57543-36-9|5-BROMO-2-HYDROXY-4-METHOXYBENZALDEHYDE| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 57543-36-9 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 57543-36-9 ]

CAS No. :	57543-36-9
Formula :	C₈H₇BrO₃
M.W :	231.04
SMILES Code :	O=CC1=CC(Br)=C(OC)C=C1O
MDL No. :	MFCD00839421
InChI Key :	OHSSWZLKWHLYFP-UHFFFAOYSA-N
Pubchem ID :	818108

Safety of [ 57543-36-9 ]

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

Computational Chemistry of [ 57543-36-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	48.04
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.63
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	2.24
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.98
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.	1.25
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	2.18
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.92
Solubility	0.277 mg/ml ; 0.0012 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.	-2.85
Solubility	0.324 mg/ml ; 0.0014 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	-2.76
Solubility	0.403 mg/ml ; 0.00175 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.	-6.12 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)	1.57

Application In Synthesis of [ 57543-36-9 ]

* 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 [ 57543-36-9 ]

[ 57543-36-9 ] Synthesis Path-Downstream 1~35

1
[ 673-22-3 ]
[ 57543-36-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bromine; acetic acid; at 0 - 20℃; for 2h;	In a 250 mL flask, 2-hydroxy-4-methoxybenzaldehyde (5 g, 32.9 mmol) was dissolved in acetic acid (65.7 mL), and cooled to 0 C, then Br2 (1 .862 ml, 36.1 mmol) in 10 mL acetic acid was added slowly. Upon complete addition, the reaction mixture was allowed to warm to room temperature, and stirred for 2 h. 100 mL of water was added to reaction flask, and the resulting white precipitate was filtered and washed with water. Drying under vacuum afforded the title compound (6.8 g, 29.4 mmol, 90 % yield). MS (M+1 ) = 233.3. 1H NMR (400 MHz, CHLOROFORM-d) delta 1 1.45 (s, 1 H), 9.70 (s, 1 H), 7.69 (s, 1 H), 6.49 (s, 1 H), 3.96 (s, 3H).
87%	With bromine; acetic acid; at 0 - 20℃; for 1h;	To a solution of a commercially available 2-hydroxy-4-methoxybenzaldehyde (1.18 g, 7.76 mmol) in glacial acetic acid (15 mL) was added a solution of Br2 (0.44 mL, 8.62 mmol) in glacial acetic acid (5 mL) at 0 C and the reaction mixture was warmed up and stirred at room temperature for 1 h. Water (30 mL) was added and the precipitate was collected by filtration. Water (30 mL) and CH2Cl2 (30 mL) were added to the white solid and the two phases were separated. The aqueous layer was extracted with CH2Cl2 (3 x 25 mL) and the combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude product 5-bromo-2-hydroxy-4-methoxybenzaldehyde which was further recrystallized from CH2Cl2 to furnish the desired product as a white solid (1.56 g, 6.75 mmol, 87 %).
80%	With bromine; In dichloromethane; at 0 - 20℃; for 3h;	2-HYDROXY-4-METHOXYBENZALDEHYDE (6.0 g, 39 mmol) was dissolved in dichloromethane (50 ML) and cooled to 0 C using an ice-water bath. Bromine (6.8 g, 43 mmol) in dichloromethane (2 mL) was added dropwise to the cooled solution and stirred for 2 h at 0 C. The mixture was warmed to room temperature and stirred for an additional 1 h and the resulting yellow precipitate was collected. Recrystallization (ethyl acetate/hexanes) yielded 7.1 g (80%) of 5-bromo-2-hydroxy-4- methoxybenzaldehyde as white needles, m. p. 63-64'C.'H-NMR (300 MHz, CDC13) 6 11.43 (s, 1 H), 9.69 (s, 1 H), 7.68 (s, 1 H), 6.48 (s, 1 H), 3.95 (s, 3 H). Anal. Calcd. for C8H7BRO3 : C, 41.59 ; H, 3.05. Found: C, 41.86 ; H, 3.05.

76%	With tetra-n-butylammonium tribromide; sodium hydrogencarbonate; sodium chloride; In dichloromethane; water;	a. 3-Bromo-6-hydroxy-4-methoxy-benzaldehyde. A mixture of 2-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and tetrabutylammonium tribromide (6.40 g, 20 mmol) in anhydrous dichloromethane (200 mL) was stirred at room temperature for 24 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40M cartridge, eluding with 5% ethyl acetate/95% hexane to give 3-bromo-6-hydroxy-4-methoxy-benzaldehyde as a white solid (3.50 g, 76%). 1H NMR (500 MHz; CDCl3): delta3.94 (s, 3 H), 6.47 (s, 1 H), 7.67 (s, 1 H), 9.68 (s, 1 H), 11.43 (s, 1 H).
76%	With tetra-n-butylammonium tribromide; sodium hydrogencarbonate; sodium chloride; In dichloromethane; water;	a. 3-Bromo-6-hydroxy-4-methoxy-benzaldehyde A mixture of 2-hydroxy-4-methoxy-benzaldehyde (3.04 g, 20 mmol) and tetrabutylammonium tribromide (6.40 g, 20 mmol) in anhydrous dichloromethane (200 mL) was stirred at room temperature for 24 hours. The solution was washed successively with a saturated aqueous solution of NaHCO3 (150 mL), water (150 mL), a saturated aqueous solution of NaCl (150 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave a solid which was purified by column chromatography, using a Biotage 40M cartridge, eluding with 5% ethyl acetate/95% hexane to give 3-bromo-6-hydroxy-4-methoxy-benzaldehyde as a white solid (3.50 g, 76%). 1H NMR (500 MHz; CDCl3): delta3.94 (s, 3H), 6.47 (s, 1H), 7.67 (s, 1H), 9.68 (s, 1H), 11.43 (s, 1H).
	With bromine; In dichloromethane; ethyl acetate;	Example 62 3-[5-(Benzo[b]thien-2-yl)-2-carboxymethoxy-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one, Sodium Salt Ex-62A: A solution of 2-hydroxy-4-methoxybenzaldehyde (3.03 g, 20 mmol) in 25 mL of dichloromethane was cooled to 0 C. and treated dropwise with a solution of bromine (3.41 g, 21 mmol) in 10 mL of dichloromethane. The reaction mixture was stirred at 0 C. for 1.5 hours. The solvent was removed by rotary evaporation to give a residue. The residue was taken up in EtOAc and washed with 3 portions of water. The organic layer was dried over MgSO4. The drying agent was removed by filtration, and solvent was removed by rotary evaporation to give 3.9 g of the desired 5-bromo-2-hydroxy-4-methoxybenzaldehyde as a solid, m.p. 111-115 C.
	With bromine;	2-Hydroxy-4-methoxybenzaldehyde (20 g, 131.4 mmol) was brominated to give 5-bromo-2-hydroxy-4-methoxybenzaldehyde as a light yellow solid, followed by coupling with 4-methoxyphenylboronic acid (750 mg, 4.94 mmol) using method A to give 800 mg (75%) of 4-hydroxy-6,4'-dimethoxybiphenyl-3-carbaldehyde as a light yellow solid.

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 2360 - 2367.
[2]Journal of the Iranian Chemical Society,2011,vol. 8,p. 531 - 536.
[3]Patent: WO2015/17589,2015,A1 .Location in patent: Page/Page column 83.
[4]Tetrahedron,2011,vol. 67,p. 3904 - 3914.
[5]Journal of Medicinal Chemistry,2007,vol. 50,p. 1304 - 1315.
[6]Patent: WO2004/56727,2004,A2 .Location in patent: Page 58.
[7]Patent: US2003/83357,2003,A1 .
[8]Patent: US6515003,2003,B1 .
[9]Journal of Medicinal Chemistry,2017,vol. 60,p. 362 - 372.
[10]Journal of Organic Chemistry,2009,vol. 74,p. 4009 - 4012.
[11]Journal of the Chemical Society,1929,p. 1580.
[12]Proceedings - Indian Academy of Sciences, Section A,1942,vol. <A> 16,p. 135.
[13]Proceedings - Indian Academy of Sciences, Section A,1942,vol. <A> 16,p. 135.
[14]Journal of the Chemical Society,1929,p. 1580.
[15]Patent: US6608101,2003,B1 .
[16]Patent: US6689806,2004,B1 .Location in patent: Page/Page column 70.
[17]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3727 - 3731.
[18]Chemistry - An Asian Journal,2015,vol. 10,p. 1050 - 1064.

2
[ 6615-24-3 ]
[ 57543-36-9 ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

3
[ 57543-36-9 ]
[ 114-70-5 ]
6-bromo-7-methoxy-3-phenyl-coumarin [ No CAS ]

References: [1]Journal Of Scientific and Industrial Research,1952,vol. 11 B,p. 39,43.

4
[ 57543-36-9 ]
[ 130333-46-9 ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

5
[ 57543-36-9 ]
2-ethoxy-5-bromo-4-methoxy-benzaldehyde [ No CAS ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

6
[ 57543-36-9 ]
[ 633357-97-8 ]

References: [1]Journal of the Chemical Society,1932,p. 524,525, 526.

7
[ 57543-36-9 ]
[ 117238-61-6 ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

8
[ 57543-36-9 ]
[ 873980-72-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With nitric acid; acetic acid; at 85℃; for 2h;	0.1 mol of <strong>[57543-36-9]5-bromo-2-hydroxy-4-methoxybenzaldehyde</strong> is dissolved in 20 ml of acetic acid and the solution is heated to 85[deg.] C. with stirring. Under this condition, 6.9 ml is added dropwise to the solution. 65% nitric acid solution was reacted for 2 h after the addition. After completion of the reaction, 50 ml of ice water was added to the solution to precipitate a yellow precipitate which was filtered and dried. It was then purified by column chromatography eluting with dichloromethane:methanol=40:1 to give a yellow solid, 59% yield.

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 362 - 372.
[2]Patent: CN108069929,2018,A .Location in patent: Paragraph 0062-0063.
[3]Journal of the Chemical Society,1932,p. 524,525, 526.

9
[ 57543-36-9 ]
5-bromo-2-hydroxy-4-methoxy-benzaldehyde phenylhydrazone [ No CAS ]

References: [1]Journal of the Chemical Society,1930,p. 2279,2287.

10
[ 116096-90-3 ]
[ 77-78-1 ]
[ 57543-36-9 ]

References: [1]Journal Of Scientific and Industrial Research,1952,vol. 11 B,p. 39,43.

11
[ 57543-36-9 ]
[ 874-86-2 ]
[ 84224-30-6 ]

References: [1]Liebigs Annalen der Chemie,1982,p. 1836 - 1869.

12
[ 626-35-7 ]
[ 43192-31-0 ]
[ 57543-36-9 ]
(4α,5β)-ethyl 4,6-dibromo-8-oxo-1-oxa-2-azaspiro<4,5>deca-2,6,9-triene-3-carboxylate [ No CAS ]
(4α,5β)-ethyl 4,6,9-tribromo-8-oxo-1-oxa-2-azaspiro<4,5>deca-2,6,9-triene-3-carboxylate [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 4255 - 4270.

13
ethyl (Z)-3-(3'-bromo-4'-methoxyphenyl)-2-nitroacrylate [ No CAS ]
[ 57543-36-9 ]
(4α,5β)-ethyl 7-bromo-4-chloro-8-oxo-1-oxa-2-azaspiro<4,5>-2,6,9-triene-3-carboxylate [ No CAS ]
(E)-ethyl 3-chloro-(5'-bromo-2'-chloro-4'-methoxyphenyl)-2-hydroxyiminopropionate [ No CAS ]

References: [1]Tetrahedron,1999,vol. 55,p. 4255 - 4270.

14
[ 673-22-3 ]
[ 64-18-6 ]
[ 7726-95-6 ]
[ 127-09-3 ]
[ 57543-36-9 ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

15
[ 673-22-3 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 57543-36-9 ]

References: [1]Journal of the Chemical Society,1929,p. 1580.

16
[ 673-22-3 ]
[ 60-29-7 ]
[ 7726-95-6 ]
[ 24967-79-1 ]
[ 57543-36-9 ]
[ 117238-61-6 ]

References: [1]Proceedings - Indian Academy of Sciences, Section A,1942,vol. <A> 16,p. 135.

17
[ 673-22-3 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 24967-79-1 ]
[ 57543-36-9 ]
[ 117238-61-6 ]

References: [1]Proceedings - Indian Academy of Sciences, Section A,1942,vol. <A> 16,p. 135.

19
[ 57543-36-9 ]
[ 7697-37-2 ]
[ 633357-97-8 ]

References: [1]Journal of the Chemical Society,1932,p. 524,525, 526.

20
[ 57543-36-9 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 873980-72-4 ]

References: [1]Journal of the Chemical Society,1932,p. 524,525, 526.

21
[ 6165-68-0 ]
[ 57543-36-9 ]
[ 552845-71-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium fluoride;bis(tri-t-butylphosphine)palladium(0); In tetrahydrofuran; at 60℃; for 1.5h;	5-BROMO-2-HYDROXY-4-METHOXYBENZALDEHYDE obtained from Ex-lA (1.5 g, 6.5 mmol) and thiophene-2-boronic acid (0.91 g, 7.1 mmol) were dissolved in tetrahydrofuran (15 mL). Nitrogen was bubbled into the solution for 10 min followed by the sequential addition of potassium fluoride (0.80 G, 14 mmol, spray-dried) and bis (tri-t-butylphosphine) palladium (0) (0.033 g, 0.065 MMOL). The solution was immediately heated to 60 C and aged for 1.5 h. Upon completion, as determined by HPLC, the reaction was diluted with water (25 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were dried over sodium sulfate and concentrated to a brown solid. Silica gel chromatography (ethyl acetate/hexanes, 1: 3) gave 1.46 g (97%) of 2-hydroxy-4-methoxy-5-thiophen-2-yl-benzaldehyde as a yellow solid, m. p. 118-119 C.'H-NMR (300 MHz, CDC13) 8 11.48 (s, 1 H), 9.79 (s, 1 H), 7.72 (s, 1 H), 7.37 (dd, 1 H), 7.31 (dd, 1 H), 7.08 (dd, 1 H), 6.54 (s, 1 H), 3.98 (s, 3 H). Anal. Calcd. for CSH703S : C, 61.52 ; H, 4.30 ; S, 13.69. Found: C, 61.12 ; H, 4.34 ; S, 13.56.

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1304 - 1315.
[2]Patent: WO2004/56727,2004,A2 .Location in patent: Page 58-59.

22
[ 130333-46-9 ]
[ 57543-36-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5300 - 5315.

23
[ 673-22-3 ]
[ 57543-36-9 ]
[ 63638-85-7 ]
[ 117238-61-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5300 - 5315.

24
[ 57543-36-9 ]
C₈H₉BrO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 5300 - 5315.
[2]Chemistry - An Asian Journal,2015,vol. 10,p. 1050 - 1064.

25
[ 57543-36-9 ]
[ 552845-72-4 ]