Product Name

  • Name

    METHYL 4-FORMYL-3-NITROBENZOATE 97

  • EINECS
  • CAS No. 153813-69-5
  • Article Data16
  • CAS DataBase
  • Density 1.386 g/cm3
  • Solubility
  • Melting Point 62-66 °C(lit.)
  • Formula C9H7NO5
  • Boiling Point 380 °C at 760 mmHg
  • Molecular Weight 209.158
  • Flash Point 190.2 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 153813-69-5 (METHYL 4-FORMYL-3-NITROBENZOATE 97)
  • Hazard Symbols
  • Synonyms 4-Formyl-3-nitrobenzoicacid methyl ester;Methyl 4-formyl-3-nitrobenzoate;
  • PSA 89.19000
  • LogP 1.71710

Synthetic route

(E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene
104447-80-5

(E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

Conditions
ConditionsYield
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
133831-27-3

methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

Conditions
ConditionsYield
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
88089-94-5

methyl 4-bromomethyl-3-nitrobenzoate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

Conditions
ConditionsYield
With 4-methylmorpholine N-oxide In acetonitrile at 20℃; for 1.16667h;66%
4-methyl-3-nitro-benzoic acid methyl ester
7356-11-8

4-methyl-3-nitro-benzoic acid methyl ester

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

Conditions
ConditionsYield
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
623-51-8

ethyl 2-sulfanylacetate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

2-ethyl 6-methyl benzo[b]thiophene-2,6-dicarboxylate
850074-42-9

2-ethyl 6-methyl benzo[b]thiophene-2,6-dicarboxylate

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 3-azido-4-formylbenzoate
1279718-17-0

methyl 3-azido-4-formylbenzoate

Conditions
ConditionsYield
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%
2-(pentafluorosulfanyl)benzyl acetate

2-(pentafluorosulfanyl)benzyl acetate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 4-(3-(benzyloxy)-1-hydroxy-3-oxo-2-pentafluorosulfanylpropyl)-3-nitrobenzoate

methyl 4-(3-(benzyloxy)-1-hydroxy-3-oxo-2-pentafluorosulfanylpropyl)-3-nitrobenzoate

Conditions
ConditionsYield
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)
18006-13-8

methyltriisopropoxytitanium(IV)

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

C10H11NO5
1582753-59-0

C10H11NO5

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 1.16667h; Inert atmosphere;87%
methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 3-amino-4-formylbenzoate
212322-17-3

methyl 3-amino-4-formylbenzoate

Conditions
ConditionsYield
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
108-00-9

N,N-dimethylethylenediamine

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 2-(2-(dimethylamino)ethyl)-2H-indazole-6-carboxylate

methyl 2-(2-(dimethylamino)ethyl)-2H-indazole-6-carboxylate

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

cyanomethylene triphenylphosphorane
16640-68-9

cyanomethylene triphenylphosphorane

(E)-methyl 4-(2-cyanovinyl)-3-nitrobenzoate

(E)-methyl 4-(2-cyanovinyl)-3-nitrobenzoate

Conditions
ConditionsYield
In dichloromethane at -15 - 20℃; for 1.5h;79%
ethylene glycol
107-21-1

ethylene glycol

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 4-( 1,3-dioxolan-2-yl)-3-nitrobenzoate
773095-63-9

methyl 4-( 1,3-dioxolan-2-yl)-3-nitrobenzoate

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

methyl 2-(3-hydroxypropyl)-2H-indazole-6-carboxylate

methyl 2-(3-hydroxypropyl)-2H-indazole-6-carboxylate

Conditions
ConditionsYield
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
67-56-1

methanol

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

4-dimethoxymethyl-3-nitro-benzoic acid methyl ester
332082-19-6

4-dimethoxymethyl-3-nitro-benzoic acid methyl ester

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane at 90℃; for 0.5h;76%
2-tert-butylfuran
7040-43-9

2-tert-butylfuran

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

C25H29NO6
1378569-12-0

C25H29NO6

Conditions
ConditionsYield
With perchloric acid In 1,4-dioxane; water at 70℃;72%
tert-butyl 3-cyano-2-(triphenylphosphoranylidene)propanoate

tert-butyl 3-cyano-2-(triphenylphosphoranylidene)propanoate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 4-(3-(tert-butoxy)-2-(cyanomethyl)-3-oxoprop-1-en-1-yl)-3-nitrobenzoate

methyl 4-(3-(tert-butoxy)-2-(cyanomethyl)-3-oxoprop-1-en-1-yl)-3-nitrobenzoate

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

(Z)-1-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)pyrrolidine

(Z)-1-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)pyrrolidine

methyl 3-nitro-4-[(1E)-4,4,4-trifluoro-3-oxo-2-phenylbut-1-en-1-yl]benzoate

methyl 3-nitro-4-[(1E)-4,4,4-trifluoro-3-oxo-2-phenylbut-1-en-1-yl]benzoate

Conditions
ConditionsYield
With acetic acid at 80 - 90℃; stereoselective reaction;70%
methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

C17H17NO6

C17H17NO6

Conditions
ConditionsYield
With formic acid at 110℃; for 18h; Inert atmosphere;66%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 3-nitro-4-[(4-trifluoromethylphenylimino)methyl]benzoate
860007-73-4

methyl 3-nitro-4-[(4-trifluoromethylphenylimino)methyl]benzoate

Conditions
ConditionsYield
In ethanol at 20℃; for 5h;64%
methyl ethynyl ketone
1423-60-5

methyl ethynyl ketone

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

C13H11NO3

C13H11NO3

Conditions
ConditionsYield
With formic acid at 110℃; for 18h; Inert atmosphere;62%
methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

methyl 4-(hydroxymethyl)-3-nitrobenzoate
89950-93-6

methyl 4-(hydroxymethyl)-3-nitrobenzoate

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 0 - 25℃;61%
With sodium tetrahydroborate In methanol54%
methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

(Z)-methyl 4-(2-bromo-3-methoxy-3-oxoprop-1-enyl)-3-nitrobenzoate
1586740-49-9

(Z)-methyl 4-(2-bromo-3-methoxy-3-oxoprop-1-enyl)-3-nitrobenzoate

Conditions
ConditionsYield
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
75-16-1

methylmagnesium bromide

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

A

C10H11NO5
1582753-59-0

C10H11NO5

B

methyl 4-(hydroxymethyl)-3-nitrobenzoate
89950-93-6

methyl 4-(hydroxymethyl)-3-nitrobenzoate

Conditions
ConditionsYield
In diethyl ether at 20℃; for 4h;A n/a
B 13%
...Expand
carbon tetrabromide
558-13-4

carbon tetrabromide

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

4-(2,2-dibromovinyl)-3-nitrobenzoic acid methyl ester

4-(2,2-dibromovinyl)-3-nitrobenzoic acid methyl ester

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

3,4-dichloro-5H-furan-2-one
62674-12-8

3,4-dichloro-5H-furan-2-one

methyl 4-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)methyl)-3-nitrobenzoate

methyl 4-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)methyl)-3-nitrobenzoate

methyl 4-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)methyl)-3-nitrobenzoate

methyl 4-((3,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)(hydroxy)methyl)-3-nitrobenzoate

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 3h; Title compound not separated from byproducts.;
...Expand
Methyl thioglycolate
2365-48-2

Methyl thioglycolate

methyl 4-formyl-3-nitrobenzoate
153813-69-5

methyl 4-formyl-3-nitrobenzoate

dimethyl benzo[b]thiophene-2,6-dicarboxylate
850073-71-1

dimethyl benzo[b]thiophene-2,6-dicarboxylate

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester
850073-74-4

2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid
850073-75-5

2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

2-hydroxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester

2-hydroxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

C35H26N2SO3

C35H26N2SO3

Conditions
ConditionsYield
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
153813-69-5

methyl 4-formyl-3-nitrobenzoate

benzo[b]thiophene-2,6-dicarboxylic acid 2-hydroxyamide 6-phenylamide

benzo[b]thiophene-2,6-dicarboxylic acid 2-hydroxyamide 6-phenylamide

Conditions
ConditionsYield
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

Benzoic acid,4-formyl-3-nitro-, methyl ester Specification

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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