[ CAS No. 4151-80-8 ] {[proInfo.proName]}

Name: 4151-80-8|[1,1'-Biphenyl]-4,4'-diyldiboronic acid|97%
Brand: Ambeed
SKU: A151518
Price: 5.0 USD
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2D 3D

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Quality Control of [ 4151-80-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4151-80-8 ]

SDS Specification

Alternatived Products of [ 4151-80-8 ]

Product Details of [ 4151-80-8 ]

CAS No. :	4151-80-8	MDL No. :	MFCD00151795
Formula :	C₁₂H₁₂B₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SLHKDOGTVUCXKX-UHFFFAOYSA-N
M.W :	241.84	Pubchem ID :	2734608
Synonyms :

Calculated chemistry of [ 4151-80-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	4.0
Molar Refractivity :	71.53
TPSA :	80.92 Å²

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) :	-6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.36
Log Po/w (WLOGP) :	-1.29
Log Po/w (MLOGP) :	0.15
Log Po/w (SILICOS-IT) :	-1.72
Consensus Log Po/w :	-0.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.78 mg/ml ; 0.00322 mol/l
Class :	Soluble
Log S (Ali) :	-2.66
Solubility :	0.527 mg/ml ; 0.00218 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.7
Solubility :	0.479 mg/ml ; 0.00198 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.05

Safety of [ 4151-80-8 ]

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 [ 4151-80-8 ]

* 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 [ 4151-80-8 ]
Downstream synthetic route of [ 4151-80-8 ]

[ 4151-80-8 ] Synthesis Path-Upstream 1~6

1
[ 92-86-4 ]
[ 4151-80-8 ]

Yield	Reaction Conditions	Operation in experiment
64.5%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -30 - 20℃; for 1 h; Stage #3: With hydrogenchloride In water	To a solution of 4,4'-dibromo-l,l'-biphenyl (5. OOg, 16.03 mmol) in dry THF (100 mL) was added dropwise n-butylithium (1.0M solution in hexane, 40.1 mL, 64.1 mmol) at -78°C and stirred for Ihr. The reaction mixture was warm to -30°C and dropwise added trimethyl borate (4.83 mL, 43.3 mmol) and allowed to stir at room temperature for Ihr. Then the reaction mixture was acidified to pH=2 by 1.5 N HCl. The precipitate was filtered to obtained [l,l'-biphenyl]-4,4'-diyldiboronic acid (2.5 g, 10.34 mmol, 64.5 percent yield) as off white solid. NMR (DMSO-d₆, δ = 2.50 ppm, 400 MHz): δ 8.06 (br. s., 4 H), 7.88 (d, J= 8.53 Hz, 4 H), 7.65 (d, J= 8.4 Hz, 4 H)

Reference： [1] Patent: WO2015/5901, 2015, A1, . Location in patent: Page/Page column 490
[2] Chemistry Letters, 2008, vol. 37, # 11, p. 1122 - 1123
[3] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6607 - 6613
[4] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4502 - 4510
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 51, p. 14144 - 14148[6] Angew. Chem., 2014, vol. 127, # 51, p. 14368 - 14372,5

2
[ 5467-74-3 ]
[ 92-86-4 ]
[ 4151-80-8 ]

Reference： [1] Advanced Synthesis and Catalysis, 2005, vol. 347, # 1, p. 185 - 195

3
[ 3001-15-8 ]
[ 4151-80-8 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 7, p. 3620 - 3626
[2] Journal of the American Chemical Society, 2014, vol. 136, # 22, p. 7899 - 7906

4
[ 5419-55-6 ]
[ 92-86-4 ]
[ 4151-80-8 ]

Reference： [1] Chemistry - A European Journal, 2003, vol. 9, # 24, p. 6167 - 6176

5
[ 5487-93-4 ]
[ 4151-80-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 51, p. 14144 - 14148[2] Angew. Chem., 2014, vol. 127, # 51, p. 14368 - 14372,5

6
[ 624-38-4 ]
[ 4151-80-8 ]

Reference： [1] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571

[ 4151-80-8 ] Synthesis Path-Downstream 1~88

1
[ 624-38-4 ]
[ 4151-80-8 ]

Reference： [1]Journal of the Chemical Society C: Organic,1966,p. 566 - 571

2
C₁₂H₈Br₂Mg₂ [ No CAS ]
[ 4151-80-8 ]

Reference： [1]Journal of the Chemical Society C: Organic,1970,p. 488 - 493

3
[ 4151-80-8 ]
[ 126-30-7 ]
[ 5487-93-4 ]

Reference： [1]Journal of the Chemical Society C: Organic,1966,p. 566 - 571
[2]Journal of the Chemical Society C: Organic,1970,p. 488 - 493

4
[ 4151-80-8 ]
[ 111-42-2 ]
[ 26076-51-7 ]

Reference： [1]Journal of the Chemical Society C: Organic,1970,p. 488 - 493

5
[ 92160-61-7 ]
[ 4151-80-8 ]
[ 243465-09-0 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

6
[ 4151-80-8 ]
[ 312924-92-8 ]
C₄₈H₄₈N₂S₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 8619 - 8624

7
[ 4151-80-8 ]
[ 495383-59-0 ]
[ 495383-63-6 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1827 - 1832

8
[ 4151-80-8 ]
[ 328249-41-8 ]
[ 618903-42-7 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 7129 - 7132

9
[ 4151-80-8 ]
[ 618903-41-6 ]
[ 618903-43-8 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 7129 - 7132

10
[ 4151-80-8 ]
C₄₇H₇₉BrO₁₈ [ No CAS ]
C₁₀₆H₁₆₆O₃₆ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8082 - 8083

11
[ 4151-80-8 ]
C₈₅H₇₃BrN₈O₈ [ No CAS ]
C₁₈₂H₁₅₄N₁₆O₁₆ [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3893 - 3896

12
[ 5467-74-3 ]
[ 92-86-4 ]
[ 4151-80-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2005,vol. 347,p. 185 - 195

13
[ 10522-47-1 ]
[ 4151-80-8 ]
[ 910231-05-9 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 6485 - 6496

14
[ 910231-23-1 ]
[ 4151-80-8 ]
C₃₄H₂₈N₂O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 6485 - 6496

15
5-bromo-8-(methoxymethoxy)-2-methylquinoline [ No CAS ]
[ 4151-80-8 ]
C₃₆H₃₂N₂O₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 6485 - 6496

16
[ 5419-55-6 ]
[ 92-86-4 ]
[ 4151-80-8 ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 6167 - 6176

17
C₄₉H₄₇IO₁₀ [ No CAS ]
[ 4151-80-8 ]
[(CH₂C₆H₂(OH)(CH₃))4CH₂C₆H₂(OH)]2C₆H₄C₆H₄ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2005,vol. 78,p. 768 - 770

18
[ 4151-80-8 ]
[ 107-21-1 ]
[ 135615-38-2 ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 6167 - 6176

19
[ 4151-80-8 ]
[ 113999-02-3 ]
4,4’-bis(5-carboethoxy-3,4-diethylpyrrol-2-yl)biphenyl [ No CAS ]
C₄₆H₄₈N₂O₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 7541 - 7544

20
[ 4877-80-9 ]
[ 4151-80-8 ]
polymer; monomer(s): 2,3,6,7,10,11-hexahydroxytriphenylene; 4,4'-biphenyldiboronic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12914 - 12915

21
[ 4151-80-8 ]
[ 495383-64-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2002,vol. 75,p. 1827 - 1832

22
[ 4151-80-8 ]
4,4'''''-diiodo-[1,4';1',1'';4'',1''';4''',1'''';4'''',1''''']sexiphenyl-3,2',2'''',3'''''-tetraol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

23
[ 4151-80-8 ]
[ 243465-10-3 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

24
[ 4151-80-8 ]
[ 243465-11-4 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

25
[ 4151-80-8 ]
[ 243465-12-5 ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

26
[ 4151-80-8 ]
C₇₄H₇₈O₁₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 7961 - 7962

27
4-{(2S,3R)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenyl trifluoromethanesulfonate [ No CAS ]
[ 4151-80-8 ]
(3R,4S,3'R,4'S)-4,4'-(1,1':4',1'':4'',1'''-quaterphenyl-4,4'''-diyl)bis{1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one} [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 5h;Heating / reflux;	4- {(2S, 3R)-1-(4-FLUOROPHENYL)-3-[(3S)-3-(4-FLUOROPHENYL)-3-HYDROXYPROPYL]-4- oxoazetidin-2-yl} phenyl trifluoromethanesulfonate (80.1 mg, 0.148 mmol) and tetrakis (TRIPHENYLPHOSPHINE) palladium (0) (8. 5 mg, 0.00736 mmol) were dissolved in toluene (1.0 ML). 2.0 M aqueous potassium carbonate (0.148 ML) and a solution of 4, 4'-biphenyldiboronic acid (17.9 mg, 0.074 mmol) in ethanol (0.5 mL) were added. The reaction was stirred vigorously for 5 h at refluxing temperature under a nitrogen atmosphere and then diluted with water (2.5 mL), extracted with ethyl acetate (3 X 10 mL), washed with brine (10 mL), dried over sodium sulfate, filtered, concentrated and purified by chromatography (12 g silica gel, 10% to 100% ethyl acetate-hexane) to afford (3R, 4S, 3 R, 4 S)-4, 4 -(1, 1 : 4', 1" : 4", 1" -QUATERPHENYL-4, 4" -DIYL) BIS F 1- (4- FLUOROPHENYL)-3- [ (3)-3- (4-FLUOROPHENYL)-3-HYDROXYPROPYL] AZETIDIN-2-ONE} 102 (58 mg, 42% yield) as an off-white solid. RF = 0.4, silica gel, 1: 1 ethyl ACETATE/HEXANES. NMR 1H (CDC13) 7.7-6. 9 (M, 32H), 4.7 (m, 2H), 4.6 (s, 2H), 3.2 (M, 2H), 2.1-1. 9 (M, 8H).

Reference： [1]Patent: WO2005/21497,2005,A2 .Location in patent: Page/Page column 53

28
[ 887918-07-2 ]
[ 4151-80-8 ]
4,4'-biphenylenebis(3,6,8-triphenylpyrene) [ No CAS ]

Reference： [1]Patent: WO2006/57325,2006,A1 .Location in patent: Page/Page column 30-31

29
3,6,8-tris(m-tolyl)-1-bromopyrene [ No CAS ]
[ 4151-80-8 ]
4,4'-biphenylenebis(3,6,8-tri-m-tolylpyrene) [ No CAS ]

Reference： [1]Patent: WO2006/57325,2006,A1 .Location in patent: Page/Page column 34-36

30
[ 23790-75-2 ]
[ 4151-80-8 ]
[ 958891-96-8 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 14240 - 14250
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 7693 - 7696

31
[ 847152-22-1 ]
[ 4151-80-8 ]
Ir₂(NC₁₁H₈)4((N₂C₁₀H₇C₆H₄C₆H₄)2)⁽²⁺⁾*2PF₆^(1-)=[Ir₂(NC₁₁H₈)4((N₂C₁₀H₇C₆H₄C₆H₄)2)](PF₆)2 [ No CAS ]

Reference： [1]Dalton Transactions,2003,p. 2080 - 2084

32
ammonium hexafluorophosphate [ No CAS ]
[Ru(2,2'-bipyridine)2[4-(4'-bromophenyl)-[2,2']bipyridinyl]](PF₆)2 [ No CAS ]
[ 4151-80-8 ]
(Ru(C₁₀N₂H₈)2(C₅NH₄C₅NH₃(C₆H₄)2))2⁽⁴⁺⁾*4PF₆^(1-)=(Ru(C₁₀H₈N₂)2(C₅NH₄C₅NH₃(C₆H₄)2))2(PF₆)4 [ No CAS ]

Reference： [1]Inorganic Chemistry,2005,vol. 44,p. 4706 - 4718

33
[ 4877-80-9 ]
[ 4151-80-8 ]
C₆H₃BO [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 12914 - 12915

34
[ 860438-20-6 ]
[ 4151-80-8 ]
poly(5,5''''-dibromo-3'',4''-dibutyl-3',4'''-diperfluorobutyl[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene-co-4,4'-biphenylbisboric acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; benzene; for 24h;Heating / reflux;	COMPARATIVE EXAMPLE 2Comparative Compound (B) shown below was prepared for comparison with Exemplifying compound (IV-10), a ?-conjugated compound of the present invention. The preparation process is described below.Tetrakis(triphenylphosphine)palladium (0.02 mmol) and 3 mL of an aqueous 2N sodium carbonate solution were added to a mixture liquid of 5,5-dibromo-3,4-dibutyl-3',4'-diperfluorobutyl-[2,2';5',2;5,2';5',2]quinquethiophene (1.0 mmol), 4,4'-biphenyl-bisboric acid (1.0 mmol), and 8 mL of benzene in a nitrogen atmosphere. The resulting mixture was refluxed for 24 hours. The reaction mixture was poured into a large amount of acetone to obtain a crude product. This crude product was purified by repeated reprecipitation to obtain the intended Comparative Compound (B) in a 29% yield. The obtained Comparative Compound (B) had a molecular weight of Mn: 21,300; Mw: 30,000 according to GPC measurement (solvent: chloroform).A field effect type organic transistor was prepared in the same manner as in Example 5 except that Comparative Compound (B) was used in place of Exemplifying compound (IV-10) used in Example 5. The mobility was measured in the same manner as in Example 4. The results are shown below.

Reference： [1]Patent: US7462726,2008,B2 .Location in patent: Page/Page column 26

35
[ 1008133-51-4 ]
[ 4151-80-8 ]
[(Ir(1,3-di(2-pyridyl)-4,6-dimethylbenzene-N,C2,N))2(μ-mtbpy-.vphi.4-mtbpy)](hexafluorophosphate)2 [ No CAS ]

Reference： [1]Inorganic Chemistry,2008,vol. 47,p. 6596 - 6607

36
[ 4151-80-8 ]
[ 120362-71-2 ]
[ 1088716-93-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 3h;Heating / reflux;	(Example 2) [Production Method of Exemplified Compound No. 607](Intermediate 1-2)The following reagents and solvents were charged in a reaction vessel under nitrogen atmosphere, and a reaction solution was suspended. ?Intermediate 1-2: 305 mg (0.80 mmolj ?Biphenyl-4, 4' -diboronic acid: 92 mg (0.38 mmol) -Tetrakistriphenylphosphin palladium: 44 mg (0.04 mmol) ?Toluene: 9 ml ?Ethanol: 9 ml <n="67"/>10% sodium carbonate solution: 6 mlNext, the reaction solution was stirred for 3 hours under heating and reflux. After that, the reaction solution was cooled to room temperature, and water was added to terminate the reaction. Next, the solution was filtrated, and the resultant solid was purified by alumina column chromatography (developing solvent: chlorobenzene) . After that, the purified product was further subjected to slurry washing with chlorobenzene, and was filtered off, whereby 200 mg of Exemplified Compound No. 607 were obtained.Then, 754.2 as M+ of the compound was confirmed by Matrix Assisted Laser Desorption/Ionization - Time of Flight Mass Spectrometry (MALDI-TOFMS) . A PL spectrum in a toluene solution (1.0 * 10~5 mol/L) of Exemplified Compound No. 607 was measured. As a result, a PL spectrum shown in FIG. 7 was obtained. The PL spectrum was a blue emission spectrum having an emission peak at 441 nm and a full width at half maximum of 74 nm.

Reference： [1]Patent: WO2008/146720,2008,A1 .Location in patent: Page/Page column 65-66

37
[ 1080498-61-8 ]
[ 4151-80-8 ]
[ 1082540-29-1 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 5365 - 5368

38
[ 918959-37-2 ]
[ 4151-80-8 ]
[ 1146616-52-5 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 2915 - 2917

39
[ 1232143-83-7 ]
[ 4151-80-8 ]
[ 1232143-86-0 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4852 - 4855

40
[ 67-56-1 ]
(dimethylglyoxime)2(H₂O)CoMe [ No CAS ]
[ 539-48-0 ]
[ 4151-80-8 ]
[ 7732-18-5 ]
[(cobalt(III)(methyl)(dimethylglyoxime(-H))(dimethylglyoxime(-2H)))2(CH3OBC6H4)2(α,,alpha.'-diamino-p-xylene)]*3.5H2O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2010,vol. 363,p. 2113 - 2124

41
[ 67-56-1 ]
(dimethylglyoxime)2(H₂O)CoMe [ No CAS ]
[ 3114-70-3 ]
[ 4151-80-8 ]
[ 7732-18-5 ]
[(cobalt(III)(methyl)(dimethylglyoxime(-H))(dimethylglyoxime(-H₂)))2(CH₃OBC₆H₄)2(1,6-diaminohexane)]*2H₂O [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2010,vol. 363,p. 2113 - 2124

42
[ 67-56-1 ]
[ 553-26-4 ]
(dimethylglyoxime)2(H₂O)CoMe [ No CAS ]
[ 4151-80-8 ]
[(cobalt(III)(methyl)(dimethylglyoxime(-H))(dimethylglyoxime(-2H)))2(CH₃OBC₆H₄)2(4,4'-bipyridine)] [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2010,vol. 363,p. 2113 - 2124

43
[ 67-56-1 ]
[ 553-26-4 ]
(dimethylglyoxime)2(H₂O)CoMe [ No CAS ]
[ 4151-80-8 ]
[(cobalt(III)(methyl)(bis(dimethylglyoximate))((CH₃OBC₆H₄)2)2)2(4,4'-bipyridine)] methanol hexasolvate [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2010,vol. 363,p. 2113 - 2124

44
[ 4151-80-8 ]
[ 120-80-9 ]
[ 1101928-52-2 ]

Reference： [1]Chemistry Letters,2008,vol. 37,p. 1122 - 1123
[2]Chemistry Letters,2008,vol. 37,p. 1122 - 1123

45
cis-1,4-bis(4-bromophenyl)-1,4-bis(methoxymethylether)cyclohexane [ No CAS ]
[ 4151-80-8 ]
C₅₆H₆₀Br₂O₈ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 10202 - 10205

46
[ 1240575-39-6 ]
[ 4151-80-8 ]
[ 1240575-46-5 ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 1585 - 1592

47
[ 1112364-21-2 ]
[ 4151-80-8 ]
C₁₀₀H₆₆N₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 7352 - 7359

48
[ 92-86-4 ]
[ 4151-80-8 ]

Yield	Reaction Conditions	Operation in experiment
64.5%		To a solution of 4,4'-dibromo-l,l'-biphenyl (5. OOg, 16.03 mmol) in dry THF (100 mL) was added dropwise n-butylithium (1.0M solution in hexane, 40.1 mL, 64.1 mmol) at -78C and stirred for Ihr. The reaction mixture was warm to -30C and dropwise added trimethyl borate (4.83 mL, 43.3 mmol) and allowed to stir at room temperature for Ihr. Then the reaction mixture was acidified to pH=2 by 1.5 N HCl. The precipitate was filtered to obtained [l,l'-biphenyl]-4,4'-diyldiboronic acid (2.5 g, 10.34 mmol, 64.5 % yield) as off white solid. NMR (DMSO-d6, delta = 2.50 ppm, 400 MHz): delta 8.06 (br. s., 4 H), 7.88 (d, J= 8.53 Hz, 4 H), 7.65 (d, J= 8.4 Hz, 4 H)

Reference： [1]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 490
[2]Chemistry Letters,2008,vol. 37,p. 1122 - 1123
[3]Journal of Materials Chemistry,2011,vol. 21,p. 6607 - 6613
[4]Journal of Materials Chemistry,2012,vol. 22,p. 4502 - 4510
[5]Angewandte Chemie - International Edition,2014,vol. 53,p. 14144 - 14148
Angew. Chem.,2014,vol. 127,p. 14368 - 14372,5

49
[ 4151-80-8 ]
N-(4-bromophenyl)dodecanamide [ No CAS ]
[ 1265679-01-3 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 226 - 233

50
[ 4151-80-8 ]
[ 95-54-5 ]
[ 1309370-63-5 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 6607 - 6613

51
[ 1313207-02-1 ]
[ 1313207-86-1 ]
[ 4151-80-8 ]
[ 1335315-65-5 ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydrogencarbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; isopropyl alcohol; at 20 - 150℃; for 0.216667h;microwave irradiation;	To a suspension of methyl N-[(1S)-1 -[(2S,4S)-2-(5-iodo-1 H-benzimidazol-2-yl)-4- methyl-pyrrolidine-1 -carbonyl]-2-methyl-propyl]carbamate (52.40 mg, 0.1082 mmol), methyl ((S)-1 -((2S,4S)-2-(4-iodo-1 H-imidazol-2-yl)-4-methylpyrrolidin-1 - yl)-3-methyl-1 -oxobutan-2-yl)carbamate (47 mg, 0.1082 mmol), [1 , 1 -biphenyl]- 4,4'-diyldiboronic acid (26.17 mg, 0.1082 mmol), Pd(DPPF)(Cl)2.CH2Cl2 (4.418 mg, 0.005410 mmol) and 1 mL of 2-propanol in a microwave vial is added 1M aqueous NaHC03 (541.0 muIota_, 0.5410 mmol). The reaction mixture is stirred for 3 minutes at room temperature and is heated to 150C in the microwave for 10 minutes. The reaction mixture is concentrated to dryness. The residue is purified by flash column chromatography on silica gel (0 to 10% methanol in CH2Cl2) and is further purified by reverse phase preparative HPLC to give ((S)-1 - {(2S,4S)-2-[5-(4'-{2-[(2S,4S)-1 -((S)-2-methoxycarbonylamino-3-methyl-butyryl)- 4-methyl-pyrrolidin-2-yl]-1 H-imidazol-4-yl}-biphenyl-4-yl)-1 H-benzoimidazol-2- yl]-4-methyl-pyrrolidine-1 -carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (12 mg, 25%).LC/MS: m/z = 817.62 (M+H+).

Reference： [1]Patent: WO2011/119853,2011,A1 .Location in patent: Page/Page column 105

52
C₇₄H₁₁₆INO₂₂ [ No CAS ]
[ 4151-80-8 ]
C₁₆₀H₂₄₀N₂O₄₄ [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 15327 - 15331

53
[ 4151-80-8 ]
2B⁽³⁺⁾*2O^(2-)*C₆H₄C₆H₄^(2-)=OBC₆H₄C₆H₄BO [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 2943 - 2945

54
[ 1369968-48-8 ]
[ 4151-80-8 ]
[ 1369968-55-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 3620 - 3626

55
[ 3001-15-8 ]
[ 4151-80-8 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 3620 - 3626
[2]Journal of the American Chemical Society,2014,vol. 136,p. 7899 - 7906

56
[ 736928-20-4 ]
[ 4151-80-8 ]
[ 1361152-08-0 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 4502 - 4510

57
[ 4151-80-8 ]
[ 64413-90-7 ]
[ 849637-43-0 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 4502 - 4510

58
[ 125143-53-5 ]
[ 4151-80-8 ]
C₃₄H₃₀S₄ [ No CAS ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9519 - 9521

59
[ 32294-60-3 ]
[ 4151-80-8 ]
[ 130746-56-4 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 117 - 125

60
(6-bromo-naphthalene-2-yl)-diphenyl amine [ No CAS ]
[ 4151-80-8 ]
6-(4-(2-(diphenylamino)naphthalen-6-yl)-4'-biphenyl)-N,N-diphenylnaphthalen-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In water; at 155℃; for 0.0833333h;Inert atmosphere;	To a solution of 6-bromo-N,N-diphenylnaphthalen-2-amine (1.0028 g, 2.65 mmols), 4,4'- diphenyldiboronic acid (0.3188 g, 1.32 mmols), sodium carbonate (0.87 g, 8 mmols), and TBAB (0.856 g) in water (6.1 mL) was added Pd(OAc)2 (0.035 g, 0.03 mmols). The solution was degassed with nitrogen, and heated to 155 C for 5 min. The reaction solution was then poured into ethyl acetate and water. A precipitate was filtered off and redissolved in hot toluene, and the organic layer was concentrated, and the crude product was chromatographed (2.5-100% ethyl acetate in hexanes, and then hot toluene, silica gel) to give the title compound (0.200 g, 20%>) as a yellow, crystalline compound: 1H NMR (400 MHz, CDC13) delta 8.03 (s, 2H), 7.77-7.83 (m, 10H), 7.74 (d, J= 8.8, 2.0 Hz, 2H), 7.68 (d, J= 8.4 Hz, 2H), 7.46 (d, J= 2.0 Hz, 2H), 7.33 (dd, J= 9.2, 2.4 Hz, 2H), 7.29 (t, J= 7.6 Hz, 8H), 7.17 (d, J= 8.4 Hz, 8 H), 7.07 (t, J= 8.4 Hz, 4H); 13C NMR (100 MHz, CDC13) delta 147.6, 145.6, 140.0, 139.4, 136.5, 133.6, 130.1, 129.3, 129.1, 127.6, 127.5, 127.4, 125.7, 125.3, 124.7, 124.4, 123.0, 119.6; LCMS (M+H)+ Calc'd for C56H4iN2 741.3269, found 741.3270.

Reference： [1]Patent: WO2013/169918,2013,A1 .Location in patent: Paragraph 0022

61
[ 18242-39-2 ]
[ 4151-80-8 ]
[ 1569868-42-3 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 3972 - 3980

62
[ 4151-80-8 ]
[ 1569868-34-3 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 3972 - 3980

63
[ 4151-80-8 ]
8F₆P^(1-)*8Cu⁽¹⁺⁾*4C₅₂H₄₂N₈ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 3972 - 3980

64
[ 1304287-51-1 ]
[ 4151-80-8 ]
[ 1611490-50-6 ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 7899 - 7906

65
[ 23683-68-3 ]
[ 4151-80-8 ]
[ 1616624-27-1 ]

Reference： [1]Chemical Physics Letters,2014,vol. 605-606,p. 126 - 130

66
methyl 3-acetoxy-2-methylene-5-phenylpent-4-ynoate [ No CAS ]
[ 4151-80-8 ]
[ 1618099-37-8 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3792 - 3795

67
[ 5487-93-4 ]
[ 4151-80-8 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 14144 - 14148
Angew. Chem.,2014,vol. 127,p. 14368 - 14372,5

68
(S)-tert-butyl (1-(5-bromo-1-methyl-1H-imidazol-2-yl)-2-methylpropyl)carbamate [ No CAS ]
[ 4151-80-8 ]
ditert-butyl ((1S,1‘S)-(S,S’-([1,1‘-biphenyl]-4,4’-diyl)bis(1-methyl-1H-imidazole-5,2-diyl))bis(2-methylpropane-1,1-diyl))dicarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.59%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 90℃;	To a solution of [l,l'-biphenyl]-4,4'-diyldiboronic acid (0.65 g, 2.419 mmol) in DMF (2 mL), was added (S)-tert-butyl (l-(5-bromo-l-methyl-lH-imidazol-2-yl)- 2-methylpropyl)carbamate (1.688 g, 5.08 mmol), potassium phosphate tribasic (2.054 g, 9.68 mmol) and PdC dppf) (0.177 g, 0.242 mmol). The reaction mixture was degassed and heated to 90C for overnight. The volatile component was removed in vacuo. The resulting residue was dissolved in EtOAc (100 mL) and filtered through celite bed. The filtrate was washed with brine, dried over Na2S04and concentrated in vacuo. The crude material was purified by ISCO using 40 g Redisep silica column (MeOH:CHCi3, 3:97) and further purified by reverse phase prep HPLC to obtain di- tert-butyl (( 1 S, 1 'S)-(5,5'-([ 1 , 1 '-biphenyl]-4,4'-diyl)bis( 1 -methyl- 1 H-imidazole-5,2- diyl))bis(2-methylpropane-l,l-diyl))dicarbamate (0.2 g, 0.304 mmol, 12.59 % yield) as off white solid. NMR (DMSO-d6, delta = 2.50 ppm, 300 MHz): delta 7.81 (d, J=8.31 Hz, 4 H), 7.56 (d, J = 8.1 Hz ,4 H), 7.18 (s, 2 H), 7.04 (s, 2 H), 4.42 - 4.51 (m, 2 H), 3.83 (s, 6 H), 2.21 - 2.33 (m, 2 H), 1.39 (s, 18 H), 0.99 (d, J= 6.52 Hz, 6 H), 0.84 (d, J = 6.61 Hz, 6H). LCMS : (Condition-B12) Rt: 2.45 -200 Step i

Reference： [1]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 491

69
[ 4151-80-8 ]
C₄₂H₅₂F₄N₆O₂ [ No CAS ]

Reference： [1]Patent: WO2015/5901,2015,A1

70
[ 4151-80-8 ]
(1S,1'S)-1,1‘-(5,5‘-([1,1‘-biphenyl]-4,4’-diyl)bis(1-methyl-1H-imidazole-5,2-diyl))bis(2-methylpropan-1-amine) dihydrochloride [ No CAS ]

Reference： [1]Patent: WO2015/5901,2015,A1

71
[ 504-29-0 ]
[ 4151-80-8 ]
N-([1,1'-biphenyl]-4-yl)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With potassium phosphate monohydrate; copper(II) acetate monohydrate; In dimethyl sulfoxide; at 40℃; for 24h;Sealed tube;	General procedure: An oven-dried 25 mL sealed tube with stir bar was charged with arylboronic acid (1 equiv.),2-amino pyridine (1 equiv.), Cu(OAc)2·H2O (1.2 equiv.), K3PO4·H2O(2 equiv.) and 3 or 5 mL of DMSO was added and closed the sealed tube. The reactionmixture was heated at the indicated temperature for 24 h. After the reaction finished, theproduct was extracted with ethyl acetate (5 × 3 mL). The organic layers werewashed with brine, dried over Na2SO4, and evaporated toyield the crude reaction mixture. The purification was done by combi flashmachine flash chromatography on silica gel (eluent: heptanes:EtOAc = 60:40).

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4843 - 4847

72
syn-tetrahydroxypentiptycenequinone [ No CAS ]
[ 4151-80-8 ]
C₉₂H₄₈B₄O₁₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 4880 - 4884

73
di(n-octyl)glyoxime [ No CAS ]
[ 4151-80-8 ]
[ 1692-15-5 ]
iron(II) chloride [ No CAS ]
C₅₈H₆₄B₄Fe₂N₁₄O₁₂ [ No CAS ]

Reference： [1]Chimia,2015,vol. 69,p. 191 - 195

74
[ 4151-80-8 ]
N-(4-bromophenyl)-3,5-bis(dodecyloxy)benzamide [ No CAS ]
C₈₆H₁₂₄N₂O₆ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2017,vol. 12,p. 52 - 59

75
[ 1315511-62-6 ]
[ 4151-80-8 ]
C₁₁₀H₁₇₂N₂O₈ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2017,vol. 12,p. 52 - 59

76
[ 4151-80-8 ]
4-bromophenyl 3,5-bis(dodecyloxy)benzoate [ No CAS ]
C₈₆H₁₂₂O₈ [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2017,vol. 12,p. 52 - 59

77
[ 4151-80-8 ]
[ 685517-67-3 ]
4,4’-bis(2,6-difluoropyridin-4-yl)-1,1':4’,1”-terphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 12h;Reflux;	A mixture of 4,4-biphenyldiboronic acid (25mg, 0.10mmol) and 2,6-difluoro-3-iodopyridine (50mg, 0.21mmol) was added to a suspension of Pd(PPh3)4 (14mg, 0.012mmol) in 1,2-dimethoxyethane (4mL) and aqueous Na2CO3 (0.5mL, 2mol/L). The mixture was subsequently maintained at reflux for 12h, allowed to cool and then poured into H2O (10mL) and extracted with CH2Cl2 (3×30mL). The organic extracts were dried (MgSO4), concentrated in vacuo and the residue was purified by column chromatography (CH2Cl2/pentane=1:9, v/v) to give the product as a white powder (29mg, 76%). 1H NMR (400MHz, CDCl3): delta 8.03 (dd, 2H, J=7.9, 17.3), 7.75 (d, 4H, J=8.5), 7.64 (d, 4H, J=8.4), 6.96 (dd, 2H, J=2.9, 8.1). 19F NMR (376MHz, CDCl3): delta -69.8, -70.8. HRMS m/z calcd. for C22H12F4N2Na [M+Na+]: 403.0834, found: 403.0837. MP: 193-195C.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 525 - 530

78
[ 685517-71-9 ]
[ 4151-80-8 ]
4,4'-bis(2,6-difluoropyridin-4-yl)-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 14h;Reflux;	A mixture of 4,4-biphenyldiboronic acid (25mg, 0.10mmol) and 2,6-difluoro-4-iodopyridine (50mg, 0.21mmol) was added to a suspension of Pd (PPh3)4 (14mg, 0.012mmol) in 1,2-dimethoxyethane (4mL) and aqueous Na2CO3 (0.5mL, 2mol/L). The mixture was subsequently maintained at reflux for 14h, allowed to cool, poured into H2O (10mL), and extracted with CH2Cl2 (3×30mL). The organic extracts were dried (MgSO4), concentrated in vacuo, and the residue was purified by column chromatography (CH2Cl2/pentane=1:9, v/v) to give the product as a white powder (32mg, 82%). 1H NMR (400MHz, DMSO-d6): delta 8.00 (dd, 8H, J=8.5, 38.9), 7.65 (s, 4H). 19F NMR (376MHz, CDCl3): delta -68.6. MALDI-TOF-MS m/z calcd. for C22H12F4N2 [M+]: 380.094, found: 379.848. MP: 240-242C.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 525 - 530

79
[ 4151-80-8 ]
C₂₂H₁₇BrO₂ [ No CAS ]
C₅₆H₄₂O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2017,vol. 23,p. 10058 - 10067

80
5-bromoquinolin-8-yl 4-methylbenzenesulfonate [ No CAS ]
[ 4151-80-8 ]
4,4’-bis(8-tosyloxyquinolin-5-yl)biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 80℃; for 18h;Inert atmosphere;	General procedure: The synthesis of 1,4-bis-(8-benzyloxyquinolin-5-yl)benzene 15 will be used as representative example for the synthesis of bis-8-tosyloxyquinolines 17. 5-Bromo-8-benzyloxyquinoline 14 (314 mg, 1 mmol, 1 equiv), benzene-1,4-diboronic acid (82.8 mg, 0.5 mmol, 0.5 equiv), sodium carbonate (217 mg, 2.05 mmol, 2.05 equiv) and tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.06 mmol, 0.06 equiv) were added to a flask (50 mL). Meanwhile, a solvent mixture of toluene/ethanol/water (3/1/1, 15 mL/5 mL/5 mL) was degassed under argon atmosphere by a freeze-thaw procedure. The degassed solvent mixture was added to the reagents and the mixture was stirred for 18 hours at 80C under argon atmosphere. When the reaction was finished, the mixture was cooled and the crude product was extracted with CH2Cl2 (25 mL) and water (25 mL). The organic fraction was washed three times with water (25 mL), dried (MgSO4) and evaporated to obtain the crude product. Recrystallization from CHCl3 yielded 1,4-bis-(8-benzyloxyquinolin-5-yl)benzene 15 in 52% (141 mg, 0.26 mmol).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 3803 - 3807

81
[ 4151-80-8 ]
C₈F₁₈Zn*2C₆H₁₂N₂O [ No CAS ]
4,4'-bis(1,1,2,2,3,3,4,4,4-nonafluorobutyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 463 - 468

82
[ 4151-80-8 ]
2-(3-bromothiophen-2-yl)-3-((triisopropylsilyl)ethynyl)quinoxaline [ No CAS ]
4,4′-bis(5-(3-((triisopropylsilyl)ethynyl)quinoxalin-2-yl)thiophen-2-yl)-1,1′-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; methanol; at 100℃; for 16h;Inert atmosphere; Schlenk technique;	General procedure: Starting material 1a (236 mg, 0.50 mmol) in dry 1,4-dioxane(2.00 mL) was placed under nitrogen atmosphere in a sinteredscrew-cap Schlenk tube and degassed with nitrogen(5 min). Then tetrakis(triphenylphosphane)palladium (0)(118 mg, 0.10 mmol, 10 mol%), Na2CO3 (132 mg,1.25 mmol), bisboronic acids 4 (0.55 mmol) and methanol(1.00 mL) were successively added (for experimental detailssee Table 3). The reaction mixture was stirred at 100 C for16 h. After cooling to room temperature (5 min, water bath)deionized water (10 mL) was added and the aqueous phasewas extracted with dichloromethane (3×10 mL, monitoredby TLC). The combined organic layers were dried (anhydroussodium sulfate) and filtered. After removal of the solvents in vacuo, the residue was absorbed onto celite andpurified by chromatography on silica gel (petroleum ether(boiling range 40-60 C)/ethyl acetate or dichloromethane)to give the bis(3-ethynyl quinoxaline thienyl) dumbbells 5.

Reference： [1]Science China Chemistry,2018,vol. 61,p. 909 - 924

83
2-bromo-[1]-benzothieno[3,2-b][1]benzothiophene [ No CAS ]
[ 4151-80-8 ]
4,4’-bis([1]benzothieno[3,2-b][1]benzothiophene-2-yl)-1,1’-biphenyl [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 16595 - 16602

84
[ 106-39-8 ]
[ 4151-80-8 ]
[ 21711-52-4 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 13670 - 13673

85
[ 4151-80-8 ]
2-bromo-3,3',4,4'-tetrakis(pentyloxy)-1,1'-biphenyl [ No CAS ]
3,3''''',4,4',4'''',4''''',5',5''''-octakis(pentyloxy)-1,1':2',1'':4'',1''':4''',1'''':2'''',1'''''-sexiphenyl [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 462 - 470

86
[ 96-26-4 ]
[ 4151-80-8 ]
C₆₀H₉₆N₁₄O₁₃ [ No CAS ]
C₇₈H₁₁₄N₁₄O₁₇ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 2700 - 2704
Angew. Chem.,2019,vol. 131,p. 2726 - 2730,5

87
1-bromo-2,4-dibutoxybenzene [ No CAS ]
[ 4151-80-8 ]
C₄₀H₅₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;	1.2 g of 1-bromo-2,4-dibutoxybenzene was completely dissolved in an aqueous 1,4-dioxane solution (dioxane: water = 5: 1), and then 0.5 g of 2,4- Dimethoxyphenylboronic acid, 0.4 g of tetratriphenylphosphine palladium, 1.6 g of sodium carbonate, the mixed system was heated to 100 C under reflux overnight. After the reaction, the reaction solution was cooled to room temperature, the solvent was spin-dried, dissolved in dichloromethane, and extracted three times with water. The organic layer was dried over anhydrous Na2SO4, re-spinned and stirred, and separated by column chromatography to obtain monomer M25.

Reference： [1]Patent: CN110642684,2020,A .Location in patent: Paragraph 0041; 0066-0068

88
[ 4151-80-8 ]
C₁₂H₁₆Br₂O₂ [ No CAS ]
C₃₆H₄₀Br₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;	1.5g of 4-bromo-2- (5-bromo-n-pentyloxy) -5-methoxybenzene was completely dissolved in an aqueous solution of 1,4-dioxane (dioxane: water = 5: 1) Then, 0.5 g of 2,4-dimethoxyphenylboronic acid, 0.4 g of tetratriphenylphosphine palladium, and 1.6 g of sodium carbonate were added, and the mixed system was heated to 100 C under reflux overnight. After the reaction, the reaction solution was cooled to room temperature, the solvent was spin-dried, dissolved in dichloromethane, and extracted three times with water. The organic layer was dried over anhydrous Na2SO4, re-spinned and stirred, and separated by column chromatography to obtain monomer M26.

Reference： [1]Patent: CN110642684,2020,A .Location in patent: Paragraph 0041; 0069; 0070

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P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 4151-80-8 ] {[proInfo.proName]}

Quality Control of [ 4151-80-8 ]

Related Doc. of [ 4151-80-8 ]

Product Details of [ 4151-80-8 ]

Calculated chemistry of [ 4151-80-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4151-80-8 ]

Application In Synthesis of [ 4151-80-8 ]

[ 4151-80-8 ] Synthesis Path-Upstream 1~6

[ 4151-80-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 4151-80-8 ]

Organoboron

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 4151-80-8 ]