555-06-6

Basic information

• Product Name: 4-AMINOBENZOIC ACID SODIUM SALT
• Synonyms: 4-amino-benzoicacimonosodiumsalt;antergyl;Benzoicacid,4-amino-,monosodiumsalt;monosodium4-aminobenzoate;pabavit;p-Aminobenzoicacid,sodiumsal;p-amino-benzoicacimonosodiumsalt;sodiumaminobenzoate
• CAS NO: 555-06-6
• Molecular Formula: C₇H₆NO₂*Na
• Molecular Weight: 159.12
• EINECS: 209-080-3
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 555-06-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 339.9 °C at 760 mmHg
• Flash Point: 159.4 °C
• Appearance: yellow/powder
• Vapor Pressure: 3.45E-05mmHg at 25°C
• Storage Temp.: Store at RT.
• Water Solubility: Soluble in water (50 mg/ml).
• CAS DataBase Reference: 4-AMINOBENZOIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOBENZOIC ACID SODIUM SALT(555-06-6)
• EPA Substance Registry System: 4-AMINOBENZOIC ACID SODIUM SALT(555-06-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DG2975000
• TSCA: Yes
• Hazardous Substances Data: 555-06-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow powder

Uses

Different sources of media describe the Uses of 555-06-6 differently. You can refer to the following data:
1. Analgesic.
2. 4-Aminobenzoic acid sodium salt is used as a Pharmaceutical intermediate.

Purification Methods

Recrystallise it from water. [Hermann Helv Chim Acta 9 786 1926, Beilstein 14 II 247.]

InChI:InChI=1/C7H7NO2.Na/c8-6-3-1-5(2-4-6)7(9)10;/h1-4H,8H2,(H,9,10);/q;+1/p-1

Synthetic route

4-amino-benzoic acid (150-13-0) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
With sodium hydroxide In ethanol at 69.84℃; for 1h;	92%
With sodium hydroxide In water	90%

1,1,3,3-Tetramethoxypropan-2-on-(4-ethoxycarbonyl)phenylhydrazon (81494-74-8) → sodium p-aminobenzoate (555-06-6) + 2-Amino-1,1,3,3-tetramethoxypropan (81494-56-6)

Conditions	Yield
With sodium hydroxide; hydrogen; nickel In methanol at 100℃; under 91938.4 Torr; for 100h;	A n/a B 75%

p-aminoethylbenzoate (94-09-7) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
With sodium hydroxide In ethanol at 25℃; Rate constant; var. solv.;

4-methoxycarbonyl aniline (619-45-4) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
With sodium hydroxide In ethanol at 25℃; Rate constant; var. solv.;

Mesoxaldialdehyd-2-(4-ethoxycarbonyl)phenylhydrazon (81494-73-7) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / conc. HCl / methanol / 1.) r. t., 2.) reflux, 30 min 2: H2, NaOH / Raney Ni / methanol / 100 h / 100 °C / 91938.4 Torr View Scheme

sodium 4-nitrobenzoate (3847-57-2) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
With sodium tetrahydroborate In water at 39.84℃;
With sulfuric acid; tin(IV) oxide at 85℃; for 2h; Temperature;
With sodium tetrahydroborate; water at 0 - 20℃; for 24h; chemoselective reaction;

1-methyl-4-nitrobenzene (99-99-0) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: chromium(VI) oxide; acetic acid; hydrogenchloride / water / 0.5 h / 25 °C / pH 6 2: sodium hydroxide; titanium(IV) oxide / 70 °C 3: sulfuric acid; tin(IV) oxide / 2 h / 85 °C View Scheme

4-nitro-benzoic acid (62-23-7) → sodium p-aminobenzoate (555-06-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; titanium(IV) oxide / 70 °C 2: sulfuric acid; tin(IV) oxide / 2 h / 85 °C View Scheme

(3-chloropropyl)trimethylsilane (2344-83-4) + sodium p-aminobenzoate (555-06-6) → trimethylsilyl-propyl-p-aminobenzoate

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Reflux;	97%

sodium p-aminobenzoate (555-06-6) + acetaldehyde (75-07-0) → sodium 4-hydroxy-2-methyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Conditions	Yield
In water at 25℃; for 24h; Doebner-Miller reaction;	95%

sodium p-aminobenzoate (555-06-6) + 1,3-Dichloropropane (142-28-9) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
In N-methyl-acetamide; water	95%
With sodium carbonate; dimethyl sulfoxide; 1,2-dichloro-ethane In water	91.5%

methanol (67-56-1) + nickel(II) chloride hexahydrate + sodium p-aminobenzoate (555-06-6) → [(4-amino-benzoate)2 nickel(II) (methanol)2]*methanol

Conditions	Yield
In methanol NiCl2*6H2O in methanol added to sodium 4-aminobenzoate in methanol; mixture refluxed for 2 h; light green crystals formed within one week; elem. anal.;	95%

vanadyl(IV) sulfate hydrate + sodium p-aminobenzoate (555-06-6) → oxovanadium(IV) bis(4-aminobenzoate)*H2O

Conditions	Yield
In methanol; water dropwise addn. of VO(SO4) in 50% MeOH/H2O soln. to sodium aminobenzoate in water, immediate pptn. of complex; filtered, washed (hot 50% MeOH/H2O), dried (vac., anhyd. silica gel); elem. anal.;	94%

water (7732-18-5) + europium(III) chloride (10025-76-0) + sodium p-aminobenzoate (555-06-6) → europium(III) p-aminobenzoate monohydrate

Conditions	Yield
In water byproducts: NaCl; elem. anal., TGA;	93%

water (7732-18-5) + sodium p-aminobenzoate (555-06-6) + terbium(III) chloride (10042-88-3) → terbium(III) p-aminobenzoate monohydrate

Conditions	Yield
In water byproducts: NaCl; elem. anal.;	92%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + sodium p-aminobenzoate (555-06-6) → (C5H5)2Ti(OCOC6H4NH2)2

Conditions	Yield
In benzene a mixt. of (η-C5H5)2TiCl2 and Na salt of the substituted benzoic acid in anhydrous benzene stirred at 30°C for 4 h; orange soln. filtered, concd., crystn. (refrigerator), recrystd. (benzene);	88%
In not given

copper(II) choride dihydrate + 1,10-phenanthroline hydrochloride (3829-86-5) + sodium p-aminobenzoate (555-06-6) → [Cu(phen)2Cl]Cl*2p‑aminobenzoic acid*4H2O

Conditions	Yield
In methanol for 1h;	88%

tripropyltin chloride (2279-76-7) + sodium p-aminobenzoate (555-06-6) → tri-n-propyltin(IV) p-aminobenzoate (112402-78-5)

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by extn. with light pertoleum; elem. anal.;	85%

4,4'-bipyridine (553-26-4) + (2,2'-bipyridine)copper(II) nitrate + sodium perchlorate + sodium p-aminobenzoate (555-06-6) → ([(2,2'-bipyridine)semi(4,4'-bipyridine)(p-aminobenzoate)copper(II)] perchlorate semihydrate)(n)

Conditions	Yield
In methanol refluxed for 2 h, cooled to room temp., a soln. of perhclorate added; ppt. dried (vac.); elem. anal.;	85%

4,4'-bipyridine (553-26-4) + copper (II) nitrate tetrahydrate + sodium p-aminobenzoate (555-06-6) → catena-poly[[[μ-4,4'-bipyridyl-bis[aqua(p-aminobenzoato)copper(II)]]-di-μ-4,4'-bipyridyl] dinitrate tetrahydrate]

Conditions	Yield
In methanol solns. of 4,4'-bipyridine and sodium p-NH2-benzoate in methanol added tosoln. of Cu(NO3)2*4H2O in methanol (1:1:1 molar ratio); heated under re flux for 2 h; ppt. filtered off and dried under vac.; elem. anal.;	81%

furfural (98-01-1) + sodium p-aminobenzoate (555-06-6) → Sodium; 4-[(tetrahydro-furan-2-ylmethyl)-amino]-benzoate

Conditions	Yield
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr; Rate constant; Thermodynamic data; E(a);	80%
With hydrogen; AV-17-8-Pd In ethanol at 45℃; under 750.06 Torr;	80%

trimethyltin(IV)chloride (1066-45-1) + sodium p-aminobenzoate (555-06-6) → trimethyltin(IV) p-aminobenzoate (77928-13-3)

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by recrystn. from EtOH; elem. anal.;	80%

tributyltin chloride (1461-22-9) + sodium p-aminobenzoate (555-06-6) → tri-n-butyltin(IV) p-aminobenzoate (23059-99-6)

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by extn. with light pertoleum; elem. anal.;	80%

sodium p-aminobenzoate (555-06-6) + triphenyltin chloride (639-58-7) → triphenyltin(IV) p-aminobenzoate (61057-42-9)

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by washing with light petroleum; elem. anal.;	80%

tricyclohexyltin(IV) chloride (3091-32-5) + sodium p-aminobenzoate (555-06-6) → tricyclohexyltin(IV) p-aminobenzoate (87414-52-6)

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by recrystn. from EtOH; elem. anal.;	78%

sodium p-aminobenzoate (555-06-6) + tri(α-naphthyl)antimony(III) dichloride (444307-81-7, 52762-61-5) → tri(α-naphthyl)antimony(V) (OOCC6H4NH2-para)(Cl)

Conditions	Yield
In methanol; benzene byproducts: NaCl; at reflux temp.; elem. anal.;	78%

D-Glucose (2280-44-6) + sodium p-aminobenzoate (555-06-6) → Sodium; 4-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylamino)-benzoate (72108-61-3)

Conditions	Yield
In ethanol; water	76%

diphenylantimony(III) chloride (2629-47-2) + sodium p-aminobenzoate (555-06-6) → Sb(3+)*2C6H5(1-)*OCOC6H4NH2(1-)=(C6H5)2Sb(OCOC6H4NH2)

Conditions	Yield
In methanol byproducts: NaCl; at 40-80°C under anhydrous and oxygen free conditions; elem. anal.;	75%

sodium p-aminobenzoate (555-06-6) + 1,2-dichloro-ethane (107-06-2) → O,O'-bis(p-aminobenzoyl)-1,2-ethylebediol (10505-05-2)

Conditions	Yield
With sodium benzoate In N,N-dimethyl-formamide at 120℃; for 3h;	74%

tribenzyltin(IV) chloride (3151-41-5) + sodium p-aminobenzoate (555-06-6) → tribenzyltin(IV) p-aminobenzoate

Conditions	Yield
In ethanol byproducts: NaCl; refluxed in abs. EtOH for 3-4 h; concd., cooled, filtered, benzene was added to the filtrate, mixt. was refluxed for ca. 2 h in a Dean-Stark apparatus filtering off any sepd. NaCl, solvent was removed, residue was purified by washing with light petroleum; elem. anal.;	70%

sodium p-aminobenzoate (555-06-6) + chlorobis(4-methylphenyl)antimony (87856-04-0) → Sb(3+)*2CH3C6H4(1-)*OCOC6H4NH2(1-)=(CH3C6H4)2Sb(OCOC6H4NH2)

Conditions	Yield
In methanol byproducts: NaCl; at 40-80°C under anhydrous and oxygen free conditions; elem. anal.;	65%

mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin (67217-55-4) + sodium p-aminobenzoate (555-06-6) → mono-6-O-p-aminobenzoyl-β-cyclodextrin (864380-54-1)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 72h; Inert atmosphere;	51%

(Cd(1,4,7,10-tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetrazacyclododecane))(ClO4)2 + sodium p-aminobenzoate (555-06-6) → (Cd(1,4,7,10-tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetrazacyclododecane)(p-aminobenzoate))ClO4

Conditions	Yield
In acetonitrile sodium p-aminobenzoate was added to soln. (Cd((S)-thphpc12))(ClO4)2 in MeCN and refluxed for 2 h; react. mixt. was cooled to room temp., solvent was removed, residue was suspended in water and heated to boiling, MeCN was added, soln. was cooled slowly, ppt. was filtered; elem. anal.;	50%

sodium p-aminobenzoate (555-06-6) → 4-azidobenzoic acid (6427-66-3)

Conditions	Yield
Stage #1: sodium p-aminobenzoate With p-toluenesulfonic acid monohydrate; sodium nitrite In water at 20℃; for 0.333333h; Stage #2: With sodium azide In water at 20℃; for 0.5h;	50%

Tris(2-chloroethyl) phosphate (115-96-8) + sodium p-aminobenzoate (555-06-6) → tris[2-(p-aminobenzoyloxy)ethyl] phosphate

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; N-benzyl-N,N,N-triethylammonium chloride In N,N-dimethyl-formamide 1.) 110 deg C, 2 h, 2.) 130 deg C, 1 h;	46%

sodium p-aminobenzoate (555-06-6) + pantolactone (79-50-5) → (+/-)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid (70006-36-9)

Conditions	Yield
at 190℃; for 72h;	45%

Upstream product

• 62-23-7 4-nitro-benzoic acid 
• 99-99-0 1-methyl-4-nitrobenzene 
• 3847-57-2 sodium 4-nitrobenzoate 
• 150-13-0 4-amino-benzoic acid 
• 81494-73-7 Mesoxaldialdehyd-2-(4-ethoxycarbonyl)phenylhydrazon 
• 619-45-4 4-methoxycarbonyl aniline 
• 81494-74-8 1,1,3,3-Tetramethoxypropan-2-on-(4-ethoxycarbonyl)phenylhydrazon 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 72108-61-3 Sodium; 4-((3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-ylamino)-benzoate 
• 193750-57-1 NH₂C₆H₄COOI 
• 70006-36-9 (+/-)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid 
• 77928-13-3 trimethyltin(IV) p-aminobenzoate 
• 864380-54-1 mono-6-O-p-aminobenzoyl-β-cyclodextrin 
• 488786-75-0 4-((2S,6R)-3,5-Dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl)-benzoic acid 2-(3,4-dimethyl-phenyl)-2-oxo-ethyl ester 
• 352672-09-4 4-(1,3-dioxo-1,3,3a,4,7,7a-hexahydro-isoindol-2-yl)-benzoic acid 2-(3,4-dimethyl-phenyl)-2-oxo-ethyl ester 

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