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Product Details of [ 6269-89-2 ]

CAS No. :6269-89-2 MDL No. :MFCD00005961
Formula : C10H13N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VWOJSRICSKDKAW-UHFFFAOYSA-N
M.W : 207.23 Pubchem ID :80447
Synonyms :

Calculated chemistry of [ 6269-89-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 66.62
TPSA : 61.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.01
Log Po/w (WLOGP) : 0.24
Log Po/w (MLOGP) : 0.34
Log Po/w (SILICOS-IT) : -0.59
Consensus Log Po/w : 0.53

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.93
Solubility : 2.46 mg/ml ; 0.0119 mol/l
Class : Very soluble
Log S (Ali) : -1.88
Solubility : 2.72 mg/ml ; 0.0131 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.28
Solubility : 1.09 mg/ml ; 0.00524 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.92

Safety of [ 6269-89-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6269-89-2 ]

* 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.

  • Upstream synthesis route of [ 6269-89-2 ]
  • Downstream synthetic route of [ 6269-89-2 ]

[ 6269-89-2 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 6269-89-2 ]
  • [ 67455-41-8 ]
YieldReaction ConditionsOperation in experiment
90% With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol for 3 h; 1-(4-Nitrophenyl)piperazine 22A (414 mg, 2 mM) was dissolved in ethanol (15 mL) and tetrahydrofuran (15 mL), 10percent palladium/carbon (50 mg) was added, and reacted under hydrogen conditions for 3 hours. The reaction was monitored by TLC and was filtered through celite. The filtrate was concentrated to give product 22B (319 mg, yield 90.0percent).
Reference: [1] Synthetic Communications, 2012, vol. 42, # 2, p. 213 - 222
[2] RSC Advances, 2015, vol. 5, # 113, p. 93433 - 93437
[3] Green Chemistry, 2017, vol. 19, # 14, p. 3400 - 3407
[4] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[5] Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry, 2011, vol. 41, # 1, p. 114 - 119
[6] Patent: CN107540636, 2018, A, . Location in patent: Paragraph 0234-0236
[7] Chemical Science, 2018, vol. 9, # 45, p. 8553 - 8560
[8] Collection of Czechoslovak Chemical Communications, 1934, vol. 6, p. 211,218
[9] Journal of the American Chemical Society, 1951, vol. 73, p. 3100,3101
[10] Journal of Materials Chemistry A, 2018, vol. 6, # 34, p. 16680 - 16689
  • 2
  • [ 110-85-0 ]
  • [ 100-00-5 ]
  • [ 6269-89-2 ]
YieldReaction ConditionsOperation in experiment
81% at 100℃; for 6 h; A solution of l-chloro-4-nitro benzene (650g, 4.140mol) in diglyme (1L) was added to a solution of piperazine (2.84Kg, 33.12mol) in diglyme (500mL) at 100°C and the resultant mass was stirred at 100°C for 6h. The mixture was cooled to 40-45°C, water (5L) was added; warmed to room temperature and stirred for lh. The precipitated solid was filtered, washed with water (IL), pet ether (500mL) and dried to give 700g (81percent) of 4-nitro phenyl piperazine G as yellow colour solid. [TLC system: Ethyl acetate: pet ether (3 :7); Rf value: 0.70].
81% at 100℃; for 6 h; Large scale A solution of 1-chloro-4-nitro benzene (650g, 4.l4Omol) in diglyme (1L) was added to a solution of piperazine (2.84Kg, 33.l2mol) in diglyme (500mL) at 100°C and the resultant mass was stirred at 100°C for 6h. The mixture was cooled to 40-45°C, water (5L) wasadded; warmed to room temperature and stirred for lh. The precipitated solid was filtered, washed with water (1L), pet ether (500mL) and dried to give 700g (81percent) of 4-nitro phenyl piperazine G as yellow colour solid. [TLC system: Ethyl acetate: pet ether (3:7); &value:0.70].
80% With tetra-(n-butyl)ammonium iodide; potassium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere j00133J 4-Chioro nitrohenzene (1.57 g, 10 mrnoi, I eq). piperazine (1.12 g, 13 mmol. 1.3 eq), potassium carbon (2.07 g, 15 mmoi, 1.5 eq) and tetra-N-butyl ammonium iodide (37 mg, 0.1 mrnol, 0.01 eq) were added to a reaction vessel, then dimethyl sulfoxide (25 mL) was added under an inert atmosphere. The resulting suspension was heated at 120 °C overnight. The reaction mixture was cooled, diluted with ice water (40 mL). neutralized with 2N hydrochloric acid and then extracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to yield i-(4-nitrophenvl)piperazine as a yellow solid. Yield 1.65 g, 80percent; ‘H NMR (CDCI3, 500M1-Tz) d 301-303 (t, 4H. J 5.15 Hz), 3.37-3.39 (t, 4H, 4.9 FIz). 6.81-6.82 (d, 2H, J:::: 9.3 Hz). 8.11-8. 13 (d, 2H, 9.35 Hz).
80% With tetra-(n-butyl)ammonium iodide; potassium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere 4-Chloro nitrobenzene (1.57 g, 10 mmol, 1 eq), piperazine (1.12 g, 13 mmol, 1.3 eq), potassium carbonate (2.07 g, 15 mmol, 1.5 eq) and tetra-N-butyl ammonium iodide (37 mg, 0.1 mmol, 0.01 eq) were added to a reaction vessel, then dimethyl sulfoxide (25 mL) was added under an inert atmosphere. The resulting suspension was heated at 120 °C overnight. The reaction mixture was cooled, diluted with ice water (40 mL), neutralized with 2N hydrochloric acid and then extracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with water and brine, dried over Na2S04, and concentrated under reduced pressure to yield l-(4-nitrophenyl)piperazine as a yellow solid. Yield = 1.65 g, 80percent; *H N.V1R (CDC13, 500 MHz) δ 3.01-3.03 (t, 4H, ./ 5.15 Hz), 3.37-3.39 (t, 4H, 4.9 Hz), 6.81-6.82 (d, 2H, J ------ 9.3 Hz), 8, 1 1 -8.13 (d, 2H, .7 = 9.35 Hz).
70%
Stage #1: Reflux
Stage #2: With sodium hydroxide In water at 10 - 20℃;
Reference Example 29; 1-(4-nitro-phenyl)-piperazine; A solution of 1-chloro-4-nitrobenzene (15 g, 94.5 mmol) in 1-butanol (75 mL) was added over 20-30 minutes to a refluxing solution of anhydrous piperazine (24.4 g, 284 mmol) in 1-butanol (75 mL) and the mixture maintained at reflux overnight. The solvent was removed under reduced pressure to afford a solid, to which was added 2N hydrochloric acid (400 mL). The aqueous layer was washed twice with ethyl acetate, cooled to below 10° C. and basified with a cold solution of 40percent sodium hydroxide to pH 10, keeping temperature below 20° C. The mixture was extracted with ethyl acetate (4.x.200 mL) then the combined organic layers were washed with brine and dried over sodium sulfate. Filtration and concentration under reduced pressure afforded 1-(4-nitro-phenyl)-piperazine (13.7 g, 70percent) as a yellow solid.

Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[2] Organic Letters, 2016, vol. 18, # 20, p. 5272 - 5275
[3] Patent: WO2016/79536, 2016, A1, . Location in patent: Page/Page column 34-35
[4] Patent: WO2017/203270, 2017, A1, . Location in patent: Page/Page column 30; 33; 34
[5] Patent: WO2018/45106, 2018, A1, . Location in patent: Paragraph 00133
[6] Patent: WO2018/45104, 2018, A1, . Location in patent: Paragraph 00158
[7] Patent: US2011/9390, 2011, A1, . Location in patent: Page/Page column 16-17
[8] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 7, p. 650 - 654
[9] Journal of the American Chemical Society, 1951, vol. 73, p. 3100,3101
[10] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5661 - 5665
[11] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11357 - 11360
  • 3
  • [ 182618-86-6 ]
  • [ 6269-89-2 ]
YieldReaction ConditionsOperation in experiment
90% With trifluoroacetic acid In dichloromethane at 20℃; for 1 h; Step: 5bSynthesis of l-(4-Nitro-phenyl)-piperazine.Procedure:TFA (6ml) and was added to a solution of 4-(4-Nitro-phenyl)-piperazine-l -carboxylic acid tert-butyl ester (2g, 0.07166mol) in DCM (20ml) and stirred for lhr at RT. The reaction was monitored by TLC (10percent MeOH: CHC13). The reaction mixture was concentrated and the residue was washed with water and and dried at reduced pressure to afford a 2.2g (90percent yield) of solid l-(4-Nitro-phenyl)-piperazine.
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2549 - 2552
[2] Patent: WO2012/59932, 2012, A1, . Location in patent: Page/Page column 118
[3] Tetrahedron Letters, 1997, vol. 38, # 23, p. 4091 - 4094
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3086 - 3090
  • 4
  • [ 110-85-0 ]
  • [ 586-78-7 ]
  • [ 6269-89-2 ]
YieldReaction ConditionsOperation in experiment
55% With potassium carbonate In N,N-dimethyl-formamideReflux A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 1.16 g (6 mmol) piperazine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 30:1, 15:1, 10:1 ) to afford 566 mg (55percent) yellow solid.
49.4% With potassium phosphate In isopropyl alcohol for 48 h; Heating / reflux 8.10 g p-nitro-bromobenzene was added into a 250 ml round-bottom flask containing 50 mL isopropanol, then 7.00 g anhydrous piperazine, 15.00g anhydrous K3PO4 and 4 ml glycol was added, then 2.00g CuI was added as catalyster under nitrogen atmosphere (the small-scale reaction was carried out in the absence of nitrogen atmosphere, the results showed that the yield was low probably because of the oxidation of CuI).
The reaction mixture was refluxed for two days under nitrogen atmosphere.
The crude product was filterd and concentrated.
The concentrate was extracted with chloroform/water.
The chloroform extract was dried by anhydrous Na2SO4.
Based on higher polarity of product and lower polarity of the starting material, the extract was purified by column-chromatography with gradient elution of petroleum ether: ethyl acetate: ethanol in differ ratio, concentrated the elude, to produce N-4-nitro-phenyl piperazine as yellow solid (4.10g, 49.4percent yield). Mp: 126-128°C (lit.: 130-132°C.)
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[3] Patent: EP2036909, 2009, A1, . Location in patent: Page/Page column 11-12
[4] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5661 - 5665
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6666 - 6678
[6] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 117 - 125
  • 5
  • [ 110-85-0 ]
  • [ 350-46-9 ]
  • [ 6269-89-2 ]
YieldReaction ConditionsOperation in experiment
85.1% Reflux A mixture of 4-nitrofluorobenzene (70.7 g), piperazine (49.8 g) and acetonitrile (400 mL) was stirred at refluxing overnight. The reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool down to room temperature, basified with saturated K2CO3 solution (500 mL), and then extracted with ethyl acetate. The combined organic layers was washed with water and brine, dried over Na2SO4, and concentrated under reduced pressure to afforded 1 -(4-nitrophenyl)piperazme 2 (88.4 g, 85.1percent, M+.H+= 208.5) as a yellow solid.
Reference: [1] RSC Advances, 2015, vol. 5, # 113, p. 93433 - 93437
[2] Patent: WO2015/6754, 2015, A2, . Location in patent: Paragraph 00285
[3] Patent: US5008267, 1991, A,
[4] Patent: WO2007/53095, 2007, A1, . Location in patent: Page/Page column 52
[5] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 12, p. 3513 - 3516
  • 6
  • [ 821-48-7 ]
  • [ 100-01-6 ]
  • [ 6269-89-2 ]
YieldReaction ConditionsOperation in experiment
14% With potassium carbonate In butan-1-ol PREPARATION 6
1-(4-Nitrophenyl)Piperazine
This compound was prepared according to the procedure of Preparation 1.
A mixture of 100.0 g (0.56 mol) of bis(2-chloroethyl)amine hydrochloride, 77.3 g (0.56 mol) of p-nitroaniline and 160.0 g (1.2 mol) of solid potassium carbonate in a total volume of 1 L of n-butanol gave an oil that solidified upon trituration with ethyl acetate.
The hydrochloric acid salt was converted to the base which solidified.
The solid was triturated with ethyl ether/methanol to give 16.1 g (14percent) of the product.
Concentration of the ethyl ether/methanol mixture gave 1.3 g as a light yellow solid, mp 121°-123° C.
Anal. Calculated for C10 H13 N3 O2: C, 57.96; H, 6.32; N, 20.28. Found: C, 57.84; H, 6.29; N, 20.37.
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 46, p. 7921 - 7922
[2] Patent: US5086055, 1992, A,
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6766 - 6769,4
[4] European Journal of Pharmaceutical Sciences, 2016, vol. 88, p. 166 - 177
  • 7
  • [ 110-85-0 ]
  • [ 100-25-4 ]
  • [ 6269-89-2 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
  • 8
  • [ 350-46-9 ]
  • [ 6269-89-2 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2549 - 2552
[2] Tetrahedron Letters, 1997, vol. 38, # 23, p. 4091 - 4094
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 8, p. 3086 - 3090
[4] Patent: WO2012/59932, 2012, A1,
  • 9
  • [ 110-85-0 ]
  • [ 636-98-6 ]
  • [ 6269-89-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 22, p. 6245 - 6249
  • 10
  • [ 586-78-7 ]
  • [ 6269-89-2 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2549 - 2552
  • 11
  • [ 43204-63-3 ]
  • [ 100-01-6 ]
  • [ 6269-89-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1934, vol. 6, p. 211,218
  • 12
  • [ 6269-89-2 ]
  • [ 540-51-2 ]
  • [ 5521-38-0 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine In chloroform at 50℃; A mixture of 1-(4-nitrophenyl)piperazine (5, 2.5 g, 12 mmol), 2-bromoethanol (1.28 mL, 18 mmol) and Et3N (1.6 mL, 18 mmol) wereheated at 50° C in CHCl3 (15 mL) for 30-35 h. Reaction mixturewasthen concentrated under reduced pressure and residue was dissolvedin EtOAc (15 mL). The organic layer was washed with water(10 mL x 3). The combined organic layer was then dried (anhyd.Na2SO4) and was concentrated under reduced pressure. The solidseparated out was washed with distilled hexane and again driedunder high vacuum. The pure yellow crystals were recrystallizedusing EtOAc/Hexane in excellent yield (yield 97percent); mp: 180-184 °C;IR (KBr) v (cm-1): 3019, 2399, 2344, 1597, 1535, 1507, 1476, 1350,1330; 1H NMR (400 MHz, CDCl3): δ 8.12-8.09 (2H, m), 6.83-6.81(2H, m), 3.69 (2H, t, J 5.2 Hz), 3.47-3.43 (4H, m), 2.67 (4H, t,J 5.1 Hz), 2.62 (2H, t, J 5.4 Hz), 2.33 (1H, bs); 13C NMR (100 MHz,CDCl3): δ 154.7, 138.5, 125.9, 112.7, 59.3, 57.9, 52.4, 47.0; HRMS (ESIpositive) m/z calcd. for C12H17N3O3 [M+H]+: 252.1348, found,252.1347; Anal calcd. for C12H17N3O3; C, 57.36; H, 6.82; N, 16.72,found: C, 57.13; H, 6.64; N, 16.60.
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 132, p. 204 - 218
[2] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 1, p. 63 - 70
[3] Patent: WO2005/9978, 2005, A1, . Location in patent: Page 59
[4] Patent: WO2005/42518, 2005, A2, . Location in patent: Page/Page column 59
  • 13
  • [ 6269-89-2 ]
  • [ 100-39-0 ]
  • [ 16155-08-1 ]
YieldReaction ConditionsOperation in experiment
77% With triethylamine In acetonitrile for 12 h; Reflux Benzyl bromide (1.42 mL, 11.6 mmol) was added to a solution of l-(4- nitrophenyl)piρerazine (2.0 g, 11.6 mmol) in acetonitrile (30 mL) with triethylamine (2.68mL, 19.32 mmol) and refluxed for 12 h. The mixture was concentrated in vacuo and the residue partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford l-benzyl-4-(4-nitrophenyl)piperazine (2.2 g, 77percent).
Reference: [1] Patent: WO2009/130481, 2009, A1, . Location in patent: Page/Page column 136-137
  • 14
  • [ 6269-89-2 ]
  • [ 100-44-7 ]
  • [ 16155-08-1 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 2005, vol. 55, # 3, p. 145 - 152
  • 15
  • [ 24424-99-5 ]
  • [ 6269-89-2 ]
  • [ 182618-86-6 ]
YieldReaction ConditionsOperation in experiment
77% With N-ethyl-N,N-diisopropylamine In 1,4-dioxane A.
4-(4-Nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl Ester
1-(4-Nitrophenyl)piperazine (20 g, 96.5 mmol) (Acros Organics) was dissolved in dioxane (300 mL), and diisopropylethylamine (13.7 g, 106 mmol) (Aldrich) was added.
To the solution was added di-tert-butyl dicarbonate (21 g, 96.6 mmol).
After stirring overnight, the mixture was poured into water (1 L) and stirred for 10 minutes.
The aqueous layer was extracted with ethyl acetate (2*500 mL) and the combined organic extracts were dried over MgSO4, filtered, and evaporated in vacuo.
The residue was recrystallized from a mixture of ethyl acetate/hexane to provide 4-(4-nitrophenyl)-1-piperazinecarboxylic acid, 1,1-dimethylethyl ester (22.7 g, 77percent).
Reference: [1] Patent: US2002/151554, 2002, A1,
[2] Archiv der Pharmazie, 2000, vol. 333, # 8, p. 267 - 274
[3] Patent: US2001/14682, 2001, A1,
[4] Patent: EP1215208, 2002, A2, . Location in patent: Example C(101)
[5] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[6] Patent: CN107540636, 2018, A, . Location in patent: Paragraph 0211-0213
[7] Patent: WO2008/141976, 2008, A1, . Location in patent: Page/Page column 62
[8] Patent: WO2009/141386, 2009, A1, . Location in patent: Page/Page column 71-72
[9] Patent: US2003/229067, 2003, A1, . Location in patent: Page 32
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  • [ 182618-86-6 ]
Reference: [1] Patent: US2003/105107, 2003, A1,
  • 17
  • [ 24424-99-5 ]
  • [ 6269-89-2 ]
  • [ 7087-68-5 ]
  • [ 182618-86-6 ]
Reference: [1] Patent: US2003/73668, 2003, A1,
  • 18
  • [ 6269-89-2 ]
  • [ 74853-08-0 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[2] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
  • 19
  • [ 6269-89-2 ]
  • [ 112559-81-6 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
[2] Tetrahedron Letters, 1999, vol. 40, # 31, p. 5655 - 5659
  • 20
  • [ 6269-89-2 ]
  • [ 170911-92-9 ]
Reference: [1] Patent: US5780480, 1998, A,
  • 21
  • [ 6269-89-2 ]
  • [ 170911-92-9 ]
Reference: [1] Patent: CN107540636, 2018, A,
[2] Patent: WO2008/141976, 2008, A1,
[3] Patent: US2003/229067, 2003, A1,
  • 22
  • [ 24424-99-5 ]
  • [ 6269-89-2 ]
  • [ 170911-92-9 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[2] Patent: WO2009/141386, 2009, A1,
  • 23
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  • [ 124-63-0 ]
  • [ 442549-42-0 ]
  • [ 63178-61-0 ]
Reference: [1] Patent: US2004/87575, 2004, A1,
[2] Patent: US2003/13708, 2003, A1,
[3] Patent: US2004/110745, 2004, A1,
  • 24
  • [ 6269-89-2 ]
  • [ 442549-42-0 ]
Reference: [1] Patent: WO2012/59932, 2012, A1,
  • 25
  • [ 6269-89-2 ]
  • [ 1439934-41-4 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 113, p. 93433 - 93437
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