[ CAS No. 58743-81-0 ] {[proInfo.proName]}

Name: 58743-81-0|4-Bromo-4'-propyl-1,1'-biphenyl|98%
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SKU: A243284
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Quality Control of [ 58743-81-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 58743-81-0 ]

Product Details of [ 58743-81-0 ]

CAS No. :	58743-81-0	MDL No. :	MFCD00060105
Formula :	C₁₅H₁₅Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPERLOMMOVDOHH-UHFFFAOYSA-N
M.W :	275.18	Pubchem ID :	619019
Synonyms :

Calculated chemistry of [ 58743-81-0 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	74.16
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.36
Log Po/w (XLOGP3) :	5.58
Log Po/w (WLOGP) :	5.07
Log Po/w (MLOGP) :	5.31
Log Po/w (SILICOS-IT) :	5.4
Consensus Log Po/w :	4.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.42
Solubility :	0.00105 mg/ml ; 0.00000381 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.34
Solubility :	0.00125 mg/ml ; 0.00000455 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.96
Solubility :	0.00003 mg/ml ; 0.000000109 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 58743-81-0 ]

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 [ 58743-81-0 ]

* 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 [ 58743-81-0 ]
Downstream synthetic route of [ 58743-81-0 ]

[ 58743-81-0 ] Synthesis Path-Upstream 1~9

1
[ 10289-45-9 ]
[ 58743-81-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	With iron(III) chloride; bromine In dichloromethane at 25℃; for 18 h;	Add 1 equivalent of compound 5, fifth organic solvent, 0.2 equivalent of ferric chloride to the reaction flask, and the fifth organic solvent is dichloromethane.The weight ratio of the fifth organic solvent to the compound 5 is 5:1, and the mixture is stirred well, and 1.15 equivalents of liquid bromine is slowly added thereto, and the temperature is maintained at 25 ° C for 18 hours.The reaction was quenched by adding a 15percent aqueous solution of sodium hydroxide, stirred, and allowed to stand for separation. The organic phase was washed twice with water to remove the aqueous phase.The organic phase was dried to give a crude compound (yield: Compound 6), which was beaten in methanol, filtered, and dried to give a white solid as compound 6 in a yield of 77percent.

Reference： [1] Patent: CN108129258, 2018, A, . Location in patent: Paragraph 0020; 0030; 0031; 0038; 0039; 0040; 0041; 0042

2
[ 92-86-4 ]
[ 107-08-4 ]
[ 58743-81-0 ]

Reference： [1] Chemistry - A European Journal, 2001, vol. 7, # 23, p. 5118 - 5134

3
[ 58743-84-3 ]
[ 58743-81-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1976, p. 97 - 102
[2] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900

4
[ 106-37-6 ]
[ 87942-08-3 ]
[ 58743-81-0 ]

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

5
[ 92-66-0 ]
[ 58743-81-0 ]

Reference： [1] Journal of Materials Chemistry C, 2014, vol. 2, # 5, p. 891 - 900

6
[ 92-52-4 ]
[ 58743-81-0 ]

Reference： [1] Patent: CN108129258, 2018, A,

7
[ 37940-57-1 ]
[ 58743-81-0 ]

Reference： [1] Patent: CN108129258, 2018, A,

8
[ 87292-26-0 ]
[ 58743-81-0 ]

Reference： [1] Patent: CN108129258, 2018, A,

9
[ 58743-81-0 ]
[ 544-92-3 ]
[ 58743-76-3 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1976, p. 97 - 102

[ 58743-81-0 ] Synthesis Path-Downstream 1~68

1
[ 58743-81-0 ]
[ 126334-35-8 ]
[ 121218-91-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1989,p. 2041 - 2054

2
[ 58743-81-0 ]
[ 544-92-3 ]
[ 58743-76-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1976,p. 97 - 102

3
[ 58743-84-3 ]
[ 58743-81-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1976,p. 97 - 102
[2]Journal of Materials Chemistry C,2014,vol. 2,p. 891 - 900

4
[ 106-37-6 ]
[ 87942-08-3 ]
[ 58743-81-0 ]

Reference： [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1480 - 1486
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1650 - 1656

5
[ 58743-81-0 ]
Cu₂(CN)2 [ No CAS ]
[ 58743-76-3 ]

Reference： [1]Russian Journal of Organic Chemistry,1995,vol. 31,p. 1480 - 1486
Zhurnal Organicheskoi Khimii,1995,vol. 31,p. 1650 - 1656

6
[ 58743-81-0 ]
[ 24850-33-7 ]
[ 218938-49-9 ]

Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 5118 - 5134

7
[ 92-86-4 ]
[ 107-08-4 ]
[ 58743-81-0 ]

Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 5118 - 5134

8
[ 58743-81-0 ]
[ 909122-51-6 ]

Yield	Reaction Conditions	Operation in experiment
11.2%		The resulting residue was purified by a preparative column chromatography using a mixed solvent of heptane and ethyl acetate (heptane/ethyl acetate=1/1 by volume) as a developing solvent and silica gel as a mediator, and further purified by recrystallization from a mixed solvent of toluene and ethanol (toluene/ethanol=1/1 by volume) to obtain 1.69 g of 3-chloro-4-ethoxy-2-fluoro-4"-propyl-[1,1';4',1"]terphenyl (C195). The resulting compound (C195) was colorless crystals, and the yield was 11.2% based on the compound (b60). The transition temperatures of the resulting compound (C195) were as follows. Transition temperature: C (129.2 SA) 136.8 N 183.2 Iso The resulting compound exhibited the following chemical shift delta (ppm) of 1H-NMR analysis, and thus the compound was identified as 3-chloro-4-ethoxy-2-fluoro-4"-propyl-[1,1';4',1"]terphenyl. The measuring solvent was CDCl3.

Reference： [1]Patent: US2006/198968,2006,A1

9
[ 58743-81-0 ]
1-(4'-propylbiphenyl-4-yl)-3-propanethiol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 5118 - 5134

10
[ 58743-81-0 ]
1-(4'-propylbiphenyl-4-yl)-3-acetylthiopropane [ No CAS ]

Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 5118 - 5134

11
[ 58743-81-0 ]
4-bromo-2-methyl-2H-pyrazol-3-ylamine [ No CAS ]
(4-bromo-2-methyl-2H-pyrazol-3-yl)-(4'-propyl-biphenyl-4-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30.1%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 48h;	Example 1.16; Preparation of (4-Bromo-2-methyl-2H-pyrazol-3-yl)-(4'-propyl-biphenyl-4-yl)-amine(Compound 10).A 20-mL scintillation vial was charged with 4'-bromo-4-propyl-biphenyl (275.2 mg, 1 mmol), 3-amino-4-bromo-2-methyl pyrazole (176.0 mg, 1 mmol), sodium fert-butoxide (134.5 mg, 1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (45.8 mg, 0.05 mmol), BINAP (62.3 mg, 0.1 mmol) and toluene (2 mL) under nitrogen atmosphere. The reaction mixture was heated at 800C for 48 hours. It was then allowed to cool to room temperature, taken up in ether/ethyl acetate, filtered and concentrated. The crude material was subjected to column chromatography on silica gel (Biotage, eluent hexanes/ethyl acetate 70/30) to afford Compound 10 as a yellow solid. Yield: 110.7 mg (30.1 %). LCMS m/z (%) = 370 (M+H 79Br, 100), 372 (M+H 81Br, 98).

Reference： [1]Patent: WO2006/60762,2006,A2 .Location in patent: Page/Page column 71

12
[ 58743-81-0 ]
4-n-propyl-4'-(2-tert-butoxycarbonylvinyl)biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In hexane;	Example 98 Synthesis of 4-n-propyl-4'-(2-tert-butoxycarbonylvinyl)biphenyl (Compound 98) 4-n-propyl-4'-(2-tert-butoxycarbonylvinyl)biphenyl was obtained in the same manner as in the Example 44, except for using <strong>[58743-81-0]4-n-propyl-4'-bromobiphenyl</strong> and hexane as the recrystallization solvent instead of 4-(tert-butoxycarbonyloxy)-4'-bromobiphenyl and methanol, respectively. 1H-NMR(CDCl3) ppm: 0.99(t, 3H, CH3), 1.55(s, 9H, tert-Bu), 1.60-1.82(m, 2H, CH2), 2.64(t, 2H, CH2), 6.39(d, 1H, CH=CH), 7.26(d, 2H, C6H4), 7.48-7.68(m, 7H, C6H4 and CH=CH).

Reference： [1]Patent: US2003/211421,2003,A1

13
[ 58743-81-0 ]
[ 88038-94-2 ]

Yield	Reaction Conditions	Operation in experiment
		(i) Synthesis of 4-(4-n-propylphenyl)benzoic acid 4-(4-n-propylphenyl)benzoic acid was obtained in the same manner as in the step (i) of the Example 109, except for using <strong>[58743-81-0]4-n-propyl-4'-bromobiphenyl</strong> instead of 1-(trans-4-n-propylcyclohexyl)-4-bromobenzene.

Reference： [1]Patent: US2003/211421,2003,A1

14
[ 58743-81-0 ]
[ 126213-50-1 ]
[ 1313877-82-5 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 4068 - 4071

15
[ 58743-81-0 ]
[ 1352615-36-1 ]
[ 1352615-39-4 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 20℃;Inert atmosphere;	To the solution of diamine, 7, (1 .06g, 2.32mmol) and 4-bromo-4'-propyl- biphenyl (1 .28g, 4.65mmol) in toluene (20ml_) was added the solution of pd2dba3 (128mg, 0.139mmol) and P(t-Bu)3 (57 mg, 0.278mmol) in toluene (10ml_), followed by the addition of NaO'Bu (0.45g, 4.65mmol) under nitrogen. The resultant mixture was stirred at room temperature overnight. The mixture was filtered through a short silica bed and the filtrate was concentrated under reduced pressure. By column chromatography (10- 30% toluene in hexane) 1 .35g of product 10 was obtained as a solid (69% yield).
69%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 20℃;Inert atmosphere;	Step 4: To the- scuUon of diamine, 7, (1 .Of3g, 2.S2mmcO and 4bomo-4?--propyb n%henyi (1,26g. .65rnrno) in eduene (2OrnL) was ahead the soh.Won of pddba3 (128mg, 0.1 39mmoi) and P(t-Bu):t (57 mg, 0.2i8mrnoi) in tohiene (1 OmL), toflowed 57 the adthton of NeOtBu (0.45g, 4.ebmrnoO under ndrogen The resultant mixture was stirred at room temperature overnqht.The mixture was tibared throuqh a short sca bed and the flitrete was concentrated under reduced pressure. By column cnrornatography (10- 30% toluene in hexane) I .35g of product 10 was obtained as a soBd (69% yle dl.
69%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 20℃;Inert atmosphere;	To the solution of diamine, 7, (1.06 g, 2.32 mmol) and 4-bromo-4?-propyl-biphenyl (1.28 g, 4.65 mmol) in toluene (20 mL) was added the solution of pd2dba3 (128 mg, 0.139 mmol) and P(t-Bu)3 (57 mg, 0.278 mmol) in toluene (10 mL), followed by the addition of NaOtBu (0.45 g, 4.65 mmol) under nitrogen. The resultant mixture was stirred at room temperature overnight. The mixture was filtered through a short silica bed and the filtrate was concentrated under reduced pressure. By column chromatography (10-30% toluene in hexane) 1.35 g of product 10 was obtained as a solid (69% yield).

Reference： [1]Patent: WO2011/159872,2011,A1 .Location in patent: Page/Page column 39-40
[2]Patent: WO2015/89027,2015,A1 .Location in patent: Page/Page column 94; 95
[3]Patent: US2016/315259,2016,A1 .Location in patent: Paragraph 0366; 0367

16
[ 58743-81-0 ]
[ 1158651-01-4 ]
[ 1158651-28-5 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium t-butanolate;1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 200℃; for 40h;Inert atmosphere;	Under an atmosphere of nitrogen, compound 3 (2.0 g, 3.03 mmol), <strong>[58743-81-0]4-bromo-4'-propylbiphenyl</strong> (1.67 g, 6.05 mmol), tris(dibenzylideneacetone)dipalladium(0) (139 mg, 5 mol %), tri-t-butylphosphine (61 mg, 10 mol %) and toluene (27 mL) were combined. Sodium t-butoxide (0.872 g, 9.08 mmol) was added and the reaction was stirred at room temperature for 40 h. <strong>[58743-81-0]4-bromo-4'-propylbiphenyl</strong> (250 mg, 0.091 mmol), tris(dibenzylideneacetone)dipalladium(0) (55 mg, 2 mol %), tri-t-butylphosphine (25 mg, 4 mol %) and sodium t-butoxide (291 mg, 3.03 mmol) were then added. After another 23 h, the reaction mixture was filtered through a pad of Celite, rinsing with toluene. The solution was concentrated on a rotary evaporator and dried under vacuum. The product was purified by medium pressure liquid chromatography on silica gel (0-40% methylene chloride gradient in hexanes) to give 1.70 g (53% yield) of a white solid. NMR analysis confirmed the structure of Intermediate Compound 33 as a mixture of 4,4'- and 4,5'-regioisomers. Purity (UPLC): 97.8%.

Reference： [1]Patent: US2012/65432,2012,A1 .Location in patent: Page/Page column 47

17
[ 61676-62-8 ]
[ 58743-81-0 ]
[ 153035-56-4 ]

Yield	Reaction Conditions	Operation in experiment
80%		[Experimental embodiment 2]: preparation of the compound in formula (I-4)Step 1: synthesize the compound in formula (2-A) (hereinafter ?compound (2-A)?).First, 10 grams of 4-bromo-1-propyl benzene in formula (2) is placed in a two-neck bottle. The two-neck bottle is heated, and waterless THF is injected into the two-neck bottle. After the two-neck bottle is cooled to -78 C., 18 mL of an n-BuLi solution is slowly dripped into the two-neck bottle. After maintaining the reaction temperature at -78 C. for 1 hour, 10 mL of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is slowly dripped into the two-neck bottle. After continuing the reaction for 1 hour, the bottle is heated to room temperature. 10 mL of distilled water is added to the above double-neck bottle, and low pressure evaporation-concentration is performed to remove the THF. Ethyl acetate and distilled water are used to extract the obtained mixture solution. Afterwards, the collected organic solution is desiccated by waterless magnesium sulfate, and the solid magnesium sulfate is removed by gravitational filtration. Then, low pressure evaporation-concentration is performed on the obtained mixture solution to remove the solvent. 9.47 grams of a white solid compound (2-A) is obtained. The yield is 80%.

Reference： [1]Patent: US2012/264984,2012,A1 .Location in patent: Page/Page column 4-5

18
[ 58743-81-0 ]
[ 1402734-19-3 ]

Reference： [1]Patent: US2012/264984,2012,A1

19
[ 58743-81-0 ]
[ 1402734-20-6 ]

Reference： [1]Patent: US2012/264984,2012,A1

20
[ 58743-81-0 ]
[ 1402734-21-7 ]

Reference： [1]Patent: US2012/264984,2012,A1

21
[ 58743-81-0 ]
[ 1402734-22-8 ]

Reference： [1]Patent: US2012/264984,2012,A1

22
[ 58743-81-0 ]
[ 1402734-15-9 ]

Reference： [1]Patent: US2012/264984,2012,A1

23
[ 688-71-1 ]
[ 58743-81-0 ]
[ 153035-56-4 ]