3-Methylthiophene supplier

Name
3-Methylthiophene
EINECS 210-482-6
CAS No. 616-44-4
Article Data52
CAS DataBase
Density 1.013 g/cm³
Solubility Insoluble in water
Melting Point -69 °C(lit.)
Formula C₅H₆S
Boiling Point 114.2 °C at 760 mmHg
Molecular Weight 98.1686
Flash Point 11.1 °C
Transport Information UN 1993 3/PG 2
Appearance clear colorless to light yellow liquid
Safety 7-16-29-33-36-37/39-26-7/9
Risk Codes 11-20/22-36/37/38-37
Molecular Structure
Hazard Symbols F, Xn, Xi
Synonyms 5-17-01-00331 (Beilstein Handbook Reference);3-Thiotolene;Thiophene,3-methyl-;beta-Methylthiophene;
PSA 28.24000
LogP 2.05650

Synthetic route

: 17249-90-0
2,5-Dichloro-3-methylthiophene

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen; potassium hydroxide In methanol at 80℃; under 60006 Torr; for 24h;	95.33%

: 872-31-1
3-Bromothiophene

bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium: bis(μ-[2-(dimethylamino)ethanolato-N,O:O]tetramethyldiindium

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
bis-triphenylphosphine-palladium(II) chloride In benzene at 80℃; for 24h;	93%

: 10486-61-0
3-thienyl iodide

: 31729-70-1
bis(iodozinc)methane

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
Stage #1: 3-thienyl iodide; bis(iodozinc)methane With tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane In tetrahydrofuran at 40℃; for 0.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; water chemoselective reaction;	73%

: 71637-34-8
3-hydroxymethyl-thiophene

: 201230-82-2
carbon monoxide

A: 6964-21-2
thiophen-3-yl-acetic acid

B: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 34% B 11%
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h;	A 34 % Spectr. B 11 % Spectr.

...Expand

: 188290-36-0
thiophene

: cis-Cp(*)W(CO)2(MeCN)(4-methyl-2-thienyl)

A: 616-44-4
3-Methylthiophene

: cis-Cp(*)W(CO)2(MeCN)(-2-thienyl)

: cis-Cp(*)W(CO)2(d3-MeCN)(-2-thienyl)

Conditions

Conditions	Yield
	A 32% B 33% C 6%

...Expand

: 33922-80-4
bis-(1-propenyl) sulfide

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 872-55-9
2-ethylthiophene

D: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
at 500 - 520℃; pyrolysis at atmospheric pressure in a nitrogen stream; Further byproducts given;	A 32% B n/a C 25% D n/a

...Expand

: 77-77-0
Divinyl sulfone

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

D: 108-88-3
toluene

E: 95-15-8
Benzo[b]thiophene

F: 71-43-2
benzene

Conditions

Conditions	Yield
With hydrogen sulfide at 580℃; thermal transformations of divinyl sulfone; further gaseous medium;	A 12% B 1.1% C 3% D 3.6% E 0.4% F 11%

...Expand

: 513-35-9
2-methyl-but-2-ene

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With aluminium oxide-chromium oxide; sulfur dioxide

: 123-51-3
i-Amyl alcohol

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With aluminium oxide-chromium oxide; sulfur dioxide

: 78-78-4
methylbutane

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With aluminium oxide-chromium oxide; sulfur dioxide

: 563-45-1
3-Methyl-1-butene

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With aluminium oxide-chromium oxide; sulfur dioxide

: 78-79-5
isoprene

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With sulfur at 350℃;

: 188290-36-0
thiophene

: 64710-12-9
dimethylfluoronium ion

A: 554-14-3
2-Methylthiophene

B: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With oxygen; trimethylamine In gas Product distribution; gas-phase methylation of furan and thiophene, pressure dependence, effect of partial pressure of NMe3, competition experiments in the presence of benzene; mechanism of methylation;

...Expand

: 188290-36-0
thiophene

: 24400-15-5
dimethylchloronium

A: 554-14-3
2-Methylthiophene

B: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With oxygen; trimethylamine In gas Product distribution; gas-phase methylation of furan and thiophene, pressure dependence, effect of partial pressure of NMe3, competition experiments in the presence of benzene; mechanism of methylation;

...Expand

: 554-14-3
2-Methylthiophene

A: 872-55-9
2-ethylthiophene

B: 638-00-6
2,4-dimethylthiophene

C: 638-02-8
2,5-DIMETHYLTHIOPHENE

D: 616-44-4
3-Methylthiophene

Conditions

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.

...Expand

: 632-16-6
2,3-dimethylthiophene

A: 188290-36-0
thiophene

B: 872-55-9
2-ethylthiophene

C: 638-02-8
2,5-DIMETHYLTHIOPHENE

D: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 3.1 % Chromat. B 1.5 % Chromat. C 1.0 % Chromat. D 12.8 % Chromat.

...Expand

: 632-16-6
2,3-dimethylthiophene

A: 554-14-3
2-Methylthiophene

B: 616-44-4
3-Methylthiophene

C: 108-88-3
toluene

D: 71-43-2
benzene

Conditions

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 6.6 % Chromat. B 12.8 % Chromat. C 4.1 % Chromat. D 24.7 % Chromat.

...Expand

: 632-16-6
2,3-dimethylthiophene

A: 632-15-5
3,4-dimethylthiophene

B: 872-55-9
2-ethylthiophene

C: 638-00-6
2,4-dimethylthiophene

D: 616-44-4
3-Methylthiophene

Conditions

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.

...Expand

: 632-15-5
3,4-dimethylthiophene

A: 632-16-6
2,3-dimethylthiophene

B: 638-00-6
2,4-dimethylthiophene

C: 638-02-8
2,5-DIMETHYLTHIOPHENE

D: 616-44-4
3-Methylthiophene

Conditions

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.

...Expand

: 632-15-5
3,4-dimethylthiophene

A: 638-00-6
2,4-dimethylthiophene

B: 638-02-8
2,5-DIMETHYLTHIOPHENE

C: 616-44-4
3-Methylthiophene

D: 71-43-2
benzene

Conditions

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.

...Expand

: 872-31-1
3-Bromothiophene

: 74-88-4
methyl iodide

: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With n-butyllithium 1.) hexane, THF, -78 deg C, 1 h; 2.) -78 deg C to RT; Yield given. Multistep reaction;

: 638-00-6
2,4-dimethylthiophene

A: 554-14-3
2-Methylthiophene

B: 632-15-5
3,4-dimethylthiophene

C: 638-02-8
2,5-DIMETHYLTHIOPHENE

D: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 6.6 % Chromat. B 2.9 % Chromat. C 3.5 % Chromat. D 9.5 % Chromat.

...Expand

: 638-02-8
2,5-DIMETHYLTHIOPHENE

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 632-16-6
2,3-dimethylthiophene

D: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
1.) glow discharge, 2.) -196 deg C -> -80 deg C; Further byproducts given. Title compound not separated from byproducts;	A 2.0 % Chromat. B 15.4 % Chromat. C 1.0 % Chromat. D 2.3 % Chromat.

...Expand

: 18888-46-5
isopropyl vinyl sulfide

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

D: 108-88-3
toluene

E: 71-43-2
benzene

Conditions

Conditions	Yield
at 550℃; Product distribution;

...Expand

: 33922-80-4
bis-(1-propenyl) sulfide

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 872-55-9
2-ethylthiophene

D: 616-44-4
3-Methylthiophene

E: 925-89-3
Prop-1-en-1-thiol

F: 71-43-2
benzene

Conditions

Conditions	Yield
at 520℃; Product distribution; Mechanism; reaction in the presence of dimethyl selenide, 2-halothiophenes and acetylene, var. temp.;

...Expand

: 16330-21-5
propyl vinyl sulfide

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

D: 108-88-3
toluene

E: 71-43-2
benzene

Conditions

Conditions	Yield
at 550℃; Product distribution;

...Expand

: 109-66-0
pentane

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

Conditions

Conditions	Yield
With cerium(IV) oxide; aluminum oxide; chromium(III) oxide; lanthanum(III) oxide; praseodymium(III) oxide; Nd3O3; hydrogen sulfide; potassium oxide at 550℃; under 760 Torr; Yield given. Yields of byproduct given;
With hydrogen sulfide; cerium(IV) oxide; chromium(III) oxide; lanthanum(III) oxide; neodymium(III) oxide; praseodymium(III) oxide; potassium oxide at 550℃; Product distribution; Further Variations:; Catalysts;

...Expand

: 109-66-0
pentane

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

D: 513-35-9
2-methyl-but-2-ene

E: 627-20-3
(Z)-pent-2-ene

F: 646-04-8
(E)-pent-2-ene

Conditions

Conditions	Yield
With hydrogen sulfide; ferrisilicate at 500℃; for 1h; Product distribution; other temperatures, other volume feed rates of n-pentane, other H2S/n-pentane molar ratios, other reaction times;	A 0.3 % Chromat. B 12.2 % Chromat. C 1.7 % Chromat. D n/a E n/a F n/a

...Expand

: 627-50-9
vinyl ethylsulfide

A: 188290-36-0
thiophene

B: 554-14-3
2-Methylthiophene

C: 616-44-4
3-Methylthiophene

D: 108-88-3
toluene

E: 71-43-2
benzene

Conditions

Conditions	Yield
at 550℃; Product distribution;

...Expand

: 2-(1-methylpropenyl)-1,3-dithiolane 1,1-dioxide

A: 616-44-4
3-Methylthiophene

B: 3,4,7,8,11,12-hexamethyl-1,5,9-trithiacyclododeca-2,6,10-triene

Conditions

Conditions	Yield
at 430 - 600℃;

: 616-44-4
3-Methylthiophene

: 123-19-3
4-heptanone

: 1567323-42-5
2-(4-hydroxy-4-heptyl)-4-methylthiophene

Conditions

Conditions	Yield
Stage #1: 3-Methylthiophene With n-butyllithium In diethyl ether; hexane for 1h; Reflux; Stage #2: 4-heptanone In diethyl ether at 20℃; for 1h;	100%

: 616-44-4
3-Methylthiophene

: 14282-76-9
2-bromo-3-methylthiophene

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;	99%
With N-Bromosuccinimide	99%
With N-Bromosuccinimide In acetic acid for 0.416667h;	97.9%

: 616-44-4
3-Methylthiophene

: 13191-36-1
2,5-dibromo-3-methylthiophene

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran Inert atmosphere;	99%
With benzyltrimethylazanium tribroman-2-uide; zinc(II) chloride In acetic acid for 15h; Ambient temperature;	97%
With potassium bromide In water; acetic acid at 30℃; for 0.25h; Temperature;	94%

: 616-44-4
3-Methylthiophene

: 27126-76-7
[hydroxy(tosyloxy)iodo]benzene

: 91228-41-0
(3-methyl-2-thienyl)(phenyl)iodonium tosylate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	98%
In 2,2,2-trifluoroethanol at 20℃; for 3h;	98%
In 2,2,2-trifluoroethanol at 0 - 20℃;	98%
In chloroform for 2h; Heating;	78.1%

: 616-44-4
3-Methylthiophene

: 27126-76-7
[hydroxy(tosyloxy)iodo]benzene

: 1118904-87-2
(3-methyl-2-thienyl)(phenyl)iodonium tosylate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 2h;	98%
In 2,2,2-trifluoroethanol at 20℃; for 2h;	84%

: 616-44-4
3-Methylthiophene

: 633337-85-6
3'-[4-(t-butyldimethylsilyloxy)-3-methylphenyl]pentan-3-ol

: 633337-86-7
3'-[4-(hydroxy)-3-methylphenyl]-3'-[4-methylthiophen-2-yl]pentane

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at -78 - 20℃; for 6.75h;	95%
With boron trifluoride diethyl etherate at -78 - 20℃; for 6.75h; Product distribution / selectivity;	95%

: 616-44-4
3-Methylthiophene

: 623-00-7
4-bromobenzenecarbonitrile

: 1101167-54-7
4-(4-methylthiophen-2-yl)benzonitrile

Conditions

Conditions	Yield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; hexane at 0℃; for 4h; Inert atmosphere; Stage #3: 4-bromobenzenecarbonitrile With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 20 - 50℃; Inert atmosphere;	95%

Yield

Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere;
Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; hexane at 0℃; for 4h; Inert atmosphere;
Stage #3: 4-bromobenzenecarbonitrile With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; diethyl ether; hexane at 20 - 50℃; Inert atmosphere;

95%

: 85-44-9
phthalic anhydride

: 616-44-4
3-Methylthiophene

: 2-(4-methylthiophene-2-carbonyl)benzoic acid

Conditions

Conditions	Yield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethylpiperidin-4-yl heptanoate; isopropylmagnesium chloride In tetrahydrofuran at 66℃; for 23h; Stage #2: phthalic anhydride With hydrogenchloride In tetrahydrofuran; water at -20 - 20℃;	94%
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; isopropylmagnesium chloride In tetrahydrofuran at 66℃; for 23h; Inert atmosphere; Stage #2: phthalic anhydride In tetrahydrofuran at -25 - -20℃; for 1.08333h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at -20 - 20℃; pH=2; regioselective reaction;	89.7%
With aluminium trichloride; nitrobenzene

: 616-44-4
3-Methylthiophene

: 16494-40-9
2-iodo-3-methylthiophene

Conditions

Conditions	Yield
With iodine; mercury(II) oxide	94%
With iodine; mercury(II) oxide In benzene for 0.5h; Ambient temperature;	94%
With iodine; mercury(II) oxide In benzene Iodination;	79%

: 616-44-4
3-Methylthiophene

: 16488-62-3
2,3,5-triiodo-4-methyl-thiophene

Conditions

Conditions	Yield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 15h; Ambient temperature;	94%
With mercury(II) diacetate; iodine; acetic acid

: 616-44-4
3-Methylthiophene

: 83781-30-0
pentaamminetrifluoromethanesulfonato osmium(III) trifluoromethanesulfonate

: 4,5-η2-[Os(NH3)5]-3-methylthiophene triflate

Conditions

Conditions	Yield
With Mg In N,N-dimethyl acetamide Kinetics; N2-atmosphere;	93%
With Z/Hg In methanol Kinetics; N2-atmosphere;	93%
In [D3]acetonitrile Kinetics; N2-atmosphere; -40°C; not isolated; detd. by (1)H NMR spectroscopy;

: 616-44-4
3-Methylthiophene

: 1873-88-7
1,1,1,3,5,5,5-heptamethyltrisiloxan

: 1,1,1,3,5,5,5-heptamethyl-3-(4-methylthiophen-2-yl)trisiloxane

Conditions

Conditions	Yield
With tert-butylethylene; C25H40O2P2Ru In neat (no solvent) at 120℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	93%
Stage #1: 1,1,1,3,5,5,5-heptamethyltrisiloxan With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; C25H35N3; cyclohexene In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: 3-Methylthiophene In tetrahydrofuran at 65℃; for 26h; Sealed tube; Inert atmosphere; regioselective reaction;	89%

: 616-44-4
3-Methylthiophene

: 16488-60-1
3-methyl-2,5-diiodothiophene

Conditions

Conditions	Yield
With N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride In acetic acid for 4h; Ambient temperature;	92%
With sulfuric acid; iodine; iodic acid In tetrachloromethane; water; acetic acid for 4h; Heating;	64%

: 616-44-4
3-Methylthiophene

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 6030-36-0
4-methylthiophene-2-carbaldehyde

Conditions

Conditions	Yield
Stage #1: 3-Methylthiophene With 2,2,6,6-tetramethyl-piperidine; tert.-butyl lithium In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;	92%
Stage #1: 3-Methylthiophene With n-butyllithium In tetrahydrofuran at -65℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -65℃; for 2h;	90%
With n-butyllithium In diethyl ether at 20℃; for 1.5h;	84%

: 616-44-4
3-Methylthiophene

: phenylthallium(III) (1,4,7,10,13,16-hexaoxacyclooctadecane)diperchlorate

: (18-crown-6)phenyl(4-methyl-2-thienyl)thallium(III) perchlorate

Conditions

Conditions	Yield
In acetonitrile addn. of solvent and thiophene to complex, degassed three times, sealed (vac.), heated at 60°C for 24 h in the dark; addn. of Et2O, pptn., filtered, addn. of Et2O to CH2Cl2 soln., filtered, dissolved in CH3CN, addn. of Et2O, recrystd. (CH2Cl2/Et2O); elem. anal.;	92%

: 616-44-4
3-Methylthiophene

: 1135-99-5
diphenyltin(IV) dichloride

: 117013-09-9
bis(4-methyl-2-thienyl)diphenyltin(IV)

Conditions

Conditions	Yield
With n-C4H9Li In not given reflux 3 h;	92%
With PhLi In not given reflux 3 h; elem. anal.;	79%

: 616-44-4
3-Methylthiophene

: C16H21IO5S

: (3-methyl-2-thienyl)(phenyl)iodonium (+/-)-10-camphorsulfonate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	92%

: 616-44-4
3-Methylthiophene

: C16H21IO5S

: (3-methyl-2-thienyl)(phenyl)iodonium 10-camphorsulfonate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	92%

: 616-44-4
3-Methylthiophene

: diphenyliodonium tetrafluoroborate

: 16939-15-4
3-methyl-4-phenylthiophene

Conditions

Conditions	Yield
With 5%-palladium/activated carbon In ethanol at 60℃; for 22h; regioselective reaction;	92%
With palladium In tetrahydrofuran at 60℃; for 24h;	71%

: 616-44-4
3-Methylthiophene

: 591-50-4
iodobenzene

: 104-15-4
toluene-4-sulfonic acid

: C7H7O3S(1-)*C17H14IS(1+)

Conditions

Conditions	Yield
Stage #1: iodobenzene With peracetic acid; acetic acid In dichloromethane; 2,2,2-trifluoroethanol at 35℃; for 1h; Stage #2: 3-Methylthiophene; toluene-4-sulfonic acid In dichloromethane; 2,2,2-trifluoroethanol at 20℃; for 3h;	91%

...Expand

: 616-44-4
3-Methylthiophene

: 34846-44-1
3-Bromomethylthiophene

Conditions

Conditions	Yield
With N-Bromosuccinimide; dihydrogen peroxide In tetrachloromethane	90%
With N-Bromosuccinimide; dibenzoyl peroxide In benzene for 0.5h; Heating;	88%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 2h; Reflux;	87%

: 616-44-4
3-Methylthiophene

: 1460-08-8
2-diazocyclohexane-1,3-dione

: 3-Hydroxy-2-(4-methylthien-2-yl)cyclohex-2-enone

Conditions

Conditions	Yield
dirhodium tetraacetate In fluorobenzene for 15h; Ambient temperature;	90%

: 616-44-4
3-Methylthiophene

A: 16494-40-9
2-iodo-3-methylthiophene

B: 16488-60-1
3-methyl-2,5-diiodothiophene

Conditions

Conditions	Yield
With ammonium iodide; dihydrogen peroxide In water; acetic acid for 20h; Green chemistry; regioselective reaction;	A 90% B 10%

: 616-44-4
3-Methylthiophene

: 591-50-4
iodobenzene

: 14300-29-9
2-phenyl-4-methylthiophene

Conditions

Conditions	Yield
Stage #1: 3-Methylthiophene With n-butyllithium In diethyl ether; hexane for 1h; Heating; Stage #2: With Trimethyl borate In diethyl ether; hexane at 20℃; for 1h; Stage #3: iodobenzene With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; diethyl ether; hexane for 5h; Heating;	89%

: 616-44-4
3-Methylthiophene

: 105551-42-6
(mesyloxyhydroxyiodo)benzene

: (3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	89%

: 616-44-4
3-Methylthiophene

: 105551-42-6
(mesyloxyhydroxyiodo)benzene

: 1205744-68-8
(3-methyl-2-thienyl)(phenyl)iodonium methanesulfonate

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 20℃; for 3h;	89%

: 616-44-4
3-Methylthiophene

: 98-58-8
4-bromobenzenesulfonyl chloride

: 3-(4-bromophenyl)-4-methylthiophene

Conditions

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); lithium carbonate In 1,4-dioxane at 140℃; for 40h; Inert atmosphere; Schlenk technique; regioselective reaction;	89%

: 1532-72-5
isoquinoline N-oxide

: 616-44-4
3-Methylthiophene

: 3-(thiopheno-2-methoxy)quinazolino-4(3H)-one

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; copper(II) sulfate; sodium iodide In decane; dichloromethane at 70℃; for 8h;	89%

3-Methylthiophene Consensus Reports

Reported in EPA TSCA Inventory.

3-Methylthiophene Specification

The IUPAC name of this chemical is 3-methylthiophene. With the CAS registry number 616-44-4, it is also named as Thiophene, 3-methyl-. The product's categories are thiophenes; heterocycles; thiophene & benzothiophene; heterocyclic compounds; 3-alkylthiophenes (for conduting polymer research); functional materials; reagents for conducting polymer research; heterocyclic building blocks. It is clear colorless to light yellow liquid which is miscible with ethanol, ether, acetone, benzene and carbon tetrachloride, soluble in chloroform, and insoluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of 3-Methylthiophene can be summarized as: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)#Freely Rotating Bonds: 0; (6)Index of Refraction: 1.531; (7)Molar Refractivity: 29.46 cm³; (8)Molar Volume: 95.1 cm³; (9)Polarizability: 11.67×10^-24 cm³; (10)Surface Tension: 32.9 dyne/cm; (11)Flash Point: 11.1 °C; (12)Enthalpy of Vaporization: 34.24 kJ/mol; (13)Boiling Point: 114.2 °C at 760 mmHg; (14)Vapour Pressure: 23.8 mmHg at 25°C; (15)Exact Mass: 98.019021; (16)MonoIsotopic Mass: 98.019021; (17)Topological Polar Surface Area: 28.2; (18)Heavy Atom Count: 6; (19)Complexity: 43.2.

Uses of 3-Methylthiophene: It can be used as pharmaceutical intermediate. And it reacts with N,N-dimethyl-formamide to get 3-methyl-thiophene-2-carbaldehyde. This reaction needs reagent phosphoryl chloride by anschliessend Hydrolysieren.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep away from sources of ignition. And it is harmful by inhalation and if swallowed. In addition, this chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:Cc1ccsc1
2. InChI:InChI=1/C5H6S/c1-5-2-3-6-4-5/h2-4H,1H3
3. InChIKey:QENGPZGAWFQWCZ-UHFFFAOYAK

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mammal (species unspecified)	LC50	inhalation	18gm/m³ (18000mg/m³)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mammal (species unspecified)	LD50	unreported	1600mg/kg (1600mg/kg)	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse	LC50	inhalation	18gm/m³/2H (18000mg/m³)	"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.
mouse	LD50	oral	1800mg/kg (1800mg/kg)	"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 87, 1982.

Product Name

3-Methylthiophene

Synthetic route

3-Methylthiophene Consensus Reports

3-Methylthiophene Specification

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