3-(thiophen-2-ylsulfanyl)propionic acid 2-ethylhexyl ester
Thiophene-2-thiol
Conditions | Yield |
---|---|
Stage #1: 3-(thiophen-2-ylsulfanyl)propionic acid 2-ethylhexyl ester With sodium methylate In methanol at 20℃; for 1h; Reflux; Stage #2: With hydrogenchloride In water at 20℃; pH=1 - 2; | 87.3% |
thiophene-2-sulfonyl chloride
Thiophene-2-thiol
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 0.166667h; Inert atmosphere; chemoselective reaction; | 85% |
thiophene
Thiophene-2-thiol
Conditions | Yield |
---|---|
With n-butyllithium; water; sulfur | 70% |
With n-butyllithium; sulfur 1.) hexane/THF, -20 - -30 deg C, 0.5 h, 2.) hexane/THF, -70 deg C, 1 h; Yield given. Multistep reaction; | |
With n-butyllithium; sulfur In tetrahydrofuran; hexane at 0 - 5℃; for 2h; |
2-thienyl chloride
A
thiophene
B
Thiophene-2-thiol
C
thiophene-3-thiol
D
sulfure de dithienyle-3,3'
E
2-thienyl 3-thienyl sulfide
F
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
With dimethylselenide; hydrogen sulfide In gas at 500℃; Product distribution; Mechanism; effect of dimethyl selenide on reaction; various temperatures; | A 46% B 10% C 3% D n/a E n/a F 1.8% |
3-(thiophen-2-ylsulfanyl)propionic acid 2-ethylhexyl ester
Thiophene-2-thiol
Conditions | Yield |
---|---|
Stage #1: 3-(thiophen-2-ylsulfanyl)propionic acid 2-ethylhexyl ester With sodium methylate In methanol at 20℃; for 1h; Reflux; Stage #2: With hydrogenchloride In water at 20℃; pH=1 - 2; | 87.3% |
thiophene-2-sulfonyl chloride
Thiophene-2-thiol
Conditions | Yield |
---|---|
With triphenylphosphine In toluene for 0.166667h; Inert atmosphere; chemoselective reaction; | 85% |
thiophene
Thiophene-2-thiol
Conditions | Yield |
---|---|
With n-butyllithium; water; sulfur | 70% |
With n-butyllithium; sulfur 1.) hexane/THF, -20 - -30 deg C, 0.5 h, 2.) hexane/THF, -70 deg C, 1 h; Yield given. Multistep reaction; | |
With n-butyllithium; sulfur In tetrahydrofuran; hexane at 0 - 5℃; for 2h; |
2-thienyl chloride
A
thiophene
B
Thiophene-2-thiol
C
thiophene-3-thiol
D
sulfure de dithienyle-3,3'
E
2-thienyl 3-thienyl sulfide
F
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
With dimethylselenide; hydrogen sulfide In gas at 500℃; Product distribution; Mechanism; effect of dimethyl selenide on reaction; various temperatures; | A 46% B 10% C 3% D n/a E n/a F 1.8% |
2-thienyl chloride
Diethyl disulfide
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 550℃; for 0.0141667h; Product distribution; gas phase copyrolysis; | A 18.4% B 36.4% C 3.4% D 14.3% |
bis(thien-2-yl)sulfide
A
thiophene
B
Thiophene-2-thiol
C
thiophene-3-thiol
D
2-thienyl 3-thienyl sulfide
E
dithieno[3,2-b;2',3'-d]thiophene
F
2,2'-Bithiophene
Conditions | Yield |
---|---|
With hydrogen sulfide at 450 - 600℃; Product distribution; | A 31.8% B 6% C 5% D 4.7% E n/a F 15.2% |
at 500 - 600℃; Product distribution; | A 17.6% B 13.1% C 1.4% D 0.5% E n/a F 3% |
bis(thien-2-yl)sulfide
A
Thiophene-2-thiol
B
thiophene-3-thiol
C
2,3'-bithienyl
D
2-thienyl 3-thienyl sulfide
E
2,2'-Bithiophene
Conditions | Yield |
---|---|
With hydrogen sulfide; sulfur at 180℃; for 8h; Product distribution; | A 29.9% B 12.6% C 5.7% D 16.6% E 7.7% |
1,2-Dichloroethylene
A
thiophene
B
Thiophene-2-thiol
C
thiophene-3-thiol
D
thieno[2,3-b]thiophene
F
cis-2-thienyl β-chlorovinyl sulfide
Conditions | Yield |
---|---|
With hydrogen sulfide In neat (no solvent) at 480℃; for 0.0125h; Product distribution; var. temp., var. ratio of reagents, var. contact time; | A 13.5% B 5.47% C 3.95% D n/a E 5.91% F 5.45% |
2-thienyl chloride
Diethyl disulfide
ethyldisulfanyl
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
thieno[3,2-b]thiophene
E
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; for 0.0166667h; Product distribution; Mechanism; different ratio; |
2-thienyl chloride
Diethyl disulfide
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
thieno[3,2-b]thiophene
E
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; for 0.0166667h; Product distribution; Mechanism; |
2-thienyl chloride
diethyl sulphide
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
thieno[3,2-b]thiophene
E
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; for 0.0166667h; Product distribution; Mechanism; |
2-thienyl chloride
diethyltrisulfane
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
thieno[3,2-b]thiophene
E
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; for 0.0166667h; Product distribution; Mechanism; |
2-thienyl chloride
2-propanethiol
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 540℃; for 0.0152778h; Product distribution; | A 2.4 % Chromat. B 20.0 % Chromat. C 1.7 % Chromat. D 32.0 % Chromat. |
2-thienyl chloride
ethanethiol
A
Thiophene-2-thiol
B
thieno[2,3-b]thiophene
C
thieno[3,2-b]thiophene
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; for 0.0166667h; Product distribution; Mechanism; |
Conditions | Yield |
---|---|
With mesna Yield given. Multistep reaction; | |
Stage #1: 2-bromothiophene With n-butyllithium In diethyl ether; hexane at -70℃; for 2.5h; Inert atmosphere; Stage #2: With sulfur In diethyl ether; hexane at -70℃; for 2h; Inert atmosphere; |
2-ethylthiophene
thieno[2,3-b]thiophene
A
thiophene
B
Thiophene-2-thiol
C
thieno[3,2-b]thiophene
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
at 560℃; Product distribution; thermolysis; | A 10 % Chromat. B 11.5 % Chromat. C n/a D 17 % Chromat. |
bis(thien-2-yl)sulfide
A
Thiophene-2-thiol
B
thiophene-3-thiol
C
3,3'-bithiophene
D
2,3'-bithienyl
E
2-thienyl 3-thienyl sulfide
F
2,2'-Bithiophene
Conditions | Yield |
---|---|
With hydrogen sulfide at 180℃; for 10h; Product distribution; other reagent, reaction time; | A 1.0 % Turnov. B 0.5 % Turnov. C 8.5 % Turnov. D 10.7 % Turnov. E 37.8 % Turnov. F 8.0 % Turnov. |
allyl(2-thiophene)sulfide
A
thiophene
B
Thiophene-2-thiol
C
bis(thien-2-yl)sulfide
D
2-methylthieno<2,3-b>thiophene
Conditions | Yield |
---|---|
In gas thermolysis above 380 deg C; |
2-thienyl disulfide
A
Thiophene-2-thiol
B
thiophene-3-thiol
C
2-thienyl 3-thienyl sulfide
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
With hydrogen sulfide at 130℃; for 7h; Product distribution; other temperatures, reaction time; | A 12.5 % Turnov. B 3.8 % Turnov. C 19.6 % Turnov. D 61.6 % Turnov. |
4-(2-thienylthio)tetrahydrothiophene-2-thione
Thiophene-2-thiol
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran Product distribution; |
thiophen-2-yl magnesium bromide
1,2,5-thiadiazole
A
Thiophene-2-thiol
B
bis(thien-2-yl)sulfide
C
3-(2-thienyl)-1,2,5-selenadiazole
Conditions | Yield |
---|---|
With sulenium monochloride 1.) tetrahydrofuran, reflux, 2 h, 2.) tetrahydrofuran, 3 h; Yield given. Multistep reaction; |
allyl(2-thiophene)sulfide
acetylene
A
thiophene
B
Thiophene-2-thiol
C
thieno[2,3-b]thiophene
D
bis(thien-2-yl)sulfide
E
2-methylthieno<2,3-b>thiophene
Conditions | Yield |
---|---|
In gas at 460℃; Product distribution; Mechanism; other allyl 2-thieno selenide, with or without acetylene, var. temperatures; | A 5 % Chromat. B 14 % Chromat. C 25 % Chromat. D 17 % Chromat. E 10 % Chromat. |
allyl(2-thiophene)sulfide
acetylene
A
Thiophene-2-thiol
B
thieno[2,3-b]thiophene
C
bis(thien-2-yl)sulfide
D
2-methylthieno<2,3-b>thiophene
Conditions | Yield |
---|---|
In gas at 460℃; thermolysis; Further byproducts given; | A 14 % Chromat. B 25 % Chromat. C 17 % Chromat. D 10 % Chromat. |
Conditions | Yield |
---|---|
With sulfur |
bis(thien-2-yl)sulfide
A
thiophene
B
Thiophene-2-thiol
C
thiophene-3-thiol
D
dithieno[2,3-b:3',2'-d]thiophene
Conditions | Yield |
---|---|
With hydrogen sulfide In gas at 500 - 600℃; Product distribution; |
2-thienyl chloride
A
Thiophene-2-thiol
B
thiophene-3-thiol
C
2-thienyl 3-thienyl sulfide
D
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
With methanol; hydrogen sulfide at 610℃; Product distribution; Further Variations:; Reagents; Temperatures; |
S-thiophen-2-yl ethanethioate
Thiophene-2-thiol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol |
ethyl 5-bromovalerate
A
Thiophene-2-thiol
2-thienyl chloride
hydrogen sulfide
A
Thiophene-2-thiol
B
bis(thien-2-yl)sulfide
Conditions | Yield |
---|---|
Kinetics; byproducts: HCl; at 500-600°C; |
Thiophene-2-thiol
2,5-dihydro-2H-2-oxothiophene
4-(Thiophen-2-ylsulfanyl)-dihydro-thiophen-2-one
Conditions | Yield |
---|---|
In neat (no solvent) at 25℃; for 18h; Product distribution; | 100% |
In neat (no solvent) at 25℃; for 18h; | 100% |
Thiophene-2-thiol
phenylhydrazine
4-(2-thienylthio)-2-phenylhydrazonotetrahydrothiophene
Conditions | Yield |
---|---|
at 18 - 20℃; for 240h; | 99% |
Conditions | Yield |
---|---|
With oxygen In water at 45℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Pressure; | 99% |
With cobalt(II)phthalocyanine-tetra-sodium sulfonate In water at 60℃; for 6h; Schlenk technique; | 91% |
With (bis(2,1-phenylene)bis(azanediyl)bis(methylene)diphenol)diselenide In acetonitrile at 20℃; for 7h; | 89% |
Thiophene-2-thiol
3-Methylbutenoic acid
3-methyl-3-(thiophene-2-thio)butyric acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 98% |
With triethylamine In tetrahydrofuran for 20h; Reflux; Inert atmosphere; | 63.35% |
With triethylamine In tetrahydrofuran for 20h; Reflux; Inert atmosphere; | 63.35% |
With triethylamine In tetrahydrofuran for 20h; Inert atmosphere; Reflux; | 63.35% |
With triethylamine In tetrahydrofuran for 20h; Inert atmosphere; Reflux; | 63.4% |
Conditions | Yield |
---|---|
With sodium chloride; triethylamine In tetrahydrofuran | 98% |
Thiophene-2-thiol
1-bromo-2,2-dimethoxyethane
2-(2,2-dimethoxy-ethylsulfanyl)-thiophene
Conditions | Yield |
---|---|
With potassium carbonate In acetone | 97% |
With ethanol; sodium ethanolate |
Thiophene-2-thiol
tert-butyldimethylsilyl p-methoxycinnamate
3-(4-Methoxy-phenyl)-3-(thiophen-2-ylsulfanyl)-propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 97% |
Thiophene-2-thiol
ethyl 2-bromoisobutyrate
ethyl 2-methyl-2-(thien-2-ylthio)propanoate
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol Heating; | 97% |
Thiophene-2-thiol
2-bromo-N-(5-tert-butyl-isoxazol-3-yl)-2-methyl-propionamide
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol for 18h; Heating / reflux; | 97% |
Thiophene-2-thiol
N-methyl bromomaleimide
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; | 97% |
Thiophene-2-thiol
(Z)-3-(pyridin-3-yl)acrylic acid
3-Pyridin-3-yl-3-(thiophen-2-ylsulfanyl)-propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 96% |
Thiophene-2-thiol
poly(methacrylic acid)
2-Methyl-3-(thiophen-2-ylsulfanyl)-propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 95% |
Thiophene-2-thiol
cis-cinnamic acid
3-(2-mercaptothiopheneyl)-3-phenyl propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 95% |
Thiophene-2-thiol
(Z)-3-(4-methoxyphenyl)acrylic acid
3-(4-Methoxy-phenyl)-3-(thiophen-2-ylsulfanyl)-propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 95% |
Thiophene-2-thiol
(Z)-3-(2-nitrophenyl)acrylic acid
3-(2-thienylthio)-3-(o-nitrophenyl)-propionic acid
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 21h; Heating; | 95% |
Thiophene-2-thiol
1,3-chlorobromopropane
2-(3-Chloropropylsulfanyl)thiophene
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In isopropyl alcohol at 100℃; for 1h; | 95% |
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; |
Conditions | Yield |
---|---|
With potassium carbonate at 20 - 78℃; Inert atmosphere; | 95% |
With potassium carbonate at 78℃; for 3h; Inert atmosphere; | 95% |
With potassium carbonate; potassium iodide In acetone at 20℃; | 32.9% |
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 76℃; for 6.5h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; ammonium carbamate In methanol at 25℃; for 24h; Inert atmosphere; chemoselective reaction; | 95% |
With ammonium hydroxide; manganese(IV) oxide; oxygen In water; N,N-dimethyl-formamide at 90℃; under 7500.75 Torr; for 20h; Autoclave; | 59% |
Thiophene-2-thiol
ethyl (Z)-3-iodopropenoate
(Z)-3-(thiophen-2-ylthio)-acrylic acid ethyl ester
Conditions | Yield |
---|---|
With potassium phosphate; copper(l) iodide; cis-1,2-cyclohexane In N,N-dimethyl-formamide at 40 - 50℃; for 2h; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 94% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran | 93% |
With triethylamine In tetrahydrofuran | 93% |
With triethylamine In tetrahydrofuran | 93% |
In 1,4-dioxane at 70 - 80℃; | 92% |
Thiophene-2-thiol
A
2-thienyl disulfide
B
4-(2-thienylthio)tetrahydrothiophene-2-thione
Conditions | Yield |
---|---|
Product distribution; Mechanism; | A n/a B 93% |
1,4-diaza-bicyclo[2.2.2]octane
Thiophene-2-thiol
2-(trimethylsilyl)phenyl trifluoromethanesulfonate
Conditions | Yield |
---|---|
Stage #1: 1,4-diaza-bicyclo[2.2.2]octane; 2-(trimethylsilyl)phenyl trifluoromethanesulfonate With cesium fluoride In acetonitrile at 20℃; Stage #2: Thiophene-2-thiol In acetonitrile at 100℃; for 18h; | 93% |
Thiophene-2-thiol
2-hydroxycyclobutanone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane at 20℃; | 93% |
Thiophene-2-thiol
2-((4-((4-aminophenyl)sulfonyl)phenyl)amino)-3-chloronaphthalene-1,4-dione
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 93% |
Conditions | Yield |
---|---|
Stage #1: Thiophene-2-thiol With potassium tert-butylate In ethanol at 0℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromo-octane In ethanol at 80℃; for 12h; Inert atmosphere; | 92.4% |
With potassium hydroxide; hydrazine hydrate for 1h; Ambient temperature; | 63% |
With potassium tert-butylate In ethanol; dichloromethane for 2h; Heating; | 60% |
With potassium hydroxide | |
With potassium carbonate |
Molecular Structure of 2-Thiophenethiol (CAS NO.7774-74-5):
IUPAC Name: Thiophene-2-thiol
Canonical SMILES: C1=CSC(=C1)S
InChI: InChI=1S/C4H4S2/c5-4-2-1-3-6-4/h1-3,5H
InChIKey: SWEDAZLCYJDAGW-UHFFFAOYSA-N
Molecular Weight: 116.20456 [g/mol]
Molecular Formula: C4H4S2
XLogP3: 2.2
EINECS: 231-881-1
Appearance: Clear yellowish to orange liquid
Index of Refraction: 1.636
Molar Refractivity: 32.81 cm3
Molar Volume: 91.5 cm3
Surface Tension: 46.4 dyne/cm
Density: 1.269 g/cm3
Flash Point: 54.7 °C
Enthalpy of Vaporization: 38.68 kJ/mol
Boiling Point: 166.9 °C at 760 mmHg
Vapour Pressure: 2.3 mmHg at 25 °C
storage temp.: Store under inert gas
Sensitive: Air Sensitive
Product Categories: THIOL;Thiophene & Benzothiophene; thiol Flavor
2-Thiophenethiol (CAS NO.7774-74-5) is used to deploy flavor for candy and baking food.
Safety Information of 2-Thiophenethiol (CAS NO.7774-74-5):
Hazard Codes:Xi,Xn
Risk Statements:36/37/38-36/38-21/22-20/22
36/37/38:Irritating to eyes, respiratory system and skin
36/38:Irritating to eyes and skin
21/22:Harmful in contact with skin and if swallowed
20/22:Harmful by inhalation and if swallowed
Safety Statements:26-36-36/37/39
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
RIDADR:UN3334
WGK Germany:3
F:10-13-23
Hazard Note:Irritant
2-Thiophenethiol (CAS NO.7774-74-5), its Synonyms are 2-Mercaptothiophene ; 2-Thienyl mercaptan ; FEMA No. 3062 ; alpha-Thienyl mercaptan ; Thiophene-2-thiol .
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