4-bromo-2-methylthiophene
methylmagnesium chloride
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 22h; | 79% |
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether Kumada coupling; Heating; |
Conditions | Yield |
---|---|
With potassium hydroxide; hydrazine hydrate In diethylene glycol | 76% |
Conditions | Yield |
---|---|
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 4h; Further stages.; | 73% |
Stage #1: 3-Methylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 0 - 20℃; for 3h; Stage #2: methyl iodide at 0 - 20℃; for 5h; | 68% |
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran; pentane at -78 - 20℃; for 2h; |
methyl magnesium iodide
4-bromo-2-methylthiophene
2,4-dimethylthiophene
Conditions | Yield |
---|---|
nickel 1,3-bis(diphenylphosphino)propane In diethyl ether for 22h; Heating; | 66% |
Conditions | Yield |
---|---|
Bildung ueber das Hydrazon; |
2,5-Dimethyl-[1,4]dithiin
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With sulfur at 200℃; |
Conditions | Yield |
---|---|
With diphosphorus trisulfide | |
With phosphorous (V) sulfide |
Conditions | Yield |
---|---|
With sulfur at 260℃; |
methyloxirane
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With aluminum oxide; hydrogen sulfide at 400℃; |
2-Methylthiophene
Methyl fluoride
A
2,3-dimethylthiophene
B
2,4-dimethylthiophene
C
2,5-DIMETHYLTHIOPHENE
Conditions | Yield |
---|---|
With oxygen; trimethylamine In gas at 37.5℃; Product distribution; Kinetics; Mechanism; radiolysis: 1.5*104 Gy at 5*105 Gy h-1; variable pressures; |
2-Methylthiophene
A
2-ethylthiophene
B
2,4-dimethylthiophene
C
2,5-DIMETHYLTHIOPHENE
D
3-Methylthiophene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 11.7 % Chromat. B 0.6 % Chromat. C 4.9 % Chromat. D 9.2 % Chromat. |
2,3-dimethylthiophene
A
3,4-dimethylthiophene
B
2-ethylthiophene
C
2,4-dimethylthiophene
D
3-Methylthiophene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 2.3 % Chromat. B 1.5 % Chromat. C 1.5 % Chromat. D 12.8 % Chromat. |
3,4-dimethylthiophene
A
thiophene
B
2-Methylthiophene
C
2,4-dimethylthiophene
D
toluene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 1.9 % Chromat. B 1.4 % Chromat. C 6.2 % Chromat. D 2.4 % Chromat. |
3,4-dimethylthiophene
A
2,3-dimethylthiophene
B
2,4-dimethylthiophene
C
2,5-DIMETHYLTHIOPHENE
D
3-Methylthiophene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 5.1 % Chromat. B 6.2 % Chromat. C 1.1 % Chromat. D 12.2 % Chromat. |
3,4-dimethylthiophene
A
2,4-dimethylthiophene
B
2,5-DIMETHYLTHIOPHENE
C
3-Methylthiophene
D
benzene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 6.2 % Chromat. B 1.1 % Chromat. C 12.2 % Chromat. D 17.6 % Chromat. |
2,5-DIMETHYLTHIOPHENE
A
2-Methylthiophene
B
2,4-dimethylthiophene
C
toluene
D
benzene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 15.4 % Chromat. B 3.3 % Chromat. C 2.6 % Chromat. D 36.9 % Chromat. |
3-Methylthiophene
A
thiophene
B
2,3-dimethylthiophene
C
2,4-dimethylthiophene
D
benzene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 13.6 % Chromat. B 13.6 % Chromat. C 1.7 % Chromat. D 7.7 % Chromat. |
3-Methylthiophene
A
2-Methylthiophene
B
2,3-dimethylthiophene
C
3,4-dimethylthiophene
D
2,4-dimethylthiophene
Conditions | Yield |
---|---|
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts; | A 14.4 % Chromat. B 13.6 % Chromat. C 1.7 % Chromat. D 1.7 % Chromat. |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With diphosphorus trisulfide |
Conditions | Yield |
---|---|
at 400℃; |
Conditions | Yield |
---|---|
at 260℃; |
3-Methylthiophene
methyl iodide
A
2,3-dimethylthiophene
B
2,4-dimethylthiophene
Conditions | Yield |
---|---|
Stage #1: 3-Methylthiophene With methyllithium In tetrahydrofuran at 20℃; for 1h; Stage #2: methyl iodide In tetrahydrofuran at 20℃; Further stages.; | |
Stage #1: 3-Methylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane Stage #2: methyl iodide In diethyl ether; hexane Further stages. Title compound not separated from byproducts.; |
2-bromo-4-methylthiophene
methylmagnesium chloride
2,4-dimethylthiophene
Conditions | Yield |
---|---|
1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran; diethyl ether Kumada coupling; Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C 1.2: 80 percent / methanol / tetrahydrofuran; hexane 2.1: 79 percent / Ni(dppp)Cl2 / diethyl ether / 22 h View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: butyl lithium; diethyl ether / Behandeln mit Dimethylformamid und Hydrolysieren 2: Bildung ueber das Hydrazon View Scheme |
2,4-dimethyl-2,5-dihydrothiophene
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With bunazosin In benzene |
Conditions | Yield |
---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride In diethyl ether for 24h; Inert atmosphere; Reflux; |
thiophene
Dimethyldisulphide
A
2-Methylthiophene
B
3,4-dimethylthiophene
C
2,4-dimethylthiophene
D
2,3,4-trimethylthiophene
E
2,5-DIMETHYLTHIOPHENE
F
tetramethylthiophene
G
3-Methylthiophene
H
methylthiol
I
dimethylsulfide
J
hydrogen sulfide
Conditions | Yield |
---|---|
With Co/HZSM-5 at 300℃; under 760.051 Torr; Inert atmosphere; Flow reactor; |
2,4-dimethylthiophene
2,4-dibromo-3,5-dimethylthiophene
Conditions | Yield |
---|---|
With bromine for 0.05h; Ambient temperature; | 96% |
With bromine In acetic acid | 65% |
With carbon disulfide; bromine Erwaermen des Reaktionsprodukts mit methanol. Kalilauge; |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Inert atmosphere; | 95% |
2,4-dimethylthiophene
N,N-bis(4-methylphenyl)-N-(4-iodophenyl) amine
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at 20℃; for 2h; Stage #2: With zinc(II) chloride In diethyl ether at 20℃; for 5h; Stage #3: N,N-bis(4-methylphenyl)-N-(4-iodophenyl) amine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20 - 50℃; for 7h; | 92% |
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In diethyl ether; hexane at -30 - 20℃; for 6h; Metallation; Stage #2: iodobenzene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 50℃; for 12h; Phenylation; | 90% |
Yield given. Multistep reaction; |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With sulfuryl dichloride In dichloromethane for 2h; Reflux; | 85% |
28% | |
With sulfuryl dichloride In dichloromethane |
2,4-dimethylthiophene
(E)-4-bromostilbene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethylthiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; zinc(II) chloride In diethyl ether; hexane at -30 - 20℃; for 6h; Metallation; Stage #2: (E)-4-bromostilbene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 50℃; for 12h; Arylation; | 80% |
2,4-dimethylthiophene
N,N-dimethyl-formamide
3,5-dimethyl-2-thiophenecarboxaldehyde
Conditions | Yield |
---|---|
With trichlorophosphate 1.) r.t., 1 h, 2.) heating, 30 min; | 77% |
With trichlorophosphate at 70 - 75℃; for 3h; | 66% |
With diethyl ether anschliessendes Hydrolysieren; |
2,4-dimethylthiophene
trifluoroacetic anhydride
1-(3,5-dimethylthiophen-2-yl)-2,2,2-trifluoroethanone
Conditions | Yield |
---|---|
With magnesium perchlorate dihydrate In 1,2-dichloro-ethane at 60℃; for 12h; Friedel-Crafts Acylation; regioselective reaction; | 76% |
3,5-dimethylthiophene-2-carbonyl chloride
2,4-dimethylthiophene
bis(3,5-dimethyl-2-thienyl) ketone
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane for 4h; | 72% |
Conditions | Yield |
---|---|
With 4-(ethylthio)-N,N-dimethylaniline; palladium diacetate; acetic acid; hydroquinone at 60℃; for 3h; | 65% |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -78℃; for 3h; Inert atmosphere; | 44% |
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -78℃; | 44 % Chromat. |
2,4-dimethylthiophene
oxalyl dichloride
1,2-bis(3,5-dimethyl-2-thienyl)ethane-1,2-dione
Conditions | Yield |
---|---|
With aluminium trichloride In n-heptane; 1,2-dichloro-ethane at -20℃; for 2.3h; Friedel-Crafts reaction; | 44% |
2,4-dimethylthiophene
2-bromoaniline
2-(2'-bromophenyl)-3,5-dimethylthiophene
Conditions | Yield |
---|---|
With isopentyl nitrite at 70℃; for 4h; | 43% |
2,4-dimethylthiophene
1-(2,3,3,4,4,5,5-Heptafluoro-1-cyclopenten-1-yl)-2-methylnaphthalene
3,5-dimethyl-2-[3,3,4,4,5,5-hexafluoro-2-(2-methyl-1-naphthalenyl)-1-cyclopenten-1-yl]thiophene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethylthiophene With N,N,N,N,-tetramethylethylenediamine In diethyl ether at 0℃; Inert atmosphere; Stage #2: With n-butyllithium In diethyl ether; hexane Inert atmosphere; Reflux; Stage #3: 1-(2,3,3,4,4,5,5-Heptafluoro-1-cyclopenten-1-yl)-2-methylnaphthalene In diethyl ether; hexane at -70 - 20℃; Inert atmosphere; | 43% |
2,4-dimethylthiophene
1-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazolyl-4'-yl)-3-thienyl]perfluorocyclopentene
1-(3,5-dimethyl-2-thienyl)-2-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazol-4'-yl)-3-thienyl]perfluorocyclopentene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 1-[2,4-dimethyl-5-(2'',4'',5''-triphenylimidazolyl-4'-yl)-3-thienyl]perfluorocyclopentene In tetrahydrofuran at -78℃; for 1h; Further stages.; | 42% |
2,4-dimethylthiophene
3,3-dimethoxy-4-oxo-cyclohexa-1,5-dienecarbonitrile
Conditions | Yield |
---|---|
for 5h; Diels-Alder reaction; Heating; | A 3% B 40% |
2,4-dimethylthiophene
4-acetyl-6,6-dimethoxy-cyclohexa-2,4-dienone
Conditions | Yield |
---|---|
for 5h; Diels-Alder reaction; Heating; | A 33% B 21% |
2,4-dimethylthiophene
3,3-dimethoxy-4-oxo-cyclohexa-1,5-dienecarboxylic acid methyl ester
Conditions | Yield |
---|---|
for 5h; Diels-Alder reaction; Heating; | A 6% B 12% C 32% |
2,4-dimethylthiophene
chloromethyl methyl ether
2,4-bis(chloromethyl)-3,5-dimethylthiophene
Conditions | Yield |
---|---|
With titanium tetrachloride In carbon disulfide Ambient temperature; | 22% |
2,4-dimethylthiophene
carbamic chloride
3,5-dimethyl-thiophene-2-carboxylic acid amide
Conditions | Yield |
---|---|
With carbon disulfide; aluminium trichloride |
2,4-dimethylthiophene
acetic anhydride
1-(3,5-dimethyl-[2]thienyl)-ethanone
Conditions | Yield |
---|---|
With phosphoric acid; benzene |
Conditions | Yield |
---|---|
With tin(IV) chloride; benzene |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With iodine; mercury(II) oxide; benzene |
2,4-dimethylthiophene
3,5-dimethyl-2-thiophenecarboxaldehyde
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide Erwaermen des Dinatrium-Salzes der erhaltenen Disulfonsaeure mit Phosphor(V)-chlorid; |
2,4-dimethylthiophene
Conditions | Yield |
---|---|
With ethanol; sodium acetate; mercury dichloride |
The Thiophene, 2, 4-dimethyl-, with the CAS registry number 638-00-6, is also known as 2, 4-Dimethyl thiophene. Its EINECS registry number is 211-312-3. This chemical's molecular formula is C6H8S and molecular weight is 112.19. What's more, its IUPAC name is 2, 4-Dimethylthiophene. Besides, this chemical is highly flammable, and it may catch fire on contacting with an ignition source. Hence, keep it away from sources of ignition.
Physical properties about Thiophene, 2, 4-dimethyl- are: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.82; (4)ACD/LogD (pH 7.4): 2.82; (5)ACD/BCF (pH 5.5): 81.38; (6)ACD/BCF (pH 7.4): 81.38; (7)ACD/KOC (pH 5.5): 811.24; (8)ACD/KOC (pH 7.4): 811.24; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 28.24 Å2; (13)Index of Refraction: 1.527; (14)Molar Refractivity: 34.28 cm3; (15)Molar Volume: 111.4 cm3; (16)Polarizability: 13.59×10-24 cm3; (17)Surface Tension: 32.2 dyne/cm; (18)Density: 1.006 g/cm3; (19)Flash Point: 23 °C; (20)Enthalpy of Vaporization: 36.05 kJ/mol; (21)Boiling Point: 138.7 °C at 760 mmHg; (22)Vapour Pressure: 8.26 mmHg at 25 °C.
Preparation of Thiophene, 2, 4-dimethyl-: this chemical is prepared by reaction of 4-Bromo-2-methyl-thiophene with Methylmagnesium iodide by heating. This reaction needs catalyst Nickel 1, 3-bis(diphenylphosphino)propane and solvent Diethyl ether. The reaction time is 22 hours. The yield is about 66 %.
Uses of Thiophene, 2, 4-dimethyl-: it is used to produce other chemicals. For example, it is used to produce 2, 4-Dibromo-3, 5-dimethyl-thiophene at ambient temperature. The reaction needs reagent Br2. The reaction time is 3 minutes. The yield is about 96 %.
You can still convert the following datas into molecular structure:
(1) SMILES: s1c(cc(c1)C)C
(2) InChI: InChI=1/C6H8S/c1-5-3-6(2)7-4-5/h3-4H,1-2H3
(3) InChIKey: CPULIKNSOUFMPL-UHFFFAOYAR
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