153813-69-5

Basic information

• Product Name: METHYL 4-FORMYL-3-NITROBENZOATE 97
• Synonyms: METHYL 4-FORMYL-3-NITROBENZOATE 97;4-FORMYL-3-NITROMETHYLBENZOATE4-FORMYL-3-NITROBENZOIC ACID METHYL ESTER;4-Methoxycarbonyl-2-nitrobenzaldehyde;Methyl 4-forMyl-3-nitrobenzoate 97%
• CAS NO: 153813-69-5
• Molecular Formula: C₉H₇NO₅
• Molecular Weight: 209.156
• Product Categories: Aldehydes;C9;Carbonyl Compounds
• Mol File: 153813-69-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 62-66 °C(lit.)
• Boiling Point: 380 °C at 760 mmHg
• Flash Point: 190.2 °C
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 5.61E-06mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: METHYL 4-FORMYL-3-NITROBENZOATE 97(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-FORMYL-3-NITROBENZOATE 97(153813-69-5)
• EPA Substance Registry System: METHYL 4-FORMYL-3-NITROBENZOATE 97(153813-69-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 153813-69-5(Hazardous Substances Data)

Usage

General Description

Methyl 4-formyl-3-nitrobenzoate 97 is a chemical compound with the molecular formula C9H7NO5. It is a nitro compound that consists of a methyl ester group, a formyl group, and a nitro group attached to a benzene ring. Methyl 4-formyl-3-nitrobenzoate 97 is commonly used in organic synthesis for the production of various pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as a precursor in the manufacture of dyes, pigments, and other specialty chemicals. The compound is known for its bright yellow color and has a purity of 97%. It is important to handle this chemical with caution as it may cause skin and eye irritation, and should be stored and handled according to proper safety guidelines.

InChI:InChI=1/C9H7NO5/c1-15-9(12)6-2-3-7(5-11)8(4-6)10(13)14/h2-5H,1H3

Synthetic route

(E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene (104447-80-5) → methyl 4-formyl-3-nitrobenzoate (153813-69-5)

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 (133831-27-3) → methyl 4-formyl-3-nitrobenzoate (153813-69-5)

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 (88089-94-5) → methyl 4-formyl-3-nitrobenzoate (153813-69-5)

Conditions	Yield
With 4-methylmorpholine N-oxide In acetonitrile at 20℃; for 1.16667h;	66%

4-methyl-3-nitro-benzoic acid methyl ester (7356-11-8) → methyl 4-formyl-3-nitrobenzoate (153813-69-5)

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 (623-51-8) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → 2-ethyl 6-methyl benzo[b]thiophene-2,6-dicarboxylate (850074-42-9)

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 (153813-69-5) → methyl 3-azido-4-formylbenzoate (1279718-17-0)

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%

2-(pentafluorosulfanyl)benzyl acetate + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 4-(3-(benzyloxy)-1-hydroxy-3-oxo-2-pentafluorosulfanylpropyl)-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) (18006-13-8) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → C10H11NO5 (1582753-59-0)

Conditions	Yield
In tetrahydrofuran at 0℃; for 1.16667h; Inert atmosphere;	87%

methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 3-amino-4-formylbenzoate (212322-17-3)

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 (108-00-9) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 2-(2-(dimethylamino)ethyl)-2H-indazole-6-carboxylate

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 (153813-69-5) + cyanomethylene triphenylphosphorane (16640-68-9) → (E)-methyl 4-(2-cyanovinyl)-3-nitrobenzoate

Conditions	Yield
In dichloromethane at -15 - 20℃; for 1.5h;	79%

ethylene glycol (107-21-1) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 4-( 1,3-dioxolan-2-yl)-3-nitrobenzoate (773095-63-9)

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 (153813-69-5) + propan-1-ol-3-amine (156-87-6) → methyl 2-(3-hydroxypropyl)-2H-indazole-6-carboxylate

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 (67-56-1) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → 4-dimethoxymethyl-3-nitro-benzoic acid methyl ester (332082-19-6)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 90℃; for 0.5h;	76%

2-tert-butylfuran (7040-43-9) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → C25H29NO6 (1378569-12-0)

Conditions	Yield
With perchloric acid In 1,4-dioxane; water at 70℃;	72%

tert-butyl 3-cyano-2-(triphenylphosphoranylidene)propanoate + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 4-(3-(tert-butoxy)-2-(cyanomethyl)-3-oxoprop-1-en-1-yl)-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 (153813-69-5) + (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

Conditions	Yield
With acetic acid at 80 - 90℃; stereoselective reaction;	70%

methyl 4-formyl-3-nitrobenzoate (153813-69-5) + acetylenedicarboxylic acid diethyl ester (762-21-0) → C17H17NO6

Conditions	Yield
With formic acid at 110℃; for 18h; Inert atmosphere;	66%

4-trifluoromethylphenylamine (455-14-1) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 3-nitro-4-[(4-trifluoromethylphenylimino)methyl]benzoate (860007-73-4)

Conditions	Yield
In ethanol at 20℃; for 5h;	64%

methyl ethynyl ketone (1423-60-5) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → C13H11NO3

Conditions	Yield
With formic acid at 110℃; for 18h; Inert atmosphere;	62%

methyl 4-formyl-3-nitrobenzoate (153813-69-5) → methyl 4-(hydroxymethyl)-3-nitrobenzoate (89950-93-6)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 25℃;	61%
With sodium tetrahydroborate In methanol	54%

methyl (triphenylphosphoranylidene)acetate (21204-67-1) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → (Z)-methyl 4-(2-bromo-3-methoxy-3-oxoprop-1-enyl)-3-nitrobenzoate (1586740-49-9)

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 (75-16-1) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → C10H11NO5 (1582753-59-0) + methyl 4-(hydroxymethyl)-3-nitrobenzoate (89950-93-6)

Conditions	Yield
In diethyl ether at 20℃; for 4h;	A n/a B 13%

carbon tetrabromide (558-13-4) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → 4-(2,2-dibromovinyl)-3-nitrobenzoic acid methyl ester

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 (153813-69-5) + 3,4-dichloro-5H-furan-2-one (62674-12-8) → 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	Yield
With triethylamine In methanol at 20℃; for 3h; Title compound not separated from byproducts.;

Methyl thioglycolate (2365-48-2) + methyl 4-formyl-3-nitrobenzoate (153813-69-5) → dimethyl benzo[b]thiophene-2,6-dicarboxylate (850073-71-1)

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 (153813-69-5) → 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester (850073-74-4)

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 (153813-69-5) → 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid (850073-75-5)

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 (153813-69-5) → 2-hydroxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester

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 (153813-69-5) → C35H26N2SO3

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 (153813-69-5) → benzo[b]thiophene-2,6-dicarboxylic acid 2-hydroxyamide 6-phenylamide

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

Upstream product

• 133831-27-3 methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate 
• 96-98-0 4-methyl-3-nitrobenzoic acid 
• 88089-94-5 methyl 4-bromomethyl-3-nitrobenzoate 
• 7356-11-8 4-methyl-3-nitro-benzoic acid methyl ester 
• 104447-80-5 (E)-1-(dimethylamino)-2-[4-(methoxycarbonyl)-2-nitrophenyl]ethene 

Downstream Products

• 850073-74-4 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester 
• 850073-75-5 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid 
• 850073-72-2 benzo[b]thiophene-2,6-dicarboxylic acid 6-methyl ester 
• 850074-43-0 benzo[b]thiophene-2,6-dicarboxylic acid 2-ethyl ester 
• 850072-65-0 6-hydroxymethyl-benzo[b]thiophene-2-carboxylic acid ethyl ester 
• 850074-44-1 6-formyI-benzo[b]thiophene-2-carboxylic acid ethyl ester 
• 947513-35-1 C₁₈H₁₇NSO₂ 
• 850074-74-7 6-(benzylamino-methyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester 
• 947513-38-4 C₂₀H₂₁NSO₂ 
• 205058-62-4 methyl 4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-3-nitrobenzoate 

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