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Name |
2-Nitrothiophene |
EINECS | 210-190-9 |
CAS No. | 609-40-5 | Density | 1.422 g/cm3 |
PSA | 74.06000 | LogP | 2.17950 |
Solubility | N/A | Melting Point |
43-45 °C(lit.) |
Formula | C4H3NO2S | Boiling Point | 224.5 °C at 760 mmHg |
Molecular Weight | 129.139 | Flash Point | 93.9 °C |
Transport Information | N/A | Appearance | white to light yellow crystal powder |
Safety | 24/25-36-26 | Risk Codes | 68-36/37/38-20/21/22 |
Molecular Structure | Hazard Symbols | Xn | |
Synonyms |
Thiophene, 2-nitro-;2-Nitrothiophene 85%;2-Nitro thiophene; |
Article Data | 36 |
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 |
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 |
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℃; |
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