3-octylthiophene
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; Darkness; | 99% |
With N-Bromosuccinimide; acetic acid at 15℃; for 2h; | 98% |
With N-Bromosuccinimide; acetic acid In chloroform at 0℃; for 0.5h; Inert atmosphere; | 97.9% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide Multistep reaction; |
octylmagnesium bromide
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 78 percent / Ni(dppp)Cl2 / tetrahydrofuran / 12 h / 20 °C 2.1: N-bromosuccinimide / CHCl3 / 4 h / 20 °C 2.2: 90 percent / N-bromosuccinimide / CHCl3 / 4 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: Mg / diethyl ether 1.2: 73 percent / Ni(dppp)Cl2 / diethyl ether / 24 h / Heating 2.1: 82 percent / NBS / acetic acid; CHCl3 View Scheme |
octylmagnesium bromide
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 61 percent / Ni(dppp)Cl2 / diethyl ether / 35 °C 2: 40 percent / Br2 / acetic acid / 0.5 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 15 h / Reflux 2: N-Bromosuccinimide / tetrahydrofuran / 15 h / 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether / 0.25 h / 0 - 5 °C / Inert atmosphere 2: N-Bromosuccinimide; acetic acid / chloroform / 0.5 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / tetrahydrofuran / 15 h / Reflux 2: N-Bromosuccinimide / tetrahydrofuran / 15 h / 0 - 5 °C View Scheme |
1-bromo-octane
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: magnesium; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / diethyl ether 2: N-Bromosuccinimide / N,N-dimethyl-formamide View Scheme |
2-bromo-3-octylthiophene
N,N-dimethyl-formamide
3-octyl-2-thiophenecarboxaldehyde
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; hexane at -60 - 20℃; | 96% |
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran Reflux; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran Reflux; | 48% |
With n-butyllithium |
2-bromo-3-octylthiophene
5,5'-dibromo-4,4'-bis(oktyl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With silver fluoride; bis(benzonitrile)palladium(II) dichloride In dimethyl sulfoxide at 30℃; for 16h; | 96% |
With potassium fluoride; cis-dichlorobis(benzonitrile)palladium(II); silver nitrate In dimethyl sulfoxide at 60℃; for 6h; | |
With bis(benzonitrile)palladium(II) dichloride; silver fluoride In dimethyl sulfoxide |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water Suzuki cross-coupling; | 92% |
tri-n-butylstannyl chloride
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran for 2h; Reflux; Stage #2: tri-n-butylstannyl chloride In tetrahydrofuran at 0 - 20℃; | 92% |
2-bromo-3-octylthiophene
4-methoxycarbonylphenylboronic acid
methyl 4-(3-octylthiophen-2-yl)benzoate
Conditions | Yield |
---|---|
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; Suzuki-Miyaura cross-coupling; Continuous flow reactor; Inert atmosphere; | 91% |
2-thienyl chloride
2-bromo-3-octylthiophene
3-octyl-5'-chloro-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate; palladium diacetate In N,N-dimethyl-formamide at 80℃; Heck-type coupling reaction; | 86% |
5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,7-dioctylnaphtho[1,2-b:5,6-b']dithiophene
2-bromo-3-octylthiophene
2,7-dioctyl-5,10-bis(3-octylthiophen-2-yl)naphtho[1,2-b:5,6-b']dithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tripotassium phosphate "n" hydrate; water In tetrahydrofuran for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux; | 86% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux; | 85% |
2,5-dibromothiophen
2-bromo-3-octylthiophene
3,3”-dioctyl-2,2’:5’,2”-terthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium; ethylene dibromide In diethyl ether for 4h; Reflux; Inert atmosphere; Stage #2: 2,5-dibromothiophen With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 18h; Reflux; Inert atmosphere; | 84% |
Stage #1: 2-bromo-3-octylthiophene With magnesium; ethylene dibromide In diethyl ether for 4h; Reflux; Inert atmosphere; Stage #2: 2,5-dibromothiophen With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 18h; Reflux; | 84% |
Stage #1: 2-bromo-3-octylthiophene With magnesium In diethyl ether Metallation; Stage #2: 2,5-dibromothiophen With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 20h; Alkylation; Heating; Further stages.; | 68% |
2-bromo-3-octylthiophene
5,5'-bis(tri-n-butylstannyl)-2,2'-bithiophene
3,3'''-dioctyl-2,2’:5’,5'':2'',2'''-quaterthiophene
Conditions | Yield |
---|---|
With triphenylphosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran; N,N-dimethyl-formamide at 75℃; for 48h; Stille coupling; | 84% |
With tetrakis(triphenylphosphine) palladium(0) In toluene Stille Cross Coupling; Inert atmosphere; Reflux; | 78.1% |
5,5″-dibromo-3,3″-dioctyl-2,2′:5′,2″-trithiophene
2-bromo-3-octylthiophene
3,3′,3′″,3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium; ethylene dibromide In diethyl ether for 4h; Reflux; Inert atmosphere; Stage #2: 5,5″-dibromo-3,3″-dioctyl-2,2′:5′,2″-trithiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 20h; Reflux; Inert atmosphere; | 83% |
2-bromo-3-octylthiophene
2,2-Dimethyl-1,3-propanediol
[1',3'-(2',2'-dimethylpropylene)]-3-octyl-2-thienyl boronate
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran for 3h; Heating; Stage #2: With Trimethyl borate In tetrahydrofuran at 20℃; Stage #3: 2,2-Dimethyl-1,3-propanediol In diethyl ether | 82% |
2-bromo-3-octylthiophene
3,3'-dioctyl-2,2'-bithiophene
Conditions | Yield |
---|---|
With bis(tri-n-butyltin); bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 85℃; for 24h; | 78% |
With bis-triphenylphosphine-palladium(II) chloride; bis(tri-n-butyltin) | 67% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 110℃; for 12h; |
trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; Inert atmosphere; | 77% |
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 24h; |
chloro-trimethyl-silane
2-bromo-3-octylthiophene
3-octyl-2-trimethylsilylthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran for 2h; Heating; Stage #2: chloro-trimethyl-silane for 6h; Heating; | 76% |
2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-one
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In water; toluene at 115℃; for 20h; Suzuki Coupling; Inert atmosphere; | 74.4% |
2-bromo-3-octylthiophene
5'-methyl-3-octyl-2,2'-bithiophene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 11h; Kumada coupling; Heating; | 73% |
3,4-difluoro-2,5-bis-trimethylstannanylthiophene
2-bromo-3-octylthiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 110℃; for 24h; Stille Cross Coupling; Schlenk technique; Inert atmosphere; | 73% |
2-bromo-3-octylthiophene
N,N-dimethyl-formamide
5-bromo-3-n-octyl-2-thiophenecarbaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate In 1,2-dichloro-ethane at 0℃; for 0.25h; Vilsmeier-Haack Formylation; Inert atmosphere; Stage #2: 2-bromo-3-octylthiophene In 1,2-dichloro-ethane for 4h; Vilsmeier-Haack Formylation; Inert atmosphere; Reflux; | 72.7% |
With trichlorophosphate In 1,2-dichloro-ethane Vilsmeier-Haack reaction; | |
Stage #1: 2-bromo-3-octylthiophene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 6h; |
2,5-dibromo-3,4-dimethylthieno[2,3-b]thiophene
2-bromo-3-octylthiophene
2,5-bis(3-octylthiophen-2-yl)-3,4-dimethylthieno[2,3-b]thiophene
Conditions | Yield |
---|---|
In tetrahydrofuran | 72% |
5,5″″-dibromo-3,3′,3′″3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene
2-bromo-3-octylthiophene
3,3',3'',3'''',3''''',3''''''-hexaoctyl-2,5’:2’,5’’:2’’,2’’’:5’’’,2’’’’:5’’’’,2’’’’’:5’’’’’,2''''''-heptathiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium; ethylene dibromide In diethyl ether for 4h; Reflux; Inert atmosphere; Stage #2: 5,5″″-dibromo-3,3′,3′″3″″-tetraoctyl-2,5′:2′,5″:2″,2′″:5′″,2″″-pentathiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 20h; Reflux; Inert atmosphere; | 72% |
5,5'-dibromo-2,2'-bisthiophene
2-bromo-3-octylthiophene
3,3'''-dioctyl-2,2’:5’,5'':2'',2'''-quaterthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium; ethylene dibromide In diethyl ether for 3h; Inert atmosphere; Reflux; Stage #2: 5,5'-dibromo-2,2'-bisthiophene In diethyl ether Reflux; Inert atmosphere; | 71% |
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran; ethylene dibromide Inert atmosphere; Sonication; Stage #2: 5,5'-dibromo-2,2'-bisthiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; ethylene dibromide at 0 - 40℃; for 0.5h; Kumada Cross-Coupling; Inert atmosphere; | 65.7% |
2,5-dibromothiophen
2-bromo-3-octylthiophene
4,4''-dioctyl-2,2':5',2''-terthiophene
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium In tetrahydrofuran; ethylene dibromide Inert atmosphere; Sonication; Stage #2: 2,5-dibromothiophen With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; ethylene dibromide at 0 - 40℃; for 0.5h; Kumada Cross-Coupling; Inert atmosphere; | 68.5% |
Conditions | Yield |
---|---|
With Ni(ddpf)2Cl2 In tetrahydrofuran at 0℃; Reflux; | 65% |
2-bromo-3-octylthiophene
3-octyl-2-thiophenecarboxaldehyde
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With magnesium; iodine In tetrahydrofuran at 40℃; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene at 5 - 25℃; | 64% |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2-bromo-3-octylthiophene
2-(3-octylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3-octylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2.25h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 25℃; for 17h; | 64% |
Stage #1: 2-bromo-3-octylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78℃; for 5h; Inert atmosphere; | 64% |
Stage #1: 2-bromo-3-octylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; n-heptane Inert atmosphere; Schlenk technique; | 54% |
Stage #1: 2-bromo-3-octylthiophene With n-butyllithium In tetrahydrofuran; hexane at -80 - -50℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -80 - 20℃; for 4h; Inert atmosphere; | 14.83 g |
Conditions | Yield |
---|---|
Stage #1: 1-bromo-octane With magnesium In diethyl ether for 1.5h; Reflux; Stage #2: 2-bromo-3-octylthiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; Reflux; | 64% |
2,5-bis-trimethylstannanyl-thiophene
2-bromo-3-octylthiophene
3,3”-dioctyl-2,2’:5’,2”-terthiophene
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In toluene at 90℃; for 12h; | 63% |
2-bromo-3-octylthiophene
2-bromo-5-iodo-3-octylhiophene
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 0 - 20℃; Inert atmosphere; Darkness; | 60% |
The CAS register number of 2-Bromo-3-octylthiophene is 145543-83-5. It also can be called as Thiophene,2-bromo-3-octyl- and the systematic name about this chemical is 2-bromo-3-octylthiophene. The molecular formula about this chemical is C12H19BrS and the molecular weight is 275.25. It belongs to the Thiophenes.
Physical properties about 2-Bromo-3-octylthiophene are: (1)ACD/LogP: 6.87; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7; (4)ACD/LogD (pH 7.4): 7; (5)ACD/BCF (pH 5.5): 108376; (6)ACD/BCF (pH 7.4): 108376; (7)ACD/KOC (pH 5.5): 139824; (8)ACD/KOC (pH 7.4): 139824; (9)#Freely Rotating Bonds: 7; (10)Polar Surface Area: 28.24Å2; (11)Index of Refraction: 1.526; (12)Molar Refractivity: 69.674 cm3; (13)Molar Volume: 226.955 cm3; (14)Polarizability: 27.621x10-24cm3; (15)Surface Tension: 36.08 dyne/cm; (16)Enthalpy of Vaporization: 52.579 kJ/mol; (17)Boiling Point: 307.088 °C at 760 mmHg; (18)Vapour Pressure: 0.001 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: Brc1sccc1CCCCCCCC
(2)InChI: InChI=1/C12H19BrS/c1-2-3-4-5-6-7-8-11-9-10-14-12(11)13/h9-10H,2-8H2,1H3
(3)InChIKey: ISONQKSIWXLJOQ-UHFFFAOYAZ
(4)Std. InChI: InChI=1S/C12H19BrS/c1-2-3-4-5-6-7-8-11-9-10-14-12(11)13/h9-10H,2-8H2,1H3
(5)Std. InChIKey: ISONQKSIWXLJOQ-UHFFFAOYSA-N
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