thiophene
2-nitrothiophene
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% |
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In tetrahydrofuran -190 deg C -> room temperature; | 76% |
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
A
2-nitrothiophene
B
2,2'-dinitro-5,5'-dithienyl
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; |
Conditions | Yield |
---|---|
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at -35℃; for 4h; Nitration; Ipso-nitration; | 23% |
Conditions | Yield |
---|---|
With nitric acid Beim Durchleiten eines mit Thiophendampf beladenen Luftstromes; | |
With nitric acid |
2-iodo-5-nitrothiophene
A
2-nitrothiophene
B
2,2'-dinitro-5,5'-dithienyl
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
2-nitrothiophene
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
nitric acid
acetic anhydride
acetic acid
2-nitrothiophene
Conditions | Yield |
---|---|
at 10℃; |
2-thiophenylcarboxylic acid
nitric acid
acetic anhydride
A
2-nitrothiophene
B
5-nitrothiophene-2-carboxylic acid
C
4-nitro-2-thiophenecarboxylic acid
Conditions | Yield |
---|---|
at -5℃; |
thiophene
nitric acid
A
2-nitrothiophene
B
2,5-dinitrothiophene
Conditions | Yield |
---|---|
beim Durchleiten von Luft; |
thiophene
cyclohexane
nitric acid
A
2-nitrothiophene
B
oxalic acid
C
maleic acid
D
2,5-dinitrothiophene
2-nitrothiophene
2-chlorobutyronitrile
2-(2-nitro-thiophen-3-yl)-butyronitrile
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -78℃; | 96% |
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
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
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% |
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
2-nitrothiophene
A
benzophenone
B
1,1-diphenyl-2-(2-thienyl)-ethylene
Conditions | Yield |
---|---|
In acetonitrile for 2h; Irradiation; | A 88% B 10% |
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.); |
Conditions | Yield |
---|---|
In acetonitrile for 4.5h; Heating; | 84% |
2-nitrothiophene
N,N-bis(tert-butoxycarbonyl)allylamine
(E)-N,N-bis(tert-butoxycarbonyl)-3-(5-nitrothiophen-2-yl)prop-2-en-1-amine
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
4-iodo-4’-methoxybiphenyl
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
1-chloro-N,N-dimethylmethane sulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran for 1h; | 81% |
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating; | 81% |
pyrrolidine
2-nitrothiophene
methyl iodide
1-[(1E,3Z)-1-methylsulfanyl-4-nitrobuta-1,3-dienyl]pyrrolidine
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; |
Conditions | Yield |
---|---|
dirhodium tetraacetate In fluorobenzene for 15h; Ambient temperature; | A 78% B 19% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; ammonia for 2h; | 78% |
Conditions | Yield |
---|---|
In acetonitrile for 2h; Irradiation; | 78% |
2-nitrothiophene
Conditions | Yield |
---|---|
With sodium acetate; palladium diacetate; silver carbonate In tert-Amyl alcohol at 130℃; for 4h; | 77% |
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating; | 76% |
2-nitrothiophene
chloromethyl phenyl sulfone
(2-nitro-3-thienyl)methyl phenyl sulfone
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
2-nitro-thiophen-3-ol
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
1-(1-chloroethyl)phenyl sulfone
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -40 - -30℃; for 0.5h; | 70% |
2-nitrothiophene
4-((phenylthio)methyl)benzonitrile
Conditions | Yield |
---|---|
With potassium hydroxide In tetrahydrofuran; ammonia for 1h; Heating; | 70% |
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
2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride
molybdenum hexacarbonyl
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
(trifluoromethyl)trimethylsilane
2-nitro-5-trimethylsilylthiophene
Conditions | Yield |
---|---|
With rubidium fluoride at 0℃; for 2h; Reagent/catalyst; Inert atmosphere; regioselective reaction; | 68% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tri tert-butylphosphoniumtetrafluoroborate; molybdenum hexacarbonyl In toluene at 140℃; for 14h; Sealed tube; Inert atmosphere; | 67% |
Conditions | Yield |
---|---|
In acetonitrile for 1h; Irradiation; | 66% |
2-nitrothiophene
1-indene
A
2-nitro-indene
B
2-(o-tolyl)-2-oxo-ethanale
C
2-indanone
D
2-(2-thienyl)indene
Conditions | Yield |
---|---|
In acetonitrile for 1h; | A 20% B 6% C 8% D 66% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; N,N-dimethyl-formamide at -73 - -68℃; for 0.0166667h; | 64% |
2-nitrothiophene
1-(1-chloroethyl)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% |
Reported in EPA TSCA Inventory.
The 2-Nitrothiophene is an organic compound with the formula C4H3NO2S. The IUPAC name of this chemical is 2-nitrothiophene. With the CAS registry number 609-40-5, it is also named as Thiophene, 2-nitro-. The product's categories are Thiophenes; Heterocycles; Thiophene & Benzothiophene; Thiophens; Building Blocks; Heterocyclic Building Blocks. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place. It is used in organic synthesis.
Physical properties about 2-Nitrothiophene are: (1)ACD/LogP: 1.65; (2)ACD/LogD (pH 5.5): 1.65; (3)ACD/LogD (pH 7.4): 1.65; (4)ACD/BCF (pH 5.5): 10.5; (5)ACD/BCF (pH 7.4): 10.5; (6)ACD/KOC (pH 5.5): 187.33; (7)ACD/KOC (pH 7.4): 187.33; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 1; (10)Polar Surface Area: 74.06 Å2; (11)Index of Refraction: 1.603; (12)Molar Refractivity: 31.18 cm3; (13)Molar Volume: 90.7 cm3; (14)Polarizability: 12.36×10-24cm3; (15)Surface Tension: 53.9 dyne/cm; (16)Density: 1.422 g/cm3; (17)Flash Point: 93.9 °C; (18)Enthalpy of Vaporization: 44.22 kJ/mol; (19)Boiling Point: 224.5 °C at 760 mmHg; (20)Vapour Pressure: 0.136 mmHg at 25°C.
Preparation: this chemical can be prepared by thiophene. This reaction will need reagent acetic acid anhydride and copper (II)-nitrate trihydrate.
Uses of 2-Nitrothiophene: it can be used to produce 3-dichloromethyl-2-nitro-thiophene at temperature of -70 °C. It will need reagent t-BuOK and solvent tetrahydrofuran, dimethylformamide with reaction time of 1 min. The yield is about 74%.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed and possible risk of irreversible effects. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)c1sccc1
(2)InChI: InChI=1/C4H3NO2S/c6-5(7)4-2-1-3-8-4/h1-3H
(3)InChIKey: JIZRGGUCOQKGQD-UHFFFAOYAL
(4)Std. InChI: InChI=1S/C4H3NO2S/c6-5(7)4-2-1-3-8-4/h1-3H
(5)Std. InChIKey: JIZRGGUCOQKGQD-UHFFFAOYSA-N
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View