[ CAS No. 37909-95-8 ] {[proInfo.proName]}

Name: 37909-95-8|4-Butyl-1,1'-Biphenyl|98%
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SKU: A109663
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Quality Control of [ 37909-95-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 37909-95-8 ]

Product Details of [ 37909-95-8 ]

CAS No. :	37909-95-8	MDL No. :	MFCD00100665
Formula :	C₁₆H₁₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JZDZRFNMDCBTNS-UHFFFAOYSA-N
M.W :	210.31	Pubchem ID :	2775237
Synonyms :

Calculated chemistry of [ 37909-95-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.25
Num. rotatable bonds :	4
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	71.27
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.2
Log Po/w (XLOGP3) :	6.01
Log Po/w (WLOGP) :	4.7
Log Po/w (MLOGP) :	5.83
Log Po/w (SILICOS-IT) :	5.11
Consensus Log Po/w :	4.97

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.22
Solubility :	0.00126 mg/ml ; 0.00000601 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.79
Solubility :	0.000343 mg/ml ; 0.00000163 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.52
Solubility :	0.0000632 mg/ml ; 0.000000301 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.61

Safety of [ 37909-95-8 ]

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 [ 37909-95-8 ]

* 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 [ 37909-95-8 ]
Downstream synthetic route of [ 37909-95-8 ]

[ 37909-95-8 ] Synthesis Path-Upstream 1~2

1
[ 37909-95-8 ]
[ 52709-83-8 ]

Reference： [1] Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 1187 - 1191[2] Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 6, p. 1305 - 1310

2
[ 37909-95-8 ]
[ 63619-54-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 853 - 862

[ 37909-95-8 ] Synthesis Path-Downstream 1~79

1
[ 108-30-5 ]
[ 37909-95-8 ]
[ 102553-53-7 ]

Reference： [1]Nippon Kagaku Zasshi,1957,vol. 78,p. 1577,1580
Chem.Abstr.,1960,p. 1413

2
[ 13211-01-3 ]
[ 37909-95-8 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 845
    Chem.Abstr.,1955,p. 10898
[2]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
    Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376
[3]Journal of the American Chemical Society,1975,vol. 97,p. 4620 - 4626
[4]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191
    Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310
[5]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 853 - 862

3
[ 93017-33-5 ]
[ 37909-95-8 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 608,611; engl. Ausg. S. 589, 591

4
[ 92-52-4 ]
[ 71-36-3 ]
[ 37909-95-8 ]
[ 7641-81-8 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 413,416; engl. Ausg. S. 405, 407
[2],1957,vol. IV 14,p. 49,56
Chem.Abstr.,1960,p. 24565

5
[ 37909-88-9 ]
[ 37909-95-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1972,p. 1581 - 1587

6
[ 37909-95-8 ]
[ 93189-65-2 ]

Reference： [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376

7
[ 37909-95-8 ]
[ 141-75-3 ]
[ 102168-20-7 ]

Reference： [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376

8
[ 37909-95-8 ]
[ 84941-14-0 ]
[ 93972-13-5 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310

11
[ 109-72-8 ]
(η⁶:η⁶-biphenyl)bis(tricarbonylchromium) [ No CAS ]
[ 37909-95-8 ]
[ 54532-97-7 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 2073 - 2076

12
4-butyl-N,N,N-trimethylphenylaminium trifluoromethanesulfonate [ No CAS ]
[ 98-80-6 ]
[ 37909-95-8 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 6046 - 6047

13
[ 109-65-9 ]
[ 1137-79-7 ]
[ 37909-95-8 ]

Reference： [1]Synthesis,2003,p. 2811 - 2814

14
[ 693-03-8 ]
[ 2051-62-9 ]
[ 37909-95-8 ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 15922 - 15934

15
[ 698378-27-7 ]
[ 37909-95-8 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557

16
[ 15499-27-1 ]
[ 98-80-6 ]
[ 37909-95-8 ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 1871 - 1876
[2]Journal of the American Chemical Society,2005,vol. 127,p. 4685 - 4696
[3]Organometallics,2018,vol. 37,p. 1876 - 1883

17
[ 92-66-0 ]
[ 15676-66-1 ]
[ 37909-95-8 ]

Reference： [1]Synthesis,2005,p. 485 - 492

18
[ 41492-05-1 ]
[ 3958-47-2 ]
[ 37909-95-8 ]

Reference： [1]Synthesis,2005,p. 485 - 492

19
[ 15499-27-1 ]
[ 29540-83-8 ]
[ 960-16-7 ]
[ 644-08-6 ]
[ 37909-95-8 ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 6343 - 6348

20
[ 41492-05-1 ]
[ 98-80-6 ]
[ 37909-95-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With C24H20Cl2NPPdS; potassium carbonate; palladium; In toluene; at 100℃; for 2h;	General procedure: A 100 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer bar. The flask was charged with toluene (15 ml) and the appropriate amount of catalyst reagents and the internal standard (n-Decane: 2.59 mmol). The contents were thoroughly mixed and an initial sample (t0) was then taken. The reaction flask was placed in an oil bath at the desired temperature and the reaction mixture allowed to heat/reflux with stirring. A sample was taken and analyzed every 10 min for the first hour and every 30 min thereafter until t3h. In cases where conversionwas not complete after 3 h, the reaction mixturewas then allowed to stir for a total of 24 h. The reaction at 140 C was performed in a sealed tube. All catalytic reactions were done under aerobic conditions. Percentage conversions were determined by GC with n-decane as the internal standard and the coupling products were characterized by mass spectrometry (Table 4) as well as 1H NMR spectroscopy (Entry 5, Table 4 only).

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 3190 - 3198
[2]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 551 - 555
[3]Applied Organometallic Chemistry,2015,vol. 29,p. 87 - 89
[4]Journal of Organometallic Chemistry,2012,vol. 703,p. 34 - 42
[5]Angewandte Chemie - International Edition,2006,vol. 45,p. 2868 - 2871
[6]Chemistry - A European Journal,2010,vol. 16,p. 1812 - 1818
[7]Organometallics,2010,vol. 29,p. 1729 - 1739
[8]Applied Catalysis A: General,2011,vol. 393,p. 231 - 241
[9]Organometallics,2011,vol. 30,p. 6270 - 6282
[10]Journal of Organometallic Chemistry,2018,vol. 868,p. 76 - 85

21
[ 37909-95-8 ]
[ 63619-54-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 853 - 862

22
[ 92-52-4 ]
[ 37909-95-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310

23
[ 37909-95-8 ]
[ 52709-83-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310

24
[ 37909-95-8 ]
[ 93972-06-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1984,vol. 20,p. 1187 - 1191
Zhurnal Organicheskoi Khimii,1984,vol. 20,p. 1305 - 1310

25
[ 3218-36-8 ]
KMnO₄ [ No CAS ]
[ 37909-95-8 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557
[2]European Journal of Organic Chemistry,2004,p. 1544 - 1557

26
[ 698377-55-8 ]
[ 37909-95-8 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 1544 - 1557
[2]European Journal of Organic Chemistry,2004,p. 1544 - 1557

27
[ 37909-95-8 ]
[ 102168-34-3 ]

Reference： [1]Nippon Kagaku Zasshi,1957,vol. 78,p. 1577,1580
Chem.Abstr.,1960,p. 1413

28
[ 92-52-4 ]
sodium [ No CAS ]
[ 37909-95-8 ]

Reference： [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376

29
[ 37909-95-8 ]
[ 7641-81-8 ]

Reference： [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376

30
[ 37909-95-8 ]
[ 96624-48-5 ]

Reference： [1]Journal of general chemistry of the USSR,1960,vol. 30,p. 393 - 399
Zhurnal Obshchei Khimii,1960,vol. 30,p. 369 - 376

31
aluminiumchlorid [ No CAS ]
[ 37909-95-8 ]
[ 75-36-5 ]
[ 59662-37-2 ]

Yield	Reaction Conditions	Operation in experiment
	In nitrobenzene;	Example 58 Intermediate 58A 1-(4'-butyl[1,1'-biphenyl]-4-yl)-1-ethanone 5g (24mmol) <strong>[37909-95-8]4-butylbiphenyl</strong> and 3.96g (30mmol) aluminiumchlorid are dissolved in 30ml nitrobenzene. At a temperature below 20C 1.87g (30mmol) acetylchloride is added dropwise and the reactionmixture is stirred at roomtemperature for 2hrs. The solution is poured onto icewater, the organic phase is separated, the aqueous phase extracted with ethylacetate, the combined organic phases are washed with water and brine, dried and concentrated. The product is obtained by trituration with petrolether. Yield: 3.07g (51%). 200 MHz 1H-NMR (CDCl3): 0.96, t, 3H; 1.40, m, 2H; 1.65, m, 2H; 2.62, s, 3H; 2.68, t, 2H; 7.30, d, 2H; 7.58, d, 2H; 7.69, d, 2H; 8.02, d, 2H.

Reference： [1]Patent: EP1031349,2000,A1

32
[ 37909-95-8 ]
[ 13211-01-3 ]
[ 92-92-2 ]

Reference： [1]Synlett,2009,p. 117 - 121

33
[ 693-03-8 ]
[ 1009828-67-4 ]
[ 37909-95-8 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 9566 - 9569

34
[ 1625-92-9 ]
[ 92-52-4 ]
[ 7116-95-2 ]
[ 644-08-6 ]
[ 5707-44-8 ]
[ 37909-95-8 ]
[ 10289-45-9 ]

Reference： [1]Petroleum Chemistry,2010,vol. 50,p. 149 - 153

35
[ 109-65-9 ]
[ 3315-91-1 ]
[ 37909-95-8 ]

Reference： [1]Asian Journal of Chemistry,2011,vol. 23,p. 4087 - 4089
[2]Asian Journal of Chemistry,2013,vol. 25,p. 6303 - 6305

36
[ 15499-27-1 ]
[ 100-58-3 ]
[ 37909-95-8 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 936 - 938

37
[ 92-69-3 ]
[ 37909-95-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 96 - 99
[2]Organic Letters,2013,vol. 15,p. 96 - 99

38
[ 76996-40-2 ]
[ 693-04-9 ]
[ 37909-95-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2329 - 2336
[2]Organic Letters,2013,vol. 15,p. 96 - 99
[3]ChemSusChem,2018,vol. 11,p. 1290 - 1294
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 7271 - 7276

39
[ 405201-85-6 ]
[ 693-04-9 ]
[ 37909-95-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 96 - 99

40
[ 20651-67-6 ]
[ 71-43-2 ]
[ 37909-95-8 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 2983 - 2985

41
[ 15499-27-1 ]
[ 71-43-2 ]
[ 37909-95-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 6016 - 6024

42
[ 15499-27-1 ]
[ 591-51-5 ]
[ 37909-95-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5114 - 5117
[2]Chemistry - A European Journal,2016,vol. 22,p. 3991 - 3995

43
[ 15499-27-1 ]
[ 591-51-5 ]
[ 37909-95-8 ]
[ 7641-81-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5114 - 5117

44
C₂₁H₂₂OSi [ No CAS ]
[ 74-88-4 ]
[ 37909-95-8 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 12719 - 12722
Angew. Chem.,2013,vol. 125,p. 12951 - 12954,4

45
[ 542-69-8 ]
C₂₁H₂₂OSi [ No CAS ]
[ 37909-95-8 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 12719 - 12722
Angew. Chem.,2013,vol. 125,p. 12951 - 12954,4

46
[ 20651-67-6 ]
[ 98-80-6 ]
[ 37909-95-8 ]

Reference： [1]Green Chemistry,2013,vol. 15,p. 3396 - 3403

47
[ 591-50-4 ]
[ 145240-28-4 ]
[ 37909-95-8 ]

Yield	Reaction Conditions	Operation in experiment
34%		In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.

Reference： [1]Journal of Materials Chemistry A,2014,vol. 2,p. 12739 - 12745
[2]Tetrahedron,2017,vol. 73,p. 5784 - 5793
[3]Chemical Communications,2014,vol. 50,p. 12356 - 12359

48
[ 37909-95-8 ]
C₁₀₀H₁₂₀N₈O₁₂ [ No CAS ]
2C₁₀₀H₁₂₀N₈O₁₂*C₁₆H₁₈ [ No CAS ]

Reference： [1]Journal of Physical Organic Chemistry,2015,vol. 28,p. 187 - 190

49
[ 15499-27-1 ]
[ 591-51-5 ]
[ 104-51-8 ]
[ 37909-95-8 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 3991 - 3995

50
[ 109-72-8 ]
[ 1591-31-7 ]
[ 37909-95-8 ]

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 3043 - 3046

51
[ 591-50-4 ]
[ 2525-42-0 ]
[ 18162-48-6 ]
[ 145240-28-4 ]
[ 37909-95-8 ]
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%; 64%		In N2 (purity of 99.999%) filled glove box (O2 < 0.1ppm, H2O < 0.1 ppm), to an oven-dried screwed 20 mL vial were added Palladium catalyst (5 mol%), Ligand (5 or 10 mol%), Base (2 eq.), Boronic acids 3 (1.5 eq.) and THF (3 mL), then allene 1a (0.2 mmol, 36 mg) and phenyl iodide 2a (1.2 eq., 49 mg) were also charged into the formed suspension above. The joint position between vial and cap was sealed with black electric tape to save the nitrogen in it and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13-15 hours on the IKA electric stirring machine. The reaction process was monitored by TLC (Hexane/Ethyl acetate = 2:1) method to show that the precursor of allyllic alcohol was formed completely. Then, imidazole (8 eq. 108 mg) and TBSCl (3 eq. 90 mg) were added into the vial under air and kept stirring for around 2 hours, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the reaction of producing the protected allyl alcohol by TBS group 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a. The results were summarized in Table 1 as below.

Reference： [1]Tetrahedron,2017,vol. 73,p. 5784 - 5793

52
C₅₄H₄₅O₃P₂PdS⁽¹⁺⁾*BF₄^(1-) [ No CAS ]
[ 18162-48-6 ]
[ 145240-28-4 ]
[ 37909-95-8 ]
[(2Z)-3-(benzenesulfonyl)-2-phenylprop-2-en-1-yl]oxy}(tert-butyl)dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%; 80%		In an N2 charged glove box with oxygen and water levels ?0.1 ppm, to an oven-dried screwed vial were added complex 8 (51 mg, 0.05 mmol), K2CO3 (13.8 mg, 0.1 mmol, 2 eq.), boronic acids 3a (9 mg, 0.05mmol, 1 eq.) and THF (3 mL), then phenyl iodide 2a (10 mg, 0.05 mmol, 1 eq.) were also charged into the reaction mixture. The joint position between the vial and cap was sealed with black electric tape to save the nitrogen in the vial and heat the reaction vial up at 70 oC using aluminum heating plate outside of glove box for 13 hours on the IKA electric stirring machine. After 15 hours, imidazole (17 mg, 0.25 mmol, 5 eq.) and TBSCl (22 mg, 0.15 mmol, 3 eq.) were added into the vial under air and stirred for another 2 hours at room temperature, which was monitored by TLC (Hexane/Ethyl acetate = 7:1) method as well to confirm the formation of TBS protected allyl alcohol 4a was completed. Then product was isolated and purified by short column chromatography (Hexane/Ethyl acetate = 20:1) to get pure product of 4a (7 mg, 80%). The spectrum was same as above. The biphenyl product 4aa is also formed with about 1.6 mg (15% yield). There is no reaction occur without the presence of phenyl iodide, which was confirmed by the analysis of 31P NMR of crude reaction mixture.

Reference： [1]Tetrahedron,2017,vol. 73,p. 5784 - 5793

53
[ 109-69-3 ]
[ 2920-38-9 ]
[ 74-88-4 ]
[ 37909-95-8 ]
4-butyl-4-phenylcyclohexa-2,5-dienone [ No CAS ]
trans-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]
cis-4-butyl-1-methyl-4-phenylcyclohexa-2,5-dienecarbonitrile [ No CAS ]