
[2]Organic and Biomolecular Chemistry,2003,vol. 1,p. 2865 - 2876.
[3]Science China Chemistry,2012,vol. 55,p. 1097 - 1100.
[4]Patent: CN104151240,2017,B .Location in patent: Paragraph 0027; 0029; 0031; 0032; 0033.
[5]Journal of Organic Chemistry,2019,vol. 84,p. 5855 - 5862.

21
[ 4096-34-8 ]
[ 126717-59-7 ]
[ 875757-98-5 ]

References: [1]Heterocycles,2009,vol. 79,p. 791 - 804.
[2]Tetrahedron Letters,2006,vol. 47,p. 553 - 556.

22
[ 126717-59-7 ]
[ 459856-12-3 ]