[ CAS No. 1215857-68-3 ]

Name: 1215857-68-3|2-(2-Hexyldecyl)thiophene|95%
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Quality Control of [ 1215857-68-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1215857-68-3 ]

CAS No. :	1215857-68-3	MDL No. :	MFCD31567256
Formula :	C₂₀H₃₆S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OEKNWJQSAYEBFD-UHFFFAOYSA-N
M.W :	308.56	Pubchem ID :	67507457
Synonyms :

Calculated chemistry of [ 1215857-68-3 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.8
Num. rotatable bonds :	14
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	101.39
TPSA :	28.24 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-1.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	5.21
Log Po/w (XLOGP3) :	9.73
Log Po/w (WLOGP) :	7.63
Log Po/w (MLOGP) :	5.77
Log Po/w (SILICOS-IT) :	8.47
Consensus Log Po/w :	7.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-7.14
Solubility :	0.0000226 mg/ml ; 0.0000000732 mol/l
Class :	Poorly soluble
Log S (Ali) :	-10.24
Solubility :	0.0000000177 mg/ml ; 0.0000000001 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-7.74
Solubility :	0.00000567 mg/ml ; 0.0000000184 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.76

Safety of [ 1215857-68-3 ]

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 [ 1215857-68-3 ]

* 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 [ 1215857-68-3 ]

[ 1215857-68-3 ] Synthesis Path-Downstream 1~47

1
[ 2786-07-4 ]
[ 52997-43-0 ]
[ 1215857-68-3 ]

Reference： [1]Chemistry Letters,2010,vol. 39,p. 60 - 61

2
[ 1215857-68-3 ]
[ 1215857-69-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-Bromosuccinimide; acetic acid In chloroform at -20 - 20℃; for 4.5h; Schlenk technique; Inert atmosphere;
90%	With N-Bromosuccinimide; acetic acid In chloroform at 20℃; for 0.5h; Inert atmosphere; Cooling with ice;	1 EXAMPLE 1 Synthesis of 2-bromo-5-(2-hexyldecyl)thiophene (2). A solution of 2-(2-hexyldecyl)thiophene (1.01 g, 3.27 mmol) in CHCl3 (8 mL) and AcOH (8 mL) was chilled in an ice/salt bath under N2 and NBS (0.580 g, 3.27 mmol) was added in four equal portions over 0.5 h. The mixture was allowed to reach ambient temperature and stirred overnight. The solvents were evaporated under reduced pressure and the residue was filtered through a plug of silica gel using hexanes as eluent to yield 1.13 g (90%) colorless liquid. 1H NMR (400 MHz, CDCl3) δ 6.83 (d, 1H), 6.49 (d, 1H), 2.66 (d, 2H), 1.55 (m, 1H), 1.25 (m, 24H), 0.87 (m, 6H).
88%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 69.5h;

Reference： [1]Zhou, Jiaoyan; Zuo, Yi; Wan, Xiangjian; Long, Guankui; Zhang, Qian; Ni, Wang; Liu, Yongsheng; Li, Zhi; He, Guangrui; Li, Chenxi; Kan, Bin; Li, Miaomiao; Chen, Yongsheng [Journal of the American Chemical Society, 2013, vol. 135, # 23, p. 8484 - 8487]
[2]Current Patent Assignee: POLYERA CORP - US2017/104160, 2017, A1 Location in patent: Paragraph 0186
[3]Lu, Ming; Nagamatsu, Shuichi; Yoshida, Yuji; Chikamatsu, Masayuki; Azumi, Reiko; Yase, Kiyoshi [Chemistry Letters, 2010, vol. 39, # 1, p. 60 - 61]

3
[ 188290-36-0 ]
[ 52997-43-0 ]
[ 1215857-68-3 ]

Yield	Reaction Conditions	Operation in experiment
75%		To a solution of thiophene (5 g, 60 mmol) in THF (50 mL) was added n-BuLi (25 mL, 2.5 M in hexane) at -78 C. The solution was stirred for 30 min at -78 C and 1 h at 0 C. The 2-hexyldecyl bromide (20 g, 66 mmol) was then added at 0 C and the mixture was stirring for overnight before pouring into water and extracting with hexane. The hexane phase was dried over Na2SO4. After removing the solvent, the crude product was purified by distillation to give a colorless liquid (13.7 g, 75 %). 1H NMR (300 MHz, CDCl3, delta): 7.15 (dd, 1H), 6.96 (t, 1H), 6.77 (m, 1H), 2.80 (d, J = 6.66 Hz, 2H), 1.65 (br, 1H), 1.29 (br, 24H), 0.93-0.89 (m, 6H). 13C NMR (125 MHz, CDCl3, delta): 144.57, 126.75, 125.18, 123.12, 40.25, 34.45, 33.39, 32.12, 30.20, 29.85, 29.56, 26.79, 22.91, 14.35. GC-MS (m/z): calcd for C20H36S, 308.56; found, 308.

Reference： [1]Polymer,2016,vol. 82,p. 228 - 237
[2]Journal of Materials Chemistry A,2013,vol. 1,p. 8270 - 8279
[3]Journal of Polymer Science, Part A: Polymer Chemistry,2017,vol. 55,p. 1209 - 1218
[4]Journal of the American Chemical Society,2013,vol. 135,p. 8484 - 8487
[5]Journal of Materials Chemistry A,2015,vol. 3,p. 23149 - 23161
[6]Journal of Polymer Science, Part A: Polymer Chemistry,2018,vol. 56,p. 653 - 660
[7]Journal of Polymer Science, Part A: Polymer Chemistry,2019,vol. 57,p. 60 - 69

4
[ 1215857-68-3 ]
[ 1422748-36-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 4.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 2 h / 50 °C 2.3: 2 h / 0 °C

5
[ 1215857-68-3 ]
[ 1439861-99-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 4.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere 2.1: magnesium; ethylene dibromide / diethyl ether / 4 h / Schlenk technique; Inert atmosphere; Reflux 2.2: 18 h / 20 °C / Reflux 3.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Schlenk technique; Inert atmosphere 3.2: 2 h / 50 °C 3.3: 2 h / 0 °C

6
[ 1215857-68-3 ]
[ 1439862-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 4.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Schlenk technique; Inert atmosphere 2.2: 2 h / 50 °C 2.3: 2 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran / 1.67 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 3.2: 14.5 h / 0 - 20 °C

7
[ 1215857-68-3 ]
[ 1439862-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 4.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere 2.1: magnesium; ethylene dibromide / diethyl ether / 4 h / Schlenk technique; Inert atmosphere; Reflux 2.2: 18 h / 20 °C / Reflux 3.1: n-butyllithium / tetrahydrofuran / 2.5 h / -78 °C / Schlenk technique; Inert atmosphere 3.2: 2 h / 50 °C 3.3: 2 h / 0 °C 4.1: n-butyllithium / tetrahydrofuran / 1.67 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 4.2: 14.5 h / 0 - 20 °C

8
[ 1215857-68-3 ]
[ 1400788-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; acetic acid / chloroform / 4.5 h / -20 - 20 °C / Schlenk technique; Inert atmosphere 2.1: magnesium; ethylene dibromide / diethyl ether / 4 h / Schlenk technique; Inert atmosphere; Reflux 2.2: 18 h / 20 °C / Reflux

9
[ 1215857-68-3 ]
[ 1446139-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux
	Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 120 °C / Inert atmosphere 3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 120 °C / Inert atmosphere

10
[ 1215857-68-3 ]
[ 1446139-66-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux 3: N-Bromosuccinimide; acetic acid / chloroform / 20 °C

Reference： [1]Jiang, Youyu; Yu, Di; Lu, Luhua; Zhan, Chun; Wu, Di; You, Wei; Xie, Zhizhong; Xiao, Shengqiang [Journal of Materials Chemistry A, 2013, vol. 1, # 28, p. 8270 - 8279]

11
[ 1215857-68-3 ]
[ 1446139-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux 3: N-Bromosuccinimide; acetic acid / chloroform / 20 °C 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux

Reference： [1]Jiang, Youyu; Yu, Di; Lu, Luhua; Zhan, Chun; Wu, Di; You, Wei; Xie, Zhizhong; Xiao, Shengqiang [Journal of Materials Chemistry A, 2013, vol. 1, # 28, p. 8270 - 8279]

12
[ 1215857-68-3 ]
[ 1446139-68-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / Inert atmosphere; Reflux 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux 3: N-Bromosuccinimide; acetic acid / chloroform / 20 °C 4: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 7 h / Inert atmosphere; Reflux 5: N-Bromosuccinimide; acetic acid / chloroform; acetic acid / 20 °C

Reference： [1]Jiang, Youyu; Yu, Di; Lu, Luhua; Zhan, Chun; Wu, Di; You, Wei; Xie, Zhizhong; Xiao, Shengqiang [Journal of Materials Chemistry A, 2013, vol. 1, # 28, p. 8270 - 8279]

13
[ 1215857-68-3 ]
[ 1461-22-9 ]
[ 1448462-04-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(2'-hexyldecyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.5h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 20℃; for 1h; Inert atmosphere;
	With n-butyllithium In tetrahydrofuran
	Stage #1: 2-(2'-hexyldecyl)thiophene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 2h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference： [1]Jiang, Youyu; Yu, Di; Lu, Luhua; Zhan, Chun; Wu, Di; You, Wei; Xie, Zhizhong; Xiao, Shengqiang [Journal of Materials Chemistry A, 2013, vol. 1, # 28, p. 8270 - 8279]
[2]Xu, Xiaopeng; Feng, Kui; Li, Kai; Peng, Qiang [Journal of Materials Chemistry A, 2015, vol. 3, # 46, p. 23149 - 23161]
[3]Zhu, Xiaolei; Hessin, Cheriehan; Salamé, Aude; Sosa-Vargas, Lydia; Kreher, David; Adachi, Chihaya; Proust, Anna; Mialane, Pierre; Marrot, Jérome; Bouchet, Aude; Sliwa, Michel; Méry, Stéphane; Heinrich, Benoît; Mathevet, Fabrice; Izzet, Guillaume [Angewandte Chemie - International Edition, 2021, vol. 60, # 15, p. 8419 - 8424][Angew. Chem., 2021, vol. 133, # 15, p. 8500 - 8505,6]

14
[ 15155-41-6 ]
[ 1215857-68-3 ]
[ 1446139-63-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran Inert atmosphere; Reflux;

Reference： [1]Jiang, Youyu; Yu, Di; Lu, Luhua; Zhan, Chun; Wu, Di; You, Wei; Xie, Zhizhong; Xiao, Shengqiang [Journal of Materials Chemistry A, 2013, vol. 1, # 28, p. 8270 - 8279]

15
[ 61676-62-8 ]
[ 1215857-68-3 ]
C₂₆H₄₇BO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-(2'-hexyldecyl)thiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Scheuble; Gross; Trefz; Brinkmann; López Navarrete; Ruiz Delgado; Ludwigs [Macromolecules, 2015, vol. 48, # 19, p. 7049 - 7059]

16
[ 1215857-68-3 ]
C₂₈H₃₈BrClS₃Zn [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336 / tetrahydrofuran; water; toluene / 20 h / 100 °C / Inert atmosphere 3.1: N-Bromosuccinimide / chloroform; N,N-dimethyl-formamide / 18 h / 0 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 4.2: 0.83 h / 20 °C / Inert atmosphere

Reference： [1]Scheuble; Gross; Trefz; Brinkmann; López Navarrete; Ruiz Delgado; Ludwigs [Macromolecules, 2015, vol. 48, # 19, p. 7049 - 7059]

17
[ 1215857-68-3 ]
C₂₈H₄₀S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336 / tetrahydrofuran; water; toluene / 20 h / 100 °C / Inert atmosphere

Reference： [1]Scheuble; Gross; Trefz; Brinkmann; López Navarrete; Ruiz Delgado; Ludwigs [Macromolecules, 2015, vol. 48, # 19, p. 7049 - 7059]

18
[ 1215857-68-3 ]
C₂₈H₃₉BrS₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere 1.2: 12 h / 20 °C / Inert atmosphere 2.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336 / tetrahydrofuran; water; toluene / 20 h / 100 °C / Inert atmosphere 3.1: N-Bromosuccinimide / chloroform; N,N-dimethyl-formamide / 18 h / 0 °C / Inert atmosphere

Reference： [1]Scheuble; Gross; Trefz; Brinkmann; López Navarrete; Ruiz Delgado; Ludwigs [Macromolecules, 2015, vol. 48, # 19, p. 7049 - 7059]

19
[ 1215857-68-3 ]
[ 1446139-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 12 h / 120 °C / Inert atmosphere