609-40-5

Basic information

• Product Name: 2-Nitrothiophene
• Synonyms: 2-Nitrothiofene;2-nitro-thiophen;2-NITROTHIOPHENE;AKOS BBS-00004367;AKOS 93624;2-NITROTHIOPHENE, TECH., 85%;2-Nitrothiophene,98+%;2-Nitrothiophene85%
• CAS NO: 609-40-5
• Molecular Formula: C₄H₃NO₂S
• Molecular Weight: 129.14
• EINECS: 210-190-9
• Product Categories: Thiophenes;Heterocycles;Thiophene&Benzothiophene;Thiophens;Building Blocks;Heterocyclic Building Blocks;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-oher series
• Mol File: 609-40-5.mol
• Article Data: 18

Chemical Properties

• Melting Point: 43-45 °C(lit.)
• Boiling Point: 224-225 °C(lit.)
• Flash Point: 201 °F
• Appearance: /solid
• Density: 1,364 g/cm3
• Vapor Pressure: 0.136mmHg at 25°C
• Refractive Index: 1.5740 (estimate)
• Storage Temp.: Keep Cold
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 2-Nitrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrothiophene(609-40-5)
• EPA Substance Registry System: 2-Nitrothiophene(609-40-5)

Safety Data

• Hazard Codes: Xn
• Statements: 68-36/37/38-20/21/22
• Safety Statements: 24/25-36-26-36/37
• WGK Germany: 3
• RTECS: XN0030000
• TSCA: T
• Hazardous Substances Data: 609-40-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2-Nitrothiophene is a useful compound in the synthesis of thiophene containing compounds.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits very toxic fumes of NOxand SOx.

InChI:InChI=1/C4H3NO2S/c6-5(7)4-2-1-3-8-4/h1-3H

Synthetic route

thiophene (188290-36-0) → 2-nitrothiophene (609-40-5)

Conditions	Yield
With Vilsmeier reagent; potassium nitrate In neat (no solvent) at 100℃; under 1500.15 Torr; Reagent/catalyst; Temperature; Microwave irradiation;	88%
With sodium nitrite for 0.0333333h; Reagent/catalyst; Microwave irradiation;	85%
With nitric acid; acetic anhydride In acetic acid at 20℃; for 2.5h; Nitration;	81%

2-thienyl lithium (2786-07-4) → 2-nitrothiophene (609-40-5)

Conditions	Yield
With dinitrogen tetraoxide In tetrahydrofuran -190 deg C -> room temperature;	76%

thiophene (188290-36-0) → 3-nitrothiophene (822-84-4) + 2-nitrothiophene (609-40-5)

Conditions	Yield
With (NH4)2Ce(NO3)5; acetic anhydride at 25℃; for 17h;	A 12% B 58%
With nitric acid In acetic anhydride; acetic acid at 10℃; for 2h; Yield given. Yields of byproduct given;
durch Nitrierung;
With molecular sieve; nitric acid; acetic anhydride for 0.5h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With nitric acid; acetic anhydride

2-bromo-5-nitrothiophene (13195-50-1) → 2-nitrothiophene (609-40-5) + 2,2'-dinitro-5,5'-dithienyl (41085-77-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; palladium diacetate In toluene at 105℃; for 5h;	A 28% B 58%
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide Pt cathode; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

thiophene boronic acid (6165-68-0) → 2-nitrothiophene (609-40-5)

Conditions	Yield
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at -35℃; for 4h; Nitration; Ipso-nitration;	23%

thiophene (188290-36-0) + nitro acetate (591-09-3) → 2-nitrothiophene (609-40-5)

thiophene (188290-36-0) → 2-nitrothiophene (609-40-5) + 2,5-dinitrothiophene (59434-05-8)

Conditions	Yield
With nitric acid Beim Durchleiten eines mit Thiophendampf beladenen Luftstromes;
With nitric acid

2-iodo-5-nitrothiophene (6277-18-5) → 2-nitrothiophene (609-40-5) + 2,2'-dinitro-5,5'-dithienyl (41085-77-2)

Conditions	Yield
With tetrabutylammonium perchlorate In N,N-dimethyl-formamide Pt cathode; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2-nitro-5-trimethylsilylthiophene (77998-65-3) → 2-nitrothiophene (609-40-5)

Conditions	Yield
In sulfuric acid; acetic acid at 50℃;
In sulfuric acid; acetic acid at 50℃; Rate constant; 1.) other solvents, 2.) k (excit.);
With sodium methylate In methanol at 50℃; Rate constant; deuterium isotope effect;

thiophene (188290-36-0) + nitric acid (7697-37-2) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → 2-nitrothiophene (609-40-5)

Conditions	Yield
at 10℃;

thiophene (188290-36-0) + benzoyl nitrate → 2-nitrothiophene (609-40-5)

2-thiophenylcarboxylic acid (527-72-0) + nitric acid (7697-37-2) + acetic anhydride (108-24-7) → 2-nitrothiophene (609-40-5) + 5-nitrothiophene-2-carboxylic acid (6317-37-9) + 4-nitro-2-thiophenecarboxylic acid (13138-70-0)

Conditions	Yield
at -5℃;

thiophene (188290-36-0) + nitric acid (7697-37-2) → 2-nitrothiophene (609-40-5) + 2,5-dinitrothiophene (59434-05-8)

Conditions	Yield
beim Durchleiten von Luft;

thiophene (188290-36-0) + cyclohexane (110-82-7) + nitric acid (7697-37-2) → 2-nitrothiophene (609-40-5) + oxalic acid (144-62-7) + maleic acid (110-16-7) + 2,5-dinitrothiophene (59434-05-8)

2-nitrothiophene (609-40-5) + 2-chlorobutyronitrile (4158-37-6) → 2-(2-nitro-thiophen-3-yl)-butyronitrile (476427-34-6)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78℃;	96%

2-nitrothiophene (609-40-5) + chloroform (67-66-3) → 3-(dichloromethyl)-2-nitrothiophene (113388-38-8)

Conditions	Yield
Stage #1: 2-nitrothiophene; chloroform With potassium tert-butylate In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide at -78℃; for 0.0833333h; Stage #2: With methanol; acetic acid at 0℃;	94%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -78℃; for 0.0833333h;	94%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -70℃; for 0.0166667h;	74%
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -73 - -68℃; for 0.0166667h;	74%

2-nitrothiophene (609-40-5) + N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (93102-05-7) → (3aR*, 6aR*)-5-benzyl-6a-nitro-4,5,6,6a-tetrahydro-3aH-thieno[2,3-c]pyrrole

Conditions	Yield
Stage #1: 2-nitrothiophene; N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In dichloromethane Saturated solution; diastereoselective reaction;	94%
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;	94%

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;

1,1-Diphenylethylene (530-48-3) + 2-nitrothiophene (609-40-5) → benzophenone (119-61-9) + 1,1-diphenyl-2-(2-thienyl)-ethylene (68969-38-0)

Conditions	Yield
In acetonitrile for 2h; Irradiation;	A 88% B 10%

2-nitrothiophene (609-40-5) + acetic anhydride (108-24-7) → 2-acetylaminothiophene (13053-81-1)

Conditions	Yield
With hydrogen; nickel In N,N-dimethyl-formamide	84%
Stage #1: 2-nitrothiophene With hydrogenchloride; tin at 40 - 45℃; for 0.666667h; Reduction; Stage #2: acetic anhydride With sodium hydroxide; water In diethyl ether for 0.166667h; Acetylation;	64%
With iron; acetic acid at 100℃; for 5h;	40%
With hydrogen; nickel In N,N-dimethyl-formamide at 49.9℃; Kinetics; Rate constant; Thermodynamic data; various temperatures ΔH(activ.), ΔH(activ.);

2-nitrothiophene (609-40-5) + phenylacetylene (536-74-3) → 2-nitrobiphenyl (86-00-0)

Conditions	Yield
In acetonitrile for 4.5h; Heating;	84%

2-nitrothiophene (609-40-5) + N,N-bis(tert-butoxycarbonyl)allylamine (115269-99-3) → (E)-N,N-bis(tert-butoxycarbonyl)-3-(5-nitrothiophen-2-yl)prop-2-en-1-amine (1436419-29-2)

Conditions	Yield
With copper diacetate; palladium diacetate; silver carbonate In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 120℃; for 14h; regioselective reaction;	83%

2-nitrothiophene (609-40-5) + 4-iodo-4’-methoxybiphenyl (126971-87-7) → 2-(4'-methoxybiphenyl-4-yl)-5-nitrothiophene

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; silver (II) carbonate; triphenylphosphine In tetrahydrofuran; water at 60℃; for 168h; Heck Reaction; Inert atmosphere; Schlenk technique;	82%

2-nitrothiophene (609-40-5) + 1-chloro-N,N-dimethylmethane sulfonamide (35427-68-0) → N,N-dimethyl-(2-nitro-3-thienyl)methanesulfonamide

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 1h;	81%
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating;	81%

pyrrolidine (123-75-1) + 2-nitrothiophene (609-40-5) + methyl iodide (74-88-4) → 1-[(1E,3Z)-1-methylsulfanyl-4-nitrobuta-1,3-dienyl]pyrrolidine (200815-33-4)

Conditions	Yield
Stage #1: pyrrolidine; 2-nitrothiophene With silver nitrate In ethanol at 20℃; for 72h; Stage #2: methyl iodide In ethanol Further stages.;	80%
With silver nitrate 1.) EtOH, 0 deg C, 10 d; 2.) 30 deg C, 30 min; Yield given. Multistep reaction;

2-nitrothiophene (609-40-5) + 2-diazocyclohexane-1,3-dione (1460-08-8) → 2-Nitro-3a,6,7,8a-tetrahydro-5H-8-oxa-3-thiacyclopentainden-4-one + 3-Hydroxy-2-(5-nitrothien-2-yl)cyclohex-2-enone

Conditions	Yield
dirhodium tetraacetate In fluorobenzene for 15h; Ambient temperature;	A 78% B 19%

2-nitrothiophene (609-40-5) + α-chlorobenzyl phenyl sulfone (5533-31-3) → α-(2-nitro-5-thienyl)benzyl phenyl sulfone

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; ammonia for 2h;	78%

styrene (292638-84-7) + 2-nitrothiophene (609-40-5) → C-phenyl-C-formyl-N-(2-thienyl)-nitrone

Conditions	Yield
In acetonitrile for 2h; Irradiation;	78%

2-nitrothiophene (609-40-5) + N1,N1-diisopropyl-N2-(2-methoxyphenethyl)oxalamide → N1,N1-diisopropyl-N2-[2-methoxy-6-(5-nitrothiophen-2-yl)phenethyl]oxalamide

Conditions	Yield
With sodium acetate; palladium diacetate; silver carbonate In tert-Amyl alcohol at 130℃; for 4h;	77%

2-nitrothiophene (609-40-5) + chloromethyl p-tolylsulfone (7569-26-8) → (2-nitro-3-thienyl)methyl p-tolyl sulfone

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating;	76%

2-nitrothiophene (609-40-5) + chloromethyl phenyl sulfone (7205-98-3) → (2-nitro-3-thienyl)methyl phenyl sulfone (93418-92-9)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 1h;	74%
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating;	74%
Stage #1: chloromethyl phenyl sulfone With potassium tert-butylate In N,N-dimethyl-formamide at -40℃; for 0.00833333h; Inert atmosphere; Stage #2: 2-nitrothiophene In N,N-dimethyl-formamide at -40℃; for 0.0833333h; Inert atmosphere;	74%

2-nitrothiophene (609-40-5) → 2-nitro-thiophen-3-ol (128496-62-8)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;	72%
With tert.-butylhydroperoxide; potassium tert-butylate In ammonia at -33℃;	72%

2-nitrothiophene (609-40-5) + 1-(1-chloroethyl)phenyl sulfone (13557-25-0) → 1-(2-nitro-3-thienyl)ethyl phenyl sulfone

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -40 - -30℃; for 0.5h;	70%

2-nitrothiophene (609-40-5) + 4-((phenylthio)methyl)benzonitrile (51229-54-0) → 2-nitro-3-(4-cyanophenylmethyl)thiophene

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating;	70%

styrene (292638-84-7) + 2-nitrothiophene (609-40-5) + carbon monoxide (201230-82-2) → C13H13NOS

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; potassium tetrachloropalladate(II); boric acid In tetrahydrofuran at 80℃; under 26252.6 Torr; for 20h; Autoclave; regioselective reaction;	70%

2-nitrothiophene (609-40-5) + 2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride (1160967-80-5) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → 3-(thiophen-2-yl)-2-(trifluoromethyl)quinazolin-4(3H)-one

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; sodium carbonate; palladium dichloride In 1,4-dioxane at 120℃; for 24h; Inert atmosphere; Sealed tube;	70%

2-nitrothiophene (609-40-5) + (trifluoromethyl)trimethylsilane (81290-20-2) → 2-nitro-5-trimethylsilylthiophene (77998-65-3)

Conditions	Yield
With rubidium fluoride at 0℃; for 2h; Reagent/catalyst; Inert atmosphere; regioselective reaction;	68%

2-nitrothiophene (609-40-5) + 2-iodophenylamine (615-43-0) + acetic anhydride (108-24-7) → C13H10N2OS

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tri tert-butylphosphoniumtetrafluoroborate; molybdenum hexacarbonyl In toluene at 140℃; for 14h; Sealed tube; Inert atmosphere;	67%

2-nitrothiophene (609-40-5) + 1-indene (95-13-6) → 2-(2-thienyl)indene (150994-10-8)

Conditions	Yield
In acetonitrile for 1h; Irradiation;	66%

2-nitrothiophene (609-40-5) + 1-indene (95-13-6) → 2-nitro-indene (16021-01-5) + 2-(o-tolyl)-2-oxo-ethanale (63440-60-8) + 2-indanone (615-13-4) + 2-(2-thienyl)indene (150994-10-8)

Conditions	Yield
In acetonitrile for 1h;	A 20% B 6% C 8% D 66%

2-nitrothiophene (609-40-5) + Bromoform (75-25-2) → 3-Dibromomethyl-2-nitro-thiophene (122947-91-5)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -73 - -68℃; for 0.0166667h;	64%

2-nitrothiophene (609-40-5) + 1-(1-chloroethyl)phenyl sulfone (13557-25-0) → 1-(2-nitro-3-thienyl)ethyl phenyl sulfone + 1-(2-nitro-5-thienyl)ethyl phenyl sulfone

Conditions	Yield
With sodium methylate In tetrahydrofuran for 1h;	A 64% B 16%
With potassium tert-butylate In tetrahydrofuran; ammonia for 2h;	A 64% B 16%

Upstream product

• 188290-36-0 thiophene 
• 591-09-3 nitro acetate 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 6165-68-0 thiophene boronic acid 
• 110-82-7 cyclohexane 
• 2786-07-4 2-thienyl lithium 
• 77998-65-3 5-nitro-2-trimethylsilylthiophene 
• 6277-18-5 2-iodo-5-nitrothiophene 
• 13195-50-1 2-bromo-5-nitrothiophene 

Downstream Products

• 13195-50-1 2-bromo-5-nitrothiophene 
• 5347-12-6 2,4-dinitrothiophene 
• 59434-05-8 2,5-dinitrothiophene 
• 136-34-5 N-(thiophen-2-yl)benzamide 
• 40492-18-0 2,3-dibromo-5-nitro-thiophene 
• 3958-03-0 Tetrabromothiophene 
• 616-46-6 thiophen-2-ylamine 

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