-
Name
Methyl 4-aminobenzoate
- EINECS 210-598-7
- CAS No. 619-45-4
- Article Data313
- CAS DataBase
- Density 1.166 g/cm3
- Solubility Soluble in alcohol and ether, slightly soluble in water
- Melting Point 110-113 °C
- Formula C8H9NO2
- Boiling Point 299.2 °C at 760 mmHg
- Molecular Weight 151.165
- Flash Point 154.9 °C
- Transport Information
- Appearance white to beige crystals or crystalline powder
- Safety 26-37/39-36/37/39
- Risk Codes 36/37/38-20/21/22
-
Molecular Structure
-
Hazard Symbols
Xn, 
Xi
- Synonyms Benzoicacid, p-amino-, methyl ester (6CI,7CI,8CI);(4-(Methoxycarbonyl)phenyl)amine;4-(Carbomethoxy)aniline;4-(Methoxycarbonyl)aniline;4-Aminobenzenecarboxylicacid methyl ester;4-Aminobenzoic acid methyl ester;Methyl 4-aminobenzoate;Methyl 4-aminophenylcarboxylate;Methyl aniline-4-carboxylate;Methylp-aminobenzoate;NSC 3783;p-(Methoxycarbonyl)aniline;p-Aminobenzoic acidmethyl ester;p-Carbomethoxyaniline;
- PSA 52.32000
- LogP 1.63660
Synthetic route
| 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% |
| Conditions | Yield |
|---|---|
| With thionyl chloride for 2h; Esterification; Heating; | 100% |
| With acetyl chloride at 20℃; for 168h; Inert atmosphere; | 100% |
| With thionyl chloride at 0 - 20℃; | 100% |
-
-
20442-96-0
methyl 4-azidobenzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With sodium tetrahydroborate; tin bis(1,2-benzenethiolate) In tetrahydrofuran; phosphate buffer at 10℃; for 0.25h; pH=10; Reduction; | 100% |
| With hydrazine hydrate In ethanol at 20℃; chemoselective reaction; | 99% |
| With ammonium chloride; zinc In ethanol; water for 0.5h; Heating; | 98% |
| Conditions | Yield |
|---|---|
| In 1,2-dimethoxyethane at 20℃; for 96h; | 100% |
-
-
106896-49-5
methyl 4-amino-3-bromobenzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With formic acid; tributyl-amine; 10-phenyl-10H-phenothiazine In acetonitrile at 20℃; for 49h; Inert atmosphere; UV-irradiation; | 100% |
| With dihydroxyborane; potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 100℃; Suzuki Coupling; | 71% |
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2.5h; Sealed tube; Irradiation; Inert atmosphere; | 100% |
-
-
67-56-1
methanol
-
-
201230-82-2
carbon monoxide
-
-
540-37-4
p-aminoiodobenzene
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With triethylamine at 100℃; under 3750.38 Torr; for 1.5h; Inert atmosphere; | 99% |
| With triethylamine at 80℃; under 3750.38 Torr; for 3h; Autoclave; | 80% |
-
-
150-13-0
4-amino-benzoic acid
-
-
616-38-6
carbonic acid dimethyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With sulfuric acid for 18h; Reflux; Inert atmosphere; | 95% |
| With layered double hydroxide - supported L-methionine at 180℃; for 6h; Autoclave; chemoselective reaction; | 90% |
| With sulfuric acid for 16h; Neat (no solvent); Reflux; | 89.64% |
-
-
303120-71-0
2-[(4-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With ethylenediamine In ethanol at 20℃; for 2.15h; | 95% |
-
-
123876-56-2
methyl 4-(benzylamino)benzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With ammonium formate; zinc In ethylene glycol for 0.0333333h; microwave irradiation; | 93% |
| With hydrogen; palladium on activated charcoal In ethanol for 24h; | 100 % Turnov. |
| Conditions | Yield |
|---|---|
| With sodium azide; copper; L-proline In water; dimethyl sulfoxide at 150℃; under 37503.8 Torr; for 0.583333h; Flow reactor; chemoselective reaction; | 93% |
| With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry; | 85% |
| With copper (II)-fluoride; trimethylsilylazide; triethylamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere; | 66% |
| Multi-step reaction with 2 steps 1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C 2: hydrogenchloride; water / methanol / 1 h / 20 °C View Scheme |
-
-
19718-49-1
4-amino-3-iodobenzoic acid methyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With formic acid; tributyl-amine; fac-tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile at 25 - 30℃; for 8h; Inert atmosphere; Irradiation; | 93% |
-
-
20442-96-0
methyl 4-azidobenzoate
-
-
70978-37-9
1-(azidomethyl)-4-methoxybenzene
-
A
-
874-90-8
4-methoxybenzonitrile
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With [2,5-Me2-3,4-Ph2(η5-C4CNHPh)]Ru(CO)2H at 70℃; for 16h; Irradiation; Inert atmosphere; | A 90% B 92% |
-
-
619-50-1
4-nitrobenzoic acid methyl ester
-
A
-
24226-29-7
N-[(4-methoxycarbonyl)phenyl]hydroxylamine
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With methyldiazene In acetonitrile at 28℃; for 0.75h; Irradiation; Sealed tube; Inert atmosphere; | A 91% B n/a |
| With [Co(κS,N-4-(trifluoromethyl)pyrimidine-2-thiolate)3]; methylhydrazine In d(4)-methanol at 70℃; for 1.5h; Sealed tube; | A 80% B 20% |
| With 1,2-bis(mercaptomethyl)benzene; tetraethylammonium chloride; iron(II) chloride In acetonitrile at 40℃; for 6h; | A 47% B 11% |
| Conditions | Yield |
|---|---|
| Stage #1: 4-methoxycarbonylphenyl bromide With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 6h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 91% |
| With potassium phosphate; bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia In 1,4-dioxane at 70℃; under 4137.29 Torr; for 12h; Inert atmosphere; | 83% |
| With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In 1,4-dioxane at 90℃; for 2h; Glovebox; Sealed tube; | 47% |
| Conditions | Yield |
|---|---|
| With sulfuric acid In methanol at 100℃; for 20h; | 90.3% |
| In methanol; water |
-
-
100192-88-9
4-allyloxycarbonylamino-benzoic acid methyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide at 20℃; allyl carbamate cleavage; Electrochemical reaction; Zn/stainless steel couple electrodes; current intensity 60 mA; supporting electrolite: tetrabutylammonium tetrafluoroborate; | 90% |
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With hydroxylamine hydrochloride; sodium acetate; palladium on activated charcoal In methanol Ambient temperature; | 88% |
| Conditions | Yield |
|---|---|
| With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h; | 88% |
| With N'',N'''''-1,8-naphthalenediyl bis[N,N,N',N'-tetramethyl]guanidine In N,N-dimethyl-formamide at 20℃; Kinetics; |
-
-
17012-22-5
methyl 4-acetamidobenzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| Stage #1: methyl 4-acetamidobenzoate With Schwartz's reagent In tetrahydrofuran at 20℃; for 0.0666667h; Inert atmosphere; Stage #2: With water In tetrahydrofuran Inert atmosphere; chemoselective reaction; | 87% |
-
-
875118-61-9
methyl 4-(((benzyloxy)carbonyl)amino)benzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction; | 87% |
-
-
619-50-1
4-nitrobenzoic acid methyl ester
-
-
1104416-85-4
2-(p-trifluoromethylphenyl)benzothiazoline
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With camphor-10-sulfonic acid In toluene for 24h; Molecular sieve; Reflux; Inert atmosphere; | A 10% B 87% |
-
-
164596-20-7
4-tert-butoxycarbonylamino-benzoic acid methyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| HY-Zeolite In dichloromethane for 2h; Heating; | 86% |
| Conditions | Yield |
|---|---|
| Stage #1: Methyl 4-chlorobenzoate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 90℃; for 18h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether | 85% |
| With potassium phosphate; bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia In 1,4-dioxane at 70℃; under 4137.29 Torr; for 12h; Inert atmosphere; | 79% |
| With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C50H70NO4PPdS; C50H70NO4PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere; | 53% |
| With C46H71Cl3N2Pd; ammonia; sodium t-butanolate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Schlenk technique; | 51% |
-
-
842-74-0
4-benzylidene-2-phenyloxazole-5(4H)-one
-
A
-
130814-94-7
(Z)-N-(3-hydrazinyl-3-oxo-1-phenylprop-1-en-2-yl)benzamide
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With hydrazine hydrate In ethanol for 3h; Reflux; | A 85% B n/a |
-
-
619-50-1
4-nitrobenzoic acid methyl ester
-
-
67-63-0
isopropyl alcohol
-
A
-
18144-43-9
isopropyl 4-aminobenzoate
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With potassium tert-butylate; bis(pinacol)diborane at 110℃; for 2h; | A n/a B 85% |
-
-
17012-22-5
methyl 4-acetamidobenzoate
-
A
-
79663-14-2
methyl 4-(ethylamino)benzoate
-
B
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With dihydridocarbonyl(1,1,1-tris(diphenylphosphinomethyl)ethane)ruthenium(II) complex; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid In tetrahydrofuran at 120℃; under 38002.6 Torr; for 16h; Glovebox; Autoclave; Inert atmosphere; | A 85% B n/a |
| With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); formic acid; bis(trifluoromethanesulfonyl)amide; triethylamine; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In dibutyl ether at 130℃; for 24h; | A n/a B 83% |
| Conditions | Yield |
|---|---|
| With dipotassium peroxodisulfate; sodium azide; water; silver carbonate In N,N-dimethyl-formamide at 120℃; Sealed tube; | 85% |
| With sodium azide In dimethyl sulfoxide at 125℃; for 19h; | 20% |
-
-
84851-56-9
methyl 4-(1-hydroxy ethyl)benzoate
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube; | 84% |
| With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 10h; | 78% |
| Conditions | Yield |
|---|---|
| In dichloromethane at 20℃; Inert atmosphere; | 100% |
| With pyridine In dichloromethane at 0 - 20℃; | 100% |
| With acetic acid for 2h; Reflux; | 91.32% |
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
13170-28-0
methyl p-nitrosobenzoate
| Conditions | Yield |
|---|---|
| With selenium(IV) oxide; dihydrogen peroxide In dichloromethane; water at 20℃; for 22h; | 100% |
| With oxone(R) In dichloromethane; water at 20℃; for 1h; Inert atmosphere; | 95% |
| With oxone In dichloromethane; water at 20℃; | 89% |
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
19718-49-1
4-amino-3-iodobenzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane Heating / reflux; | 100% |
| With N,N,N-trimethylbenzenemethanaminium dichloroiodate; calcium carbonate In methanol; dichloromethane Heating / reflux; | 100% |
| With pyridine iodine monochloride In methanol for 2h; Reflux; Inert atmosphere; | 93% |
-
-
50-00-0
formaldehyd
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
1202-25-1
methyl 4-(N,N-dimethylamino)benzoate
| Conditions | Yield |
|---|---|
| With sodium cyanoborohydride; acetic acid at 0 - 65℃; for 2.75h; | 100% |
| With Decaborane In methanol; water at 20℃; for 0.5h; | 94% |
| With sodium cyanoborohydride; acetic acid In tetrahydrofuran at 23 - 50℃; for 18h; Inert atmosphere; | 63% |
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| With selenium(IV) oxide; dihydrogen peroxide In methanol; water at 20℃; for 22h; | 100% |
| With selenium(IV) oxide; dihydrogen peroxide In methanol; water at 20℃; for 72h; | 100 %Spectr. |
| Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane; methanol / 20 °C 2: dihydrogen peroxide; ammonium paratungstate hydrate / ethanol; water / 70 °C View Scheme |
| Conditions | Yield |
|---|---|
| Stage #1: 4-methoxycarbonyl aniline With hydrogenchloride; sodium nitrite In water for 0.5h; cooling; Stage #2: piperazine In water for 0.5h; | 100% |
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
292068-77-0
5-((tert-butoxycarbonyl)amino)benzo[b]thiophene-2-carboxylic acid
| Conditions | Yield |
|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide | 100% |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; |
-
-
407-25-0
trifluoroacetic anhydride
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
304646-56-8
methyl 4-(2,2,2-trifluoroacetamido)benzoate
| Conditions | Yield |
|---|---|
| In dichloromethane for 1h; | 100% |
| Stage #1: trifluoroacetic anhydride; 4-methoxycarbonyl aniline In dichloromethane for 1h; Stage #2: With water; sodium hydrogencarbonate In dichloromethane | 100% |
| With triethylamine In dichloromethane at 0 - 20℃; for 14h; | 97% |
-
-
536748-07-9
(2R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(4-dimethylcarbamoyl-2-fluoro-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
536748-00-2
(2R,4R)-4-Methoxy-2-(4-methoxycarbonyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
| Conditions | Yield |
|---|---|
| With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine In chloroform; ethyl acetate | 100% |
-
-
89711-08-0
N-(t-butoxycarbonyl)glycinal
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
936571-55-0
4-(2-tert-butoxycarbonylamino-ethylamino)benzoic acid methyl ester
| Conditions | Yield |
|---|---|
| Stage #1: N-(t-butoxycarbonyl)glycinal; 4-methoxycarbonyl aniline With acetic acid In methanol at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: With sodium cyanoborohydride In methanol at 20℃; Molecular sieve; Inert atmosphere; | 100% |
| Stage #1: N-(t-butoxycarbonyl)glycinal; 4-methoxycarbonyl aniline In methanol; acetic acid 4A molecular sieves; Stage #2: With sodium cyanoborohydride In methanol; acetic acid Product distribution / selectivity; | 68% |
| With 3-phenyl-propionaldehyde; sodium cyanoborohydride In methanol; acetic acid Product distribution / selectivity; Molecular sieve; |
-
-
591-31-1
3-methoxy-benzaldehyde
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
349456-93-5
4-[(3-methoxy-benzylidene) amino]-benzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
| In N,N-dimethyl-formamide at 100 - 150℃; |
-
-
1550-35-2
2,4-difluorobenzaldehyde
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
1391608-80-2
4-{[1-(2,4-difluoro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In toluene for 12h; | 100% |
| With toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
-
-
3132-99-8
m-bromobenzoic aldehyde
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
1391608-87-9
4-{[1-(3-bromo-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
| With toluene-4-sulfonic acid In toluene for 12h; Reflux; | 100% |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 80℃; for 8h; | 100% |
-
-
7677-24-9
trimethylsilyl cyanide
-
-
79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one
-
-
619-45-4
4-methoxycarbonyl aniline
| Conditions | Yield |
|---|---|
| In acetic acid at 0 - 20℃; | 100% |
| In acetic acid at 0 - 20℃; |
| Conditions | Yield |
|---|---|
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; | 100% |
| With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 100℃; for 10h; | 10% |
| Conditions | Yield |
|---|---|
| In dichloromethane at 20℃; for 18h; Inert atmosphere; Molecular sieve; | 100% |
| Conditions | Yield |
|---|---|
| With 10wt%Cu-5wt%Co/γ-Al2O3 at 170℃; for 6h; Autoclave; Inert atmosphere; | 100% |
| With zinc oxide-supported iridium catalyst at 150℃; under 3750.38 Torr; for 12h; Inert atmosphere; | 76 %Chromat. |
| Conditions | Yield |
|---|---|
| Stage #1: 4-methoxycarbonyl aniline With hydrogenchloride; sodium nitrite In water at 0 - 40℃; for 1h; Stage #2: edaravone With sodium hydroxide In water at 2 - 5℃; for 1h; | 99.6% |
-
-
42558-54-3
Methyl 4-methyl-3-oxopentanoate
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
936847-59-5
methyl 4-(4-methyl-3-oxopentanamido)benzoate
| Conditions | Yield |
|---|---|
| With ethylenediamine In toluene for 20 - 25h; Heating / reflux; | 99.45% |
| In toluene for 24h; Reflux; Dean-Stark; | 85% |
-
-
2515-30-2
6-chloro-N,N'-di-p-tolyl-[1,3,5]triazine-2,4-diamine
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
84689-00-9
4-(4,6-Bis-p-tolylamino-[1,3,5]triazin-2-ylamino)-benzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With sodium hydroxide In 1,4-dioxane at 80℃; for 2h; | 99.1% |
| Conditions | Yield |
|---|---|
| With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; Inert atmosphere; | 99% |
| With triethylamine In dichloromethane at 0 - 20℃; | 80% |
| With sodium acetate |
-
-
122-04-3
4-nitro-benzoyl chloride
-
-
619-45-4
4-methoxycarbonyl aniline
-
-
39799-74-1
methyl 4-<(4'-nitrobenzoyl)amino>benzoate
| Conditions | Yield |
|---|---|
| In dichloromethane at 20℃; | 99% |
| With triethylamine In dichloromethane at 0 - 20℃; for 12h; | 87% |
| With pyridine; chloroform |
| Conditions | Yield |
|---|---|
| With bromine; acetic acid at 25℃; for 0.5h; Bromination; | 99% |
| With bromine In acetic acid at 25℃; for 0.5h; Bromination; Heating; | 98% |
| With bromine; acetic acid at 25℃; for 0.5h; Bromination; | 98% |
Methyl 4-aminobenzoate Consensus Reports
Methyl 4-aminobenzoate Specification
The IUPAC name of p-Aminobenzoic acid methyl ester is methyl 4-aminobenzoate. With the CAS registry number 619-45-4 and EINECS 210-598-7, it is also named as Methyl aniline-4-carboxylate. The product's categories are Carboxylicester; Aromatic Esters; C8 to C9; Carbonyl Compounds; Esters; Aromatic Amino Acids; Peptide Synthesis; Unnatural Amino Acid Derivatives. It is white to beige crystals or crystalline powder which is soluble in alcohol and ether, slightly soluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): 1.41; (5)ACD/BCF (pH 5.5): 6.99; (6)ACD/BCF (pH 7.4): 6.99; (7)ACD/KOC (pH 5.5): 139.88; (8)ACD/KOC (pH 7.4): 140.01; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 129.6 cm3; (16)Surface Tension: 46.2 dyne/cm; (17)Enthalpy of Vaporization: 53.92 kJ/mol; (18)Vapour Pressure: 0.00121 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 151.063329; (22)MonoIsotopic Mass: 151.063329; (23)Topological Polar Surface Area: 52.3; (24)Heavy Atom Count: 11; (25)Complexity: 139.
Preparation of p-Aminobenzoic acid methyl ester: It can be obtained by 4-amino-benzoic acid and methanol. This reaction which is a kind of Esterification needs reagent SOCl2 by heating. The reaction time is 2 hours. The yield is 100%.
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Uses of p-Aminobenzoic acid methyl ester: It is used in organic synthesis and as dye intermediate. It also can react with 2-acetylamino-benzoic acid to get 4-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid methyl ester. This reaction needs reagent PCl3 and solvent toluene by heating. The reaction time is 1.5 hours. The yield is 63%.
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When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC)c1ccc(N)cc1
2. InChI:InChI=1/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3
3. InChIKey:LZXXNPOYQCLXRS-UHFFFAOYAA
The following are the toxicity data which has been tested.
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 237mg/kg (237mg/kg) | Journal of Medicinal Chemistry. Vol. 17, Pg. 900, 1974. |
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