• Name

  Methyl 4-nitrobenzoate

• EINECS 210-599-2
• CAS No. 619-50-1
• Article Data445
• CAS DataBase
• Density 1.301 g/cm³
• Solubility
• Melting Point 94-96 °C(lit.)
• Formula C₈H₇NO₄
• Boiling Point 302.6 °C at 760 mmHg
• Molecular Weight 181.148
• Flash Point 149.2 °C
• Transport Information
• Appearance light yellow to yellow fine crystalline powder
• Safety 22-24/25
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms Benzoicacid, p-nitro-, methyl ester (6CI,8CI);4-Methoxycarbonylnitrobenzene;4-nitrobenzoic acid methyl ester;Methyl 4-nitrobenzoate;Methylp-nitrobenzoate;NSC 4137;p-Carbomethoxynitrobenzene;p-Nitrobenzoic acidmethyl ester;
• PSA 72.12000
• LogP 1.90460

Synthetic route

67-56-1

methanol

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;	100%
Stage #1: 4-nitro-benzoic acid With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 0.0833333h; Garegg-Samuelsson type reaction; Stage #2: methanol In dichloromethane at 20℃; Garegg-Samuelsson type reaction;	100%
With dmap; 2-chloro-1-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl)pyridinium trifluoromethanesulfonate; triethylamine In N,N-dimethyl-formamide at 20℃; for 1h;	100%

636-98-6

p-nitrobenzene iodide

201230-82-2

carbon monoxide

1067-21-6

triethylmethoxystannane

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With iodophenylbis(triphenylphosphine)palladium under 760 Torr; for 1h;	100%

...Expand

18107-18-1

diazomethyl-trimethyl-silane

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
In methanol; toluene at 20℃; for 2h;	100%
In ethyl acetate	60%
In methanol; diethyl ether; hexane at 20℃; for 2h; Inert atmosphere;	178 mg

5564-73-8

1-(dimethoxymethyl)pyrrolidine

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 30℃; for 25h;	100%

67-56-1

methanol

diethyl N-(4-nitrobenzoyloxy)-4-fluorobenzimidoylphosphonate

A

619-50-1

4-nitrobenzoic acid methyl ester

B

154109-07-6

diethyl [N-(hydroxy)imino](p-fluorophenyl)methylphosphonate

Conditions

Conditions	Yield
for 6h; Inert atmosphere; Reflux;	A 100% B 100%

...Expand

67-56-1

methanol

555-16-8

4-nitrobenzaldehdye

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With water; iodine; sodium nitrite at 20 - 70℃; chemoselective reaction;	99%
With ammonium peroxydisulfate at 60℃; for 2.5h;	99%
With potassium hydroxide; iodine at 0℃; for 0.0166667h;	98%

67-56-1

methanol

619-73-8

4-nitrobenzyl chloride

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With sodium carbonate; palladium; silver(l) oxide at 80℃; for 48h; Molecular sieve;	99%
With dihydrogen peroxide for 3h; Irradiation;	95%
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;	94%

67-56-1

methanol

99-77-4

ethyl 4-nitrobenzoate

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
scandium tris(trifluoromethanesulfonate) at 64℃; for 168h;	98%
With dipotassium hydrogenphosphate for 5h; Reflux;	98%
With potassium ethoxide
acrylonitrile; triphenylphosphine at 25℃; for 24h;	71 % Chromat.

88470-26-2

N,N-dimethoxyamine

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
In benzene for 3h; Heating;	98%
In benzene Product distribution; Mechanism; Heating; other nucleophiles; var. reaction conditions;	98%
In benzene for 3h; Mechanism; Heating;	98%

4525-33-1

dimethyl dicarbonate

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
magnesium(II) perchlorate In nitromethane at 40℃; for 16h;	98%
With 2,6-dimethylpyridine; fac-tris(2-phenylpyridinato-N,C2')iridium(III) In N,N-dimethyl-formamide at 20℃; for 48h; Sealed tube; Inert atmosphere; Irradiation;

67-56-1

methanol

636-98-6

p-nitrobenzene iodide

201230-82-2

carbon monoxide

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;	98%
With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere;	95%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; under 5250.53 Torr; continuous flow reactor;	81%

...Expand

80-11-5

N-methyl-N-nitrosotoluene-p-sulfonamide

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃;	98%
Stage #1: N-methyl-N-nitrosotoluene-p-sulfonamide With potassium hydroxide In methanol; water; N,N-dimethyl-formamide Flow reactor; Stage #2: 4-nitro-benzoic acid In methanol; diethyl ether; water; N,N-dimethyl-formamide at 0 - 25℃; Sonication;	90%

67-56-1

methanol

636-97-5

N-amino-(4-nitrophenyl)carboxamide

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate at 20℃; for 0.25h; Esterification;	97%
With Oxone at 20℃; for 6h; oxidative esterification;	84%

poly(p-methyltriazenestyrene)

poly(p-methyltriazenestyrene)

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
In 1,2-dimethoxyethane for 16h;	97%

79-22-1

methyl chloroformate

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In acetonitrile	97%

681-84-5

tetramethylorthosilicate

555-16-8

4-nitrobenzaldehdye

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride; (t-Bu2POH)2PdCl2 In acetonitrile at 50℃; for 24h;	97%

121-45-9

phosphorous acid trimethyl ester

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With diethylazodicarboxylate In tetrahydrofuran for 2h;	96%
With diethylazodicarboxylate In tetrahydrofuran for 2h; Mechanism; other phosphite, other carboxylic acid, phenols, imides and C-H acids;	92%

67-56-1

methanol

50-00-0

formaldehyd

120-46-7

1,3-diphenylpropanedione

A

619-50-1

4-nitrobenzoic acid methyl ester

B

21600-84-0

bis-1,5(4-nitrophenyl)-1,5-pentanedione

Conditions

Conditions	Yield
hydroxocobalt(III) Schiff base at 60℃; for 1.5h; Product distribution; Mechanism; var. 4-subst. educts; var. reaction conditions;	A 92% B 96%

...Expand

67-56-1

methanol

3758-70-1

1-(4-nitrophenyl)propan-1-one

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;	95%

17302-46-4

methyl 2-hydroxy-5-nitrobenzoate

62-23-7

4-nitro-benzoic acid

A

619-50-1

4-nitrobenzoic acid methyl ester

B

96-97-9

5-nitrosalicylic acid

Conditions

Conditions	Yield
Stage #1: 4-nitro-benzoic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl 2-hydroxy-5-nitrobenzoate at 110℃; for 24h; Temperature;	A 95% B n/a

...Expand

67-56-1

methanol

N,N-(Boc)2-4-nitrobenzamide

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With C26H28N3O3S(1+)*F6P(1-); nickel diacetate; potassium carbonate; triethylamine at 25℃; for 2h;	95%

616-38-6

carbonic acid dimethyl ester

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With sulfuric acid at 80 - 85℃; for 9.5h; Neat (no solvent);	94.2%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide for 0.0180556h; microwave irradiation;	90%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;	86%

67-56-1

methanol

122-04-3

4-nitro-benzoyl chloride

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane for 0.166667h;	94%
With pyridine at 70℃; for 3h;	91%
at 25℃; Thermodynamic data; ΔH;

100-51-6

benzyl alcohol

62-23-7

4-nitro-benzoic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride at 20℃; for 2.5h; Esterification;	94%

67-56-1

methanol

201230-82-2

carbon monoxide

586-78-7

para-nitrophenyl bromide

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane In N,N-dimethyl-formamide at 80℃; under 2327.23 Torr;	94%
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; under 11251.1 Torr; continuous flow reactor;	77%
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; hydrazine In tetrahydrofuran; 1,4-dioxane at 100℃; under 11251.1 Torr; Temperature; Flow reactor;	77%
With ruthenium(III) trichloride hydrate; 1,4-bis(2'-diphenylphosphino-3'-methylimidazolium)butane triflate; triethylamine In 1-methyl-pyrrolidin-2-one at 140℃; under 15001.5 Torr; for 16h; Autoclave;	80 %Chromat.

...Expand

67-56-1

methanol

54914-77-1

1-(4-nitrophenyl)-3-phenyl-1-propanone

A

104-53-0

3-phenyl-propionaldehyde

B

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With N,N-dimethyl-formamide dimethyl acetal for 16h; Heating;	A n/a B 93%

...Expand

186581-53-3, 908094-01-9

diazomethane

619-73-8

4-nitrobenzyl chloride

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: 4-nitrobenzyl chloride With sodium chlorite; sodium dihydrogenphosphate; Me-AZADO+Cl- In dichloromethane; water at 25℃; for 1.5h; Stage #2: With 2-methyl-but-2-ene In dichloromethane; water Stage #3: diazomethane With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;	93%
Stage #1: 4-nitrobenzyl chloride With sodium chlorite; sodium dihydrogenphosphate; 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride In dichloromethane; water at 25℃; for 1.5h; Stage #2: With 2-methyl-but-2-ene In dichloromethane; water Stage #3: diazomethane With hydrogenchloride; sodium hydroxide Product distribution / selectivity; more than 3 stages;	63%

99768-12-4

4-methoxycarbonylphenylboronic acid

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; N–nitrosaccharin at 60℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	93%
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere;	86%
With dipotassium peroxodisulfate; bismuth (III) nitrate pentahydrate In benzene at 70℃; for 12h; Inert atmosphere;	74%
With copper(I) oxide; tetrabutylammonium nitrite In acetonitrile at 20℃;	53%

67-56-1

methanol

25393-54-8

N-(4-nitrobenzoyl)oxazolidinone

619-50-1

4-nitrobenzoic acid methyl ester

Conditions

Conditions	Yield
With [t-Bu2SnCl(OH)]2 In toluene at 85℃; for 14h;	92%

64-17-5

ethanol

619-50-1

4-nitrobenzoic acid methyl ester

99-77-4

ethyl 4-nitrobenzoate

Conditions

Conditions	Yield
With tert-butylamine for 10h; Heating;	100%
Stage #1: ethanol With platinum(IV) oxide; hydrogen at 60℃; under 750.075 - 1500.15 Torr; for 2h; Autoclave; Green chemistry; Stage #2: 4-nitrobenzoic acid methyl ester at 60℃; Autoclave; Inert atmosphere; Green chemistry; chemoselective reaction;	93%
With dichlorobis(1-butylimidazolium) zinc at 70 - 80℃;	93%

619-50-1

4-nitrobenzoic acid methyl ester

24226-29-7

N-[(4-methoxycarbonyl)phenyl]hydroxylamine

Conditions

Conditions	Yield
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;	100%
With 5% rhodium-on-charcoal; hydrazine hydrate In tetrahydrofuran at 0℃; Inert atmosphere;	100%
With rhodium contaminated with carbon; hydrazine hydrate In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;	100%

619-50-1

4-nitrobenzoic acid methyl ester

619-45-4

4-methoxycarbonyl aniline

Conditions

Conditions	Yield
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h;	100%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h;	100%
With sodium tetrahydroborate; water In ethanol at 25℃; for 1h; Solvent; chemoselective reaction;	100%

619-50-1

4-nitrobenzoic acid methyl ester

75-05-8

acetonitrile

79663-14-2

methyl 4-(ethylamino)benzoate

Conditions

Conditions	Yield
With palladium 10% on activated carbon; ammonium acetate; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;	100%

619-50-1

4-nitrobenzoic acid methyl ester

62-23-7

4-nitro-benzoic acid

Conditions

Conditions	Yield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;	99%
With methanesulfonic acid; 1-methylimidazolium hydrobromide at 120℃; for 2h;	96%
With iron(III) sulfate; water In toluene at 110℃; for 4h; Ionic liquid;	95%

619-50-1

4-nitrobenzoic acid methyl ester

100-51-6

benzyl alcohol

14786-27-7

benzyl 4-nitrobenzoate

Conditions

Conditions	Yield
With lanthanum(III) nitrate hexahydrate; TOP at 110℃; for 5h; Reagent/catalyst; Molecular sieve;	99%
With N,N'-biscyclohexyl-imidazol-2-ylidene; 4 A molecular sieve In tetrahydrofuran at 20℃; for 0.25h;	96%
1,3-dicyclohexyl-imidazol-2-ylidene In tetrahydrofuran at 20℃; for 0.25h;	96%

112-92-5

1-octadecanol

619-50-1

4-nitrobenzoic acid methyl ester

56426-96-1

octadecyl 4-nitro-benzoate

Conditions

Conditions	Yield
Stage #1: 1-octadecanol; 4-nitrobenzoic acid methyl ester In xylene for 0.5h; Heating; Stage #2: With TiO(acac)2 In xylene for 4.5h; Heating;	99%

109-80-8

1.3-propanedithiol

619-50-1

4-nitrobenzoic acid methyl ester

1,3-di(4-methoxycarbonylphenylthio)propane

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 25℃; for 1.5h;	99%
With magnesium methanolate In N,N-dimethyl-formamide at 80℃; for 8h;	78%

619-50-1

4-nitrobenzoic acid methyl ester

71-36-3

butan-1-ol

120-48-9

butyl p-nitrobenzoate

Conditions

Conditions	Yield
With Zn4(OCOCF3)6O In di-isopropyl ether for 40h; Heating;	99%

619-50-1

4-nitrobenzoic acid methyl ester

111-27-3

hexan-1-ol

6268-24-2

4-nitrophenyl hexanoate

Conditions

Conditions	Yield
With tetrabutylammonium acetate; oxiranyl-methanol In hexane for 2h; Reflux;	99%

619-50-1

4-nitrobenzoic acid methyl ester

23663-92-5

dimethyl 4,4'-azoxydibenzoate

Conditions

Conditions	Yield
With potassium hydroxide In water; isopropyl alcohol at 30℃; under 760.051 Torr; for 10h; Inert atmosphere;	98%
With manganese; acetic acid In tetrahydrofuran; water at 20℃; for 15h;	70%
With triethylsilane; indium(III) bromide In N,N-dimethyl-formamide at 60℃; for 12h;	64%
With bismuth; sodium hydroxide; sodium tetrahydroborate; oxygen 1.) methanol, room temperature, 0.5 h, 2.) methanol, room temperate, 4 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: 78 percent / Sb, NaBH4 / methanol / 1 h / Ambient temperature 2: 88 percent / NaOH, O2 / 4 h / Ambient temperature View Scheme

619-50-1

4-nitrobenzoic acid methyl ester

156-87-6

propan-1-ol-3-amine

90690-76-9

N-(3-Hydroxy-propyl)-4-nitro-benzamid

Conditions

Conditions	Yield
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry;	98%
In toluene at 97℃; for 4h; Acylation;	79%

619-50-1

4-nitrobenzoic acid methyl ester

100-36-7

N,N-diethylethylenediamine

1664-52-4

N-(2-(diethylamino)ethyl)-4-nitrobenzamide

Conditions

Conditions	Yield
With ammonium nitrate In neat (no solvent) at 20℃; for 12h; Green chemistry;	98%

619-50-1

4-nitrobenzoic acid methyl ester

619-80-7

4-nitrobenzamide

Conditions

Conditions	Yield
With ammonia In methanol at 70℃;	98%

Methyl 4-nitrobenzoate Chemical Properties

MF: C₈H₇NO₄
MW: 181.15
EINECS: 210-599-2
METHYL-p-NITROBENZOATE,it's melting point is about  94-96 °C(lit.);It's appearance is white or yellow crystal.Soluble in ethanol, Ether, Chloroform, insoluble in water.
Following is the molecular structure of METHYL-p-NITROBENZOATE:

Methyl 4-nitrobenzoate Toxicity Data With Reference

Methyl 4-nitrobenzoate Consensus Reports

Methyl 4-nitrobenzoate Safety Profile