Production Method 1

629-27-6

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  15 min, -78 °C
1.2 overnight, -80 °C → rt

Reference

Synthesis of soluble oligothiophenes bearing cyano groups, their optical and electrochemical properties

Balandier, Jean-Yves; et al, Tetrahedron, 2010, 66(49), 9560-9572

Production Method 2

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 50 min, -78 °C
1.2 -78 °C → rt; 16 h, rt

Reference

Photochromism of 1,2-bis(2-n-alkyl-5-formyl-3-thienyl)perfluorocyclopentene derivatives

Pu, Shouzhi; et al, Journal of Molecular Structure, 2009, 921(1-3), 89-100

Production Method 3

3248-78-0

880-36-4

Reaction Conditions

Reference

Product subclass 39: tetraaryl- and tetraalkylborates and related organometallic compounds

Kaufmann, D. E.; et al, Science of Synthesis, 2004, 6, 1217-1233

Production Method 4

2786-07-4

3248-78-0

880-36-4

Reaction Conditions

1.1 Reagents: Iodine

Reference

2-Alkylation reactions of thiophene and 1-methylpyrrole with trialkylboranes

Sotoyama, Toshiki; et al, Bulletin of the Chemical Society of Japan, 1979, 52(6), 1865-6

Production Method 5

69340-26-7

693-04-9

880-36-4

Reaction Conditions

1.1 Catalysts: 1,3-Butadiene ,  Dicarbonylchloro(η5-2,4-cyclopentadien-1-yl)iron Solvents: Tetrahydrofuran ;  -78 °C; 2 h, 0 °C; 22 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Cross-coupling reaction of alkyl halides with alkyl Grignard reagents catalyzed by Cp-iron complexes in the presence of 1,3-butadiene

Iwasaki, Takanori; et al, Chemistry Letters, 2018, 47(6), 763-766

Production Method 6

1160755-78-1

14403-26-0

880-36-4

Reaction Conditions

1.1 Reagents: 1,2-Dibromoethane Catalysts: Iron(III) acetylacetonate Solvents: Tetrahydrofuran ;  rt → 0 °C; 0 °C; 0 °C → rt; 3 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Iron-catalyzed oxidative heterocoupling between aliphatic and aromatic organozinc reagents: a novel pathway for functionalized aryl-alkyl cross-coupling reactions

Cahiez, Gerard; et al, Angewandte Chemie, 2009, 48(16), 2969-2972

Production Method 7

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -20 °C → 10 °C; 10 min, 10 °C; 10 °C → rt
1.2 rt → 50 °C; 30 min, 50 °C

Reference

The synthesis, structural features and thermal behavior of thiophene-containing dithiocarboxylate complexes of zinc(II)

Thomas, Mary S.; et al, Polyhedron, 2006, 25(18), 3562-3568

Production Method 8

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  0 °C; 0 °C → 20 °C
1.2 4 h, reflux

Reference

Bent-core mesogens with thiophene units

Geese, Karina; et al, Journal of Materials Chemistry, 2010, 20(43), 9658-9665

Production Method 9

1003-09-4

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Tetrahydrofuran ;  reflux; 1 h, reflux
1.2 Catalysts: Dichloro[1,1′-(1,3-propanediyl)bis[1,1-diphenylphosphine-κP]]nickel Solvents: Tetrahydrofuran ;  overnight, reflux
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Micro continuous flow-through synthesis of triangular silver nanoprisms and their incorporation in complexly composed polymer microparticles

Knauer, Andrea; et al, Chemical Engineering Journal (Amsterdam, 2013, 227, 191-197

Production Method 10

1003-09-4

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium
1.2 1 h, -78 °C

Reference

Suppressing the Surface Recombination and Tuning the Open-Circuit Voltage of Polymer/Fullerene Solar Cells by Implementing an Aggregative Ternary Compound

Galli, Diana; et al, ACS Applied Materials & Interfaces, 2018, 10(34), 28803-28811

Production Method 11

629-27-6

5713-61-1

880-36-4

Reaction Conditions

1.1 Catalysts: Cobalt chloride (CoCl2) ,  trans-(-)-N,N,N′,N′-Tetramethyl-1,2-cyclohexanediamine Solvents: Tetrahydrofuran ;  15 min, 25 °C

Reference

Cobalt(diamine)-Catalyzed Cross-coupling Reaction of Alkyl Halides with Arylmagnesium Reagents: Stereoselective Constructions of Arylated Asymmetric Carbons and Application to Total Synthesis of AH13205

Ohmiya, Hirohisa; et al, Journal of the American Chemical Society, 2006, 128(6), 1886-1889

Production Method 12

1003-09-4

3386-35-4

880-36-4

Reaction Conditions

1.1 Reagents: Magnesate(1-), dichloro(1-methylethyl)-, lithium (1:1) Solvents: Tetrahydrofuran ;  20 min, -40 °C
1.2 Reagents: Zinc iodide ,  Magnesium, chloro[(trimethylsilyl)methyl]- Solvents: Tetrahydrofuran ;  -40 °C; 1 h, < 0.1 torr
1.3 Reagents: N,N,N′,N′-Tetramethylethylenediamine Catalysts: Iron chloride (FeCl3) Solvents: Tetrahydrofuran ;  0 °C; 12 h, 40 °C
1.4 Reagents: Ammonium chloride Solvents: Water

Reference

Iron-catalyzed cross-coupling of alkyl sulfonates with arylzinc reagents

Ito, Shingo; et al, Organic Letters, 2009, 11(19), 4306-4309

Production Method 13

30711-41-2

880-36-4

Reaction Conditions

1.1 Reagents: Hydrazine hydrate (1:1) Solvents: Diethylene glycol ,  Water

Reference

Further studies in the synthesis of long chain hydroxy acids

Miller, Kenneth E.; et al, Journal of Organic Chemistry, 1961, 26, 5217-19

Production Method 14

30711-41-2

880-36-4

Reaction Conditions

1.1 Reagents: Mercury ,  Zinc ,  Hydrochloric acid

Reference

Some derivatives of 2-acylthiophenes

Campaigne, E.; et al, Journal of the American Chemical Society, 1948, 70, 391-2

Production Method 15

3248-78-0

880-36-4

Reaction Conditions

1.1 Reagents: Butyllithium ,  N,N,N′,N′-Tetramethylethylenediamine ,  Iodine ,  Hydrogen peroxide Solvents: Diethyl ether ,  Water

Reference

Formation of carbon-carbon and carbon-heteroatom bonds via organoboranes and organoborates

Negishi, Ei-Ichi; et al, Organic Reactions (Hoboken, 1985, 33,

Production Method 16

69340-26-7

693-04-9

880-36-4

Reaction Conditions

1.1 Catalysts: Cupric chloride Solvents: Tetrahydrofuran ;  rt; rt → -78 °C
1.2 Reagents: 1,3-Butadiene Solvents: Tetrahydrofuran ;  -78 °C; 48 h, 40 °C
1.3 Reagents: Hydrochloric acid Solvents: Water

Reference

Copper-Catalyzed Alkyl-Alkyl Cross-Coupling Reactions Using Hydrocarbon Additives: Efficiency of Catalyst and Roles of Additives

Iwasaki, Takanori; et al, Journal of Organic Chemistry, 2014, 79(18), 8522-8532

Production Method 17

111-83-1

5713-61-1

880-36-4

Reaction Conditions

1.1 Catalysts: 1,3-Bis(diphenylphosphino)propane ,  Cobalt chloride (CoCl2) Solvents: Tetrahydrofuran ;  0.5 h, -15 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Cobalt-catalyzed cross-coupling reactions of alkyl halides with aryl Grignard reagents and their application to sequential radical cyclization/cross-coupling reactions

Ohmiya, Hirohisa; et al, Tetrahedron, 2006, 62(10), 2207-2213

Production Method 18

193978-23-3

111-83-1

880-36-4

Reaction Conditions

1.1 Reagents: Ethanamine, N-methyl-, lithium salt Catalysts: 2413474-02-7 (THF-deficient (≈ 0.75)) Solvents: Benzene ;  rt → 50 °C; 24 h, 50 °C
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Rational Design of an Iron-Based Catalyst for Suzuki-Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles

Crockett, Michael P.; et al, Angewandte Chemie, 2020, 59(13), 5392-5397

Production Method 19

880-36-4

Reaction Conditions

1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane
1.2 Reagents: Potassium hydroxide ,  Hydrazine hydrate (1:1) Solvents: Diethylene glycol ;  reflux

Reference

Exploring the mesomorphic potential of 2,4-disubstituted thiophenes: a structure-property study

Matharu, A. S.; et al, Liquid Crystals, 2011, 38(2), 207-232

2-N-Octylthiophene Raw materials

• 4,4,5,5-tetramethyl-2-(thiophen-2-yl)-1,3,2-dioxaborolane
• 2-Octanoylthiophene
• 2-(4-Bromobutyl)-thiophene
• 2-Bromothiophene
• 1-Iodooctane
• Butylmagnesium chloride
• 1-Bromooctane
• THIOPHEN-2-YL-MAGNESIUM BROMIDE 1.0M
• n-Octyl-p-Toluenesulfonate
• 2-Thienyl-lithium
• Zinc, dioctyl-
• Borane, trioctyl-

2-N-Octylthiophene Preparation Products

• 2-N-Octylthiophene (880-36-4)

• 1. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 2. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 3. An approach to C–N activation: coupling of arenesulfonyl hydrazides and arenesulfonyl chlorides with tert-amines via a metal-, oxidant- and halogen-free anodic oxidation??
  M. Sheykhan,S. Khani,S. Shaabanzadeh,M. Joafshan Green Chem., 2017,19, 5940-5948
• 4. Acetyl group orientation modulates the electronic ground-state asymmetry of the special pair in purple bacterial reaction centers
  P. K. Wawrzyniak,M. T. P. Beerepoot,H. J. M. de Groot,F. Buda Phys. Chem. Chem. Phys., 2011,13, 10270-10279
• 5. An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening
  Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai Kong Analyst, 2017,142, 3579-3587

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Heteroaromatic compounds Heteroaromatic compounds
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Heteroaromatic compounds

• 103696-17-9(Thiophene, butyl-)
• 146436-27-3(Thiophene, 2-hexadecyl-5-methyl-)
• 146670-63-5(Thiophene, 2-decyl-5-methyl-)
• 59782-29-5(Thiophene, 2-tridecyl-)
• 24769-39-9(Thiophene, 2-decyl-)
• 57640-14-9(Thiophene, 2,2'-(1,4-butanediyl)bis-)
• 392686-53-2(Thiophene, 2-propyl-5-tridecyl-)
• 339315-91-2(Thiophene, 2-methyl-5-nonyl-)
• 57754-07-1(Thiophene, 2-nonyl-)
• 50865-10-6(Thiophene, 2-methyl-5-octyl-)