[ CAS No. 51554-93-9 ] {[proInfo.proName]}

Name: 51554-93-9|1-Bromo-4-octylbenzene|95%
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SKU: A289474
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Quality Control of [ 51554-93-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 51554-93-9 ]

CAS No. :	51554-93-9	MDL No. :	MFCD00038348
Formula :	C₁₄H₂₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OOZQSVXPBCINJF-UHFFFAOYSA-N
M.W :	269.22	Pubchem ID :	142854
Synonyms :

Calculated chemistry of [ 51554-93-9 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	7
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.76
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.82
Log Po/w (XLOGP3) :	6.26
Log Po/w (WLOGP) :	5.35
Log Po/w (MLOGP) :	5.32
Log Po/w (SILICOS-IT) :	5.49
Consensus Log Po/w :	5.25

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.29
Solubility :	0.00139 mg/ml ; 0.00000516 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.05
Solubility :	0.000241 mg/ml ; 0.000000897 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.47
Solubility :	0.0000912 mg/ml ; 0.000000339 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.84

Safety of [ 51554-93-9 ]

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

Application In Synthesis of [ 51554-93-9 ]

* 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.

Upstream synthesis route of [ 51554-93-9 ]
Downstream synthetic route of [ 51554-93-9 ]

[ 51554-93-9 ] Synthesis Path-Upstream 1~13

1
[ 106-37-6 ]
[ 17049-49-9 ]
[ 51554-93-9 ]

Reference： [1] Russian Journal of Organic Chemistry, 1995, vol. 31, # 11, p. 1480 - 1486[2] Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 11, p. 1650 - 1656
[3] Patent: WO2017/53990, 2017, A1, . Location in patent: Paragraph 00148

2
[ 76287-60-0 ]
[ 51554-93-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2233 - 2237

3
[ 1041479-71-3 ]
[ 130447-21-1 ]
[ 92-86-4 ]
[ 51554-93-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2009, vol. 351, # 4, p. 630 - 634

4
[ 76287-55-3 ]
[ 51554-93-9 ]

Reference： [1] Journal of the American Chemical Society, 1937, vol. 59, p. 1176
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2233 - 2237

5
[ 1122-91-4 ]
[ 51554-93-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2233 - 2237
[2] Journal of the American Chemical Society, 1937, vol. 59, p. 1176

6
[ 13125-66-1 ]
[ 51554-93-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 2233 - 2237

7
[ 111-83-1 ]
[ 106-37-6 ]
[ 51554-93-9 ]

Reference： [1] Journal of the American Chemical Society, 1997, vol. 119, # 20, p. 4622 - 4632

8
[ 2189-60-8 ]
[ 51554-93-9 ]

Reference： [1] Journal of Materials Chemistry, 2001, vol. 11, # 4, p. 1063 - 1071
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2012, vol. 50, # 10, p. 1953 - 1966

9
[ 108-90-7 ]
[ 51554-93-9 ]

Reference： [1] Journal of Materials Chemistry, 2001, vol. 11, # 4, p. 1063 - 1071

10
[ 2189-60-8 ]
[ 51554-93-9 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938

11
[ 51554-93-9 ]
[ 16245-79-7 ]
[ 101-67-7 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 20, p. 8306 - 8309
[2] Journal of Organic Chemistry, 2012, vol. 77, # 16, p. 6908 - 6916
[3] Journal of the American Chemical Society, 2010, vol. 132, # 21, p. 7478 - 7487

12
[ 51554-93-9 ]
[ 133997-05-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 183 - 194
[2] Journal of Organic Chemistry, 2006, vol. 71, # 15, p. 5752 - 5760
[3] Patent: US2010/137611, 2010, A1, . Location in patent: Page/Page column 12-13
[4] Macromolecules, 2010, vol. 43, # 24, p. 10231 - 10240

13
[ 121-43-7 ]
[ 51554-93-9 ]
[ 133997-05-4 ]

Reference： [1] Patent: US2010/276672, 2010, A1,

[ 51554-93-9 ] Synthesis Path-Downstream 1~88

1
[ 156-60-5 ]
[ 51554-93-9 ]
[ 135329-93-0 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1991,vol. 201,p. 147 - 160

2
[ 51554-93-9 ]
[ 76287-47-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 307 - 316
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2233 - 2237

3
[ 76287-60-0 ]
[ 51554-93-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2233 - 2237

4
[ 92-86-4 ]
[ 51554-93-9 ]
4,4'''-di-n-octyl-p-quaterphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 16559 - 16566

5
[ 51554-93-9 ]
[ 133997-05-4 ]

Yield	Reaction Conditions	Operation in experiment
		Under nitrogen atmosphere, 10 ml of a solution of 1.6M n-butyl lithium (16 mmol) in hexane is put into a 100 ml three-necked flask cooled at -80 C. After cooling to -80 C., 10 ml of THF is added dropwise thereto using a dropping funnel while the THF is maintained at -60 C. Thereafter, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise thereto using a dropping funnel. The resultant mixture is stirred at -40 C. for 1 hour, and a solution of 2.3 g (22 mmol) of trimethyl borate in 10 ml of THF is added dropwise to the mixture using a dropping funnel while the temperature of the added solution is maintained at -40 C. Thereafter, the temperature of the mixture is gradually increased to 10 C. over 2 hours, and 50 ml of a 10% HCl aqueous solution is added thereto at 0 C., and extraction is performed using 100 ml of toluene. The extract is washed with 100 ml of pure water three times, and is dehydrated using sodium sulfate. Toluene is distilled off by reducing the pressure, whereby remaining matter in an amount of 3.3 g is obtained. The remaining matter is washed with a mixed solution of 100 ml pure water/100 ml hexane, whereby 2.0 g of Compound V-a, which is 4-n-octylphenyl borate, is obtained. The obtained compound is identified as the desired product by 1H-NMR and IR.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 183 - 194
[2]Journal of Organic Chemistry,2006,vol. 71,p. 5752 - 5760
[3]Patent: US2010/137611,2010,A1 .Location in patent: Page/Page column 12-13
[4]Macromolecules,2010,vol. 43,p. 10231 - 10240

6
[ 23912-79-0 ]
[ 51554-93-9 ]
5,7,12,14-tetrakis-(4-octyl-phenyl)-5,7,12,14-tetrahydro-pentacene-5,7,12,14-tetraol [ No CAS ]

Reference： [1]Synlett,2006,p. 1359 - 1362

7
[ 51554-93-9 ]
[ 143367-56-0 ]
5,5'-bis-(4-octylphenyl)-[2,2']bithiophene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2006,vol. 16,p. 4335 - 4342

8
[ 765-03-7 ]
[ 51554-93-9 ]
[ 1004539-66-5 ]

Yield	Reaction Conditions	Operation in experiment
70%	With piperidine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); at 50℃;	Example 7; 1-(dodec-1-ynyl)-4-octylbenzene is obtained via Sonogashira coupling reaction between 1- dodecyne and 0.8 equivalent of 1-bromo-4-octyl-benzene in the presence of the catalyst Pd(PPh3)4/Cul and the base piperidine at 50 0C gave 1-(dodec-1-ynyl)-4-octylbenzene in 70% yield. Subsequent Diels-Alder reaction between 990 mg (1.85 mmol) of product of example 1a and 656 mg (1.85 mmol) of 1-(dodec-1-ynyl)-4-octylbenzene using diphenylether as solvent at > 259 0C affords 880 mg (55 % yield) of the product after column chromatography from hexane.

Reference： [1]Patent: WO2008/12250,2008,A1 .Location in patent: Page/Page column 51
[2]Macromolecules,2010,vol. 43,p. 137 - 143

9
[ 51554-93-9 ]
sym-pentakis(p-octylphenyl)corannulene [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 713 - 716

10
[ 872220-16-1 ]
[ 51554-93-9 ]
C₁₄₆H₁₈₆O₂ [ No CAS ]

Reference： [1]Macromolecules,2005,vol. 38,p. 9933 - 9938

11
[ 180577-88-2 ]
[ 51554-93-9 ]
[ 872220-14-9 ]

Reference： [1]Macromolecules,2005,vol. 38,p. 9933 - 9938

12
[ 51554-93-9 ]
[ 876292-95-4 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5752 - 5760

13
[ 51554-93-9 ]
[ 906001-86-3 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5752 - 5760

14
[ 51554-93-9 ]
2,8-dibromo-6,6,12,12-tetrakis-(4-octyl-phenyl)-6,12-dihydro-indeno[1,2-<i>b</i>]fluorene [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 8240 - 8245

15
[ 51554-93-9 ]
[ 635321-91-4 ]

Reference： [1]Macromolecules,2003,vol. 36,p. 8240 - 8245

16
[ 111-83-1 ]
p-ClC₆H₄CH₂Hal [ No CAS ]
[ 51554-93-9 ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1063 - 1071

17
[ 51554-93-9 ]
1,2-bis(4-octylphenyl)-ethane-1,2-dione [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1063 - 1071

18
[ 108-90-7 ]
[ 51554-93-9 ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1063 - 1071

19
[ 51554-93-9 ]
[ 190131-07-8 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632

20
[ 51554-93-9 ]
[ 190131-10-3 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632

21
[ 51554-93-9 ]
[ 190131-14-7 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632

22
[ 51554-93-9 ]
[6-(2,5-Diiodo-4-octyl-phenyl)-hexyl]-{4-[(E)-2-(4-methanesulfonyl-phenyl)-vinyl]-phenyl}-methyl-amine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 4622 - 4632

23
[ 13125-66-1 ]
[ 51554-93-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2233 - 2237

24
[ 1122-91-4 ]
[ 51554-93-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2233 - 2237
[2]Journal of the American Chemical Society,1937,vol. 59,p. 1176

25
[ 624-28-2 ]
[ 51554-93-9 ]
[ 603-35-0 ]
5-bromo-2-(4-octylphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With magnesium;Pd(TPP)4; In tetrahydrofuran;	(3) A Grignard reagent was prepared from magnesium (2.3 g) and <strong>[51554-93-9]4-octyl-1-bromobenzene</strong> (25 g) dissolved in dry tetrahydrofuran (hereinafter abbreviated to THF, 200 ml). To this Grignard reagent were added 2,5-dibromopyridine (23 g) and tetrakistriphenylphosphin paradiun (0) complex (hereinafter abbreviated to Pd(TPP)4, 0.57 g). The reaction mixture was heated to keep refluxing for about 2 hours. After cooling the mixture, organic matter was extracted from the mixture with ether, followed by sequential washing the extract with aqueous ammonium chloride and distilled water to separate an organic layer which was dried over MgSO4. Filtering off the desiccant and distilling off the solvent from the organic layer, the layer gave a residue which was purified by silica gel column chromatography to give 5-bromo-2-(4-octylphenyl)pyridine (35 g). This product showed phase transition temperature ( C.) as the followings: C 45 Sm 66.4 Iso wherein C, Sm and Iso represent a crystal phase, a smectic phase and an isotropic liquid phase, respectively.

Reference： [1]Patent: US6146547,2000,A

26
[ 121-43-7 ]
[ 51554-93-9 ]
p-octylphenylboric acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tetrahydrofuran;	Example 1 50 ml of THF (tetrahydrofuran) was added to 2.91 g (0.12 mol) of metallic magnesium, and the mixture was stirred. 100 ml of a solution of 26.89 g (0.1 mol) of p-octylbromobenzene in THF was added dropwise thereto, and the mixture was heated. After the initiation of the reaction was confirmed, the mixture was refluxed for one hr. The mixture was cooled to -78C, 12.46 g (0.12 mol) of trimethylboric acid was added dropwise thereto, and the mixture was stirred for 30 min. The temperature was returned to room temperature, followed by stirring for additional one hr. Dilute hydrochloric acid was added thereto, and the mixture was stirred for one hr. The aqueous layer was extracted with ether, and the oil layer was washed with water and then with an aqueous sodium hydrogencarbonate. The oil layer was then dried over sodium sulfate, the solvent was removed by distillation, and the resultant crude product was purified by chromatography on silica gel to give p-octylphenylboric acid.

Reference： [1]Patent: EP860417,1998,A2

27
[ 51554-93-9 ]
[ 5720-05-8 ]
4'-Methyl-4-octyl-biphenyl [ No CAS ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 1445 - 1449

28
[ 51554-93-9 ]
[ 98-80-6 ]
[ 7116-97-4 ]

Reference： [1]Applied Organometallic Chemistry,2015,vol. 29,p. 87 - 89
[2]Tetrahedron Letters,2008,vol. 49,p. 1445 - 1449

29
[ 930-30-3 ]
[ 51554-93-9 ]
[ 160678-59-1 ]

Yield	Reaction Conditions	Operation in experiment
		A 250 mL round-bottomed flask equipped with a rubber septum and nitrogen inlet needle is charged with l-bromo-4-octylbenzene (5.77 g, 21.43 mmol) in Et2O (10.7 ml) at room temperature. The resulting solution is cooled to 0 0C. After 5 min BuLi (8.21 ml, 21.43 mmol) solution is added dropwise via syringe over 20 min. The reaction mixture was allowed to stir at 0 0C for 30 min. The resulting solution is then cooled to -78 0C. After 10 min trimethyl borate (2.395 ml, 21.43 mmol) is added dropwise via syringe over 5 min. The reaction mixture is allowed to stir at -78 0C for 30 min. The reaction mixture is treated with 20 mL of saturated NH4Cl and 50 ml of toluene. The aqueous phase is separated and extracted with two 50-mL portions of toluene. The organic phases are combined and concentrated. The residue is further diluted with toluene and concentrated to remove water and then dried in vacuo. The resulting white pasty solid is used directly in the next transformation. The crude borate is transferred to a 200 ml round-bottomed flask equipped with a reflux condenser outfitted with a nitrogen inlet adapter while acetylacetonatobis(ethylene)rhodium(I) (0.166 g, 0.643 mmol) and (R)-BINAP enantiomer (0.480 g, 0.772 mmol) are added in one portion each. The flask is evacuated and filled with nitrogen (three cycles to remove oxygen). To the solid is added dioxane (40 ml), cyclopent-2-enone (1.796 ml, 21.43 mmol), and water (4 ml) each dropwise via syringe. The resulting suspension is heated at 100 0C for 16 h. The resulting orange/brown solution is allowed to cool to room temperature. The orange/brown solution is concentrated and the brown residue is taken up in ether and washed with IN HCl solution. A tan emulsion forms. The emulsified mixture is separated and extracted with EtOAc. The aqueous phases are also extracted with EtOAc. The combined organic phases are washed with 10% NaOH and Brine, then concentrated to afford a brown oil. The crude sample is purified via chromatography on silica gel to afforded 1258 mg of colorless oil.

Reference： [1]Patent: WO2008/79380,2008,A1 .Location in patent: Page/Page column 16

30
[ 51554-93-9 ]
[ 86-74-8 ]
[ 1046127-03-0 ]

Reference： [1]Chemistry Letters,2008,vol. 37,p. 650 - 651

31
[ 5323-87-5 ]
[ 51554-93-9 ]
[ 1036387-13-9 ]

Yield	Reaction Conditions	Operation in experiment
65.9%		General Procedure W: Synthesis of an alpha-beta unsaturated ketoneAn organometalic reagent (1-3 equivalents, preferably 1.1 equivalents) is added to a solution of a beta-alkoxy enone in an organic solvent (preferably THF) at about -78 C-room temperature (preferably 0 0C). Following the addition the reaction mixture is allowed to warm to about room temperature. After Ih IN HCl is added until a pH of 1 is obtained. The reaction mixture is taken through an aqueous work-up and the crude product can be purified by chromatography.Exemplification of General Procedure W: Preparation of 3-(4-octylphenyl)cyclohex-2-enoneTo a suspension of magnesium (1.477 g, 60.8 mmol) in THF (56 mL) was added 1-bromo- 4-octylbenzene (15.00 g, 55.7 mmol). After stirring for about 6h the reaction mixture was added with filtering to a solution of 3-ethoxycyclohex-2-enone (7.10 g, 50.6 mmol) in THF (28.0 mL) at 0 0C. Following the addition the reaction mixture was allowed to warm to room temperature. After Ih IN HCl was added until a pH of 1 was obtained. The reaction mixture was diluted with Et2O and the organic layer was separated, washed with NaHCO3, and brine, dried with Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/Hep) to provide 3-(4-octylphenyl)cyclohex-2 -enone (9.5 g, 33.4 mmol, 65.9 % yield) as a colorless oil.LCMS (Table 1, Method a) R1 = 4.53 min; m/z: 285 (M-H)-; IH NMR (400 MHz, DMSO- d6) 5 7.57 (d, 2H), 7.25 (d, 2H), 6.34 (s, IH), 2.76 (dd, 2H), 2.60 (dd, 2H), 2.40 (dd, 2H), 2.03 (dddd, 2H), 1.58-1.55 (m, 2H), 1.27-1.24 (m, 10H), 0.85 (t, 3H).

Reference： [1]Patent: WO2008/79382,2008,A1 .Location in patent: Page/Page column 76

32
[ 1041479-71-3 ]
[ 130447-21-1 ]
[ 92-86-4 ]
[ 51554-93-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 630 - 634

33
[ 220389-34-4 ]
[ 51554-93-9 ]
[ 1130165-75-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1540 - 1545

34
[ 1130165-74-0 ]
[ 51554-93-9 ]
[ 1130165-76-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1540 - 1545

35
[ 920270-28-6 ]
[ 51554-93-9 ]
2-(2-pyridyl)ethyl 3-fluoro-4'-octyl-[1,1'-biphenyl]-4-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1540 - 1545

36
[ 920270-48-0 ]
[ 51554-93-9 ]
[ 920270-56-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1540 - 1545

37
[ 5751-83-7 ]
[ 51554-93-9 ]
[ 1130165-77-3 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1540 - 1545

38
[ 6165-69-1 ]
[ 51554-93-9 ]
3-(4-n-octyl)-phenylthiophene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 14160 - 14161
[2]Journal of Materials Chemistry,2012,vol. 22,p. 14236 - 14245

39
[ 51554-93-9 ]
copper(l) cyanide [ No CAS ]
4-n-octylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In 1-methyl-pyrrolidin-2-one; for 2h;Reflux;	To a solution of l-bromo-4-octylbenzene (XX) (2.69g, lO.Ommol) in NMP(20 mL) was added CuCN (1.34g, 15mmol) and the mixture was heated to reflux for 2 hours. The mixture was cooled to rt, diluted with 200 mL of EtOAc and hexanes (1:1). The resulting mixture was washed with water (three times), brine, dried over sodium sulfate. After removal of solvent the residue was chromatographed with CombiFlash (0-20% EtOAc in hexanes) to give 4- octylbenzonitrile as a colorless solid (2.1g, 99%). 1HNMR (CDCl3): 7.60-7.55(m, 2H), 7.32- 7.25(m, 2H), 2.72-2.65(m, 2H), 1.70-1.68(m, 2H), 1.40-1.20(m, 10H), 0.95-0.87(m, 3H).

Reference： [1]Patent: WO2010/33701,2010,A2 .Location in patent: Page/Page column 85

40
[ 6165-68-0 ]
[ 51554-93-9 ]
[ 190788-69-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 10h;Inert atmosphere; Reflux;	According to the following scheme, in an atmosphere of nitrogen, tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (2.3 g) and 2N aqueous sodium carbonate solution (10 ml) are added to a mixed solution of 1-bromo-4-n-octyl benzene (25.0 g), 2-thiopheneboronic acid (10.8 g) and tetrahydrofuran (THF) (100 ml), and the mixture is refluxed for 10 hours. After the reaction is finished, the mixture is subjected to extraction with toluene, and the resultant organic phase is sufficiently washed with pure water. Subsequently, after the organic phase is dried with anhydrous sodium sulfate, the solvent is distilled away under reduced pressure, and the resultant product is subjected to a silica gel column chromatographic process (eluent: hexane) to separate the aimed product, thereby obtaining 26.2 g of Intermediate 1.

Reference： [1]Patent: US2010/197942,2010,A1 .Location in patent: Page/Page column 4-5

41
[ 51554-93-9 ]
[ 16245-79-7 ]
[ 101-67-7 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 8306 - 8309
[2]Journal of Organic Chemistry,2012,vol. 77,p. 6908 - 6916
[3]Journal of the American Chemical Society,2010,vol. 132,p. 7478 - 7487

42
[ 98437-24-2 ]
[ 51554-93-9 ]
[ 1260184-88-0 ]

Reference： [1]Journal of Photochemistry and Photobiology A: Chemistry,2010,vol. 213,p. 141 - 146

43
[ 121-43-7 ]
[ 51554-93-9 ]
[ 133997-05-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;	Synthesis Example 2 Synthesis of Exemplified Compound 4 <Synthesis of Compound V-a> In a nitrogen atmosphere, 10 ml (16 mmol) of a 1.6 M n-butyllithium/hexane solution is added to a 100-ml three-necked flask cooled to -80 C. This solution is cooled to -80 C., and then 10 ml of THF maintained at -60 C. is added dropwise thereto from a dropping funnel. Subsequently, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise to the mixture from a dropping funnel. This mixture is stirred for one hour at -40 C., and then a solution of 2.3 g (22 mmol) of trimethyl borate in THF (10 ml) maintained at -40 C. is added thereto from a dropping funnel. Thereafter, the mixture is slowly heated to 10 C. over 2 hours, and then 50 ml of a 10% aqueous solution of HCl at 0 C. is added thereto. The mixture is extracted with 100 ml of toluene. This extract is washed three times with 100 ml of purified water, and then is dried with sodium sulfate. Toluene is distilled off under reduced pressure, and 3.3 g of a residue is obtained. This residue is further washed with a mixed liquid of 100 ml of purified water and 100 ml of hexane, and thus 2.0 g of the compound V-a, which is 4-n-octylphenylboronic acid, is obtained. It is confirmed by 1H-NMR and IR that the compound is consistent with the intended product.

Reference： [1]Patent: US2010/276672,2010,A1

44
[ 51554-93-9 ]
[ 1246018-79-0 ]
[ 1246018-84-7 ]

Reference： [1]Molecular Crystals and Liquid Crystals,2009,vol. 506,p. 47 - 55

45
[ 51554-93-9 ]
[ 1257423-29-2 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9231 - 9238

46
[ 51554-93-9 ]
[ 1257423-30-5 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9231 - 9238

47
[ 51554-93-9 ]
[ 1257423-31-6 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9231 - 9238

48
[ 51554-93-9 ]
[ 1257423-32-7 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9231 - 9238

49
[ 51554-93-9 ]
[ 74-31-7 ]
[ 1257423-28-1 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9231 - 9238

50
[ 51554-93-9 ]
[ 1256466-12-2 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 10231 - 10240

51
[ 51554-93-9 ]
[ 1256466-13-3 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 10231 - 10240

52
[ 51554-93-9 ]
3,4-bis(4-octylphenyl)thiophene [ No CAS ]

Reference： [1]Macromolecules,2010,vol. 43,p. 10231 - 10240

53
[ 51554-93-9 ]
[ 913729-42-7 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 137 - 143

54
[ 51554-93-9 ]
C₅₄H₅₈Br₂ [ No CAS ]

Reference： [1]Macromolecules,2010,vol. 43,p. 137 - 143

55
[ 51554-93-9 ]
[ 79887-13-1 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 137 - 143

56
[ 51554-93-9 ]
[ 79887-13-1 ]
[ 913729-42-7 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 137 - 143

57
[ 51554-93-9 ]
[ 1066-54-2 ]
[ 340038-96-2 ]

Reference： [1]Macromolecules,2010,vol. 43,p. 137 - 143

58
[ 4746-97-8 ]
[ 51554-93-9 ]
[ 1353879-53-4 ]