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Product Details of [ 626-39-1 ]

CAS No. :626-39-1 MDL No. :MFCD00000080
Formula : C6H3Br3 Boiling Point : -
Linear Structure Formula :- InChI Key :YWDUZLFWHVQCHY-UHFFFAOYSA-N
M.W :314.80 Pubchem ID :12279
Synonyms :

Calculated chemistry of [ 626-39-1 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.54
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.69
Log Po/w (XLOGP3) : 4.51
Log Po/w (WLOGP) : 3.97
Log Po/w (MLOGP) : 4.51
Log Po/w (SILICOS-IT) : 3.9
Consensus Log Po/w : 3.92

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.13
Solubility : 0.00235 mg/ml ; 0.00000747 mol/l
Class : Moderately soluble
Log S (Ali) : -4.23
Solubility : 0.0185 mg/ml ; 0.0000587 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.93
Solubility : 0.00366 mg/ml ; 0.0000116 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.5

Safety of [ 626-39-1 ]

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

Application In Synthesis of [ 626-39-1 ]

* 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 [ 626-39-1 ]
  • Downstream synthetic route of [ 626-39-1 ]

[ 626-39-1 ] Synthesis Path-Upstream   1~51

  • 1
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  • [ 124-38-9 ]
  • [ 633-12-5 ]
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  • 2
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  • [ 633-12-5 ]
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  • 3
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  • [ 108-86-1 ]
  • [ 591-17-3 ]
  • [ 1611-92-3 ]
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  • 4
  • [ 626-39-1 ]
  • [ 626-44-8 ]
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[3] Journal of the American Chemical Society, 1997, vol. 119, # 17, p. 3907 - 3917
[4] Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3757 - 3766
[5] Synthetic Communications, 2012, vol. 42, # 2, p. 170 - 175
[6] Canadian Journal of Chemistry, 2002, vol. 80, # 8, p. 908 - 916
[7] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 150 - 158
  • 5
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  • [ 626-00-6 ]
  • [ 626-44-8 ]
  • [ 149428-64-8 ]
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  • 6
  • [ 127-19-5 ]
  • [ 626-39-1 ]
  • [ 14401-73-1 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 6, p. 2104 - 2117
[2] Journal of Organic Chemistry, 1998, vol. 63, # 21, p. 7399 - 7407
[3] Molecular Crystals and Liquid Crystals, 2007, vol. 462, # 1, p. 159 - 167
[4] Journal of the American Chemical Society, 1992, vol. 114, # 3, p. 1018 - 1025
[5] Angewandte Chemie - International Edition, 2004, vol. 43, # 44, p. 5936 - 5940
  • 7
  • [ 626-39-1 ]
  • [ 141-78-6 ]
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  • [ 14401-73-1 ]
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[2] Australian Journal of Chemistry, 1997, vol. 50, # 4, p. 425 - 434
  • 8
  • [ 626-39-1 ]
  • [ 75-36-5 ]
  • [ 108-36-1 ]
  • [ 14401-73-1 ]
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[2] Australian Journal of Chemistry, 1997, vol. 50, # 4, p. 425 - 434
  • 9
  • [ 626-39-1 ]
  • [ 7567-63-7 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 30, p. 7120 - 7132
[2] Angewandte Chemie - International Edition, 2005, vol. 44, # 35, p. 5679 - 5682
[3] Macromolecules, 2003, vol. 36, # 22, p. 8225 - 8230
[4] Journal of the American Chemical Society, 2004, vol. 126, # 13, p. 4094 - 4095
[5] Angewandte Chemie - International Edition, 1998, vol. 37, # 12, p. 1714 - 1717
[6] Synthetic Communications, 1996, vol. 26, # 12, p. 2309 - 2316
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1995, # 18, p. 2275 - 2280
[8] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 1251 - 1258
[9] Chemistry - A European Journal, 2011, vol. 17, # 11, p. 3262 - 3273
[10] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 426 - 431
[11] Journal of the American Chemical Society, 2012, vol. 134, # 1, p. 734 - 742
[12] Journal of Materials Chemistry, 2012, vol. 22, # 7, p. 3075 - 3081
[13] Supramolecular Chemistry, 2011, vol. 23, # 7, p. 501 - 508
[14] Chemical Communications, 2012, vol. 48, # 88, p. 10877 - 10879
[15] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 107, p. 377 - 385
[16] Macromolecules, 2013, vol. 46, # 12, p. 4754 - 4763
[17] Chinese Journal of Chemistry, 2012, vol. 30, # 12, p. 2861 - 2868
[18] Chemical Communications, 2014, vol. 50, # 91, p. 14175 - 14178
[19] Chemical Communications, 2016, vol. 52, # 87, p. 12881 - 12884
[20] RSC Advances, 2017, vol. 7, # 75, p. 47681 - 47688
[21] Journal of Materials Chemistry C, 2017, vol. 5, # 21, p. 5135 - 5142
[22] Organic Letters, 2018, vol. 20, # 3, p. 542 - 545
[23] European Journal of Inorganic Chemistry, 2018, vol. 2018, # 22, p. 2533 - 2540
[24] Chemical Communications, 2018, vol. 54, # 67, p. 9274 - 9277
[25] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 2242 - 2249
  • 10
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  • [ 1066-54-2 ]
  • [ 7567-63-7 ]
Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 44, p. 11985 - 11998
[2] Chemical Communications, 2016, vol. 52, # 81, p. 12032 - 12035
[3] Tetrahedron Letters, 2001, vol. 42, # 14, p. 2697 - 2699
  • 11
  • [ 626-39-1 ]
  • [ 74-86-2 ]
  • [ 7567-63-7 ]
Reference: [1] Chemistry Letters, 1998, # 11, p. 1081 - 1082
  • 12
  • [ 626-39-1 ]
  • [ 7511-49-1 ]
Reference: [1] Patent: CN107915753, 2018, A,
  • 13
  • [ 626-39-1 ]
  • [ 14862-52-3 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With n-butyllithium In hexanes; diethyl ether at -78℃; for 0.333333 h; Cooling with acetone-dry ice
Stage #2: With hexachloroethane In hexanes; diethyl ether at -78 - 20℃; for 3.5 h;
A solution of 1,3,5-tribromobenzene (9.44 g, 30 mmol) in 120 mL of ether was cooled to -78 °C in a dry ice/acetone bath. n-Butyllithium (13.2 mL of 2.5 M solution in hexanes, 33 mmol) was added dropwise over 10 min. The resulting mixture was stirred at -78 °C for an additional 10 min, then hexachloroethane (7.15 g, 30.2 mmol) was added in small portions over 3 min. The reaction mixture was then stirred for 15 min at -78 °C, followed by 3.2 h at rt. The mixture was partitioned between 100 mL of water and 100 mL of EtOAc. The aqueous layer was separated and extracted with an additional 100 mL of EtOAc. The combined organic layers were then dried over MgSO4 filtered, and concentrated in vacuo to give 472 as a pale brown solid (7.72 g, 95percent): 1H NMR (CDCl3, 300 MHz) δ 7.57 (t, 1 H), 7.47 (d, 2 H).
Reference: [1] Patent: EP1208091, 2006, B1, . Location in patent: Page/Page column 23
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 727 - 739
[3] Tetrahedron Letters, 1997, vol. 38, # 9, p. 1559 - 1562
  • 14
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  • [ 19752-57-9 ]
Reference: [1] Chemistry - A European Journal, 2008, vol. 14, # 16, p. 4948 - 4960
[2] Synthesis, 2003, # 1, p. 79 - 90
[3] Chemistry - A European Journal, 2003, vol. 9, # 20, p. 5011 - 5022
[4] Helvetica Chimica Acta, 2017, vol. 100, # 4,
[5] Helvetica Chimica Acta, 2000, vol. 83, # 11, p. 2865 - 2883
[6] Journal of Organic Chemistry, 2004, vol. 69, # 10, p. 3336 - 3339
[7] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5327 - 5332
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3436 - 3441[9] Angew. Chem., 2014, vol. 126, # 13, p. 3504 - 3509,6
  • 15
  • [ 626-39-1 ]
  • [ 98-80-6 ]
  • [ 16372-96-6 ]
YieldReaction ConditionsOperation in experiment
96% With potassium carbonate In ethanol; water at 50℃; for 5 h; Inert atmosphere; Schlenk technique General procedure: A Schlenk tube was charged with a suspension of aryl halide (1.0mmol), arylboronic acid (1.2 mmol), potassium carbonate (276 mg,2.0 mmol) and Pd/HCCP-DABP (20 mg, 0.3 molpercent) in EtOH-H2O (3 mL,v:v=1:1), evacuated, and backfilled with nitrogen. The resulting reaction mixture was stirred at 50 °C for 2.5 h. After completion of the reaction,the mixture was cooled and extracted with CH2Cl2. The combined organic phase was dried, evaporated and purified by column chromatographyon silica gel to give the coupling product. The aqueous phasewas filtered and the solid was washed with CH2Cl2 and reused in further reactions as the recovered catalyst.
69% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 90℃; for 6 h; 1,3,5-tribromobenzene (14.6 g, 46 mmol), phenylboronicacid (5.6 g, 46mmol), Pd (PPh3) 4 (1.6 g, 1.4mmol), K2CO3 (19.2 g, 14mmol), THF (100 ml), put H2O (50 ml) and the mixture was stirred under reflux for 6 hours in 90 . When the reaction is complete cool the temperature of the reaction to room temperature, and was extracted with CH2Cl2 and water wipe. The organic layer was dried over MgSO4, isolated by using silicagel column The concentrated and the organic product generated by Core 1-1-8-C1 9.8 g (69percent) is obtained.
65% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water for 8 h; Reflux; Inert atmosphere In an argon atmosphere, a mixture of 1,3,5-tribromobenzene (9.44 g, 30 mmol), phenylboronic acid (1.22 g, 10 mmol), tetrakis(triphenylphosphine) palladium (231 mg, 0.2 mmol), DME (50 mL), and a 2 M aqueous solution of sodium carbonate (10 mL, 20 mmol) was allowed to react for 8 h while refluxing under heating. After cooling the reaction solution to room temperature, the water layer was separated and removed, and the organic layer was dried over magnesium sulfate. Then, the insolubles were removed by filtration, and the organic solvent was evaporated off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the intermediate B-9 (2.03 g, yield: 65percent).
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 16 h; Intermediate I-5 4.31 g (10 mmol), 2-Chloro-4,6-diphenyl-1,3,5-triazine 2.68 g (10 mmol), Pd (PPh3) 4 ( tetra-kis(triphenylphosphine) palladium ) 0.58 g ( 0.5 mmol ) and 4.14 g K2CO3 ( 30 mmol ) and THF / H2O ( 2/1 volume ratio) mixed solution Was dissolved in 60 mL , it was stirred at 80°C for 16 hours. After cooling to room temperature the reaction solution was added to 40 mL water in aButyl ether and extracted three times with 50 mL. The combined organic layers were dried over magnesium sulfate, and the resulting glass by evaporation of the solventSeparating residues jelgwan by silica chromatography to give the compound 2A 3.38 g ( yield 63percent) . The resulting compound isAnd MS / FAB One It was confirmed.Instead of Intermediate I-5 using a phenylboronic acid and 2-Chloro-4,6-diphenyl-1,3,5-triazine in place of 1,3,5- tribromobenzene It was used except that by using the same method as that of Compound 2A of the above Synthesis Example 1 , Intermediate A-20To give the 1.97 g ( 63percent yield). The resulting compound was confirmed by LC-MS
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; for 12 h; 12.6 g (40 mmol) of 1,3,5-tribromobenzene, 3.66 g (30 mmol) of phenylboronic acid,3.4 g (1.5 mmol) of Pd (PPh3) 4 and 12.6 g (90 mmol) of K2CO3 were dissolved in 350 mL of a THF / H2O mixed solvent (in a volume ratio of 2/1)The reaction solution was stirred at a temperature of 80 ° C for 12 hours.The resulting reaction solution was cooled to room temperature,The organic layer was extracted three times by using 60 mL of water and 60 mL of ethyl acetate.The organic layer thus collected was dried with magnesium sulfate,The residue obtained after the solvent was evaporated from the silica gel column chromatography was used to separate and purify the residue,To obtain 5.9 g of intermediate I-8 (yield: 63percent).The compounds thus produced were determined by using LC-MS.
60.56% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In toluene for 3 h; Reflux [173] After mixing 1,3,5-tribromobenzen (40 g, 127.06 mmol), phenyl boronic acid (17.04 g, 139.7 mmol), PdCl(PPh3)2 (1.78 g, 2.54 mmol), toluene 500 mL, and Na2CO3 (2 M, 130 mL), the mixture was stirred under reflux. After 3 hours, the mixture was cooled to room temperature, and distilled water was added. The mixture was extracted with ethyl acetate (EA) and dried with magnesium sulfate. After drying under reduced pressure, the resulting product was separated through a column to obtain compound 1-8 (24 g, 76.9 mmol, 60.56 percent).
55% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 90℃; for 8 h; Inert atmosphere Next, under an Ar atmosphere,In a 1 L three-necked flask,10.0 g of 1,3,5-tribromobenzene,7.20 g of phenyl boronic acid, 9.54 g of Pd (PPh 3) 4,And 20.4 g of sodium carbonate were added,In a mixed solvent of 430 mL of toluene and 210 mL of water at 90 ° C.,And the mixture was heated and stirred for 8 hours.After air cooling,Water was added to separate the organic layer and the solvent was distilled off.The obtained crude product was purified by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane)Recrystallization was performed with a toluene / hexane mixed solvent,5.45 g (55percent yield) of compound F as a white solid was obtained.

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  • 16
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  • [ 98-80-6 ]
  • [ 612-71-5 ]
  • [ 16372-96-6 ]
  • [ 103068-20-8 ]
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  • 17
  • [ 626-39-1 ]
  • [ 71-43-2 ]
  • [ 16372-96-6 ]
  • [ 103068-20-8 ]
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  • 18
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  • [ 124-41-4 ]
  • [ 20469-65-2 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 31, p. 5569 - 5572
  • 19
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  • [ 124-41-4 ]
  • [ 621-23-8 ]
  • [ 20469-65-2 ]
  • [ 74137-36-3 ]
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  • [ 149428-64-8 ]
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  • 24
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  • [ 149428-64-8 ]
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  • [ 626-39-1 ]
  • [ 68-12-2 ]
  • [ 56990-02-4 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: With magnesium In tetrahydrofuran at 20℃; for 0.0833333 h; Inert atmosphere; Large scale
Stage #2: With methylmagnesium chloride In tetrahydrofuran for 3.5 h; Reflux; Inert atmosphere; Large scale
Stage #3: at 0 - 10℃; for 2 h; Inert atmosphere; Large scale
under the protection of nitrogen gas the 25kg of tetrahydrofuran, 400g of tribromobenzene and Fresh magnesium tablets 500g were added to reaction kettle and stirred for 5min at room temperature. cooled down the reaction to 0°C then catalytic amount 120g of Methylmagnesium chloride was added and raised the temperature to reflux. After the initiation , control temperature to 55-60 ° C for adding tribromobenzene 4kg in batches , after about 3 hours of addition the temperature was raised to reflux insulation for 30 minutes; cooled down the reaction to 0°C, then 1.5kf of DMF was added drop wise and addition was completed within 1hour. And then slowly raising temperature to 5-10 ° C and incubated for 1 hour. After the reaction, add 15percent hydrochloric acid for acidification , temperature controlled at 10 ° C for 1 hour. The solution is then allowed to stand for separation. Water phase was extracted with ethyl acetate , The organic phase was combined, concentrated, the17.5kg of petroleum ether was added, the temperature was raised to reflux and then cooled to 0 ° C, and the temperature was maintained for 1 hour. The product subjected to centrifugation and drying to give 3,5-dibromobenzaldehyde. Content of 99.5percent (GC), the yield of 95percent.
70%
Stage #1: With n-butyllithium In diethyl ether at -78℃; for 0.75 h; Inert atmosphere; Schlenk technique
Stage #2: for 1 h; Inert atmosphere; Schlenk technique
Compound 2 was synthesized according to the literature [22].Briefly, a suspension of 1,3,5-tribromobenzene (4.0 g,12.7 mmol) inanhydrous diethyl ether (100 mL) at -78 C was treated dropwisewith butyllithium (2.5 M, 5.3 mL, 13.5 mmol). After 45 min, DMF(2.8 g, 38.3 mmol) was droped into the mixture, which was thenstirred for another 1 h. Diluted HCl (40 mL, 2 mol/L) was added,then organic phase was removed, and a brown solid was obtained.The crude product was purified by column chromatography (silicagel) using DCM/n-hexane = 1/10 as eluent and recrystallized fromdiethyl ether/n-hexane to give needle compound 2 (2.34 g, 70percent).
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YieldReaction ConditionsOperation in experiment
45% With magnesium In hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide STR12
Preparation of 3,5-dibromobenzaldehyde
1.344G (56 mM) of magnesium was added to a solution of 15-7G(50 mM) of 1,3,5-tribromobenzene and the mixture was stirred at room temperature after 5 hours, most of the metal was digested.
To the resulting brown Grignard solution was added 7.5 mL (0.1M) of N,N-dimethylformamide at 0° under nitrogen.
The resulting mixture was stirred overnight at room temperature.
Solvent was removed in vacuo at room temperature.
The residue was taken up in 200 mL of ethyl acetate and washed with 6*50 mL of saturated sodium chloride solution, dried over anhydrous MgSO4.
Solvent was removed to give a crude solid, which was dissolved in minimum amount of CH2 Cl2 and applied on silica gel.
Elution with 1:9 mixture of ether:hexane containing methylene chloride gave 45percent yield of the desired aldehyde as white solid.
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[2] Patent: US5294610, 1994, A,
  • 32
  • [ 626-39-1 ]
  • [ 97165-77-0 ]
YieldReaction ConditionsOperation in experiment
75%
Stage #1: With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at -15℃; for 0.25 h;
Stage #2: With N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2 h;
Stage #3: With ammonia; iodine In tetrahydrofuran; water at 20℃; for 2 h;
General procedure: To a flask containing dried LiCl (0.35 g, 8.24 mmol) was added iPrMgCl (2 M in THF, 4.1 mL) and THF (5 mL) at 15° C. After beingstirred for 15 min, 3-bromo-1-benzonitrile (1.46 g, 8.03 mmol) inTHF (1 mL) was added to the reaction mixture and the obtainedmixture was stirred for 15 min. Then, DMF (1.3 mL, 12 mmol) wasadded at 0° C and the mixture was stirred for 2 h. Then, aq NH3 (7 mL, 28-30percent) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After being stirred for 2 h at room temperature, the reactionmixture was poured into satd aq Na2SO3 solution and was extracted with CHCl3 (3∗30 mL). The organic layer was dried over Na2SO4 and filtered. After removal of the solvent, the residue waspurified by short column chromatography on silica gel (eluent:hexane/ethyl acetate=9:1, v/v) to provide pure 1,3-dicyanobenzene (0.73 g) in 71percent yield. Most nitriles mentioned in this work are commercially availableand were identified by comparison with the authentic samples.
Reference: [1] Tetrahedron, 2013, vol. 69, # 5, p. 1462 - 1469
  • 33
  • [ 626-39-1 ]
  • [ 99768-12-4 ]
  • [ 50446-44-1 ]
Reference: [1] Patent: US2015/152123, 2015, A1,
[2] Patent: EP2876112, 2015, A1,
  • 34
  • [ 626-39-1 ]
  • [ 343239-58-7 ]
Reference: [1] Patent: US2018/222844, 2018, A1,
  • 35
  • [ 626-39-1 ]
  • [ 145691-59-4 ]
Reference: [1] Australian Journal of Chemistry, 1997, vol. 50, # 4, p. 425 - 434
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 5, p. 707 - 718
  • 36
  • [ 626-39-1 ]
  • [ 62-53-3 ]
  • [ 102664-66-4 ]
YieldReaction ConditionsOperation in experiment
75% With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 72 h; Inert atmosphere; Reflux A mixture of aniline (7.4 g, 79.4 mmol), 1,3,5-tribromobenzene 3 (5.0 g, 15.88 mmol), tris(dibenzylideneacetone) dipalladium(0) [Pd2(dba)3(0), 0.11 g, 0.25 mol percent], rac-2,2'-bis(diphenylphosphino)-1,1'-binapthyl (BINAP, 0.22 g, 0.75 mol percent), and sodium t-butoxide (7.63 g, 79.4 mmol) in anhydrous toluene (250 mL) was heated to refluxing temperature under nitrogen for a period of 72 h. The reaction mixture was cooled to room temperature and washed with water (100 mL). The organic layer was dried over anhydrous sodium sulfate (Na2SO4). After evaporation of the solvent, a crude brown color solid was obtained. Excess aniline was then removed by distillation at 130 °C under reduced pressure of 101 mmHg. It was further purified by chromatography (SiO2). The resulting light brown product 1,3,5-tris(phenylamino)benzene 4, TPAB, was obtained in 75percent yield (4.18 g). FT-IR (KBr) υmax 3403 (m), 3375 (m), 3078 (w), 3019 (w), 2945 (s), 1612 (m), 1591 (vs), 1518 (m), 1496 (s), 1469 (m), 1431(w), 1456 (m), 1409 (m), 1365 (w), 1295 (m), 1269 (w), 1246 (m), 1,171 (m), 1073 (w), 1030 (w), 897 (w), 834 (w), 820 (w), 802 (w), 756 (m), 721 (w), 700 (m), 688 (m), 613 (w), and 558 (w) cm−1; UV-vis (CHCl3, 1.0 × 10−5 M) λmax (ε) 289 nm (4.80 × 104 L mol−1 cm−1); 1H-NMR (500 MHz, CDCl3) δ 7.25 (t, J = 7.8 Hz, 6H), 7.08 (d, J = 7.7 Hz, 6H), 6.92 (t, J = 7.3 Hz, 3H), 6.32 (s, 3H), and 5.60 (s, 3H, N–H); 13C-NMR (125 MHz, CDCl3) δ 145.4, 142.7, 129.3, 121.3, 118.7, and 99.0.
Reference: [1] Molecules, 2015, vol. 20, # 3, p. 4635 - 4654
[2] Molecules, 2018, vol. 23, # 8,
  • 37
  • [ 626-39-1 ]
  • [ 98-80-6 ]
  • [ 103068-20-8 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water; toluene for 24 h; Reflux 500 mL reactor to tribromobenzene 25 g (79 mmol), phenyl boronic acid 23.3 g (191 mmol), potassium carbonate 32.9 g (238 mmol), tetrakistriphenylphosphinepalladium, 6.12 g (3 mmol), distilled water 50 In the mL, 125 mL toluene and 125 mL 1,4dioxaneis stirred and refluxed for 24 hours. After completion of the reaction by separating the reaction layer and the organic layer was concentrated under reduced pressure. Recrystallized with toluene and methanol to give the 8-a 21 g. (85percent yield)
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 65℃; for 12 h; Inert atmosphere 1,3,5-Tribromobenzene (20.0 g, 63.5 mmol), phenylboronic acid (18.8 g, 154 mmol), and Pd(PPh3)4 (3.75 g, 3.25 mmol)were added to 300 mL of anhydrous THF. Then, 2M K2CO3 solution(100 mL), which was dissolved in H2O, was added to the reactionmixture. The mixture was heated to 65 °C for 12 h under nitrogen. Aftercompletion of the reaction, the reaction mixture was extracted withCHCl3 and water. The organic layer was dried with anhydrous MgSO4and filtered. The solvent was evaporated. The product was isolated viasilica gel column chromatography by using CHCl3: n-hexane (1: 20) asthe eluent to afford a white solid (12.4 g, 63percent). 1H NMR (300 MHz,CDCl3): δ = 7.70 (s, 3H), 7.60 (d, 4H), 7.44(t, 4H), 7.36 (t, 2H); EI + -Mass: 310.
62% With potassium carbonate In tetrahydrofuran; water at 70℃; for 5 h; 6.3g (20.0 mmol) of 1,3,5-tribromobenzene, 4.88g (40.0 mmol) of 1-phenylboronic acid, 2.31 g (2.0 mmol) of Pd(PPh3)1, and 16.6 g (120.0 mmol) of K2CO3 were dissolved in 120 mL of a mixed solution THF/H2O (2:1) to obtain a solution, which was then stirred at about 70°C for about 5 hours. The reaction solution was cooled to room temperature, followed by three times of extraction with 120 mL of water and 100 mL of diethylether. The organic phase was collected, and was dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 3.83 g of Intermediate I-11 (Yield: 62 percent). This compound was identified using LC-MS and NMR. C18H13Br : M+ 308.2 1H NMR (CDCl3, 400MHz) δ (ppm) 7.70 (s, 3H), 7.62-7.58 (m, 4H), 7.48-7.47 (t, 1H), 7.46-7.42 (m, 3H), 7.41-7.35 (m, 2H)
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 65℃; for 5 h; Inert atmosphere 1,3,5-Tribromobenzene (20 g, 62 mmol), Pd(PPh3)4 (3.57 g, 3.1mmol) were added to 300 mL of dry THF solution, thenphenylbronic acid (32 g, 155 mmol) and 2 M K2CO3 solution (50 mL), which was dissolved in H2O, was added to the reaction mixture. The reaction mixture was heated to 65°C for 5 h under nitrogen. After the reaction was finished,extracted with diethyl ether and water. The organic layer was dried with anhydrous MgSO4 and filterd. The solvent was evaporated. The product was isolated by silica gel column chromatography using CHCl3:hexane (1:15) eluent to afforda white solid (Yield 61percent). 1H NMR (300 MHz, CDCl3) δ 7.7(s, 3H), 7.6 (d, 4H), 7.45 (t, 4H), 7.4 (t, 2H).
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 5 h; Inert atmosphere; Reflux 1,3,5-tribromobenzene (20 g, 63 mmol) and Pd(PPh3)4 (4.36 g, 3.7 mmol) were dissolved in 500 mE of an anhydrous toluene solvent under a nitrogen atmosphere to prepare a mixture. Phenylboronic acid (17 g, 140 mmol) and 50 mE of a 2M K2C03 solution were added thereto. The obtained mixture was heated for 5 hours while being refluxed under the nitrogen atmosphere. When a reaction was complete, the resultant was extracted with chloroform and distilled water and treated with anhydrous magnesium sulfate. The obtained resulting material was purified by using chloroform:hexane (a volume ratio of 1:10) as an eluting solvent through a silica gel column to obtain 11.8 g of a white solid (a yield of 60.0percent).
55.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 80℃; Inert atmosphere 4.85 g (19.88 mmol) of Intermediate (1), 5.0 g (1.90 mmol) of 1,3,5-tribromobenzene,0.92 g of Pd (pph3) 4 was placed in a flask, and 100 ml of anhydrous toluene was added under nitrogen atmosphere and stirred.To this was added 10.0 ml of 2M K2CO3.At this time, the mixture was stirred while maintaining the temperature at about 80 .After the reaction, the reaction mixture was extracted with chloroform and water.The product in the chloroform layer was separated and purified by column chromatography using a 1: 10 mixture ratio (volume ratio) of chloroform: hexane after removal of the solvent using an evaporator,To obtain 2.702 g (yield: 55.3percent) of a white solid compound (Intermediate (2)).
51% With sodium carbonate In ethanol; water; toluene for 24 h; Heating / reflux To a solution of 1,3,5-tribromobenzene (10.0 g, 31.8 mmol), phenylboronic acid (9.68 g, 79.4 mmol), and sodium carbonate (25.3 g, 0.24 mol) in a mixture of toluene (150 ml), ethanol (30 ml), and water (75 ml), tetrakis(triphenylphosphine)palladium (1.84 g, 5 mol percent) was added.
The reaction mixture was stirred while refluxing for 24 hours and quenched with conc. HCl (20 ml).
Then it was cooled to room temperature and extracted with ethyl ether (3*50 ml).
The combined organic extracts were dried over MgSO4 and concentrated under vacuum.
Purification by column chromatography (n-hexane) afforded 3,5-(diphenyl)bromobenzene (9.82 g, 51percent)
35% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 77℃; for 16 h; Inert atmosphere Under argon atmosphere, a mixture of 1, 3, 5-tribromobenzene (1000 g, 3.18 mol), phenylboronic acid (775 g, 6.35 mol), tetrakis(triphenylphosphine)palladium(0) (147 g, 128 mmol), sodium carbonate (2021 g, 19.1 mol), water (17 L), and DME (17 L) was stirred at 77° C. for 16 h. After cooling to room temperature and adding water, the reaction liquid was extracted with toluene. The toluene layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the compound B2-1 (342 g, 35percent yield).

Reference: [1] Patent: KR2015/130797, 2015, A, . Location in patent: Paragraph 0467-0472
[2] Synthesis, 2004, # 13, p. 2181 - 2185
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[4] Patent: EP2447250, 2012, A1, . Location in patent: Page/Page column 37
[5] Bulletin of the Korean Chemical Society, 2014, vol. 35, # 10, p. 3041 - 3046
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[8] Patent: US2018/19403, 2018, A1, . Location in patent: Paragraph 0071
[9] Patent: KR2016/31310, 2016, A, . Location in patent: Paragraph 0425; 0428; 0429
[10] Patent: US6998487, 2006, B2, . Location in patent: Page/Page column 52
[11] Journal of Materials Chemistry, 2010, vol. 20, # 29, p. 6131 - 6137
[12] Patent: US2018/222844, 2018, A1, . Location in patent: Paragraph 0187; 0193; 0194
[13] Patent: WO2009/21107, 2009, A1, . Location in patent: Page/Page column 32
[14] Patent: US2010/190994, 2010, A1, . Location in patent: Page/Page column 24
[15] Patent: EP2502908, 2012, A1, . Location in patent: Page/Page column 40
[16] Journal of Nanoscience and Nanotechnology, 2016, vol. 16, # 8, p. 8796 - 8799
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[18] Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2640 - 2646
  • 38
  • [ 626-39-1 ]
  • [ 24388-23-6 ]
  • [ 103068-20-8 ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; After the starting material 1,3,5-tribromobenzene (38.59g, 122.6mmol) was dissolved in THF in a round bottom flask, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (50.03 g, 245.2mmol), Pd (PPh3) 4 (4.25g, 3.7mmol), K2CO3 (101.66g, 735.5mmol), water was added and the resulting mixture was stirred at 80 C. After the reaction was completed, the organic layer was dried and extracted with water and CH2Cl2 over MgSO4, and concentrated to a silicagel column, and the resulting compound was recrystallized product 21.61g (yield: 57percent) was obtained.
Reference: [1] Journal of Materials Chemistry, 2008, vol. 18, # 28, p. 3376 - 3384
[2] Patent: KR2015/122343, 2015, A, . Location in patent: Paragraph 0162; 0173; 0175; 0176; 0177
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  • [ 626-39-1 ]
  • [ 54098-94-1 ]
  • [ 103068-20-8 ]
Reference: [1] Dyes and Pigments, 2017, vol. 146, p. 27 - 36
  • 40
  • [ 626-39-1 ]
  • [ 98-80-6 ]
  • [ 612-71-5 ]
  • [ 16372-96-6 ]
  • [ 103068-20-8 ]
Reference: [1] ChemPlusChem, 2014, vol. 79, # 9, p. 1278 - 1283
  • 41
  • [ 626-39-1 ]
  • [ 71-43-2 ]
  • [ 16372-96-6 ]
  • [ 103068-20-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3122 - 3126
  • 42
  • [ 626-39-1 ]
  • [ 128388-54-5 ]
Reference: [1] Journal of Organic Chemistry, 2001, vol. 66, # 7, p. 2358 - 2367
[2] Patent: EP2502908, 2012, A1,
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  • [ 68-12-2 ]
  • [ 120173-41-3 ]
Reference: [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 253, p. 33 - 40
[2] Journal of the American Chemical Society, 1995, vol. 117, # 20, p. 5550 - 5560
[3] Chemistry--A European Journal, 1996, vol. 2, # 3, p. 259 - 264
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  • [ 89415-43-0 ]
  • [ 118727-34-7 ]
Reference: [1] Chemical Communications, 2010, vol. 46, # 47, p. 8932 - 8934
  • 45
  • [ 626-39-1 ]
  • [ 214360-73-3 ]
  • [ 118727-34-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 35, p. 11310 - 11315[2] Angew. Chem., 2018, vol. 130, p. 11480 - 11485,6
  • 46
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  • [ 118727-34-7 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 3, p. 763 - 776
  • 47
  • [ 626-39-1 ]
  • [ 25015-63-8 ]
  • [ 24388-23-6 ]
  • [ 196212-27-8 ]
  • [ 365564-05-2 ]
  • [ 594823-67-3 ]
  • [ 408492-26-2 ]
Reference: [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901
  • 48
  • [ 626-39-1 ]
  • [ 73183-34-3 ]
  • [ 365564-05-2 ]
YieldReaction ConditionsOperation in experiment
98% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 24 h; Inert atmosphere Synthesis of Compound 1: Anhydrous DMF (10 mL) was purged with N2 and then transferred via a cannula into a three-neck round bottomed flask charged with 1, 3, 5-tribromobenzene (1.00 g, 3.17 mmol) and bis (pinacolato) diboron (2.54 g, 9.53 mmol) . Potassium acetate (1.87 g, 19.0 mmol) and Pd(dppf)Cl2 (0.087 g, 0.12 mmol) were then quickly added into the flask. The resulting mixture was stirred vigorously and heated at 90 °C for 24 hours. After cooling down to room temperature, deionized water (120 mL) was added. Black precipitate was collected by filtration, and washed with deionized water three times, which was dried under vacuum (98percent yield) .
88% With potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere A mixture of 1,3,5-tribromobenzene (7.96 g, 25.3 mmol), bis(pinacolato)diboron (21.2 g, 83.5 mmol), [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium (2.78 g, 3.79 mmol), potassium acetate (22.3 g, 228 mmol) in anhydrous 1,4-dioxane (400 mL) was degassed for 80 minutes. Mixture was then heated to 80° C. overnight under argon. After cooling to room temperature, the remaining solids were filtered off. The filtrate was dried under vacuum, redissolved in methylene chloride (400 mL) then washed with water (2.x.300 mL) and brine (300 mL). Organic layer was dried over sodium sulfate and loaded onto silica gel. A silica plug (11percent ethyl acetate in hexanes) and precipitation from methylene chloride/methanol gave 4 (9.76 g, 88percent yield).
71.3% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 85℃; for 24 h; Inert atmosphere Under a nitrogen atmosphere, 250ml three-necked flask 1,3,5-bromobenzene (15.74g, 50mmol), United pinacolato ester (41.9g, 0.165mol, TCI), potassium acetate (48.58g, 0.495mol), 1,1'- bis (diphenylphosphino) ferrocene palladium dichloride (4.08g, 5mmol) and dimethylformamide (300ml), 85 The reaction mixture was stirred under heating 24h.After completion of the reaction naturally cooled, the reaction solution was extracted with ethyl acetate, washed with saturated brine three times, the resulting organic layer was dried over anhydrous magnesium sulfate.Filtration, the resulting filtrate was removed under reduced pressure to remove the solvent.Separated by column chromatography, the mobile phase was chloroform.After the spin-dry vacuum dried to give a white powder 16.25g, yield 71.3percent.
69% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 90℃; Schlenk technique; Inert atmosphere 10108] In a flame-dried Schlenk tube under argon atmosphere, 1,3,5-tribromobenzene (200 mg, 0.64 mmol) and S2Pin2 (731.3 mg, 2.88 mmol) were dissolved in 20 ml 1,4-dioxane. Flame dried KOAc (471.1 mg, 4.8 mmol) was added quickly to the mixture followed by PdC12 (dppf) (15.5 mg, 0.029 mmol). The mixture was heated at 90° C. overnight. The progress of reaction was tracked by TLC (9 hexanes: 1 ethyl acetate) and visualization was achieved in an iodine chambet Two spots (Rf 0.20 and RI 0.25) were observed and heating was stopped and allowed to cool down to room temperature. 20-30 ml ethyl acetate was added to quench the reaction. 30 ml DI water was added to extract the aqueous phase and 30 ml brine (2x) was used to wash the organic phase, dried over anhydrous MgSO4 and filtered. After concentrating down the filtrate, hexanes: ethyl acetate (9:1) mixture was used to elute Rf 0.25 in silica column chromatography to yield white powder [6 9percent, 200 mgI. 1R NMR (300.0 MHz, CDC13): ö 8.36 (s, 3R; CR), ö 1.32 (s, 36R; CR3). 13C {1R} NMR (75.5 MRz, CDC13): ö144.14 (CR), ö 83.79 (CCR3), ö 24.96 (CR3), n.o. (CS).
57% With potassium acetate In dimethyl sulfoxide at 80℃; for 20 h; Inert atmosphere EXAMPLE 1
<Synthesis of 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6)>
8.6 g of 1,3,5-tribromobenzene, 25.0 g of bis(pinacolato)diboron, 24.1 g of potassium acetate, 250 ml of dimethyl sulfoxide previously dewatered with Molecular Sieves 4A, and 1.4 g of PdCl2(dppf)-CH2Cl2 were put into a nitrogen-purged reactor, then heated, and stirred at 80°C for 20 hours.
After cooled to room temperature, the reaction liquid was put into 1000 ml of water, and stirred for 30 minutes.
The precipitate was collected through filtration, and the precipitate was washed with methanol to obtain a crude product.
The crude product was dissolved in 200 ml of ethyl acetate, the insoluble matter was removed through filtration, and the filtrated was concentrated to dryness to obtain 7.1 g (yield 57percent) of a white powder, 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene.
2.5 g of the obtained 1,3,5-tris(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene, 3.8 g of 6-bromo-[2,2']-bipyridine, 32.3 ml of aqueous 1 M potassium carbonate solution, 0.3 g of tetrakis(triphenylphosphine)palladium(0), 108 ml of toluene and 27 ml of ethanol were put into a nitrogen-purged reactor, and heated under reflux with stirring for 18 hours.
After cooled to room temperature, this was processed for liquid-liquid separation with 100 ml of water and 100 ml of toluene added thereto, and the organic layer was further washed with 100 ml of water.
The organic layer was dewatered with anhydrous magnesium sulfate and then concentrated to obtain a crude product.
The crude product was purified through column chromatography (carrier: NH silica gel, eluent: chloroform/n-hexane) to obtain 1.1 g (yield 38percent) of a white powder, 1,3,5-tris(2,2'-bipyridin-6-yl)benzene (compound 6).

Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2641 - 2650
[2] Patent: WO2015/157239, 2015, A1, . Location in patent: Paragraph 00121; 00122
[3] Patent: US2011/196158, 2011, A1, . Location in patent: Page/Page column 7; 8
[4] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 15, p. 3431 - 3439
[5] Patent: CN103396355, 2016, B, . Location in patent: Paragraph 0062-0064
[6] Patent: US2016/178766, 2016, A1, . Location in patent: Paragraph 0106; 0107; 0108
[7] Chemical Communications, 2018, vol. 54, # 68, p. 9529 - 9532
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[9] Patent: EP2269987, 2011, A1, . Location in patent: Page/Page column 29-30
[10] Organic Electronics: physics, materials, applications, 2010, vol. 11, # 12, p. 1966 - 1973
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Reference: [1] Patent: US2015/364699, 2015, A1,
[2] Patent: US2015/364699, 2015, A1,
  • 50
  • [ 626-39-1 ]
  • [ 25015-63-8 ]
  • [ 24388-23-6 ]
  • [ 196212-27-8 ]
  • [ 365564-05-2 ]
  • [ 594823-67-3 ]
  • [ 408492-26-2 ]
Reference: [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901
  • 51
  • [ 626-39-1 ]
  • [ 25015-63-8 ]
  • [ 24388-23-6 ]
  • [ 196212-27-8 ]
  • [ 365564-05-2 ]
  • [ 594823-67-3 ]
  • [ 408492-26-2 ]
Reference: [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901
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