616-46-6

Basic information

• Product Name: 2-THIOPHENAMINE
• Synonyms: 2-THIOPHENAMINE;THIOPHEN-2-AMINE;2-Aminothiophene;thiophenine;(2-Thienyl)amine;2-Thienylamine;Thiophene-2-amine;Thiophen-2-ylaMine
• CAS NO: 616-46-6
• Molecular Formula: C₄H₅NS
• Molecular Weight: 99.15
• Mol File: 616-46-6.mol
• Article Data: 29

Chemical Properties

• Melting Point: 12-13 °C(Solv: hexane (110-54-3); dichloromethane (75-09-2))
• Boiling Point: 194.5 °C at 760 mmHg
• Flash Point: 71.4 °C
• Appearance: /
• Density: 1.221 g/cm³
• Vapor Pressure: 0.441mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 2.51±0.10(Predicted)
• CAS DataBase Reference: 2-THIOPHENAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-THIOPHENAMINE(616-46-6)
• EPA Substance Registry System: 2-THIOPHENAMINE(616-46-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 616-46-6(Hazardous Substances Data)

Usage

General Description

2-Thiophenamine, also known as 2-Aminothiophene, is a chemical compound with the molecular formula C4H5NS. It is a colorless to light yellow liquid with a strong, unpleasant odor. 2-Thiophenamine is used as a building block for the synthesis of various pharmaceuticals, agrochemicals, and dyes. It is also utilized as a stabilizer and antioxidant in the rubber and plastic industry. In addition, 2-Thiophenamine has shown potential as an intermediate in the production of pharmaceuticals and agrochemicals, making it a valuable compound in the chemical industry. However, it is important to handle this chemical with caution, as it can be harmful if ingested, inhaled, or comes in contact with the skin or eyes.

InChI:InChI=1/C4H5NS/c5-4-2-1-3-6-4/h1-3H,5H2

Synthetic route

2-Iodothiophene (3437-95-4) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;	99%
With copper(l) iodide; ammonia; potassium carbonate; L-proline In water; dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere;	50%
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 15h;	50%
With copper(l) iodide; ammonia; potassium carbonate; L-proline In water; dimethyl sulfoxide at 60℃; for 12h; Inert atmosphere;	20%

tert-butyl (2-thienyl)carbamate (56267-50-6) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 50℃; for 2h;	96%
With hydrogenchloride In 1,4-dioxane at 50℃; for 2h;	96%
With hydrogenchloride In diethyl ether at 20℃; for 0.5h;

2-nitrothiophene (609-40-5) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With triethylamine In water at 80℃; for 4h; Inert atmosphere; Green chemistry; chemoselective reaction;	91%
With sodium tetrahydroborate; copper In water at 80℃; for 0.133333h; Green chemistry;	90%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;

2-bromothiophene (1003-09-4) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With C24H32N2*ClCu; ammonia; potassium carbonate In 1-methyl-pyrrolidin-2-one; methanol at 90℃; under 5171.62 Torr; for 24h; Inert atmosphere;	88%

4-(2-tetrahydropyranoxy)-2-butyl-nitrile + Methyl thioglycolate (2365-48-2) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With sodium In methanol	48%

2-thiophenylcarboxylic acid (527-72-0) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With polystyrene Wang resin; diphenylphosphoranyl azide; triethylamine; trifluoroacetic acid 1.) toluene, 100 deg C, 16 h, 2.) CH2Cl2, 5 min; Yield given; Multistep reaction;

hydrogenchloride (7647-01-0) + 2-nitrothiophene (609-40-5) + tin → thiophen-2-ylamine (616-46-6)

1,3-dimethyl-2-(2-thienylimino)imidazolidine (592489-23-1) → thiophene-2-methylamine (111859-85-9) + thiophen-2-ylamine (616-46-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 12h;

2-nitrothiophene (609-40-5) + iron (7439-89-6) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
In acetic acid

glyoxylonitrile (4471-47-0) + cyclopentanone (120-92-3) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With hydrogen sulfide; triethylamine In methanol; ethanol

cyanoacetic acid (372-09-8) → thiophen-2-ylamine (616-46-6)

Conditions	Yield
With hydrogen sulfide In diethylamine

thiophen-2-ylamine (616-46-6) + benzoyl chloride (98-88-4) → N-(thiophen-2-yl)benzamide (136-34-5)

Conditions	Yield
for 0.0166667h; microwave irradiation;	91%

thiophen-2-ylamine (616-46-6) + 1,3,5-benzene tris(carbonyl chloride) (4422-95-1) → N1,N3,N5-trithienyltrimesamide

Conditions	Yield
In dichloromethane at 30℃; for 0.5h; Sonication;	91%

thiophen-2-ylamine (616-46-6) + ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6) + orthoformic acid triethyl ester (122-51-0) → (Z)-2-(2,6-Dichloro-5-fluoro-pyridine-3-carbonyl)-3-(thiophen-2-ylamino)-acrylic acid ethyl ester (108118-76-9)

Conditions	Yield
Stage #1: ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate; orthoformic acid triethyl ester With acetic anhydride at 140℃; for 1h; Stage #2: thiophen-2-ylamine In ethanol at 20℃; Further stages.;	90%

thiophen-2-ylamine (616-46-6) + 2,4-dichloro-1,3-dimethyl-1,3,2,4-diazadiphosphetidine-2,4-dioxide (5944-59-2) → C10H14N4O2P2S2

Conditions	Yield
In acetonitrile Reflux;	90%

thiophen-2-ylamine (616-46-6) + acetic acid (64-19-7) → 2-acetylaminothiophene (13053-81-1)

Conditions	Yield
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 96 - 100℃; for 5h; Temperature; chemoselective reaction;	90%

thiophen-2-ylamine (616-46-6) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → ethyl α-cyano-β-(N-2-thienylammonium)acrylate (65075-97-0)

Conditions	Yield
	88%

thiophen-2-ylamine (616-46-6) + carbon monoxide (201230-82-2) + p-aminoethylbenzoate (94-09-7) → C14H14N2O3S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; methyl-triphenylphosphonium iodide; palladium diacetate at 50℃; under 760.051 Torr; for 24h;	87%

thiophen-2-ylamine (616-46-6) + benzoic acid hydrazide (613-94-5) → N-(thiophen-2-yl)benzamide (136-34-5)

Conditions	Yield
With tert.-butylhydroperoxide; iron(III) chloride In 1,2-dichloro-ethane at 70℃;	85%

thiophen-2-ylamine (616-46-6) + 3-phenyl-propenal (104-55-2) → 6-phenyl-thieno[2,3-b]pyridine (100037-80-7)

Conditions	Yield
In water; acetic acid for 0.05 - 0.0583333h; Microwave irradiation;	82%

thiophen-2-ylamine (616-46-6) + 2-acetoxy-2-(4-nitrophenyl)acetic acid (29898-08-6) → acetic acid (4-nitro-phenyl)-(thiophen-2-ylcarbamoyl)-methyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran; acetonitrile Acylation;	81%

thiophen-2-ylamine (616-46-6) + methyl chloroformate (79-22-1) → methyl N-(2-thiophene)carbamate (698-78-2)

Conditions	Yield
With indium In acetonitrile at 20℃; for 10h; Inert atmosphere;	81%

thiophen-2-ylamine (616-46-6) + ortho-carborane diformaldehyde + iron(II) chloride → C12H18B10Cl2FeN2S2

Conditions	Yield
Stage #1: thiophen-2-ylamine; ortho-carborane diformaldehyde at 90℃; for 12h; Stage #2: iron(II) chloride at 20℃; for 5h;	81%

thiophen-2-ylamine (616-46-6) + 4-methoxycinnamaldehyde (1963-36-6) → 6-(4-methoxyphenyl)-thieno[2,3-b]pyridine (1228167-47-2)

Conditions	Yield
In water; acetic acid for 0.0333333 - 0.0416667h; Microwave irradiation;	80%

thiophen-2-ylamine (616-46-6) + N-formylbenzotriazole (72773-04-7) → N-(thiophen-2-yl)formamide (50624-49-2)

Conditions	Yield
In tetrahydrofuran at 67℃; for 5h;	78%

thiophen-2-ylamine (616-46-6) + 4-chlorocinnamaldehyde (1075-77-0) → 6-(4-chlorophenyl)thieno<2,3-b>pyridine (109216-78-6)

Conditions	Yield
In water; acetic acid for 0.0416667 - 0.05h; Microwave irradiation;	78%

thiophen-2-ylamine (616-46-6) + propionaldehyde (123-38-6) → 4-ethyl-5-methyl-thieno[2,3-b]pyridine (1228167-50-7)

Conditions	Yield
With triethylamine In ethanol; water for 0.0416667 - 0.05h; Microwave irradiation;	78%

thiophen-2-ylamine (616-46-6) + bis(hydroxymethyl)diisopropylphosphonium chloride (1400979-15-8) → bis(diisopropylphosphinomethyl)(2-thienylmethyl)amine

Conditions	Yield
With triethylamine In methanol at 20℃; for 14h; Schlenk technique; Inert atmosphere;	77.4%

thiophen-2-ylamine (616-46-6) + 3-nitrocinnamaldehyde (1504-76-3) → 6-(3-nitrophenyl)-thieno[2,3-b]pyridine (1228167-45-0)

Conditions	Yield
In water; acetic acid for 0.05 - 0.0583333h; Microwave irradiation;	76%

thiophen-2-ylamine (616-46-6) + 1,5-dimethyl-4-(2-oxo-5-p-tolyl-furan-3-ylideneamino)-2-phenyl-1,2-dihydro-pyrazol-3-one (425621-58-5) → 2-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylamino)-4-oxo-4-(4-tolyl)-2-butenoic acid 2-thiazolylamide

Conditions	Yield
In toluene for 3h; Heating;	75%

thiophen-2-ylamine (616-46-6) + butyraldehyde (123-72-8) → 5-ethyl-4-propyl-thieno[2,3-b]pyridine (1228167-52-9)

Conditions	Yield
With triethylamine In ethanol; water for 0.0333333 - 0.0416667h; Microwave irradiation;	75%

thiophen-2-ylamine (616-46-6) + acetaldehyde (75-07-0) → 4-methyl-thieno[2,3-b]pyridine (13362-81-7)

Conditions	Yield
With triethylamine In ethanol; water for 0.05 - 0.0583333h; Microwave irradiation;	74%

thiophen-2-ylamine (616-46-6) + methyl 2-(4-methylphenylamino)acetate (99075-46-4) → 4H-thieno[2,3-b]pyrrole-4,5-(6H)-dione

Conditions	Yield
With (R,S)-2-chloropropionic acid In toluene at 120℃; for 10h;	72.7%

thiophen-2-ylamine (616-46-6) + C17H14N4O5S → C21H17N5O5S2

Conditions	Yield
With tert.-butylhydroperoxide; iron(III) chloride In 1,4-dioxane at 80℃; for 10h;	70%

thiophen-2-ylamine (616-46-6) + acetic acid chlorocarbonyl-(4-nitro-phenyl)-methyl ester → acetic acid (4-nitro-phenyl)-(thiophen-2-ylcarbamoyl)-methyl ester

Conditions	Yield
With pyridine at 70℃; Acylation;	69%

thiophen-2-ylamine (616-46-6) + 4-chloro-1,10-phenanthroline-5,6-dione + benzaldehyde (100-52-7) → 11-chloro-1-phenyl-2-(thien-2-yl)-1H-imidazole[4,5-f][1,10]phenanthroline

Conditions	Yield
With ammonium acetate; acetic acid for 24h; Inert atmosphere; Reflux;	69%

thiophen-2-ylamine (616-46-6) + 6,7-dimethoxy-4-(1-piperazinyl)quinazoline (21584-72-5) + 1,1'-carbonyldiimidazole (530-62-1) → 4-(6,7-dimethoxy-quinazolin-4-yl)-piperazine-1-carboxylic acid thiophen-2-ylamide

Conditions	Yield
Stage #1: thiophen-2-ylamine; 1,1'-carbonyldiimidazole With triethylamine In dichloromethane at 0℃; for 1h; Stage #2: 6,7-dimethoxy-4-(1-piperazinyl)quinazoline In dichloromethane at 20℃; Further stages.;	67%

Upstream product

• 7647-01-0 hydrogenchloride 
• 609-40-5 2-nitrothiophene 
• 592489-23-1 1,3-dimethyl-2-(2-thienylimino)imidazolidine 
• 7439-89-6 iron 
• 4471-47-0 glyoxylonitrile 
• 120-92-3 cyclopentanone 
• 372-09-8 cyanoacetic acid 
• 2365-48-2 Methyl thioglycolate 
• 3437-95-4 2-Iodothiophene 
• 3221-15-6 2-(chloromethyl)thiirane 
• 1003-09-4 2-bromothiophene 
• 56267-50-6 tert-butyl (2-thienyl)carbamate 
• 527-72-0 2-thiophenylcarboxylic acid 

Downstream Products

• 56267-50-6 tert-butyl (2-thienyl)carbamate 
• 136-34-5 N-(thiophen-2-yl)benzamide 
• 1161343-34-5 3-chloro-4-methyl-N-(thiophen-2-yl)benzenesulfonamide 
• 13053-81-1 2-acetylaminothiophene 
• 203730-54-5 ethyl-[2]thienyl-amine 
• 100037-80-7 6-phenyl-thieno[2,3-b]pyridine 
• 13362-81-7 4-Methyl-thieno<2,3-b>pyridin 
• 109216-78-6 6-(4-chlorophenyl)thieno<2,3-b>pyridine 
• 1228167-45-0 6-(3-nitrophenyl)-thieno[2,3-b]pyridine 
• 1228167-47-2 6-(4-methoxyphenyl)-thieno[2,3-b]pyridine 
• 1225278-06-7 N-(2-fluoro-4-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-N'-(thiophen-2-yl)cyclopropane-1,1-dicarboxamide 
• 35454-04-7 oxalamic Acid Tert-butyl Ester 

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