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146058-82-4

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146058-82-4 Usage

General Description

Thieno[3,4-b]pyrazine, 2,3-dihexyl- is a chemical compound with the molecular formula C20H32N2S. It is a type of thienopyrazine, which is a heterocyclic compound containing a fusion of thiene and pyrazine rings. The 2,3-dihexyl- substituents on the molecule are long alkyl chains, which are primarily used to increase the solubility of the compound in organic solvents. Thieno[3,4-b]pyrazine, 2,3-dihexyl- may have applications in organic electronics, such as in the fabrication of organic thin-film transistors or organic photovoltaic devices. It is also used as a building block in the synthesis of various other organic compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 146058-82-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,6,0,5 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 146058-82:
(8*1)+(7*4)+(6*6)+(5*0)+(4*5)+(3*8)+(2*8)+(1*2)=134
134 % 10 = 4
So 146058-82-4 is a valid CAS Registry Number.

146058-82-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,3-Dihexylthieno[3,4-b]pyrazine

1.2 Other means of identification

Product number -
Other names 2,3-dihexylthieno<3,4-b>pyrazine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:146058-82-4 SDS

146058-82-4Synthetic route

thiophene-3,4-diamine
78637-85-1

thiophene-3,4-diamine

tetradecane-7,8-dione
6305-47-1

tetradecane-7,8-dione

2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

Conditions
ConditionsYield
In ethanol at 20℃; for 3h;73%
In methanol; diethyl ether Heating;
1-bromo-hexane
111-25-1

1-bromo-hexane

2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium / tetrahydrofuran / -78 °C
1.2: CuBr; LiBr / tetrahydrofuran / -100 - -75 °C
1.3: 77 percent / tetrahydrofuran / 1 h / -95 - -90 °C
2.1: 73 percent / ethanol / 3 h / 20 °C
View Scheme
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

2,3-dihexyl-5-(trimethylsilyl)thieno[3,4-b]pyrazine
1586784-63-5

2,3-dihexyl-5-(trimethylsilyl)thieno[3,4-b]pyrazine

Conditions
ConditionsYield
Stage #1: 2,3-dihexylthieno<3,4-b>pyrazine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 3.5h; Inert atmosphere;
80%
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5,7-dibromo-2,3-dihexylthieno[3,4-b]pyrazine
320365-70-6

5,7-dibromo-2,3-dihexylthieno[3,4-b]pyrazine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide80%
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5-bromo-2,3-dihexyl-thieno[3,4-b]pyrazine

5-bromo-2,3-dihexyl-thieno[3,4-b]pyrazine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 3.5h;60%
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

poly(2,3-dihexylthieno[3,4-b]pyrazine), product of electrochemical polymerization; monomer(s): 2,3-dihexylthieno[3,4-b]pyrazine

poly(2,3-dihexylthieno[3,4-b]pyrazine), product of electrochemical polymerization; monomer(s): 2,3-dihexylthieno[3,4-b]pyrazine

Conditions
ConditionsYield
Electrochemical reaction;
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

poly(2,3-dihexylthieno[3,4-b]pyrazine), obtained by oxidative polymerization induced with FeCl3; monomer(s): 2,3-dihexylthieno[3,4-b]pyrazine

poly(2,3-dihexylthieno[3,4-b]pyrazine), obtained by oxidative polymerization induced with FeCl3; monomer(s): 2,3-dihexylthieno[3,4-b]pyrazine

Conditions
ConditionsYield
With iron(III) chloride
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5-(2-decyloxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-2,3-dihexyl-thieno[3,4-b]pyrazine

5-(2-decyloxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-2,3-dihexyl-thieno[3,4-b]pyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / NBS / dimethylformamide / 3.5 h / 0 °C
2: PdCl2(PPh3)2 / toluene / 16 h / 90 °C
View Scheme
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5-(3-decyloxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-2,3-dihexyl-thieno[3,4-b]pyrazine

5-(3-decyloxymethyl-2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)-2,3-dihexyl-thieno[3,4-b]pyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / NBS / dimethylformamide / 3.5 h / 0 °C
2: PdCl2(PPh3)2 / toluene / 16 h / 90 °C
View Scheme
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

2,2',3,3'-tetrahexyl-7,70-bis(trimethylsilyl)-5,5'-bis(thieno[3,4-b]pyrazine)
1586784-66-8

2,2',3,3'-tetrahexyl-7,70-bis(trimethylsilyl)-5,5'-bis(thieno[3,4-b]pyrazine)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 3.5 h / -78 - 20 °C / Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 2.5 h / -78 - 20 °C / Inert atmosphere
2.3: 20 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 3.5 h / -78 - 20 °C / Inert atmosphere
3.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 2.5 h / -78 - 20 °C / Inert atmosphere
3.3: 20 h / Reflux; Inert atmosphere
View Scheme
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

2,2',2'',3,3',3''-hexahexyl-7,7''-bis(trimethylsilyl)-5,5':7',5''-ter(thieno[3,4-b]pyrazine)
1586784-67-9

2,2',2'',3,3',3''-hexahexyl-7,7''-bis(trimethylsilyl)-5,5':7',5''-ter(thieno[3,4-b]pyrazine)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 3.5 h / -78 - 20 °C / Inert atmosphere
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 2.5 h / -78 - 20 °C / Inert atmosphere
2.3: 20 h / Reflux; Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 2.5 h / -78 - 20 °C / Inert atmosphere
2.3: 20 h / Reflux; Inert atmosphere
View Scheme
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5,7-bis(3,4-ethylenedioxythiophen-2-yl)-2,3-dihexylthieno[3,4-b]pyrazine
866547-86-6

5,7-bis(3,4-ethylenedioxythiophen-2-yl)-2,3-dihexylthieno[3,4-b]pyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 2.5 h / -78 - 20 °C / Inert atmosphere
2.3: 20 h / Reflux; Inert atmosphere
View Scheme
2,3-dihexylthieno<3,4-b>pyrazine
146058-82-4

2,3-dihexylthieno<3,4-b>pyrazine

5-bromo-2,3-dihexyl-7-(trimethylsilyl)thieno[3,4-b]pyrazine
1586784-62-4

5-bromo-2,3-dihexyl-7-(trimethylsilyl)thieno[3,4-b]pyrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide
2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 3.5 h / -78 - 20 °C / Inert atmosphere
View Scheme

146058-82-4Downstream Products

146058-82-4Relevant articles and documents

Thieno[3,4-b]pyrazines: Synthesis, structure, and reactivity

Kenning, Don D.,Mitchell, Kari A.,Calhoun, Tessa R.,Funfar, Melanie R.,Sattler, Daniel J.,Rasmussen, Seth C.

, p. 9073 - 9076 (2002)

A general synthetic route has been developed for the efficient preparation of 2,3-disubstituted thieno[3,4-b]-pyrazines. These methods eliminate problems in the preparation of the precursor 3,4-diaminothiophene and utilize α-diones prepared through the reaction of the appropriate organocuprates with oxalyl chloride. This combination allows the convenient preparation of thieno[3,4-b]pyrazine and its 2,3-disubstituted analogues (where substituent = methyl, hexyl, octyl, decyl, dodecyl, and phenyl) in high yield. Characterization of the structure and reactivity of this class of compounds is also described, including the results of structural, electrochemical, and pKa studies.

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