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554-14-3

Basic Information
CAS No.: 554-14-3
Name: 2-Methylthiophene
Molecular Structure:
Molecular Structure of 554-14-3 (2-Methylthiophene)
Formula: C5H6S
Molecular Weight: 98.17
Synonyms: a-Methylthiophene;
EINECS: 209-063-0
Density: 1.031 g/cm3
Melting Point: -63 °C(lit.)
Boiling Point: 107.9 °C at 760 mmHg
Flash Point: 7.2 °C
Solubility: Immiscible with water
Appearance: clear colorless to slightly yellow liquid
Hazard Symbols: FlammableF, HarmfulXn, IrritantXi
Risk Codes: 11-22-36/37/38-37
Safety: 16-37/39-26-36-33-7/9
Transport Information: UN 1993 3/PG 2
PSA: 28.24000
LogP: 2.05650
Synthetic route
1795-09-1

2-methylthiolane

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
Au/X40S catalyst at 280℃; under 413.729 Torr; Product distribution / selectivity; Inert atmosphere;100%
17249-82-0

2-chloro-5-methylthiophene

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; potassium hydroxide at 80℃; under 60006 Torr; for 24h;97.11%
765-50-4

2-Chloromethylthiophene

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
Stage #1: 2-Chloromethylthiophene With lithium naphthalenide In tetrahydrofuran at 20℃; Inert atmosphere; Flow reactor;
Stage #2: With methanol Inert atmosphere; Flow reactor;
97%
110-66-7

n-pentanethiol

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
X-3R2 catalyst at 280℃; under 413.729 Torr; Product distribution / selectivity; Inert atmosphere;91%
1918-77-0

Thiophene-2-acetic acid

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;87%
In acetonitrile at 563.2℃; Kinetics; Further Variations:; Temperatures; Pyrolysis;
188290-36-0

thiophene

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
77%
54663-78-4

tributyl(thien-2-yl)stannane

74-88-4

methyl iodide

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With potassium carbonate; tris-(o-tolyl)phosphine; copper(l) chloride; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 60℃; for 0.0833333h;73%
With tris-(dibenzylideneacetone)dipalladium(0); cesium fluoride; tris-(o-tolyl)phosphine; copper(I) bromide In 1-methyl-pyrrolidin-2-one at 60℃; for 0.0833333h; Inert atmosphere;94 %Chromat.
123-76-2

levulinic acid

A

554-14-3

2-Methylthiophene

B

3970-28-3

5-methyl-2-thiophenethiol

Conditions
ConditionsYield
With Lawessons reagent In toluene at 20 - 110℃; for 3.5h; Concentration; Time;A 6%
B 66%
1918-77-0

Thiophene-2-acetic acid

110-62-3

pentanal

A

554-14-3

2-Methylthiophene

B

C10H16OS

Conditions
ConditionsYield
With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate In N,N-dimethyl acetamide at 20℃; for 16h; Irradiation; Inert atmosphere;A 21 %Chromat.
B 61%
534-22-5

2-methylfuran

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With hydrogenchloride; hydrogen sulfide In water at 50 - 60℃; for 2h; Substitution;60%
With hydrogenchloride; hydrogen sulfide at 50 - 60℃; Product distribution; other solvents (methanol, ethylene glycol, acetic acid); other acid catalysts (perchloric acid, hydrochloric acid, trifluoroacetic acid), other temperatures;5%
With hydrogenchloride; hydrogen sulfide at 50 - 60℃;5%
With hydrogen sulfide; RbNaY zeolite at 349.9℃; under 760 Torr; Product distribution; Mechanism; other catalysts (LiNaY, NaY, KNaY CsNaY zeolites);
With aluminum oxide; hydrogen sulfide at 350℃;
636-72-6

2-thiophenemethanol

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Wolff-Kishner Reduction; Sealed tube;55%
With chlorocarbonylbis(triphenylphosphine)iridium(I); hydrazine hydrate; potassium hydroxide In methanol at 160℃; for 3h; Sealed tube;55%
With carbon monoxide; hydrogen; cobalt(II) acetate
188290-36-0

thiophene

74-88-4

methyl iodide

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃;51%
With ammonia; sodium amide
Stage #1: thiophene With n-butyllithium In tetrahydrofuran at -20℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 0℃; for 1h;
16494-36-3

2-iodo-5-methylthiophene

75-89-8

2,2,2-trifluoroethanol

71-43-2

benzene

A

554-14-3

2-Methylthiophene

B

5069-26-1

2-methyl-5-phenylthiophene

C

136019-61-9

2-(2,2,2-trifluoroethoxy)thiophene

Conditions
ConditionsYield
With caesium carbonate for 6h; Inert atmosphere; Irradiation;A 25 %Chromat.
B 48%
C < 5 %Spectr.
16494-36-3

2-iodo-5-methylthiophene

108-67-8

1,3,5-trimethyl-benzene

A

554-14-3

2-Methylthiophene

B

2-(2,4,5-trimethylphenyl)-5-methylthiophene

Conditions
ConditionsYield
With caesium carbonate In 2,2,2-trifluoroethanol for 6h; Inert atmosphere; Irradiation;A 16 %Chromat.
B 44%
636-72-6

2-thiophenemethanol

A

554-14-3

2-Methylthiophene

B

98-03-3

thiophene-2-carbaldehyde

Conditions
ConditionsYield
With iodine at 150℃; for 23h; Inert atmosphere; Sealed tube;A 37%
B 42%
2004-70-8

1-methylbuta-1,3-diene

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With hydrogen sulfide; AlCrK at 490 - 510℃; Cyclization; Dehydrocyclization;41%
36953-55-6

2-(dichloromethyl)thiophene

A

554-14-3

2-Methylthiophene

B

210-80-0

benzo[1,2-b;4,3-b']dithiophene

C

13640-78-3

(E)-1,2-bis(2-thienyl)ethene

Conditions
ConditionsYield
With magnesium at 600℃; Pyrolysis;A 10%
B 6%
C 39%
16494-36-3

2-iodo-5-methylthiophene

762-72-1

allyl-trimethyl-silane

A

554-14-3

2-Methylthiophene

B

2-methyl-5-(2-propenyl)thiophene

Conditions
ConditionsYield
With caesium carbonate In 2,2,2-trifluoroethanol for 6h; Inert atmosphere; Irradiation;A 18 %Chromat.
B 37%
85455-66-9

thiophen-2-yl-methyl benzoate

A

188290-36-0

thiophene

B

554-14-3

2-Methylthiophene

C

98-03-3

thiophene-2-carbaldehyde

D

7326-80-9

1,2-bis(thiophen-2-yl)ethane

E

65-85-0

benzoic acid

F

71-43-2

benzene

Conditions
ConditionsYield
at 700℃; under 0.1 Torr; Product distribution; Mechanism; other thenyl derivatives, various temperatures;A 2%
B 1.6%
C 0.8%
D 8.4%
E 34.7%
F 11.9%
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
ConditionsYield
at 500 - 520℃; pyrolysis at atmospheric pressure in a nitrogen stream; Further byproducts given;A 32%
B n/a
C 25%
D n/a
636-72-6

2-thiophenemethanol

A

554-14-3

2-Methylthiophene

B

98-03-3

thiophene-2-carbaldehyde

C

527-72-0

2-thiophenylcarboxylic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; manganese(II) acetate; trifluoroacetic acid In acetonitrile at 80℃; under 15001.5 Torr; for 15h; Mechanism; chemoselective reaction;A 7%
B n/a
C 21%
131981-78-7

(E)-1-(thiophen-2-yl)propan-2-one oxime

A

188290-36-0

thiophene

B

554-14-3

2-Methylthiophene

C

7326-80-9

1,2-bis(thiophen-2-yl)ethane

D

75-05-8

acetonitrile

Conditions
ConditionsYield
at 800℃; under 0.001 - 0.01 Torr; approximate contact time: 0.002-0.03 s;;A 10%
B 15%
C 19%
D n/a
188290-36-0

thiophene

624-92-0

Dimethyldisulphide

A

554-14-3

2-Methylthiophene

B

1795-04-6

2,3,4-trimethylthiophene

C

638-02-8

2,5-DIMETHYLTHIOPHENE

Conditions
ConditionsYield
With zeolite HZSM-5 at 300℃; under 760.051 Torr; for 0.00236111h; Time; Flow reactor;A 19%
B 18%
C 12%
With HZSM-5 zeolite (SiO2/Al2O3 = 34) at 300℃; under 760.051 Torr; for 2h; Catalytic behavior; Temperature; Flow reactor; Gas phase; Inert atmosphere;
201230-82-2

carbon monoxide

636-72-6

2-thiophenemethanol

A

554-14-3

2-Methylthiophene

B

1918-77-0

Thiophene-2-acetic acid

Conditions
ConditionsYield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;A 12%
B 18%
188290-36-0

thiophene

624-92-0

Dimethyldisulphide

A

554-14-3

2-Methylthiophene

B

5780-36-9

2-(methylsulfanyl)thiophene

C

50878-66-5

2,5-bis(methylsulfanyl)thiophene

Conditions
ConditionsYield
With highly siliceous zeolite HZSM-5 in a hydrogen form (SiO2/Al2O3 = 34) (Ssp 500 m2/g) at 180℃; for 0.00388889h;A 6%
B 17%
C 11%
With HZSM-5 zeolite (SiO2/Al2O3 = 34) at 180℃; under 760.051 Torr; for 2h; Flow reactor; Gas phase; Inert atmosphere;
188290-36-0

thiophene

624-92-0

Dimethyldisulphide

A

554-14-3

2-Methylthiophene

B

1795-04-6

2,3,4-trimethylthiophene

Conditions
ConditionsYield
With zeolite HZSM-5 at 300℃; under 760.051 Torr; for 0.000333333h; Time; Flow reactor;A 14%
B 10%
With HZSM-5 zeolite (SiO2/Al2O3 = 34) at 350℃; under 760.051 Torr; for 2h; Catalytic behavior; Temperature; Flow reactor; Gas phase; Inert atmosphere;
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
ConditionsYield
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%
188290-36-0

thiophene

624-92-0

Dimethyldisulphide

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With zeolite HZSM-5 at 300℃; under 760.051 Torr; for 0.000166667h; Flow reactor;7%
With HZSM-5 zeolite (SiO2/Al2O3 = 34) at 300℃; under 760.051 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Temperature; Flow reactor; Gas phase; Inert atmosphere;
3437-95-4

2-Iodothiophene

74-83-9

methyl bromide

554-14-3

2-Methylthiophene

Conditions
ConditionsYield
With diethyl ether; sodium
554-14-3

2-Methylthiophene

75-07-0

acetaldehyde

19077-07-7

2-methyl-5-(1-(5-methylthiophen-2-yl)ethyl)thiophene

Conditions
ConditionsYield
With ion-exchange resin Lewatit SPC 108 (acid form) In 1,4-dioxane; water at 20℃; for 1.5h;100%
554-14-3

2-Methylthiophene

1062602-29-2

1-(p-methoxyphenyl)-3-(phenylsulfanyl)propargyl alcohol

1062602-53-2

5-methyl-2-[1-(p-anisyl)-3-(phenylsulfanyl)prop-2-ynyl]thiophene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In N,N-dimethyl-formamide at 20℃; for 72h; Friedel-Crafts alkylation; regioselective reaction;100%
554-14-3

2-Methylthiophene

5781-53-3

monomethyl oxalyl chloride

70596-06-4

(5-methyl-thiophen-2-yl)-oxo-acetic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene; monomethyl oxalyl chloride With aluminum (III) chloride In dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With water In dichloromethane at 0℃;
100%
554-14-3

2-Methylthiophene

80-59-1

Tiglic acid

1256451-40-7

2,4,5-trimethyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one

Conditions
ConditionsYield
With polyphosphoric acid Inert atmosphere;100%
With polyphosphoric acid In dichloromethane at 50℃; for 4.5h; Schlenk technique; Inert atmosphere;82%
554-14-3

2-Methylthiophene

292638-85-8

acrylic acid methyl ester

3-(5-methyl-thiophen-2-yl)-acrylic acid methyl ester

Conditions
ConditionsYield
With 3-methyl-2-(phenylthio)butanoic acid; silver(I) acetate; palladium diacetate In ethyl acetate at 60℃; for 6h; Sealed tube;100%
With 2-thienyl chloride; tetrafluoroboric acid diethyl ether; sodium 3-{(4-methoxyphenyl)thio}propane-1-sulfonate; palladium diacetate; acetic acid; hydroquinone at 60℃; for 12h; Reagent/catalyst;
554-14-3

2-Methylthiophene

29421-73-6

3,5-dibromo-2-methylthiophene

Conditions
ConditionsYield
With bromine; acetic acid at 20℃;99.7%
With N-Bromosuccinimide; acetic acid In chloroform at 20℃; for 17h;98%
With N-Bromosuccinimide; acetic acid at 20℃; for 2h;94%
554-14-3

2-Methylthiophene

68-12-2, 33513-42-7

N,N-dimethyl-formamide

13679-70-4

5-methylthiophene-2-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With ethylmagnesium chloride; N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 60℃; for 24h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; for 1h;
99%
With trichlorophosphate at 20℃;92%
Stage #1: 2-Methylthiophene; N,N-dimethyl-formamide With trichlorophosphate at 0 - 35℃; for 18h;
Stage #2: With sodium hydroxide; water In diethyl ether pH=11;
80.2%
554-14-3

2-Methylthiophene

C15H20O5

C18H22O3S

Conditions
ConditionsYield
With gold(III) chloride In nitromethane Friedel Crafts alkylation; Inert atmosphere; optical yield given as %de; diastereoselective reaction;99%
554-14-3

2-Methylthiophene

1062602-30-5

1-(4-chlorophenyl)-3-(phenylsulfanyl)prop-2-yn-1-ol

1062602-61-2

2-[1-(p-chlorophenyl)-3-(phenylsulfanyl)prop-2-ynyl]-5-methyl-thiophene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In nitromethane at 0℃; Friedel-Crafts alkylation; regioselective reaction;99%
554-14-3

2-Methylthiophene

79894-59-0

1-phenyl-3-(phenylsulfanyl)prop-2-yn-1-ol

1062602-52-1

5-methyl-2-[1'-phenyl-3'-(phenylsulfanyl)prop-2'-ynyl]thiophene

Conditions
ConditionsYield
With scandium tris(trifluoromethanesulfonate) In nitromethane at 20℃; for 1h; Friedel-Crafts alkylation; regioselective reaction;99%
With scandium tris(trifluoromethanesulfonate) In nitromethane at 20℃; for 1h;99%
554-14-3

2-Methylthiophene

106-43-4

para-chlorotoluene

85093-00-1

2-methyl-5-(4-methylphenyl)thiophene

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With ethylmagnesium chloride; N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 60℃; for 24h;
Stage #2: para-chlorotoluene With dichloro-[1,3-bis(2,6-diisopropylpenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II) In tetrahydrofuran at 60℃; for 24h;
99%
With C36H50Cl2N3OPPd; potassium tert-butylate; Trimethylacetic acid In N,N-dimethyl acetamide at 110℃; for 12h; Reagent/catalyst; Solvent;92%
With bis(tri-t-butylphosphine)palladium(0); lithium tert-butoxide In N,N-dimethyl-formamide at 100℃; for 15h; Inert atmosphere; regioselective reaction;88%
With NHC-Pd(II)-Im; potassium tert-butylate; copper(II) oxide In tetrahydrofuran at 130℃; for 12h; Inert atmosphere; Sealed tube;69%
554-14-3

2-Methylthiophene

106-38-7

para-bromotoluene

85093-00-1

2-methyl-5-(4-methylphenyl)thiophene

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With ethylmagnesium chloride; N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 60℃; for 24h;
Stage #2: para-bromotoluene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 24h;
99%
With C40H36N2O2Pd(2+)*2C2H4O2; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;92%
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); potassium carbonate; trimethylpyruvic acid In N,N-dimethyl acetamide at 140℃; for 16h;90%
554-14-3

2-Methylthiophene

90-11-9

1-Bromonaphthalene

58256-11-4

2-methyl-5-(naphthalen-1-yl)thiophene

Conditions
ConditionsYield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;99%
With C40H36N2O2Pd(2+)*2C2H4O2; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;91%
With C32H33Cl2NOPd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;86%
With [PdCl(C3H5)(dppb)]; potassium acetate at 150℃; for 24h; Inert atmosphere;20%
554-14-3

2-Methylthiophene

928712-61-2

α-Hydroxy-4-methoxy-α-phenylbenzeneacetic acid methyl ester

C21H20O3S

Conditions
ConditionsYield
With perchloric acid In 1,2-dichloro-ethane at 60℃; for 3h; Reagent/catalyst; Concentration; Time; Solvent; Friedel-Crafts Alkylation;99%
554-14-3

2-Methylthiophene

61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

476004-80-5

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; for 8h; Inert atmosphere; Schlenk technique;
99%
554-14-3

2-Methylthiophene

76-83-5

trityl chloride

2-trityl-5-methylthiophene

Conditions
ConditionsYield
With C19H10F12S In 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere; Molecular sieve;99%
554-14-3

2-Methylthiophene

49584-26-1

p-cyanobenzenesulfonyl chloride

4-(5-methylthiophen-3-yl)benzonitrile

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; tributylphosphine; 25,26,27,28-tetrakis(hydroxy)calix[4]arene; sodium carbonate In 1,4-dioxane at 105℃; for 22h; Reagent/catalyst; Solvent; Inert atmosphere;98.6%
With dichloro bis(acetonitrile) palladium(II); lithium carbonate In 1,4-dioxane at 140℃; for 40h; Schlenk technique; regioselective reaction;71%
554-14-3

2-Methylthiophene

98-74-8

4-Nitrobenzenesulfonyl chloride

2-methyl-3-(4-nitrophenyl)thiophene

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; tributylphosphine; 25,26,27,28-tetrakis(hydroxy)calix[4]arene; sodium carbonate In 1,4-dioxane at 95℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;98.5%
With dichloro bis(acetonitrile) palladium(II); lithium carbonate at 140℃; for 40h; Inert atmosphere; Schlenk technique; Green chemistry; regioselective reaction;89%
With dichloro bis(acetonitrile) palladium(II); lithium carbonate In 1,4-dioxane at 140℃; for 40h; Schlenk technique; regioselective reaction;78%
554-14-3

2-Methylthiophene

50-00-0

formaldehyd

4218-22-8

5,5'-dimethyldi-2-thienylmethane

Conditions
ConditionsYield
With ion-exchange resin Lewatit SPC 108 (acid form) In 1,4-dioxane; water at 60℃; for 2h;98%
With hydrogenchloride; zinc(II) chloride In water at -7 - 0℃; for 1h;25%
With hydrogenchloride
With hydrogenchloride
554-14-3

2-Methylthiophene

75-36-5

acetyl chloride

13679-74-8

2-Acetyl-5-methylthiophen

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0℃; for 1.5h;98%
With InIII-based[In(OTf)3] Polymeric Sulfonic Acid Catalyst In nitromethane for 0.166667h; Friedel-Crafts Acylation; Schlenk technique; Reflux;94%
With MoO4(AlCl2)2 In neat (no solvent) at 20℃; for 18h; Friedel-Crafts Acylation; Green chemistry;76%
554-14-3

2-Methylthiophene

45438-73-1

2-thenyl bromide

Conditions
ConditionsYield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane Inert atmosphere; Reflux;98%
With N-Bromosuccinimide; dibenzoyl peroxide In chloroform at 20 - 70℃;98%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1h; Reflux;78%
554-14-3

2-Methylthiophene

501-65-5

diphenyl acetylene

(E)-2-methyl-5-(1,2-diphenylvinyl)thiophene

Conditions
ConditionsYield
With tributyl borane; Pd2(methyl)2(μ-OH)(μ-N,N'-bis[2-(diphenylphosphino)phenyl]formamidinate) In tetrahydrofuran; cyclohexane at 100℃; for 17h;98%
554-14-3

2-Methylthiophene

460-00-4

1-Bromo-4-fluorobenzene

1089333-87-8

2-(4-fluorophenyl)-5-methylthiophene

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With ethylmagnesium chloride; N-cyclohexyl-cyclohexanamine In tetrahydrofuran at 60℃; for 24h;
Stage #2: 1-Bromo-4-fluorobenzene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In tetrahydrofuran at 20℃; for 24h;
98%
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 20h; Heck reaction; Inert atmosphere;87%
With C40H36N2O2Pd(2+)*2C2H4O2; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;85%
With palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid at 100℃; for 16h; Inert atmosphere;70%
With (3-phenylallyl)(chloro)-[1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(II); potassium carbonate; trimethylpyruvic acid In N,N-dimethyl acetamide at 140℃; for 16h;57%
554-14-3

2-Methylthiophene

41018-60-4

(3-(trifluoromethyl)phenyl)-λ3-iodanediyl diacetate

1330786-75-8

(5-methyl-2-thienyl)[3-(trifluoromethyl)phenyl]iodonium tosylate

Conditions
ConditionsYield
Stage #1: (3-(trifluoromethyl)phenyl)-λ3-iodanediyl diacetate With water; toluene-4-sulfonic acid In acetonitrile
Stage #2: 2-Methylthiophene In chloroform; acetonitrile for 3h; Reflux; regiospecific reaction;
98%
554-14-3

2-Methylthiophene

1426432-83-8

lithium 5-methylthiophene-2-sulfinate

Conditions
ConditionsYield
Stage #1: 2-Methylthiophene With tert.-butyl lithium In diethyl ether at -78℃; Inert atmosphere;
Stage #2: With sulfur dioxide In diethyl ether at -78 - 23℃;
98%
Stage #1: 2-Methylthiophene With tert.-butyl lithium In diethyl ether at -78℃; for 2.08333h; Inert atmosphere;
Stage #2: With sulfur dioxide at -78 - 23℃; Inert atmosphere;
Stage #1: 2-Methylthiophene With n-butyllithium In diethyl ether at -78℃; for 2h; Inert atmosphere;
Stage #2: With sulfur dioxide In diethyl ether at 23℃; for 1h; Inert atmosphere;
554-14-3

2-Methylthiophene

1532-97-4

4-bromoisoquinoline

4-(5-methylthiophene-2-yl)isoquinoline

Conditions
ConditionsYield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;98%
With C40H36N2O2Pd(2+)*2C2H4O2; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere; Schlenk technique; regioselective reaction;85%
554-14-3

2-Methylthiophene

79-10-7

acrylic acid

70329-36-1

(E)-3-(5-methyl-2-thienyl)-2-propenoic acid

Conditions
ConditionsYield
With p-benzoquinone In acetic acid; dimethyl sulfoxide at 60℃; for 10h;98%
554-14-3

2-Methylthiophene

19169-90-5

bromomethylphenylsulfone

2-methyl-5-((benzenesulfonyl)methyl)thiophene

Conditions
ConditionsYield
With tris[2-phenylpyridinato-C2,N]iridium(III); lithium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere; Irradiation;98%
554-14-3

2-Methylthiophene

C13H10O2S

Conditions
ConditionsYield
With oxygen In acetone for 5h; Irradiation;98%
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Chemistry

Product Name: 2-Methylthiophene (CAS NO.554-14-3)
Molecular formula:C5H6S
Molar mass: 98.17 g/mol
         
State: white to light yellow crystal powde
Flash Point: 45 °F
Melting point:  -63 °C(lit.)
Boiling Point: 113 °C at 760 mmHg 
Vapour Pressure: 47.6 mm Hg ( 37.7 °C)
Density: 1.014 g/mL at 25 °C(lit.)
Solubility: immiscible
Storage temp: Flammables area
Index of Refraction: 1.531 
Molar Refractivity: 29.46 cm3 
Molar Volume: 95.1 cm
XLogP3-AA: 2.3
H-Bond Donor: 0
H-Bond Acceptor: 0
Structure Descriptors of 2-Methylthiophene (CAS NO.554-14-3):
Product Categories:
  IUPAC Name: 2-methylthiophene
  Canonical SMILES: CC1=CC=CS1
  InChI: InChI=1S/C5H6S/c1-5-3-2-4-6-5/h2-4H,1H3 
  InChIKey: XQQBUAPQHNYYRS-UHFFFAOYSA-NThiophenes; Heterocycles; Thiophene&Benzothiophene; thiophene Flavor; Chemistry; Building Blocks; Heterocyclic Building Blocks

Production

By adding The carbon tetrachloride, o-nitro-toluene and azobisisobutyronitrile in aqueous solution into reaction tank, stirring heated, dropping bromine in carbon tetrachloride solution, then keep dropping back to finish and continue to return for 5-6h, at last ,bromide o-nitro benzyl bromide is generated.

Toxicity Data With Reference

1.    

orl-rat LD50:3200 mg/kg

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.
2.    

ipr-rat LD50:1 g/kg

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.
3.    

orl-mus LD50:1460 mg/kg

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.
4.    

ihl-mus LC50:11,500 mg/m3/2H

    85GMAT    Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure Izmerov, N.F., et al.,Moscow, USSR.: Centre of International Projects, GKNT,1982,87.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. A very dangerous fire hazard when exposed to heat or flame. Ignites on contact with nitric acid. When heated to decomposition it emits toxic fumes of SOx. See also SULFIDES.
Safety Information of 2-Methylthiophene (CAS NO.554-14-3):
Hazard Codes:  F,Xn,Xi
Risk Statements:
11:  Highly Flammable
22:  Harmful if swallowed
36:  Irritating to the eyes
37:  Irritating to the respiratory system
38:  Irritating to the skin
Safety Statements:
7:  Keep container tightly closed
9:  Keep container in a well-ventilated place
16:  Keep away from sources of ignition - No smoking
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
33:  Take precautionary measures against static discharges
36:  Wear suitable protective clothing
37:  Wear suitable gloves 
39:  Wear eye/face protection

Specification

 2-Methylthiophene , its CAS NO. is 554-14-3, the synonyms are alpha-Methylthiophene ;  Thiophene, 2-methyl- .