[ CAS No. 880-36-4 ] {[proInfo.proName]}

Name: 880-36-4|2-n-Octylthiophene|97%
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SKU: A765994
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Quality Control of [ 880-36-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 880-36-4 ]

Product Details of [ 880-36-4 ]

CAS No. :	880-36-4	MDL No. :	MFCD00041015
Formula :	C₁₂H₂₀S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GIFWAJGKWIDXMY-UHFFFAOYSA-N
M.W :	196.35	Pubchem ID :	70153
Synonyms :

Calculated chemistry of [ 880-36-4 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.67
Num. rotatable bonds :	7
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	62.93
TPSA :	28.24 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.48
Log Po/w (XLOGP3) :	5.5
Log Po/w (WLOGP) :	4.65
Log Po/w (MLOGP) :	3.79
Log Po/w (SILICOS-IT) :	5.37
Consensus Log Po/w :	4.56

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.34
Solubility :	0.00887 mg/ml ; 0.0000452 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.85
Solubility :	0.000276 mg/ml ; 0.00000141 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.89
Solubility :	0.00252 mg/ml ; 0.0000129 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.44

Safety of [ 880-36-4 ]

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 [ 880-36-4 ]

* 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.

Downstream synthetic route of [ 880-36-4 ]

[ 880-36-4 ] Synthesis Path-Downstream 1~88

1
[ 188290-36-0 ]
[ 111-83-1 ]
[ 880-36-4 ]

Yield	Reaction Conditions	Operation in experiment
100%		[0183] Detailed synthesis of 2-octylthiophene .[0184] A solution of thiophene (2.0 g, 1.90 mL, 23.8 mmol) in dry THF (30 mL) under argon, was cooled at - 8O0C and 1.1 equivalent of n-Buli (1.6 M in solution in hexane) was added dropwise. The mixture was then stirred for 15 min. Then 4.52 mL of 1-bromooctane (5.05 g, 26.2 mmol) was added in one time. The medium was then allowed to warm at room temperature and stirred overnight. After adding 20 mL of water, the solution was extracted by diethyl ether. The organic layers were dried over MgSO4 and the solvent removed in vacuum. Purification by Kugelrhor distillation (1500C, 30 Torr) afforded the desired alkyl thiophene as a colorless liquid (4.62g, 23.5 mmol) in quantitative yield.1H-NMR (CDCl3) : 7.10 (dd, IH, J=I.14 and 5.13 Hz), 6.91 (dd, IH, J=3.21 and 5.13 Hz), 6.78 (dd, IH, J=I.14 and 3.21 Hz) , 2.82 (t, 2H, J=7.55 Hz) , 1.68 (m, 2H) , 1.28 (m, 10H) , 0.88 (t, 3H, J=6.89 Hz) .
80.6%		After dissolution Compound 1 (50 mmol) in anhydrous THF (15 ml), cooled to -78 C., n-butyl lithium was added dropwise(hexane solution, approximately 1.6mol / L) 20 min. After completion of the dropwise addition, stirred for about 30 minutes at -30 C., then raising the reaction temperature to room temperature, stirred again for 1 hour and then added dropwise to about 10 minutes 1-bromo-octane (40 mmol) at 0 C.. After completion of the dropwise addition, followed by extraction with dichloromethane, the organic layer was washed with water, a brown oil obtained and the solvent was evaporated under reduced pressure and purified by force column chromatography to give compound 4.

Reference： [1]Patent: WO2011/20712,2011,A2 .Location in patent: Page/Page column 65-66
[2]Journal of Molecular Structure,2009,vol. 921,p. 89 - 100
[3]Journal of Materials Chemistry,2010,vol. 20,p. 9658 - 9665
[4]Patent: JP5713285,2015,B2 .Location in patent: Paragraph 0071; 0072; 0073
[5]Chemical Communications,2006,p. 871 - 873
[6]Patent: WO2006/22040,2006,A1 .Location in patent: Page/Page column 12
[7]Synlett,2004,p. 177 - 181
[8]Patent: US2585292,1950,
[9]Organic Letters,2011,vol. 13,p. 4092 - 4095
[10]Polymer,2015,vol. 65,p. 193 - 201

2
[ 3437-95-4 ]
[ 111-83-1 ]
[ 880-36-4 ]

Reference： [1]Chemische Berichte,1886,vol. 19,p. 645

3
[ 880-36-4 ]
[ 623-66-5 ]
[ 241806-30-4 ]

Reference： [1]Journal of the American Chemical Society,1956,vol. 78,p. 1958,1960

4
[ 880-36-4 ]
[ 93-61-8 ]
[ 73792-02-6 ]

Reference： [1]Journal of the Chemical Society,1955,p. 1581,1583
Errata,1957

5
[ 777952-08-6 ]
[ 880-36-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1955,p. 359,362

6
[ 30711-41-2 ]
[ 880-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; potassium hydroxide; In octanol; for 8h;Reflux;	The thiophene (4.0 g) was dissolved in anhydrous toluene (50 mL), cooled to 0 C, anhydrous SnCl 4 (6.0 mL) was added, and after stirring for 10 minutes, octanoyl chloride (7.88 mL) was added dropwise; After completion, rise to room temperature; stir for 6 hours. the reaction was quenched with water and extracted with ethyl acetate. the organic phases were combined, dried over anhydrous MgSO4, filtered and evaporated. the obtained acylated product was used in the next step without purification. The obtained oily intermediate was placed in a 100 mL single-necked flask, and potassium hydroxide (18.80 g), hydrazine hydrate (15 mL), and n-octanol (10 mL) were added thereto, and the mixture was heated to reflux; the reaction was allowed to stand for 8 hours, cooled to room temperature, and water was added thereto. The product was extracted with ethyl acetate and dried over anhydrous MgSO4. filter and spin. The crude product was separated on a silica gel column to give a colorless oil.

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725
[2]Journal of the Chemical Society,1955,p. 1581,1583
Errata,1957
[3]Chemistry - An Asian Journal,2018,vol. 13,p. 3920 - 3927
[4]Patent: CN110183419,2019,A .Location in patent: Paragraph 0013; 0017; 0018

7
[ 880-36-4 ]
[ 56555-02-3 ]
[ 111514-80-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 208 - 211

8
[ 880-36-4 ]
[ 124-38-9 ]
[ 90619-88-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 2h;Schlenk technique; Cooling with acetone-dry ice;	General procedure: In a freshly dried Schlenck tube (100mL), 4-bromo-1-octyloxylbezene (5.70g, 20mmol) was dissolved in dry THF (40mL). The solution was cooled to-78C in a dry ice/acetone bath. Then, n-BuLi (1.6M in hexane, 15mL) was added dropwise. After the lithium exchange reaction finished, dry CO2 was bubbled into the solution via a long needle for 2h. Later, the extraction with ethyl acetate was conducted before neutralized with 1M HCl. Pure product was isolated by silica gel chromatography with eluent of petroleum/EA (8:1, v/v).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 596 - 602
[2]Journal of Materials Chemistry,2010,vol. 20,p. 9658 - 9665
[3]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1983,vol. 38,p. 1669 - 1677

9
[ 880-36-4 ]
[ 68-12-2 ]
[ 73792-02-6 ]

Reference： [1]Letters in Organic Chemistry,2010,vol. 7,p. 85 - 89
[2]Journal of Molecular Structure,2009,vol. 921,p. 89 - 100
[3]Journal of Medicinal Chemistry,1983,vol. 26,p. 1378 - 1393

10
[ 880-36-4 ]
[ 111-64-8 ]
[ 241806-30-4 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

11
[ 880-36-4 ]
[ 172514-63-5 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In water; argon; N,N-dimethyl-formamide;	Synthesis of 2-bromo-5-octylthiophene <strong>[880-36-4]2-Octylthiophen</strong>e (96.1 g. 0.489 mol) and dehydrated N,N-dimethylformamide (hereinafter referred to as "DMF") (300 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube, and a solution of N-bromosuccinimide (hereinafter referred to as "NBS") (87.1 g, 0.489 mol) in DMF (200 ml) was added dropwise thereto at room temperature in an argon gas stream over a period of about one hr. After the completion of dropwise addition, the mixture was stirred with heating at 100 C. for about 2 hr. After the completion of the reaction, water (300 ml) was added to the reaction solution, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (n-hexane) to give an objective compound 2-bromo-5-octylthiophene as a yellow liquid (125.4 g, yield 93.2%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory). 1H-NMR (CDCl3, TMS/ppm): 0.88 (t, 3H, J=6.83 Hz), 1.28 (m, 10H), 1.60 (m, 2H), 2.73 (t, 2H, J=7.32 Hz), 6.52 (d, 1H, J=3.90 Hz), 6.83 (d, 1H, J=3.90 Hz).

Reference： [1]Tetrahedron,2007,vol. 63,p. 941 - 946
[2]Synlett,2004,p. 177 - 181
[3]Tetrahedron,1999,vol. 55,p. 8045 - 8064
[4]Journal of Materials Chemistry,2002,vol. 12,p. 2706 - 2721
[5]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 881 - 888
[6]Patent: US2010/224869,2010,A1
[7]Organic Letters,2011,vol. 13,p. 4092 - 4095
[8]Polymer,2015,vol. 65,p. 193 - 201
[9]CrystEngComm,2018,vol. 20,p. 1669 - 1678

Yield	Reaction Conditions	Operation in experiment
		Examples of compounds within Formula II above are: thiophene and all isomeric forms of methylthiophene, dimethylthiophene, ethyl thiophene, octyl thiophene, monochlorothiophene, monobromothiophene, monoiodothiophene, monofluorothiophene, dichlorothiophene, ...

14
[ 880-36-4 ]
2-fluoro-5-n-octylthiophene [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2003,vol. 124,p. 159 - 168

15
[ 880-36-4 ]
[ 108-24-7 ]
[ 247042-14-4 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 4003 - 4013

16
[ 188290-36-0 ]
nC₈H₁₇X [ No CAS ]
[ 880-36-4 ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 4003 - 4013

17
[ 111-83-1 ]
[ 5713-61-1 ]
[ 880-36-4 ]

Reference： [1]Tetrahedron,2006,vol. 62,p. 2207 - 2213

18
[ 880-36-4 ]
[ 183438-24-6 ]
2,5-bis[2-(5-n-octyl)thienyl]pyrimidine [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 368,p. 279 - 292

19
[ 629-27-6 ]
[ 5713-61-1 ]
[ 880-36-4 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 1886 - 1889

20
[ 2591-86-8 ]
[ 880-36-4 ]
[ 73792-02-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		In 100mL reaction flask were added <strong>[880-36-4]2-octyl thiophene</strong> 3g (15.3mmol), and 35mL of anhydrous tetrahydrofuran, pumping air in the system, which leads to an argon atmosphere, the reaction flask was placed in a cryostat reactor was cooled to -78 , stirring was added dropwise using a syringe under 5.7mL (15.3mmol) of n-butyllithium in n-hexane solution (2.7M), the reaction was continued at -78 1.5h, then slowly added dropwise 1.3mL (16.8mmol) 1- formyl piperidine, the reaction 0.5h, the reaction flask was stirred overnight at room temperature to the next. The reaction was stopped after purification treatment to give a pale yellow liquid 2.3g, 68% yield.

Reference： [1]Patent: CN105367592,2016,A .Location in patent: Paragraph 0072; 0073
[2]Chemical Communications,2006,p. 871 - 873

21
[ 880-36-4 ]
2,5-dibromo-3-(5-octyl-thienylene-vinyl)-thiophene [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 871 - 873

22
[ 880-36-4 ]
[ 925424-90-4 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 941 - 946

23
[ 880-36-4 ]
5-octyl-5'''-tridecafluorohexyl-2,2':5',2'':5'',2'''-quaterthiophene [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 941 - 946

24
[ 880-36-4 ]
C₁₈H₂₃BBr₂OS [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 881 - 888

25
[ 880-36-4 ]
4-(5-octyl-thiophen-2-yl)-phenol [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 881 - 888
[2]Journal of Materials Chemistry,2002,vol. 12,p. 2706 - 2721

26
[ 880-36-4 ]
2-(4-methoxyphenyl)-5-octylthiophene [ No CAS ]

27
[ 880-36-4 ]
2-{4-[((2E,4E)-Hexa-2,4-dienyl)oxy]-phenyl}-5-octyl-thiophene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 881 - 888

28
[ 880-36-4 ]
(2E,4E)-Hexa-2,4-dienoic acid 4-(5-octyl-thiophen-2-yl)-phenyl ester [ No CAS ]

29
[ 880-36-4 ]
(E)-Hex-2-enoic acid 4-(5-octyl-thiophen-2-yl)-phenyl ester [ No CAS ]

30
[ 880-36-4 ]
1,3,5-tris[5-(2-octylthienyl)]benzene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 4003 - 4013

31
[ 880-36-4 ]
[ 160855-05-0 ]

Reference： [1]Synlett,2004,p. 177 - 181

32
[ 880-36-4 ]
5-octyl-[3,3']bithiophenyl [ No CAS ]

Reference： [1]Synlett,2004,p. 177 - 181

33
[ 880-36-4 ]
[ 667920-02-7 ]

Reference： [1]Synlett,2004,p. 177 - 181

34
[ 880-36-4 ]
5,5'-dioctyl-[3,3']bithiophenyl [ No CAS ]

Reference： [1]Synlett,2004,p. 177 - 181

35
[ 880-36-4 ]
[ 667919-99-5 ]

Reference： [1]Synlett,2004,p. 177 - 181

36
[ 880-36-4 ]
[ 667920-03-8 ]

Reference： [1]Synlett,2004,p. 177 - 181

37
[ 880-36-4 ]
C₂₃H₂₈BrLiS₄Si [ No CAS ]

Reference： [1]Synlett,2004,p. 177 - 181

38
[ 880-36-4 ]
[ 667920-04-9 ]

Reference： [1]Synlett,2004,p. 177 - 181

39
[ 880-36-4 ]
C₂₃H₂₇BrLi₂S₄Si [ No CAS ]

Reference： [1]Synlett,2004,p. 177 - 181

40
[ 880-36-4 ]
5-pentyl-thiophene-2-carboxylic acid 4-(5-octyl-thiophen-2-yl)-phenyl ester [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2002,vol. 12,p. 2706 - 2721

41
[ 880-36-4 ]
[ 28504-81-6 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

42
[ 880-36-4 ]
[ 13090-49-8 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

43
[ 880-36-4 ]
[ 128912-54-9 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725
[2]Journal of the American Chemical Society,1956,vol. 78,p. 1958,1960

44
[ 880-36-4 ]
[ 241806-32-6 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

45
[ 880-36-4 ]
3-methyl-dithieno[3,4-<i>b</i>;3',4'-<i>d</i>]thiophene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

46
[ 880-36-4 ]
1-methyldithieno[3,4-b:3',4'-d]thiophene [ No CAS ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

47
[ 880-36-4 ]
4-(5-octyl-thiophen)-2-yl-<2,2'>-bipyridine [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 8045 - 8064

48
[ 880-36-4 ]
[ 189118-11-4 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

49
[ 880-36-4 ]
[ 241806-34-8 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

50
[ 111-64-8 ]
1.2-isopropylidene-glycerol [ No CAS ]
[ 880-36-4 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 1719 - 1725

51
[ 880-36-4 ]
[ 170656-09-4 ]

Reference： [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1983,vol. 38,p. 1669 - 1677
[2]Journal of Materials Chemistry,2010,vol. 20,p. 9658 - 9665

52
[ 880-36-4 ]
5-Octyl-2-thiophencarbonsaeurecholesterylester [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1983,vol. 38,p. 1669 - 1677

53
[ 880-36-4 ]
4,4'-Bis(5-octyl-2-thienylcarbonyloxy)biphenyl [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1983,vol. 38,p. 1669 - 1677

54
[ 880-36-4 ]
[ 86373-15-1 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1378 - 1393

55
[ 880-36-4 ]
4-[1-(5-Octyl-thiophen-2-yl)-meth-(Z)-ylidene]-amino}-benzoic acid ethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1378 - 1393

56
[ 880-36-4 ]
[ 86373-14-0 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 1378 - 1393

57
[ 880-36-4 ]
[ 15594-90-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 208 - 211

58
[ 880-36-4 ]
[ 6064-90-0 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 208 - 211

59
[ 880-36-4 ]
[ 111514-91-1 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 208 - 211

60
[ 880-36-4 ]
5-octyl-thiophene-2-carbaldehyde thiosemicarbazone [ No CAS ]

Reference： [1]Journal of the Chemical Society,1955,p. 1581,1583
Errata,1957

61
[ 111-83-1 ]
[ 880-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; thiophene; hexane; water;	Synthesis of 2-octylthiophene Thiophene (59.9 g, 0.713 mol) and dehydrated tetrahydrofuran (hereinafter referred to as "THF") (200 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube. The solution was cooled to -78 C., and a solution (200 ml) of n-butyllithium (2.6 M) in n-hexane was added dropwise to the cooled solution over a period of about one hr. After the completion of the dropwise addition, the mixture was stirred at -78 C. for about one hr. Thereafter, the reaction temperature was raised to room temperature. At that temperature, the mixture was again stirred for one hr, and 1-bromooctane (91.8 g, 0.475 mol) was added dropwise thereto at 0 C. over a period of about one hr. After the completion of the dropwise addition, the reaction temperature was raised to room temperature, and, at that temperature, the mixture was stirred overnight. After the completion of the reaction, water (200 ml) was added, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (n-hexane) to give an objective compound 2-octylthiophene as a yellow liquid (99.9 g, yield 97.8%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory; the same apparatus was also used in the following NMR measurement). 1H-NMR (CDCl3, TMS/ppm): 0.88 (t, 3H, J=6.83 Hz), 1.28 (m, 10H), 1.67 (m, 2H), 2.81 (t, 2H, J=7.32 Hz), 6.77 (dd, 1H, J=0.976 Hz, J=3.90 Hz), 6.91 (dd, 1H, J=3.90 Hz, J=4.88 Hz), 7.10 (dd, 1H, H=0.976 Hz, J=4.88 Hz).

Reference： [1]Patent: US2010/224869,2010,A1

62
[ 1160755-78-1 ]
[ 14403-26-0 ]
[ 880-36-4 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 2969 - 2972

63
[ 1003-09-4 ]
[ 3386-35-4 ]
[ 880-36-4 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4306 - 4309

64
[ 880-36-4 ]
[ 1132645-66-9 ]
[ 1194576-29-8 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 9458 - 9476

65
[ 880-36-4 ]
[ 121-43-7 ]
2-octyl-5-borondimethoxidethiophene [ No CAS ]

Reference： [1]Patent: WO2006/22040,2006,A1 .Location in patent: Page/Page column 15

66
[ 880-36-4 ]
[ 1461-22-9 ]
[ 388616-39-5 ]

Yield	Reaction Conditions	Operation in experiment
100%		In controlled atmosphere, n-butyl-lithium 2.5 M (42 ml, 0.105 mol) was added drop by drop at -78 C to a solution of <strong>[880-36-4]2-<strong>[880-36-4]n-octylthiophene</strong></strong> (20 g, 0.1 mol) in degassed THF (70 ml). The mixture was stirred for 1 h at this temperature. The tributyltin chloride was added very slowly to the mixture and stirred for 30 min at -78 C. After reaching room temperature, the reaction mixture was stirred for 12 h. The crude product was solubilized in dichloromethane, washed 3 times with a saturated solution of ammonium chlorate, dried with MgSO4 and the organic solvent was removed with roto-evaporation. The resulting crude residue was purified by column chromatography on silica gel with hexane/dichloromethane 6/4 to give an orange oil (33.38 g, 100% yield). deltaH (200 MHz, CDCl3) 7.02 (1H, d, J 3.2, 2-Harom), 6.94 (1H, d, J 3.0, 1-Harom), 2.89 (2H, t, J 8.6, -CH2-thiophene), 1.86 (2H, m, Haliph), 1.62 (2H, m, Haliph), 1.76-0.89(44H, m, Haliph); deltaC (50 MHz, CDCl3) 145, 126, 123, 33.1, 30.5, 30.3, 30.0, 29.2, 27.6, 23.1, 14, 13.7.
47%		[0185] Detailed synthesis of 2-octyl-5- tributylstannyl thiophene.Bu3Sn ^^s^^CbetaHi7 [0186] A solution of <strong>[880-36-4]2-octylthiophene</strong> (4.62 g, 23.5 mmol) in dry THF (50 mL) under argon, was cooled at -800C and 1.2 equivalent of LDA (1.8 M in solution in THF/nheptane/ethylbenzene) was added dropwise. The mixture was then stirring for 5 min. Then 6.59 mL of tributyltin chloride (7.91 g, 24.3 mmol) was slowly added. The medium was then stirred at -800C for 1 hour. After adding 30 mL of water, the solution was extracted by diethyl ether. The organic layers were dried over MgSO4 and the solvent removed in vaccum. Purification by Kugelrhor distillation (2100C, 35 Torr) afforded the desired compound as a colorless liquid (5.36 g, 11.0 mmol, 47%).1H-NMR (CDCl3): 6.97 (d, IH, J=3.15 Hz), 6.90 (d, IH, J=3.15 Hz), 2.85 (t, 2H, J=7.55 Hz), 1.60 (m, 8H), 1.32 (m, 16H), 1.06 (m, 6H), 0.89 (m, 12H).
		<strong>[880-36-4]2-<strong>[880-36-4]n-octylthiophene</strong></strong> (1.96 g) was dissolved in anhydrous THF (50 mL) and cooled to -78 C. n-BuLi (2.5 M, 4.4 mL) was added dropwise; after completion, stirring was continued at this temperature for 1 hour; the syringe was charged with 3.20 (mL) of tributyltin chloride, and the mixture was stirred at room temperature overnight, and the mixture was quenched with water and then evaporated. the organic phase was combined, washed successively with saturated brine and water, dried over anhydrous a pale yellow oil was obtained which was used in the next step without purification.

Reference： [1]Organic electronics,2014,vol. 15,p. 943 - 953
[2]Patent: WO2006/22040,2006,A1 .Location in patent: Page/Page column 13
[3]Tetrahedron Letters,2019,vol. 60
[4]Patent: WO2011/20712,2011,A2 .Location in patent: Page/Page column 66
[5]Chemistry - An Asian Journal,2018,vol. 13,p. 3920 - 3927
[6]Patent: CN110183419,2019,A .Location in patent: Paragraph 0013; 0017; 0019

67
[ 188290-36-0 ]
[ 629-27-6 ]
[ 880-36-4 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 9560 - 9572

68
[ 880-36-4 ]
[ 1260428-76-9 ]
[ 1260428-77-0 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 9560 - 9572

69
[ 880-36-4 ]
[ 1260428-82-7 ]
[ 1260428-58-7 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 9560 - 9572

70
[ 880-36-4 ]
[ 1056841-63-4 ]
[ 1260428-85-0 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 9560 - 9572

71
[ 880-36-4 ]
[ 143034-07-5 ]
[ 1263078-83-6 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 548 - 551

72
[ 880-36-4 ]
[ 1260428-85-0 ]

Reference： [1]Patent: WO2011/20712,2011,A2

73
[ 880-36-4 ]
[ 1260428-93-0 ]

Reference： [1]Patent: WO2011/20712,2011,A2

74
[ 880-36-4 ]
[ 1260428-78-1 ]

Reference： [1]Patent: WO2011/20712,2011,A2

75
[ 880-36-4 ]
[ 1260428-58-7 ]

Reference： [1]Patent: WO2011/20712,2011,A2

76
[ 880-36-4 ]
[ 1260428-77-0 ]

Reference： [1]Patent: WO2011/20712,2011,A2

77
[ 68-12-2 ]
[ 880-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane;	Synthesis of 2-fomyl-5-octylthiophene 2-Octylthiophene (40.8 g, 0.208 mol) prepared above and THF (400 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube, the solution was cooled to 0 C. in an ice bath, and a solution (100 ml) of n-butyllithium (2.6 M) in n-hexane was added dropwise to the cooled solution over a period of about one hr. After the completion of the dropwise addition, the mixture was stirred for about one hr, and dehydrated N,N-dimethylfolmamide (hereinafter referred to as "DMF?) (91.8 g, 0.475 mol) was added dropwise thereto at 0 C. over a period of about one hr. After the completion of the dropwise addition, the reaction temperature was raised to room temperature, and, at that temperature, the mixture was stirred overnight. After the completion of the reaction, a 1 N ammonium chloride solution (200 ml) was added, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (CH2Cl:hexane=1:1) to give an objective compound 2-fomyl-5-octylthiophene as a yellow liquid (45.0 g, yield 96.4%).

Reference： [1]Patent: US7935828,2011,B2

78
[ 109-99-9 ]
[ 111-83-1 ]
[ 880-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In thiophene; hexane; water;	Synthesis of 2-octylthiophene Thiophene (59.9 g, 0.713 mol) and dehydrated tetrahydrofran (hereinafter referred to as "THF?) (200 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube. The solution was cooled to -78 C., and a solution (200 ml) of n-butyllithium (2.6 M) in n-hexane was added dropwise to the cooled solution over a period of about one hr. After the completion of the dropwise addition, the mixture was stirred at -78 C. for about one hr. Thereafter, the reaction temperature was raised to room temperature. At that temperature, the mixture was again stirred for one hr, and 1-bromooctane (91.8 g, 0.475 mol) was added dropwise thereto at 0 C. over a period of about one hr. After the completion of the dropwise addition, the reaction temperature was raised to room temperature, and, at that temperature, the mixture was stirred overnight. After the completion of the reaction, water (200 ml) was added, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (n-hexane) to give an objective compound 2-octylthiophene as a yellow liquid (99.9 g, yield 97.8%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory). 1H-NMR (CDCl3, TMS/ppm): 0.88 (t, 3H, J=6.83 Hz), 1.28 (m, 10H), 1.67 (m, 2H), 2.81 (t, 2H, J=7.32 Hz), 6.77 (dd, 1H, J=0.976 Hz, J=3.90 Hz), 6.91 (dd, 1H, J=3.90 Hz, J=4.88 Hz), 7.10 (dd, 1H, J=0.976 Hz, J=4.88 Hz).

Reference： [1]Patent: US7935828,2011,B2

79
[ 880-36-4 ]
[ 1258753-81-9 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 9658 - 9665

80
[ 880-36-4 ]
[ 1268697-59-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1936 - 1939

81
[ 880-36-4 ]
[ 1268697-51-3 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1936 - 1939

82
[ 880-36-4 ]
[ 79-37-8 ]
[ 1261274-51-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1936 - 1939

83
[ 3140-93-0 ]
[ 880-36-4 ]
[ 1239368-60-5 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 5238 - 5247

84
[ 880-36-4 ]
[ 1300037-40-4 ]

Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 5238 - 5247

85
[ 880-36-4 ]
[ 4378-61-4 ]
[ 1421229-75-5 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 372 - 381

86
[ 880-36-4 ]
[ 4378-61-4 ]
[ 1421229-78-8 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 372 - 381

87
[ 880-36-4 ]
[ 13910-16-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 1947 - 1953

88
[ 880-36-4 ]
[ 40390-87-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 1947 - 1953

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[ 880-36-4 ]

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[ 880-36-4 ] Synthesis Path-Downstream 1~88

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