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94-09-7

Basic Information
CAS No.: 94-09-7
Name: Benzoicacid, 4-amino-, ethyl ester
Molecular Structure:
Molecular Structure of 94-09-7 (Benzoicacid, 4-amino-, ethyl ester)
Formula: C9H11NO2
Molecular Weight: 165.19
Synonyms: Benzocaine (USP);Benzoicacid, p-amino-, ethyl ester (8CI);(p-(Ethoxycarbonyl)phenylamine;4-(Ethoxycarbonyl)aniline;4-(Ethoxycarbonyl)phenylamine;4-Aminobenzoic acidethyl ester;4-Carbethoxyaniline;Aethoform;Amben ethyl ester;Anaesthan-syngala;Anaesthin;Anesthesine;Benzoak;Benzocaine;Diet Ayds;Ethoform;Ethyl 4-aminobenzoate;Ethyl aminobenzoate;Ethyl p-aminobenzenecarboxylate;Ethyl p-aminophenylcarboxylate;Gingicaine;Identhesin;Keloform;NSC 41531;NSC 4688;Norcain;Norcaine;Ora-jel;Orabase-B;Orthesin;Parathesin;Parathesine;Slim Mint Gum;Solu H;p-(Ethoxycarbonyl)aniline;p-Aminobenzoic acid ethyl ester;p-Carbethoxyaniline;p-Ethoxycarboxylicaniline;
EINECS: 202-303-5
Density: 1.13 g/cm>3
Melting Point: 88-90 °C
Boiling Point: 310.7 °C at 760 mmHg
Flash Point: 164.2 °C
Solubility: Soluble in ethanol, chloroform, ethyl ether and dilute acids. Sparingly soluble in water
Appearance: white odourless crystals
Hazard Symbols: IrritantXi
Risk Codes: 43-36/37/38
Safety: 22-24/25-37/39-26-24
Transport Information:
PSA: 52.32000
LogP: 2.02670
Synthetic route
99-77-4

ethyl 4-nitrobenzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With hydrogen; AV-17-8; palladium In ethanol at 45℃; under 750.06 Torr;100%
With triphenylphosphine; palladium on activated charcoal In ethanol at 40℃; atmospheric pressure;100%
With hydrazine hydrate In ethanol; water at 80℃; for 1h; chemoselective reaction;100%
38556-93-3

4-azido-benzoic acid ethyl ester

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 6h; Reagent/catalyst; chemoselective reaction;100%
With hydrogen In methanol at 20℃; for 18h; chemoselective reaction;100%
With hydrogen In methanol at 20℃; under 760.051 Torr; for 9h;97%
5338-44-3

ethyl p-acetamidobenzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With BF3 ethanol complex In ethanol100%
5798-75-4

Ethyl 4-bromobenzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With copper (II)-fluoride; trimethylsilylazide; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere;99%
Stage #1: Ethyl 4-bromobenzoate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 70℃; for 3h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
93%
With copper(I) oxide; sodium azide; L-proline In dimethyl sulfoxide at 100℃; for 2h; Inert atmosphere;93%
51934-41-9

4-iodobenzoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: 4-iodobenzoic acid ethyl ester With potassium phosphate; 2,2,2-trifluoroacetamide; N,N`-dimethylethylenediamine; copper(l) iodide In N,N-dimethyl-formamide at 45℃;
Stage #2: With methanol In N,N-dimethyl-formamide at 45℃; Further stages.;
99%
With copper(l) iodide; potassium carbonate; ammonium chloride; L-proline In water; dimethyl sulfoxide at 25℃; for 12h; Inert atmosphere;97%
With trimethylsilylazide; copper; ethanolamine In N,N-dimethyl acetamide at 95℃; for 24h; Inert atmosphere;92%

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
Stage #1: ethyl 4-oxocyclohexane-1-carboxylate With hydroxylamine hydrochloride; potassium carbonate In N,N-dimethyl acetamide at 20℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: at 130℃; for 1h; Inert atmosphere;
99%
With styrene; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 130℃; for 40h; Sealed tube; Inert atmosphere;73%
109-63-7

boron trifluoride diethyl etherate

150-13-0

4-amino-benzoic acid

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
at 120℃; for 4h;99%
64-17-5

ethanol

62-23-7

4-nitro-benzoic acid

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
Stage #1: ethanol; 4-nitro-benzoic acid With sulfuric acid at 80℃; for 6h;
Stage #2: With 5%-palladium/activated carbon; hydrogen In water at 95℃; under 5250.53 Torr; for 2h; Temperature; Pressure; Inert atmosphere;
98.6%
for 7h; Reflux;95.5%
Stage #1: ethanol; 4-nitro-benzoic acid With sulfuric acid at 80℃; for 6h; Large scale;
Stage #2: With 5%-palladium/activated carbon; hydrogen at 80℃; under 4500.45 Torr; Large scale;
64-17-5

ethanol

150-13-0

4-amino-benzoic acid

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With sulfuric acid for 5h; Reflux;96%
With sulfuric acid95%
With sulfuric acid for 5h; Reflux;94%
3289-28-9

ethyl cyclohexanecarboxylate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With ethene; 5%-palladium/activated carbon; ammonium acetate; potassium carbonate In acetonitrile at 90℃; under 760.051 Torr; for 3h; Reagent/catalyst; Schlenk technique;95%
C19H31NO4Si

C19H31NO4Si

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃;94%
4-allyloxycarbonylamino-benzoic acid ethyl ester

4-allyloxycarbonylamino-benzoic acid ethyl ester

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 1h;94%
64-17-5

ethanol

58202-83-8

p-acetamido-benzamide

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With potassium hydrogensulfate for 48h; Reflux;93%

ethyl N,N-diallyl-p-aminobenzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 40℃;91%
With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane at 40℃; for 24h; Inert atmosphere;91%
71134-92-4

N-(4-ethoxycarbonylphenyl)butyramide

A

94-32-6

ethyl 4-(N-butylamino)benzoate

B

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
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 20h; Glovebox; Autoclave; Inert atmosphere;A 89%
B n/a
451-46-7

4-fluorobenzoic acid ethyl ester

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With dipotassium peroxodisulfate; sodium azide; water; silver carbonate In N,N-dimethyl-formamide at 120℃; Sealed tube;89%
64-17-5

ethanol

540-37-4

p-aminoiodobenzene

13939-06-5, 199620-15-0

molybdenum hexacarbonyl

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N-ethyl-N,N-diisopropylamine In neat (no solvent) at 130℃; for 0.2h; Microwave irradiation;88%

C17H19NO4SSe

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In hexane; toluene; acetonitrile at 80℃; for 21h; Inert atmosphere; chemoselective reaction;87%
5338-44-3

ethyl p-acetamidobenzoate

A

42265-58-7

ethyl 4-(N-ethylamino)benzoate

B

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
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 86%
B n/a
85590-89-2

ethyl 4-<(2'-acetylamino-4',5'-methylenedioxyphenacyl)amino>benzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
In ethanol at 150℃; for 5h; Heating; sealed tube;85%
Multi-step reaction with 3 steps
1: 23 percent / 2 h / Heating
2: 78 percent / ammonia / ethanol / 5 h / 150 - 155 °C / Heating; sealed tube
3: 22.5 percent / methanolic HCl / ethanol / 6 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 14 percent / 2 h / Heating
2: 69 percent / 2 h / Heating
3: 78 percent / ammonia / ethanol / 5 h / 150 - 155 °C / Heating; sealed tube
4: 22.5 percent / methanolic HCl / ethanol / 6 h / Heating
View Scheme
14685-90-6

4-ethoxycarbonylphenylhydrazine

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 2h;85%
With titanium tetrachloride; magnesium In tetrahydrofuran at 20℃; Inert atmosphere;82%
64-17-5

ethanol

623-04-1

4-aminobenzenemethanol

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With dihydrogen peroxide for 3h; Irradiation;85%
7335-27-5

ethyl 4-chlorobenzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 110℃; for 10h; Microwave irradiation;84%
4334-88-7

p-ethoxycarbonylphenylboronic acid

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 1h; chemoselective reaction;83%
99-77-4

ethyl 4-nitrobenzoate

A

24171-85-5

ethyl 4-(hydroxylamino)benzoate

B

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With sodium tetrahydroborate; sodium selenite In water at 37℃; for 1h;A 81%
B 2%
With reduced 1% [Pd(OAc)2]3 impregnated with carbon support in trichloromethane In ethanol; water at 49.84℃; under 3750.38 Torr; for 1h; Catalytic behavior;
73779-71-2

ethyl 4-(allylamine)benzoate

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 40℃;81%
20893-30-5

2-cyanomethylthiophene

150-13-0

4-amino-benzoic acid

94-09-7

p-aminoethylbenzoate

Conditions
ConditionsYield
With potassium bromide at 15 - 65℃; for 3.5h; Temperature;79%
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History

Benzocaine was first synthesised by a German chemical firm named Ritsert, in the town of Eberbach.

Specification

Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). It can be prepared from PABA and ethanol by Fischer esterification or via the reduction of ethyl p-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, chloroform and ethyl ether. With the CAS NO.94-09-7,  it is a local anesthetic commonly used as a topical pain reliever or in cough drops.

Physical properties about Benzocaine are: (1)ACD/LogP: 1.945; (2)ACD/LogD (pH 5.5): 1.95; (3)ACD/LogD (pH 7.4): 1.95; (4)ACD/BCF (pH 5.5): 17.70; (5)ACD/BCF (pH 7.4): 17.72; (6)ACD/KOC (pH 5.5): 272.13; (7)ACD/KOC (pH 7.4): 272.41; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.554; (12)Molar Refractivity: 46.895 cm3; (13)Molar Volume: 146.113 cm3; (14)Polarizability: 18.591 10-24cm3; (15)Surface Tension: 44.6710014343262 dyne/cm; (16)Density: 1.131 g/cm3; (17)Flash Point: 164.199 °C; (18)Enthalpy of Vaporization: 55.159 kJ/mol; (19)Boiling Point: 310.731 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C

Preparation of Benzocaine: Preparation Products :4-Fluorobenzoic acid-->Benzonatate-->Ethyl 4-(butylamino)benzoate
Raw materials: 4-Aminobenzoic acid-->4-Aminophthalic acid-->Ethyl p-nitrobenzoate
Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA), it can be prepared from PABA and ethanol by Fischer esterification or via the reduction of ethyl p-nitrobenzoate.

Uses of Benzocaine:
1. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter anesthetic ointments (e.g. products for oral ulcers of Anbesol by Wyeth, Kank+a by Blistex, Orabase B and Orajel by Del Pharmaceuticals, and Ultracare by Ultradent). It is also combined with antipyrine to form A/B Otic Drops, (Brand name Auralgan) to relieve earpain and remove cerumen.
2. Benzocaine is used as a key ingredient in numerous pharmecuticals:Phenazone, an anti-inflammatory;Some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as Otitis Media and swimmers ear; Some previous diet products such as Ayds; Some condoms designed to prevent premature ejaculation. Benzocaine acts to desensitize the penis, and theoretically allows an erection to be maintained

When you are using this chemical, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable gloves and eye/face protection;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
5. Avoid contact with skin;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3;
(2)InChIKey=BLFLLBZGZJTVJG-UHFFFAOYSA-N;
(3)Smilesc1cc(C(OCC)=O)ccc1N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 56mg/kg (56mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
infant TDLo rectal 12mg/kg (12mg/kg) BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN New England Journal of Medicine. Vol. 263, Pg. 454, 1960.
mouse LD50 intraperitoneal 216mg/kg (216mg/kg)   Journal of Medicinal Chemistry. Vol. 17, Pg. 900, 1974.
mouse LD50 oral 2500mg/kg (2500mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1996.
rabbit LDLo oral 1150mg/kg (1150mg/kg)   Drugs in Japan Vol. 6, Pg. 33, 1982.
rat LD50 oral 3042mg/kg (3042mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Toksikologicheskii Vestnik. Vol. (2), Pg. 34, 1996.