(E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
With sodium periodate In tetrahydrofuran; water for 2h; Ambient temperature; | 95% |
With sodium periodate In tetrahydrofuran; water for 2h; | 93% |
With sodium periodate In tetrahydrofuran; water for 2h; | 93% |
methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
With sodium periodate In tetrahydrofuran; water at 10 - 25℃; for 18h; | 79% |
With sodium periodate In tetrahydrofuran; water at 20℃; for 16h; | |
With sodium periodate In tetrahydrofuran; water at 10 - 25℃; for 18h; | 84 g |
methyl 4-bromomethyl-3-nitrobenzoate
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
With 4-methylmorpholine N-oxide In acetonitrile at 20℃; for 1.16667h; | 66% |
4-methyl-3-nitro-benzoic acid methyl ester
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 99 percent / tetrahydrofuran / 2 h / 140 °C 2: 95 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / 105 °C 2: sodium periodate / tetrahydrofuran; water / 18 h / 10 - 25 °C View Scheme | |
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / 105 °C 2: sodium periodate / tetrahydrofuran; water / 18 h / 10 - 25 °C View Scheme |
ethyl 2-sulfanylacetate
methyl 4-formyl-3-nitrobenzoate
2-ethyl 6-methyl benzo[b]thiophene-2,6-dicarboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 60℃; for 11h; | 95% |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h; | 90.4% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 60℃; for 10.5h; | 88% |
methyl 4-formyl-3-nitrobenzoate
methyl 3-azido-4-formylbenzoate
Conditions | Yield |
---|---|
With sodium azide In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; Inert atmosphere; | 95% |
With sodium azide In N,N,N,N,N,N-hexamethylphosphoric triamide at 0 - 20℃; Inert atmosphere; | 95% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide at 20℃; | 95% |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Stage #1: 2-(pentafluorosulfanyl)benzyl acetate With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - -20℃; for 1h; Stage #2: methyl 4-formyl-3-nitrobenzoate In dichloromethane at -45℃; for 1h; | 92% |
methyltriisopropoxytitanium(IV)
methyl 4-formyl-3-nitrobenzoate
C10H11NO5
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 1.16667h; Inert atmosphere; | 87% |
methyl 4-formyl-3-nitrobenzoate
methyl 3-amino-4-formylbenzoate
Conditions | Yield |
---|---|
With iron; acetic acid In ethanol for 1h; | 85% |
With hydrogenchloride; iron; acetic acid In ethanol Heating; | 70% |
With hydrogenchloride; iron In ethanol for 0.666667h; Heating; |
N,N-dimethylethylenediamine
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Stage #1: N,N-dimethylethylenediamine; methyl 4-formyl-3-nitrobenzoate In methanol at 20℃; for 2h; Stage #2: With tributylphosphine In methanol at 50 - 70℃; | 84% |
methyl 4-formyl-3-nitrobenzoate
cyanomethylene triphenylphosphorane
Conditions | Yield |
---|---|
In dichloromethane at -15 - 20℃; for 1.5h; | 79% |
ethylene glycol
methyl 4-formyl-3-nitrobenzoate
methyl 4-( 1,3-dioxolan-2-yl)-3-nitrobenzoate
Conditions | Yield |
---|---|
In toluene for 4h; Reflux; Dean-Stark; | 78% |
With toluene-4-sulfonic acid In toluene for 4h; Dean-Stark; Reflux; | 78% |
With toluene-4-sulfonic acid In toluene for 4h; Dean-Stark; Reflux; | 78% |
methyl 4-formyl-3-nitrobenzoate
propan-1-ol-3-amine
Conditions | Yield |
---|---|
Stage #1: methyl 4-formyl-3-nitrobenzoate; propan-1-ol-3-amine In isopropyl alcohol at 80℃; for 3h; Inert atmosphere; Stage #2: With tributylphosphine In isopropyl alcohol at 80℃; for 12h; Inert atmosphere; | 78% |
methanol
methyl 4-formyl-3-nitrobenzoate
4-dimethoxymethyl-3-nitro-benzoic acid methyl ester
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane at 90℃; for 0.5h; | 76% |
Conditions | Yield |
---|---|
With perchloric acid In 1,4-dioxane; water at 70℃; | 72% |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
In toluene at 25℃; for 19h; Cooling with ice; | 72% |
In toluene at 25℃; for 19h; Cooling with ice; | 72% |
In toluene at 25℃; for 18h; | 72% |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
With acetic acid at 80 - 90℃; stereoselective reaction; | 70% |
methyl 4-formyl-3-nitrobenzoate
acetylenedicarboxylic acid diethyl ester
Conditions | Yield |
---|---|
With formic acid at 110℃; for 18h; Inert atmosphere; | 66% |
4-trifluoromethylphenylamine
methyl 4-formyl-3-nitrobenzoate
methyl 3-nitro-4-[(4-trifluoromethylphenylimino)methyl]benzoate
Conditions | Yield |
---|---|
In ethanol at 20℃; for 5h; | 64% |
Conditions | Yield |
---|---|
With formic acid at 110℃; for 18h; Inert atmosphere; | 62% |
methyl 4-formyl-3-nitrobenzoate
methyl 4-(hydroxymethyl)-3-nitrobenzoate
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate at 0 - 25℃; | 61% |
With sodium tetrahydroborate In methanol | 54% |
methyl (triphenylphosphoranylidene)acetate
methyl 4-formyl-3-nitrobenzoate
(Z)-methyl 4-(2-bromo-3-methoxy-3-oxoprop-1-enyl)-3-nitrobenzoate
Conditions | Yield |
---|---|
Stage #1: methyl (triphenylphosphoranylidene)acetate With dimethylbromosulphonium bromide In dichloromethane at 20℃; for 1h; Inert atmosphere; Stage #2: methyl 4-formyl-3-nitrobenzoate With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; | 49% |
methylmagnesium bromide
methyl 4-formyl-3-nitrobenzoate
A
C10H11NO5
B
methyl 4-(hydroxymethyl)-3-nitrobenzoate
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 4h; | A n/a B 13% |
carbon tetrabromide
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane at 0 - 20℃; | |
With triphenylphosphine In dichloromethane at 0 - 20℃; for 2.5h; Ramirez olefination; | |
With triphenylphosphine In dichloromethane at 0 - 20℃; | |
With triphenylphosphine In dichloromethane at 0℃; Corey-Fuchs olefination; | |
With triphenylphosphine In dichloromethane at 0 - 20℃; for 1.5h; |
methyl 4-formyl-3-nitrobenzoate
3,4-dichloro-5H-furan-2-one
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 3h; Title compound not separated from byproducts.; |
Methyl thioglycolate
methyl 4-formyl-3-nitrobenzoate
dimethyl benzo[b]thiophene-2,6-dicarboxylate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 25h; | |
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; |
methyl 4-formyl-3-nitrobenzoate
2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide 2: NaOH / tetrahydrofuran; methanol 3: EDC; HOBt / CH2Cl2 View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C 2: sodium hydroxide / tetrahydrofuran; methanol; water / 5 h 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 18 h View Scheme |
methyl 4-formyl-3-nitrobenzoate
2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide 2: NaOH / tetrahydrofuran; methanol 3: EDC; HOBt / CH2Cl2 4: NaOH / tetrahydrofuran; methanol View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C 2: sodium hydroxide / tetrahydrofuran; methanol; water / 5 h 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 18 h 4: sodium hydroxide / tetrahydrofuran; methanol; water View Scheme |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: K2CO3 / dimethylformamide 2: NaOH / tetrahydrofuran; methanol 3: EDC; HOBt / CH2Cl2 4: TFA / CH2Cl2 View Scheme | |
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C 2: hydroxylamine / methanol; ISOPROPYLAMIDE; water View Scheme |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: K2CO3 / dimethylformamide 2: NaOH / tetrahydrofuran; methanol 3: EDC; HOBt / CH2Cl2 4: NaOH / tetrahydrofuran; methanol 5: EDC; HOBt / CH2Cl2 View Scheme |
methyl 4-formyl-3-nitrobenzoate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: K2CO3 / dimethylformamide 2: NaOH / tetrahydrofuran; methanol 3: EDC; HOBt / CH2Cl2 4: NaOH / tetrahydrofuran; methanol 5: EDC; HOBt / CH2Cl2 6: TFA / CH2Cl2 View Scheme |
The Benzoic acid,4-formyl-3-nitro-, methyl ester, with the CAS registry number 153813-69-5, is also known as 4-Formyl-3-nitrobenzoicacid methyl ester. It belongs to the product categories of Aldehydes; C9; Carbonyl Compounds. This chemical's molecular formula is C9H7NO5 and molecular weight is 209.16. What's more, its systematic name is methyl 4-formyl-3-nitrobenzoate. It is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. What's more, it should be protected from strong oxidants.
Physical properties of Benzoic acid,4-formyl-3-nitro-, methyl ester are: (1)ACD/LogP: 2.04; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 6; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: 89.19 Å2; (7)Index of Refraction: 1.596; (8)Molar Refractivity: 51.32 cm3; (9)Molar Volume: 150.8 cm3; (10)Polarizability: 20.34×10-24cm3; (11)Surface Tension: 56 dyne/cm; (12)Density: 1.386 g/cm3; (13)Flash Point: 190.2 °C; (14)Enthalpy of Vaporization: 62.81 kJ/mol; (15)Boiling Point: 380 °C at 760 mmHg; (16)Vapour Pressure: 5.61E-06 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=[N+]([O-])c1cc(ccc1C=O)C(=O)OC
(2)InChI: InChI=1S/C9H7NO5/c1-15-9(12)6-2-3-7(5-11)8(4-6)10(13)14/h2-5H,1H3
(3)InChIKey: WGOOPYYIMZJWMA-UHFFFAOYSA-N
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