30433-91-1

Basic information

• Product Name: Thiophene-2-ethylamine
• Synonyms: THIOPHENE ETHYLAMINE;THIOPHENE-2-ETHYLAMINE;THIOPHENE-2-ETHYLAMINE HCL SALT;RARECHEM AL BW 0099;2-(2-AMINOETHYL)THIOPHENE;2-(2'-THIENYL)ETHYL AMINE;2-(2-THIENYL)ETHYLAMINE;2-(2-THIENYL)-1-ETHANAMINE
• CAS NO: 30433-91-1
• Molecular Formula: C₆H₉NS
• Molecular Weight: 127.21
• EINECS: 250-196-9
• Product Categories: Anilines, Aromatic Amines and Nitro Compounds;Thiophene&Benzothiophene;Amines;Heterocyclic Compounds;Ticlopidine Clopidogrel;Building Blocks;Heterocyclic Building Blocks;Thiophenes;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 30433-91-1.mol
• Article Data: 38

Chemical Properties

• Melting Point: 202 °C
• Boiling Point: 200-201 °C750 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.087 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.337mmHg at 25°C
• Refractive Index: n20/D 1.551(lit.)
• Storage Temp.: Refrigerator (+4°C)
• Solubility: DMSO, Methanol
• PKA: 9.47±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 106962
• CAS DataBase Reference: Thiophene-2-ethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene-2-ethylamine(30433-91-1)
• EPA Substance Registry System: Thiophene-2-ethylamine(30433-91-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: II
• Hazardous Substances Data: 30433-91-1(Hazardous Substances Data)

Usage

Chemical Properties

colorless to yellow liquid

Uses

[2-(Thiophene-2-yl)ethyl]amine is used in the synthesis of geldanamycin derivatives as HCV replication inhibitors targetting Hsp90.

Uses

2-Thiopheneethylamine (2-thiophene ethyl amine, 2-(thien-2-yl)ethylamine) is suitable to functionalize multiwall carbon nanotubes (MWCNT).It may be used as a reactant in the synthesis of pyrimidine derivatives by reacting with various isothiocyanatoketones and acylguanidines derivatives by reacting with aroyl S-methylisothiourea.

General Description

2-Thiopheneethylamine (2-(thiophen-2-yl)ethanamine) is an aromatic amine. It undergoes microwave induced condensation with iminodiacetic acid to form the corresponding piperazine-2,6-dione derivatives. Its effect as a probable substitute to the pyridine ligand on the performance of poly(3-hexylthiophene)/CdSe hybrid solar cells has been investigated.

Synthesis

N,N-Dimethylformamide (DMF) reacts with thiophene to obtain 2-thiophenecarbaldehyde, then reacts with isopropyl chloroacetate to obtain 2-thiopheneacetaldehyde, and then reacts with hydroxylamine hydrochloride to obtain 2-thiopheneacetaldehyde oxime, and finally reduced to give 2-thiopheneethylamine.

InChI:InChI=1/C6H9NS/c7-4-3-6-2-1-5-8-6/h1-2,5H,3-4,7H2/p+1

Synthetic route

2-(2-nitroethenyl)thiophene (874-84-0, 34312-77-1) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran Cooling with ice; Reflux;	92%
With lithium aluminium tetrahydride In tetrahydrofuran Reflux; Cooling with ice;	92%
With lithium aluminium tetrahydride In tetrahydrofuran Cooling with ice; Reflux;	92%

2-(2-azidoethyl)thiophene (149551-70-2) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 16h;	100%
With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; tri-n-butyl-tin hydride In tetrahydrofuran at 0℃; for 0.5h; Reduction;	89%

2-cyanomethylthiophene (20893-30-5) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere;	98%
With lithium aluminium tetrahydride In tetrahydrofuran	71%
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 1h; Ambient temperature;	56%

3-(thiophen-2-yl)-propionamide (26359-22-8) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite Zusatz von Kaliumhydroxid;
With bromine at 70℃; for 1h; Hofmann Rearrangement; Large scale;	1110g

2-(thiophen-2-yl)acetamide (4461-29-4) + 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (54903-50-3) + 2-(2-thienyl)ethylimide → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
In hydrogenchloride; sodium hydroxide	74.5%

1-(2-thienyl)-2-nitroethene (34312-77-1) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With diborane
With hydrogenchloride; sodium borohydrid; trifluoroborane diethyl ether In tetrahydrofuran; water; toluene

acetylacetone (123-54-6) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sodium carbonate In 2-methoxy-ethanol; water

C7H10N2OS → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With bromine at 60℃; for 1h; Hofmann Rearrangement;

4-(thiophen-2-yl)butan-2-one (59594-93-3) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With hydrogen azide at 60 - 120℃;

2-(2-nitroethyl)thiophene (30807-46-6) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With hydrogen at 120℃; for 12h; Autoclave;	1009 g

C19H17NS → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sulfuric acid; water at 20℃;

2-thiophenethanol (5402-55-1) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With dmap; trifluoromethylsulfonic anhydride; ammonia 1.) CH2Cl2, from -30 deg C to RT, 2.) THF, from -30 deg C to RT; Multistep reaction;
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 12 h / -5 °C 2: 85 percent / dimethylformamide / 6 h / 60 °C 3: 89 percent / TBTH; Ni(diphenylphosphinoethane)Cl2 / tetrahydrofuran / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: chloroform; pyridine; phosphorus (III)-bromide 2: ammonia; ethanol View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0.5 h / 20 °C 2: sodium azide / dimethyl sulfoxide / 1 h / 80 °C 3: palladium on activated charcoal; hydrogen / methanol / 16 h / 20 °C View Scheme

1,3,5-tris-(2-(2-thienyl)ethyl)isocyanurate (150177-92-7) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sodium hydroxide In butan-1-ol for 72h; Heating;	83%

thiophene-2-carbaldehyde (98-03-3) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; ammonium acetate / 10 h / Heating 2: lithium aluminium tetrahydride / tetrahydrofuran / Cooling with ice; Reflux View Scheme
Multi-step reaction with 2 steps 1: acetic acid; ammonium acetate / 10 h / 80 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / Reflux; Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / acetic acid / 10 h / 80 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / Cooling with ice; Reflux View Scheme
Multi-step reaction with 2 steps 1: ammonium acetate / 2 h / Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C View Scheme

2-(2-Bromoethyl)thiophene (26478-16-0) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With ethanol; ammonia

2-(thiophen-2-yl)acetamide (4461-29-4) + 2-(2-thienyl)ethylimide → [2-(2-thyenyl)ethyl]amine (30433-91-1)

N-(2-(thien-2-yl)ethyl)-phthalimide (60555-55-7) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With hydrazine In ethanol; water for 14h; Reflux;

N-<2-(2-Thienyl)ethyl>benzolsulfonamid (115328-17-1) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 72h; Heating;	25%

4-methyl-N-(2-(thiophen-2-yl)ethyl)benzenesulfonamide (102996-95-2) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene for 24h; Heating;	6%

diethyl N-[2-(thien-2-yl)-ethyl]-phosphoramidate (86052-66-6) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With hydrogenchloride at 80 - 85℃; for 1.5h; Yield given;

isopropyl N-[2-(thien-2-yl)-ethyl]-amino-phenylphosphinate (111512-35-7) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
With hydrogenchloride at 80 - 85℃; for 1.5h; Yield given;

2-(thiophen-2-yl)ethyl methanesulfonate (61380-07-2) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / dimethylformamide / 6 h / 60 °C 2: 89 percent / TBTH; Ni(diphenylphosphinoethane)Cl2 / tetrahydrofuran / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: sodium azide / dimethyl sulfoxide / 1 h / 80 °C 2: palladium on activated charcoal; hydrogen / methanol / 16 h / 20 °C View Scheme

Diethyl N-[β-(thien-2-yl)-vinyl]-phosphoramidate (86052-65-5) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 1 h / 50 °C 2: aq. HCl / 1.5 h / 80 - 85 °C View Scheme

Isopropyl N-[β-(thien-2-yl)-vinyl]-amino-phenylphosphinate (86423-62-3) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 1 h / 50 °C 2: aq. HCl / 1.5 h / 80 - 85 °C View Scheme

2-Chloromethylthiophene (765-50-4) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride / water-d2 2: lithium aluminium tetrahydride / tetrahydrofuran View Scheme

Thiophene-2-acetic acid (1918-77-0) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0.33 h / 20 °C 2: triethylamine / dichloromethane / 0.5 h / 20 °C 3: sodium azide / dimethyl sulfoxide / 1 h / 80 °C 4: palladium on activated charcoal; hydrogen / methanol / 16 h / 20 °C View Scheme

3-thiophen-2-yl-2-thioxo-propionic acid (89677-36-1) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; hydroxylamine 2: acetic acid anhydride 3: lithium alanate; diethyl ether View Scheme

5-(2'-thiophenemethylene)rhodamine (6319-47-7, 98800-08-9, 98800-09-0) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaOH solution 2: ethanol; hydroxylamine 3: acetic acid anhydride 4: lithium alanate; diethyl ether View Scheme

2-hydroxyimino-3-[2]thienyl-propionic acid (139109-61-8) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid anhydride 2: lithium alanate; diethyl ether View Scheme

3-(2-thienyl)propanoic acid (5928-51-8) → [2-(2-thyenyl)ethyl]amine (30433-91-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform; thionyl chloride / Behandeln des Reaktionsgemisches mit wss. Ammoniak und wss. Natronlauge 2: aqueous sodium hypochlorite solution; aq. NaOH solution / Zusatz von Kaliumhydroxid View Scheme

[2-(2-thyenyl)ethyl]amine (30433-91-1) + chloroacetyl chloride (79-04-9) → 2-chloro-N-(2-(thiophen-2-yl)ethyl)acetamide (135709-69-2)

Conditions	Yield
With potassium carbonate In dichloromethane Ambient temperature;	100%
With triethylamine In dichloromethane at 0℃;	82%
In benzene at 0℃; Reflux;

[2-(2-thyenyl)ethyl]amine (30433-91-1) + N-((tert-butyloxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)iminodiacetic acid monoamide (188625-17-4) → N-((tert-butyloxy)carbonyl)-N'-(2-(4-fluorophenyl)ethyl)-N''-(2-(2'-thienyl)ethyl)iminodiacetic acid diamide (211745-31-2)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h; Substitution;	100%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; Acylation;	93%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 16h;

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 4-biphenyl-carboxylic acid chloride (14002-51-8) → 4-phenylbenzoyl chloride

Conditions	Yield
With sodium hydroxide In water at 0℃;	100%
With triethylamine In tetrahydrofuran for 0.5h;	96%
With sodium hydroxide In water for 12h; Cooling with ice;	82%
With triethylamine In tetrahydrofuran at 20℃;	55%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 1,2,3-Benzotriazole (95-14-7) + formaldehyd (50-00-0) → benzotriazol-1-ylmethyl-(2-thiophen-2-yl-ethyl)-amine (1201693-98-2)

Conditions	Yield
In diethyl ether; water at 20℃;	100%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 2-[(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]acetic acid (73991-95-4, 114458-03-6, 119618-59-6, 113278-68-5) → C13H17NO4S (1218950-25-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide	100%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 1,4-Dihydroxynaphthalene (571-60-8) → 2-((thiophen-2-yl)ethylamino)naphthalene-1,4-dione

Conditions	Yield
With cerium(III) chloride heptahydrate; triethylamine In ethanol at 20℃; Further stages;	100%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + phenyl isothiocyanate (103-72-0) → 1-phenyl-3-(2-(thiophen-2-yl)ethyl)thiourea (59311-69-2)

Conditions	Yield
In dichloromethane at 20℃; for 2h; Addition;	99%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + Cyclohexanecarboxylic acid (98-89-5) → cyclohexanecarboxylic acid (2-thiophen-2-ylethyl)amide (308287-68-5)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 15h; Substitution;	99%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + formaldehyd (50-00-0) → 6,7-dihydro-4H-thieno[3,2-c]pyridine hydrochloride (28783-41-7)

Conditions	Yield
Stage #1: [2-(2-thyenyl)ethyl]amine; formaldehyd In dichloromethane at 40 - 45℃; Stage #2: With hydrogenchloride In dichloromethane; water; N,N-dimethyl-formamide at 20 - 70℃;	99%
Stage #1: [2-(2-thyenyl)ethyl]amine; formaldehyd In toluene for 1.5h; Reflux; Inert atmosphere; Dean-Stark; Stage #2: With hydrogenchloride In 1,4-dioxane; toluene at 60℃; for 0.5h; Inert atmosphere;	98%
Stage #1: [2-(2-thyenyl)ethyl]amine; formaldehyd In 1,2-dichloro-ethane for 4h; Heating / reflux; Stage #2: With hydrogenchloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 70℃; for 4h;	90%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + Diethyl maleate (141-05-9) → 1,4-diethyl 2-{[2-(thiophen-2-yl)ethyl]amino}butanedioate

Conditions	Yield
In acetonitrile at 20℃; for 16h;	99%
In acetonitrile at 20℃; for 16h;	99%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + p-tert-butyl benzoyl chloride (1710-98-1) → C17H21NOS

Conditions	Yield
With sodium hydroxide In water for 12h; Cooling with ice;	99%
With sodium hydroxide In water at 0℃;	98%
With sodium hydroxide In water for 12h;	80%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (2-(thiophen-2-yl)ethyl)carbamate (381666-12-2)

Conditions	Yield
With triethylamine In dichloromethane for 72h; Inert atmosphere;	98%
With triethylamine In dichloromethane at 20℃; Schlenk technique; Inert atmosphere;	98%
In chloroform for 6h; Heating;
In dichloromethane at 20℃; Inert atmosphere;

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 5-methoxy-2-tetralone (32940-15-1) → 5-methoxy-N-2'-(thien-2-yl)ethyltetralin-2-amine (102120-95-6)

Conditions	Yield
Stage #1: [2-(2-thyenyl)ethyl]amine; 5-methoxy-2-tetralone With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; Inert atmosphere; Industry scale; Stage #2: With acetic acid In dichloromethane at 20℃; Stage #3: With sodium hydroxide In dichloromethane; water Product distribution / selectivity; cooling with ice-water; Alkaline conditions;	98%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Solvent; Reagent/catalyst; Temperature; Time; Inert atmosphere;	98%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + C19H22O7 → C25H29NO6S

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	98%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + m-Toluic acid (99-04-7) → [2-(2-thienyl)ethylamino](m-tolyl)formaldehyde

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	98%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + carbon disulfide (75-15-0) → 1,3-di(2-(thiophen-2-yl)ethyl)thiourea (336804-80-9)

Conditions	Yield
In water at 20℃; for 0.166667h; Green chemistry;	98%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + formaldehyd (50-00-0) → N-(thiophen-2-ylethyl)methyleneamine (111954-31-5)

Conditions	Yield
In ethanol at 49 - 53℃; for 3h; Temperature; Solvent; Eschweiler-Clarke Methylation;	97.69%
In water Heating;
In water at 20 - 90℃; for 18h;
With titanium(IV) isopropylate at 80℃; for 2h; Inert atmosphere;

[2-(2-thyenyl)ethyl]amine (30433-91-1) + benzoyl chloride (98-88-4) → N-<2-(2-thienyl)ethyl>benzamide (76356-24-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 0.25h;	97%
With sodium hydroxide In water for 12h; Cooling with ice;	95%
With sodium hydroxide In water for 12h;	80%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + formic acid ethyl ester (109-94-4) → N-(2-(thien-2-yl)ethyl)formamide (28783-49-5)

Conditions	Yield
With sodium hydrogencarbonate at 20℃;	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + Glyoxilic acid (298-12-4) → 4,5,6,7-Tetrahydro-thieno[3,2-c]pyridine-4-carboxylic acid (77307-66-5)

Conditions	Yield
In water for 0.5h; Ambient temperature;	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + aniline (62-53-3) → N-(2-(thiophen-2-yl)ethyl)aniline (1120351-34-9)

Conditions	Yield
Shvo complex In tert-Amyl alcohol at 150℃; for 24h;	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 4-chloro-2-(4-methanesulfonylphenyl)-6-trifluoromethylpyrimidine (1018481-30-5) → C18H16F3N3O2S2 (1018480-66-4)

Conditions	Yield
With triethylamine	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 3-fluoro-5-(trifluoromethyl)benzoic acid (161622-05-5) → C14H11F4NOS (1370339-91-5)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane; acetonitrile at 20℃;	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + trans-Crotonaldehyde (123-73-9) → C10H15NS

Conditions	Yield
Stage #1: [2-(2-thyenyl)ethyl]amine; trans-Crotonaldehyde With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 16h; Inert atmosphere;	97%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 9-chloro-2-methoxyacridine (16492-13-0) → 2-methoxy-N-(2-(thiophen-2-yl)ethyl)acridin-9-amine (1217181-64-0)

Conditions	Yield
In methanol for 14h; Reflux;	96%

[2-(2-thyenyl)ethyl]amine (30433-91-1) + 5-bromo-3-chloro-1H-pyrrolo[2,3-b]pyridine (951626-91-8) → 3-chloro-N-(2-(thiophen-2-yl)ethyl)-1H-pyrrolo[2,3-b]pyridin-5-amine (1248587-77-0)

Conditions	Yield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl] [2-(2-aminoethyl)phenyl]palladium(II); lithium hexamethyldisilazane In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	96%

Upstream product

• 1310-58-3 Potassium hydroxide 
• 105-48-6 Isopropyl chloroacetate 
• 107-29-9 Acetaldoxime 
• 98-03-3 2-Thenaldehyde 
• 75-77-4 Chlorotrimethylsilane 
• 16949-15-8 Lithium borohydride 
• 67-56-1 Methanol 
• 109-99-9 Tetrahydrofuran 
• 16853-85-3 Lithium aluminium hydride 
• 75-52-5 Nitromethane 

Downstream Products

• 109213-13-0 5-(2-AMINOETHYL)THIOPHENE-2-SULFONAMIDE 
• 28783-41-7 4,5,6,7-Tetrahydrothieno[3,2,c] pyridine hydrochloride 

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• 76356-24-6  N-<2-(2-thienyl)ethyl>benzamide 
• 98-88-4  benzoyl chloride 
• 59311-69-2  1-phenyl-3-(2-(thiophen-2-yl)ethyl)thiourea 
• 103-72-0  phenyl isothiocyanate 
• 3535-37-3  3,4-dimethoxybenzoic acid chloride 
• 28783-49-5  N-(2-(thien-2-yl)ethyl)formamide 
• 109-94-4  formic acid ethyl ester 
• 26478-16-0  2-(2-Bromoethyl)thiophene 
• 874-84-0  2-(2-nitroethenyl)thiophene 
• 135709-69-2  2-chloro-N-(2-(thiophen-2-yl)ethyl)acetamide 
• 79-04-9  chloroacetyl chloride