35674-27-2|4-Iodo-3-nitrobenzoic acid| Ambeed

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Quality Control of [ 35674-27-2 ] Purity: 97% SDS Specification

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Product Details of [ 35674-27-2 ]

CAS No. :	35674-27-2
Formula :	C₇H₄INO₄
M.W :	293.02
SMILES Code :	IC1=C(C=C(C(=O)O)C=C1)[N+](=O)[O-]
MDL No. :	MFCD00502399
InChI Key :	DNMTZLCNLAIKQC-UHFFFAOYSA-N
Pubchem ID :	11208598

Safety of [ 35674-27-2 ]

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

Computational Chemistry of [ 35674-27-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	54.94
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	83.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.96
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	1.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.9
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.	1.43
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	0.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.26

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.08
Solubility	0.243 mg/ml ; 0.000828 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.	-3.3
Solubility	0.147 mg/ml ; 0.000502 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	-2.09
Solubility	2.36 mg/ml ; 0.00805 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	No
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	No
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.	-6.72 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.	0.56

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)	2.07

Application In Synthesis of [ 35674-27-2 ]

* 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 [ 35674-27-2 ]

[ 35674-27-2 ] Synthesis Path-Downstream 1~35

1
[ 64-17-5 ]
[ 35674-27-2 ]
[ 57362-77-3 ]

Yield	Reaction Conditions	Operation in experiment
90.5%	With sulfuric acid; at 0℃; for 6h;Inert atmosphere; Reflux;	Embodiment 47 ethyl 4-iodo-3-nitrobenzoate <strong>[35674-27-2]4-Iodo-3-nitrobenzoic acid</strong> (1.9g, 6.48mmol) was added to a flask, followed by addition of 10mL anhydrous ethanol under argon atmosphere. The mixture was cooled to 0C under an ice bath, then 0.6mL concentrated sulfuric acid was added dropwise. After completion of the dropwise addition, the reaction solution was heated to reflux and stirred for 6 h, meanwhile TLC was used to monitor the reaction. After completion of the reaction, the reaction solution was cooled to room temperature, treated with 1mol/L sodium hydroxide to neutralize sulfuric acid to make a neutral solution, then washed with saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic phase was dried over anhydrous sodium sulfate, filtered, dried, and purified by flash column chromatography (PE:EtOAc = 10:1) to give ethyl 4-iodo-3-nitrobenzoate (1.88g, 90.5%). 1H NMR (500 MHz, CDCl3) delta 8.39 (d, J = 2.0 Hz, 1H), 8.10 (d, J = 8.2 Hz, 1H), 7.85 (dd, J = 8.2, 2.0 Hz, 1H), 4.39 (q, J = 7.1 Hz, 2H), 1.39 (t, J = 7.1 Hz,3H). 13C NMR (126 MHz, CDCl3) delta 164.03, 153.15, 142.33, 133.47, 131.96, 125.98, 92.02, 62.16, 14.29. ESI(+)-MS: 322.1 [M+1]+.

References: [1]Patent: EP3428155,2019,A1 .Location in patent: Paragraph 0162; 0163.
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1896 - 1904.
[3]Chemische Berichte,1893,vol. 26,p. 1739.
[4]Patent: WO2010/62171,2010,A2 .Location in patent: Page/Page column 140.

2
[ 619-58-9 ]
[ 35674-27-2 ]

References: [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1896 - 1904.
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 12862 - 12867.
Angew. Chem.,2019,vol. 131,p. 12994 - 12999,6.
[3]Dalton Transactions,2015,vol. 44,p. 2047 - 2051.
[4]Chemical Communications,2017,vol. 53,p. 7808 - 7811.
[5]Journal of Medicinal Chemistry,2013,vol. 56,p. 1865 - 1877.
[6]Chemische Berichte,1875,vol. 8,p. 562.

3
[ 35674-27-2 ]
[ 51411-81-5 ]

References: [1]Zhurnal Organicheskoi Khimii,1973,vol. 9,p. 2540,2541; engl. Ausg. S. 2560, 2561.
[2]Tetrahedron Letters,1997,vol. 38,p. 7963 - 7966.

4
[ 35674-27-2 ]
4-iodosyl-3-nitro-benzoic acid [ No CAS ]

References: [1]Chemische Berichte,1893,vol. 26,p. 1361.

5
[ 101420-88-6 ]
[ 35674-27-2 ]

References: [1]Journal of the Chemical Society,1927,p. 25.

6
[ 35674-27-2 ]
[ 100-37-8 ]
4-iodo-3-nitro-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride [ No CAS ]

References: [1]Patent: US1765621,1938, .

7
[ 35674-27-2 ]
[ 160003-66-7 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 3093 - 3097.
[2]Patent: US2013/172618,2013,A1 .

8
[ 67-56-1 ]
[ 35674-27-2 ]
[ 89976-27-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sulfuric acid; at 0 - 0.7℃; for 8h;	Example 1 Preparation of 4-iodo-3-nitrobenzoic Acid Methyl Ester Using Methanol/Sulfuric Acid To a solution of <strong>[35674-27-2]4-iodo-3-nitrobenzoic acid</strong> (3 g, 10 mmol) in methanol (30 ml) cooled to 0 C., sulfuric acid (3.4 g, 34.6 mmol) is added slowly. The reaction mixture is warmed to room temperature and then refluxed (?70 C.) for 8 hours. After cooling, the reaction mixture is neutralized with solid NaHCO3 and the salts are filtered. The filtrate is evaporated under reduced pressure. To the residue obtained, water (30 ml) is added and the mixture extracted with MTBE (30 ml*2). The combined organic phase is washed with brine, dried using anhydrous sodium sulfate and filtered. After evaporating the solvent under reduced pressure, <strong>[35674-27-2]4-iodo-3-nitro-benzoic acid</strong> methyl ester is obtained as a yellow solid (2.67 g, 85% yield, 98% HPLC).
83%	With sulfuric acid; at 0 - 20℃; for 16h;Inert atmosphere;	[00095] To a stirred solution of <strong>[35674-27-2]4-iodo-3-nitrobenzoic acid</strong> 46 (15 g, 51.36 mmol) in MeOH (150 mL) under inert atmosphere was added concentrated sulphuric acid (15 mL) dropwise for 10 min at 0 C; warmed to RT at stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo. The residue was diluted with ice-cold water (500 mL) and extracted with EtOAc (3 x 100 mL). The combined organic extracts were washed saturated sodium bicarbonate solution (2 x 100 mL) dried over sodium sulfate, filtered and concentrated in vacuo to afford compound 47 (13 g, 83%) as an off-white solid. TLC: 30% EtOAc/ hexanes (R/. 0.8); 1H NMR (CDC13, 500 MHz) delta 8.45 (s, 1H), 8.15 (d, J = 8.4 Hz, 1H), 7.88 (dd, J = 8.2, 1.9 Hz, 1H), 3.97 (s, 3H).
77%	With sulfuric acid; for 6h;Heating / reflux;	b) 4-Iodo-3-nitro-benzoic acid methyl ester A methanolic solution of <strong>[35674-27-2]4-iodo-3-nitro-benzoic acid</strong> (10.0 g, 34.13 mmol, 1 eq. ) was treated with concentrated sulfuric acid (7 mL) and the reaction heated to reflux. After 6 hours, the acid was neutralized with solid sodium bicarbonate and the methanol removed in vacuo. The residual oil was diluted with water and extracted with diethyl ether. Combined the organics, washed with brine, dried, filtered, and removed the solvent in vacuo leaving an orange oil which was purified via normal phase chromatography to leave <strong>[35674-27-2]4-iodo-3-nitro-benzoic acid</strong> methyl ester (8.08 g, 77% yield) as a yellow solid.

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 12862 - 12867.
Angew. Chem.,2019,vol. 131,p. 12994 - 12999,6.
[2]Dalton Transactions,2015,vol. 44,p. 2047 - 2051.
[3]Chemical Communications,2017,vol. 53,p. 7808 - 7811.
[4]Patent: US2013/172618,2013,A1 .Location in patent: Paragraph 0025.
[5]Patent: WO2017/48954,2017,A1 .Location in patent: Paragraph 00095.
[6]Patent: WO2005/40157,2005,A2 .Location in patent: Page/Page column 68.
[7]Tetrahedron Letters,1997,vol. 38,p. 7963 - 7966.
[8]Journal of Medicinal Chemistry,2013,vol. 56,p. 1865 - 1877.

9
[ 1588-83-6 ]
[ 35674-27-2 ]

Yield	Reaction Conditions	Operation in experiment
89.7%		Example 1 Preparation of 4-iodo-3-nitrobenzoic acid (Compound V) 45 g (0.25 mol) 4-Amino-3-nitrobenzoic acid, 400 ml water and 100 ml concentrated hydrochloric acid were added into a reaction flask. Started to stir, and the mixture was cooled to 0 to 5 C., then 50 ml aqueous solution of 25.9 g sodium nitrite (0.38 mol) was added dropwise. The solid was dissolved gradually. After completing the dropwise addition, the mixture was reacted at 0 to 5 C. for 1 hour, and 200 ml aqueous solution of 88 g (0.5 mol) potassium iodide was added dropwise at this temperature. The mixture was stirred at room temperature for 2 h after completing the dropwise addition, and solid was precipitated. The solid was filtered, washed with water, and dried to obtain 4-iodo-3-nitrobenzoic acid (compound V) as a solid, 65 g (0.22 mol), yield 89.7%.
		Preparation of {l-Methanesulfonyl-6- [5- (2-phenoxy-ethylsulfanylmethyl)- [1,3, 4] oxadiazol-2-yl]-1 H-indol-2-ylmethyl}-dimethyl-amine a) 4-Iodo-3-nitro-benzoic acid An acetone solution of 4-amino-3-nitrobenzoic acid (25 g, 137.26 mmol, 1 eq. ) was cooled in an ice bath and treated with an aqueous solution of sodium nitrite (10.42 g, 150.99 mmol, 1.1 eq. ) and the reaction stirred for 30 minutes. The reaction was then treated with an aqueous solution of potassium iodide (23.01 g, 138.63 mmol, 1.01 eq. ) and the reaction warmed to 40C. After 2 hours, the acetone was removed in vacuo and the reaction extracted 2X250 mL with ethyl acetate. The organics were washed with 5M aqueous HCl and then collected, dried, filtered, and the solvent removed in vacuo. The residue was purified by normal phase chromatography using a step gradient of ethyl acetate in hexanes as the mobile phase to give 4-iodo-3-nitro-benzoic acid as an orange solid. This material was taken on to the esterification reaction as is.

References: [1]Patent: US2013/225810,2013,A1 .Location in patent: Paragraph 0081; 0082.
[2]Tetrahedron,2005,vol. 61,p. 10113 - 10121.
[3]Tetrahedron Letters,1997,vol. 38,p. 7963 - 7966.
[4]Patent: WO2005/40157,2005,A2 .Location in patent: Page/Page column 67-68.
[5]Patent: WO2010/62171,2010,A2 .Location in patent: Page/Page column 140.

10
[ 619-58-9 ]
[ 7697-37-2 ]
[ 35674-27-2 ]

References: [1]Chemische Berichte,1875,vol. 8,p. 562.

12
diazotized 4-amino-3-nitro-benzoic acid [ No CAS ]
[ 35674-27-2 ]

References: [1]Journal of Organic Chemistry,1954,vol. 19,p. 1500,1503.

13
[ 35674-27-2 ]
[ 7697-37-2 ]
4-iodosyl-3-nitro-benzoic acid [ No CAS ]

References: [1]Chemische Berichte,1893,vol. 26,p. 1361.

14
[ 7664-93-9 ]
4-iodosyl-3-nitro-benzoic acid [ No CAS ]
permanganate [ No CAS ]
[ 35674-27-2 ]

References: [1]Chemische Berichte,1893,vol. 26,p. 1739.

15
4-iodosyl-3-nitro-benzoic acid [ No CAS ]
KI [ No CAS ]
[ 35674-27-2 ]
[ 7553-56-2 ]

References: [1]Chemische Berichte,1893,vol. 26,p. 1739.

16
[ 35674-27-2 ]
[ 612825-76-0 ]

References: [1]Organic Letters,2003,vol. 5,p. 3611 - 3614.

17
C₆₆H₆₉N₅O₂^(2-)*Zn⁽²⁺⁾ [ No CAS ]
[ 35674-27-2 ]
C₇₃H₇₂N₆O₆^(2-)*Zn⁽²⁺⁾ [ No CAS ]

References: [1]Tetrahedron,2005,vol. 61,p. 10113 - 10121.

18
[ 35674-27-2 ]
[ 532406-56-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 2h;Reflux;	To 3.00 g (10.24 mmol) of <strong>[35674-27-2]4-iodo-3-nitrobenzoic acid</strong> was added 20 mL of SOCl2. The resulting solution was refluxed for 2 h. The excess thionyl chloride was removed by distillation. A residual amount of thionyl chloride was removed by N2 stream and thereafter by high vacuum manifold (0.2 mmHg). The resulting acid chloride was dissolved in 30 mL of dry CH2Cl2, followed by adding 2.38 g (10.24 mmol) of 15. To the resulting mixture was added 5.46 g (40.95 mmol, 4.0 eq) of AlCl3 in 5 portions at room temperature. The reaction was monitored by TLC. The completed reaction was quenched by pouring the reaction mixture onto 50 g of ice. The aqueous phase was extracted with 50 mL of CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:4) to give 3.86 g (74%) of 21 as a yellow solid: 1H NMR (500 MHz, CDCla) delta 8.34 (d, J=1.9 Hz, 1H), 8.23 (d, J=8.1 Hz, 1H), 7.76 (dd, J=1.9, 8.1 Hz, 1H), 7.64 (s, 1H), 7.48 (m, 5H), 3.73 (s, 3H), 3.69 (s, 2H); 13C NMR (125 MHz, CDCl3) 184.3, 170.9, 152.9, 151.4, 142.5, 139.7, 138.8, 137.8, 132.9, 132.3, 131.0, 129.3, 129.2, 129.0, 125.6, 91.1, 52.3, 34.1.
	With thionyl chloride; N,N-dimethyl-formamide; at 10 - 20℃; for 1h;	Example 14 Preparation of N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1) 10 g (0.034 mol) <strong>[35674-27-2]4-Iodo-3-nitrobenzoic acid</strong> (Compound VI-1) and 50 ml N,N-dimethylformamide were added into a reaction flask, stirred to dissolve, and cooled to below 10 C., and 7.5 ml (0.10 mol) sulfoxide chloride was added. After completion of the dropwise addition, the mixture was warmed to room temperature and reacted for one hour. The reaction mixture was poured into 200 ml aqueous solution of 30% methylamine with low temperature, stirred for 5 minutes to precipitate a solid, and then the mixture was added with 500 ml ice-water, stirred for 10 minutes, filtered. The solid was washed with water and dried to obtain N-methyl-4-iodo-3-nitrobenzamide (Compound VII-1), 6.5 g (0.021 mol), yield 62.3%. 1HNMR (400 MHz, DMSO-d6): delta 2.81 (d, 3H, J=4.1 Hz), 7.84 (d, 1H, 7.8 Hz), 8.23 (d, 1H, J=8.1 Hz), 8.33 (s, 1H), 8.75 (s, 1H); MS (m/z): 307 [M+H].
	With thionyl chloride; for 3h;Reflux;	<strong>[35674-27-2]4-iodo-3-nitro-benzoic acid</strong> (0.286g, 0.976mmol) and was heated for 3 hours the mixture under reflux of thionyl chloride (5ml). The reaction mixture was cooled to room temperature, the excess reagent and solvent were removed under reduced pressure to give the crude acid chloride. The crude acid chloride, using 2- (4-aminophenyl) -6-methoxy benzothiazole (0.25g, 0.976mmol) and Hunig's base (0.151 g, 1.17 mmol) and in dry THF (10 ml) to, the amide was prepared as described in the section amide coupling, after work-up to afford the title compound (0.403g, 78%) as a yellow solid.

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 22℃; for 0.5h;Inert atmosphere;

To an Ar purged solution of <strong>[35674-27-2]4-iodo-3-nitro-benzoic acid</strong> (50.0 mg, 0.171 mmol) in DCM (1.0 mL) added oxalyl chloride (29 muL, 0.341 mmol), followed by DMF (1 drop) at 22 C. After 30 minutes, the conversion to the acid chloride was confirmed by treating a small aliquot of the reaction mixture with MeOH and observing the resulting methyl ester by LC/MS. The reaction was concentrated and DCM (1.0 mL) was added to make a stock solution of the crude acid chloride.

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 395 - 408.
[2]Patent: US2010/260778,2010,A1 .Location in patent: Page/Page column 15.
[3]Patent: US2013/225810,2013,A1 .Location in patent: Paragraph 0105; 0106; 0107.
[4]Patent: JP5667058,2015,B2 .Location in patent: Paragraph 0591.
[5]Patent: US2018/127383,2018,A1 .Location in patent: Paragraph 0111.
[6]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5416 - 5421.

19
[ 35674-27-2 ]
[ 875271-83-3 ]