5-Nitrothiophene-2-carboxaldehyde supplier

Name
5-NITROTHIOPHENE-2-CARBOXALDEHYDE
EINECS 224-850-9
CAS No. 4521-33-9
Article Data30
CAS DataBase
Density 1.534 g/cm³
Solubility Insoluble in water.
Melting Point 75-77 °C
Formula C₅H₃NO₃S
Boiling Point 297.2 °C at 760 mmHg
Molecular Weight 157.15
Flash Point 133.5 °C
Transport Information
Appearance yellow solid
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Formyl-5-nitrothiophene;2-Nitrothiophene-5-carboxaldehyde;5-Nitro-2-formylthiophene;5-Nitro-2-thienylaldehyde;5-Nitro-2-thienylcarboxaldehyde;5-Nitro-2-thiophenealdehyde;5-Nitro-2-thiophenecarboxaldehyde;5-Nitrothiophene-2-carbaldehyde;NSC 168226;5-Nitrothiophene-2-carboxaldehyde;
PSA 91.13000
LogP 1.99200

Synthetic route

: 20898-85-5
(5-nitrothiophen-2-yl)methanol

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
With silica-supported Jones reagent In dichloromethane for 0.00269444h;	99.8%

: 14289-24-8
5-nitrothiophene-2-carboxaldehyde diacetate

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 65℃; for 8h;	80%
With ethanol; sulfuric acid
With hydrogenchloride
With sulfuric acid

: 20898-86-6
2-(chloromethyl)-5-nitrothiophene

: 147225-22-7
2-lithio-2-nitropropane

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 74786-70-2
2-isopropylidenemethyl-5-nitrothiophene

C: 2-(2-methyl-2-nitropropyl)-5-nitrothiophene

D: 1,2-bis-(5-nitro-2-thienyl)ethylene

Conditions

Conditions	Yield
In methanol for 0.25h; Ambient temperature; Irradiation;	A n/a B 61% C 7% D 5%

...Expand

: 20898-86-6
2-(chloromethyl)-5-nitrothiophene

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 74786-70-2
2-isopropylidenemethyl-5-nitrothiophene

C: 2-(2-methyl-2-nitropropyl)-5-nitrothiophene

D: 1,2-bis-(5-nitro-2-thienyl)ethylene

Conditions

Conditions	Yield
With lithium 2-nitropropane In methanol for 0.25h; Ambient temperature; Irradiation;	A n/a B 61% C 7% D 5%

...Expand

: 98-03-3
thiophene-2-carbaldehyde

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 57500-53-5
4-nitrothiophene-2-carbaldehyde

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; for 0.5h;	A 13% B 46%
With sulfuric acid; nitric acid at -10℃; for 0.0833333h;	A n/a B 40%
With sulfuric acid; potassium nitrate at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;	A n/a B 40%

: 87207-17-8
2-(1'-chloro-2',2'-dimethylpropyl)-5-nitrothiophene

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 87207-23-6
2,2-dimethyl-1-(5'-nitro-2'-thienyl)-1-propanol

C: 83054-95-9
2,2-dimethyl-1-(5'-nitro-2'-thienyl)-propane-1-one

Conditions

Conditions	Yield
With 2-lithio-2-nitropropane In dimethyl sulfoxide at 20℃; for 1.1h;	A 7% B 7% C 42%
With 2-lithio-2-nitropropane In dimethyl sulfoxide at 20℃; for 1.1h; Mechanism; Irradiation;	A 7% B 5% C 42%

...Expand

: 20898-83-3
(5'-nitro-2'-thienyl)methyl acetate

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
With sodium thiophenolate In dimethyl sulfoxide for 0.2h;	15%

: 20898-86-6
2-(chloromethyl)-5-nitrothiophene

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
With sodium thiophenolate In dimethyl sulfoxide for 0.166667h;	7%

: 98-03-3
thiophene-2-carbaldehyde

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
With nitric acid; acetic anhydride at -14℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, E, lg A, ΔH(excit.), ΔS(excit.);

: 98-03-3
thiophene-2-carbaldehyde

: 7664-93-9
sulfuric acid

: 7697-37-2
nitric acid

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 57500-53-5
4-nitrothiophene-2-carbaldehyde

...Expand

: 98-03-3
thiophene-2-carbaldehyde

: 7697-37-2
nitric acid

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 57500-53-5
4-nitrothiophene-2-carbaldehyde

Conditions

Conditions	Yield
anschl. Hydrolyse;

...Expand

: 98-03-3
thiophene-2-carbaldehyde

A: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

B: 57500-53-5
4-nitrothiophene-2-carbaldehyde

C: 58963-75-0
3-nitrothiophene-2-carbaldehyde

Conditions

Conditions	Yield
With sulfuric acid; nitric acid at 0℃; Title compound not separated from byproducts;

...Expand

: 20409-48-7
2,2-dimethyl-1-(2-thienyl)-1-propanone

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 3: 95 percent / SOCl2 / pyridine 4: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

: 87207-23-6
2,2-dimethyl-1-(5'-nitro-2'-thienyl)-1-propanol

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / SOCl2 / pyridine 2: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

: 83054-95-9
2,2-dimethyl-1-(5'-nitro-2'-thienyl)-propane-1-one

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 2: 95 percent / SOCl2 / pyridine 3: 7 percent / 2-lithio-2-nitropropane / dimethylsulfoxide / 1.1 h / 20 °C / Irradiation View Scheme

: 63011-97-2
2-thiophenecarboxaldehyde diacetate

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid anhydride; nitric acid; acetic acid 2: aqueous sulfuric acid View Scheme

: 67-56-1
methanol

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 17375-68-7
5-(dimethoxymethyl)-2-nitrothiophene

Conditions

Conditions	Yield
With hydrogenchloride for 0.75h; Heating;	100%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 149-73-5
trimethyl orthoformate

: 17375-68-7
5-(dimethoxymethyl)-2-nitrothiophene

Conditions

Conditions	Yield
With amberlyst-15 In acetonitrile for 1h; electroosmos;	99.8%
With amberlyst-15 In acetonitrile for 0.166667h;	97.5%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 3766-55-0
4-allyl-3-thiosemicarbazide

: 1198748-12-7
4-allyl-1-(5-nitrothenylidene)thiosemicarbazide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃;	99%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 6317-37-9
5-nitrothiophene-2-carboxylic acid

Conditions

Conditions	Yield
With bromine; sodium acetate; acetic acid	98.5%
With hydrogenchloride; bromine; sodium hydroxide In water	98.2%
With sodium hypobromide; sodium acetate; acetic acid	92%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 79-19-6
thiosemicarbazide

: 5351-83-7
2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide

Conditions

Conditions	Yield
In methanol for 3h; Reflux;	98%
In ethanol for 2h; Reflux;	92%
With acetic acid In methanol for 2h; Reflux;	84.2%

: 584-13-4
4-amino-1,2,4-triazole

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 31539-41-0
(5-nitro-thiophen-2-ylmethylene)-[1,2,4]triazol-4-yl-amine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene Heating;	98%
In ethanol for 0.5h; heating on a steam bath;	69%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 98-16-8
3-trifluoromethylaniline

: 140436-71-1
N-(5-nitro-2-thienomethylidene)-3-trifluoromethylaniline

Conditions

Conditions	Yield
In ethanol for 1h; Heating;	98%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 617-89-0
furan-2-ylmethanamine

: 69819-72-3
Furan-2-ylmethyl-[1-(5-nitro-thiophen-2-yl)-meth-(E)-ylidene]-amine

Conditions

Conditions	Yield
Duolite A 101 D resin In 1,2-dimethoxyethane at -20 - 25℃; for 3h;	98%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 36062-19-8
1,3-diaminoguanidine hydrochloride

: 1206770-32-2
1,3-bis-((5-nitrothiophen-2-yl-methylidene)amino)guanidine hydrochloride

Conditions

Conditions	Yield
In methanol for 5h; Reflux;	98%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 6030-18-8
5-nitrothiophene-2-carbaldehyde oxime

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In water Reflux;	98%
With pyridine; hydroxylamine hydrochloride In ethanol for 24h; Reflux;	85%
With hydroxylamine hydrochloride; sodium carbonate In dimethyl sulfoxide at 20℃;
With hydroxylamine hydrochloride In methanol at 25℃; for 0.25h;

: 461-72-3
2,4-imidazolidinedione

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: (Z)-5-((5-nitrothiophen-2-yl)methylene)imidazolidine-2,4-dione

Conditions

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.55h; Aldol Condensation; Reflux; Green chemistry;	98%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 20898-85-5
(5-nitrothiophen-2-yl)methanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol for 5h;	97.2%
Stage #1: 5-nitro-2-thiophenecarboxaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 0 - 20℃; for 20h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere;	96%
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;	90%

: 495-69-2
Hippuric Acid

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 31271-16-6, 89035-35-8
4-[1-(5-Nitro-thiophen-2-yl)-meth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one

Conditions

Conditions	Yield
With sodium acetate; acetic anhydride at 100℃; for 2h;	97%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 106-47-8
4-chloro-aniline

: 64857-14-3
N-(5-nitro-2-thienomethylidene)-4-chloroaniline

Conditions

Conditions	Yield
In ethanol for 1h; Heating;	97%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 519053-87-3
3-amino-2-(4-chloro-2-ethylthio-5-methylbenzenesulphonyl)guanidine

: 1-(4-chloro-2-ethylthio-5-methylbenzenesulfonyl)-3-(5-nitrothienylideneamino)guanidine

Conditions

Conditions	Yield
In ethanol for 4h; Heating;	97%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 107-06-2
1,2-dichloro-ethane

: 5832-01-9
methyl 5-nitrothiophene-2-carboxylate

Conditions

Conditions	Yield
With iodine; sodium hydrogencarbonate In methanol; n-heptane	96.5%

: 2295-31-0
2,4-thiazolidinedion

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: (Z)-5-((5-nitrothiophen-2-yl)methylene)thiazolidine-2,4-dione

Conditions

Conditions	Yield
With copper(II)-Para-aminobenzoic acid complex supported on Fe3O4 Magnetic nanoparticle In ethanol for 1.56667h; Aldol Condensation; Reflux; Green chemistry;	96%

: 14068-53-2
2-amino-5-ethyl-1,3,4-thiadiazole

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 762-04-9
phosphonic acid diethyl ester

: diethyl (((5-ethyl-1,3,4-thiadiazol-2-yl)amino)(5-nitrothiophen-2-yl)methyl)phosphonate

Conditions

Conditions	Yield
With phospho sulphonic acid In neat (no solvent) for 0.15h; Kabachnik-Fields Reaction; Microwave irradiation; Green chemistry;	95.5%

...Expand

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 5351-23-5
4-hydroxybenzoic acid hydrazide

: 4-hydroxybenzoic acid (5-nitrothiophen-2-ylmethylene)hydrazide

Conditions

Conditions	Yield
acetic acid In ethanol for 4h; Heating / reflux;	95%
In ethanol; water Heating;	86%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 5351-69-9
4-Phenyl-3-thiosemicarbazide

: (E)-4-phenyl-1-(5-nitrothienyl)thiosemicarbazide

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 20℃; Inert atmosphere;	95%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: [{5-(4-benzylthio-2-chloro-5-sulfamoylphenyl)-1,3,4-oxadiazol-2-yl}methyl]triphenylphosphonium chloride

: (E)-2-(benzylthio)-4-chloro-5-(5-(2-(5-nitrothiophen-2-yl)vinyl)-1,3,4-oxadiazol-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h; Wittig Olefination; Inert atmosphere;	95%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 17846-15-0
adamantane-1-carbohydrazide

: E-N'-[(5-nitrothiophen-2-yl)methylidene]adamantane-1-carbohydrazide

Conditions

Conditions	Yield
In ethanol for 1h; Reflux;	95%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 64-04-0
phenethylamine

: 69819-75-6
[1-(5-Nitro-thiophen-2-yl)-meth-(E)-ylidene]-phenethyl-amine

Conditions

Conditions	Yield
Duolite A 101 D resin In 1,2-dimethoxyethane at -20 - 25℃; for 3h;	94%

: (cyclohexa-2,4-dienyl-diphenyl-λ5-phosphanylidene)-acetic acid tert-butyl ester

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 3-(5-nitro-thiophen-2-yl)-acrylic acid tert-butyl ester

Conditions

Conditions	Yield
In water at 20℃; for 1h; Wittig reaction;	94%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 80691-81-2
2,5-diamino-thiophene-3,4-dicarboxylic acid diethyl ester

: 2-amino-5-[(5-nitrothiophen-2-ylmethylene)amino]thiophene-3,4-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
In toluene for 0.5h; Reflux;	94%
With trifluoroacetic acid In isopropyl alcohol for 0.5h; Heating;	87%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 126-81-8
dimedone

: 95-54-5
1,2-diamino-benzene

: 3,3-dimethyl-11-(5-nitrothiophen-2-yl)-2,3,4,5,10,11-hexahydro-1Hdibenzo[b,e][1,4]diazepin-1-one

Conditions

Conditions	Yield
With silica-supported nickel oxide nanocomposites In ethanol at 70℃; for 0.25h; Microwave irradiation; Green chemistry;	94%

...Expand

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 3619-22-5
p-toluic hydrazide

: (E)-4-methyl-N′-((5-nitrothiophen-2-yl)methylene)benzohydrazide

Conditions

Conditions	Yield
In ethanol; water Heating;	93%
With acetic acid In methanol for 6h; Reflux;	80%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 5351-17-7
4-aminobenzohydrazide

: C12H10N4O3S

Conditions

Conditions	Yield
In ethanol; water Heating;	93%

: 4521-33-9
5-nitro-2-thiophenecarboxaldehyde

: 1673-47-8
3-chlorobenzhydrazide

: C12H8ClN3O3S

Conditions

Conditions	Yield
In ethanol; water Heating;	93%

5-Nitrothiophene-2-carboxaldehyde Specification

The 5-Nitrothiophene-2-carboxaldehyde, with the CAS registry number 4521-33-9, it is also named as 2-Thiophenecarboxaldehyde,5-nitro-. The product's categories are Heterocycles; Thiophenes. Besides, it is yellow solid, which should be sealed in a dark, ventilated and dry place. In addition, its molecular formula is C₅H₃NO₃S and molecular weight is 157.15. Its systematic name is 5-Nitrothiophene-2-carboxaldehyde.

Physical properties about 5-Nitrothiophene-2-carboxaldehyde are: (1)EINECS: 224-850-9; (2)ACD/LogP: 1.15; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.15; (5)ACD/LogD (pH 7.4): 1.15; (6)ACD/BCF (pH 5.5): 4.41; (7)ACD/BCF (pH 7.4): 4.41; (8)ACD/KOC (pH 5.5): 100.6; (9)ACD/KOC (pH 7.4): 100.6; (10)#H bond acceptors: 4; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 2; (13)Polar Surface Area: 91.13 Å²; (14)Index of Refraction: 1.662; (15)Molar Refractivity: 37.93 cm³; (16)Molar Volume: 102.4 cm³; (17)Polarizability: 15.03×10^-24cm³; (18)Surface Tension: 65.1 dyne/cm; (19)Density: 1.534 g/cm³; (20)Flash Point: 133.5 °C; (21)Melting point: 75-77 °C; (22)Enthalpy of Vaporization: 53.7 kJ/mol; (23)Boiling Point: 297.2 °C at 760 mmHg; (24)Vapour Pressure: 0.00137 mmHg at 25 °C.

Preparation of 5-Nitrothiophene-2-carboxaldehyde: 5-Nitrothiophene-2-carboxaldehyde can be prepared by thiophene-2-carbaldehyde.

This reaction needs HNO₃, H₂SO₄at temperature of 0 °C. The reaction time is 30 min. The yield is 46 %.

Uses of 5-Nitrothiophene-2-carboxaldehyde: it can react with benzene-1,2-diamine to get 2-(5-nitro-thiophen-2-yl)-1H-benzoimidazole.

This reaction will occur at temperature of 350 °C. The yield is 50 %.

When you are using 5-Nitrothiophene-2-carboxaldehyde, please be cautious about it as the following: it is irritating to eyes, respiratory system and skin. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES:O=Cc1sc([N+](=O)[O-])cc1
(2)Std. InChI:InChI=1S/C5H3NO3S/c7-3-4-1-2-5(10-4)6(8)9/h1-3H;
(3)Std. InChIKey:CHTSWZNXEKOLPM-UHFFFAOYSA-N;

Product Name

5-NITROTHIOPHENE-2-CARBOXALDEHYDE

Synthetic route

5-Nitrothiophene-2-carboxaldehyde Specification

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