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150-13-0

Basic Information
CAS No.: 150-13-0
Name: 4-Aminobenzoic acid
Article Data: 341
Cas Database
Molecular Structure:
Molecular Structure of 150-13-0 (4-Aminobenzoic acid)
Formula: C7H7NO2
Molecular Weight: 137.138
Synonyms: Benzoic acid,4-amino-;para-aminobenzoate;Benzoic acid, 4-amino-;Anti-Chromotrichia factor;Acidum paraminobenzoicum;para-Aminobenzoic acid;Trichochromogenic factor;P.A.B.A. ( Para Aminobenzoic Acid );
EINECS: 205-753-0
Density: 1.315 g/cm3
Melting Point: 186-189 °C
Boiling Point: 339.9 °C at 760 mmHg
Flash Point: 159.4 °C
Solubility: water:4.7 g/L (20 °C)
Appearance: White to off white crystalline powder
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 22-36/37/38-43
Safety: 26-36/37/39
Transport Information: N/A
PSA: 63.32000
LogP: 1.54820
Synthetic route
62-23-7

4-nitro-benzoic acid

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 50℃; for 0.0833333h; Green chemistry;100%
With hydrogen In ethanol; water at 25℃; under 11251.1 Torr; for 6h; chemoselective reaction;99%
With hydrazine hydrate In water at 110℃; Sealed tube; Green chemistry;99%
6427-66-3

4-azidobenzoic acid

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With diphenyl sulfide; hydrogen; palladium on activated charcoal In methanol at 20℃; under 760 Torr; for 24h;100%
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;100%
With formic acid; tris(2,2'-bipyridyl)ruthenium dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Irradiation; chemoselective reaction;99%
623-04-1

4-aminobenzenemethanol

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With silica-supported Jones reagent In dichloromethane for 0.035h;99.8%
With potassium hydroxide In 1,3,5-trimethyl-benzene at 160℃; for 24h; Inert atmosphere;75%
Stage #1: 4-aminobenzenemethanol With C27H29BrFIrN2O; potassium hydroxide In toluene for 10h; Inert atmosphere; Reflux;
Stage #2: With hydrogenchloride In water
67%
Stage #1: 4-aminobenzenemethanol With ((CH3C6H4CH(CH3)2)RuI(C6H4NC3H2NCH3)); potassium hydroxide In m-xylene for 6h; Schlenk technique; Reflux; Inert atmosphere;
Stage #2: With hydrogenchloride In water; m-xylene pH=6; Schlenk technique; Inert atmosphere;
10%
62-23-7

4-nitro-benzoic acid

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
619-58-9

4-iodobenzoic acid

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;97%
With ammonium hydroxide; copper(l) iodide; phosphate potassium salt In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere;88%
586-91-4

azobenzene-4,4'-dicarboxylic acid

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With aminomethylpolystyrene-supported formate; palladium on activated charcoal In methanol at 20℃; for 4h;96%
With polystyrene-CH2-HN3(+)HCO2(-); magnesium In methanol at 20℃; for 0.283333h;95%
With aminomethyl polysterene resin formic acid salt; zinc In methanol at 20℃; for 0.333333h;94%
With sodium dithionite; water In dimethyl sulfoxide at 20℃; pH=7.4; Kinetics; phosphate buffer;
With sodium tetrahydroborate; water; fullerene-C60; sodium hydroxide at 20℃; for 5h; pH=11; UV-irradiation;
14786-27-7

benzyl 4-nitrobenzoate

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;96%
1562-93-2

4-(2-phenyldiazen-1-yl)benzoic acid

A

150-13-0

4-amino-benzoic acid

B

62-53-3

aniline

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.166667h;A 80%
B 95%
With hydrazine hydrate; aluminium In ethanol Heating;A 87%
B 95%
With zinc; hydrazinium monoformate In methanol for 0.15h; Heating;A 90%
B n/a
7681-52-9

sodium hypochlorite

6757-31-9

methyl-4-carbamoylbenzoate

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
Stage #1: methyl-4-carbamoylbenzoate With sodium hydroxide In water at 0℃; Hofmann Degradation;
Stage #2: sodium hypochlorite In water at 0 - 50℃; for 3.5h; Product distribution / selectivity;
95%
619-45-4

4-methoxycarbonyl aniline

150-13-0

4-amino-benzoic acid

Conditions
ConditionsYield
With AlBrCl3(1-)*C5H5N*H(1+) at 140℃; for 3h;95%
With water; potassium hydroxide In methanol at 55℃; for 3h; Inert atmosphere;78%
With sodium hydroxide for 1h;
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Specification

1.Introduction of 4-Aminobenzoic acid

The 4-Aminobenzoic acid, with its CAS NO of 150-13-0, is a kind of White Crystalline Powder. It has synonyms of Benzoic acid,4-amino-;para-aminobenzoate;Benzoic acid, 4-amino-;Anti-Chromotrichia factor;Acidum paraminobenzoicum;para-Aminobenzoic acid and Trichochromogenic factor. 4-Aminobenzoic acid should be stored  in a cool, dry place and keep away from direct sunlight. It is mainly used as intermediate.
 

2.Properties of 4-Aminobenzoic acid

(1) H bond acceptors: 3  (2) H bond donors: 3  (3) Freely Rotating Bonds: 2
(4) Polar Surface Area: 29.54 Å2  (5) Index of Refraction: 1.637  (6) Molar Refractivity: 37.41 cm3
(7) Molar Volume: 104.2 cm3 (8) Surface Tension: 64.3 dyne/cm (9) Density: 1.315 g/cm3
(10) Flash Point: 159.4 °C  (11) Enthalpy of Vaporization: 61.57 kJ/mol  (12) Boiling Point: 339.9 °C at 760 mmHg
(13) Vapour Pressure: 3.45E-05 mmHg at 25°C (14) Melting Point: 186-189 °C (15) Water Solubility: 4.7 g/L (20 ºC)
 

3.Structure descriptors of 4-Aminobenzoic acid

IUPAC Name: 4-aminobenzoic acid

InChI: InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)

InChIKey: ALYNCZNDIQEVRV-UHFFFAOYSA-N

Canonical SMILES : C1=CC(=CC=C1C(=O)O)N
 

4.Safety information of 4-Aminobenzoic acid

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38-43
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R43: May cause sensitization by skin contact.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
RTECS: DG1400000
HS Code: 29224995
 

5.Uses of 4-Aminobenzoic acid

In the past, 4-Aminobenzoic acid (CAS NO.150-13-0) has been widely used as a UV filter in sunscreen formulations, but then it has been determined that it increases the formation of a particular DNA defect in human cells, thus increasing the risk of skin cancer. Now,safer and more effective derivatives of 4-Aminobenzoic acid are more commonly used.
 

6.Toxity data of 4-Aminobenzoic acid

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 1gm/kg (1000mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 49, Pg. 184, 1942.
mouse LD50 oral 2850mg/kg (2850mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE WEAKNESS
Proceedings of the Society for Experimental Biology and Medicine. Vol. 49, Pg. 184, 1942.
rabbit LD50 intravenous 2gm/kg (2000mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 1, Pg. 71, 1942.
rabbit LD50 oral 1830mg/kg (1830mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 10, Pg. 289, 1951.
rat LD50 intraperitoneal > 3450mg/kg (3450mg/kg)   Bollettino Chimico Farmaceutico. Vol. 112, Pg. 53, 1973.
rat LD50 oral > 6gm/kg (6000mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 49, Pg. 184, 1942.