133-10-8

Usage

Safety Profile

Moderately toxic by intraperitoneal, subcutaneous, and intravenous routes. Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of NO, and Na2O

InChI:InChI=1/C7H7NO3.Na.2H2O/c8-4-1-2-5(7(10)11)6(9)3-4;;;/h1-3,9H,8H2,(H,10,11);;2*1H2/q;+1;;/p-1

Synthetic route

4-Aminosalicylic acid (65-49-6) → sodium p-aminosalicylate (133-10-8)

Conditions	Yield
With sodium carbonate
With sodium hydroxide In water at 20℃;

cytosinium 4-aminosalicylate (65944-71-0) → sodium p-aminosalicylate (133-10-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / Milling 2: sodium hydroxide / water / 20 °C View Scheme

1,3,5-trichloro-2,4,6-triazine (108-77-0) + disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid (7336-20-1) + sodium p-aminosalicylate (133-10-8) + methylamine (74-89-5) → C36H28N12O12S2(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid Stage #2: sodium p-aminosalicylate Stage #3: methylamine	98%

N-ethoxycarbonylphthalimide (22509-74-6) + sodium p-aminosalicylate (133-10-8) → 2-hydroxy-4-(1,3-dioxoisoindolin-2-yl)benzoic acid (36467-52-4)

Conditions	Yield
With sodium hydrogencarbonate; triethylamine In water at 5℃; for 5h;	95.1%

copper(II) chloride monohydrate + sodium p-aminosalicylate (133-10-8) → [Cu2(p-aminosalicylato)4(H2O)2] (1277176-65-4)

Conditions	Yield
In ethanol reacted for 0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	88%

diethylenetriaminepentaacetic dianhydride (23911-26-4) + sodium p-aminosalicylate (133-10-8) → C28H28N5O14(5-)*5Na(1+)

Conditions	Yield
In dimethyl sulfoxide at 20℃; for 2h;	85%
In dimethyl sulfoxide for 1.5h; Ambient temperature;	55%

acetic anhydride (108-24-7) + sodium p-aminosalicylate (133-10-8) → 4-acetamidosalicylic acid (50-86-2)

Conditions	Yield
In water at 45℃; for 4h;	84.12%

copper(II) chloride monohydrate + sodium p-aminosalicylate (133-10-8) + Trimethylenediamine (109-76-2) → [Cu(p-aminosalicylato)2(1,3-propanediamine)2] (1277176-70-1)

Conditions	Yield
In ethanol a soln. of Cu salt added to a soln. of Na salt, CH2(CH2NH2)2 added after0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	84%

sodium p-aminosalicylate (133-10-8) + 2-methylsulfanyl-thiazol-4-one (20949-66-0) → 2-(4-carboxy-3-hydroxyphenyl)amino-Δ2-thiazolin-4-one (81059-99-6)

Conditions	Yield
In ethanol for 1.5h; Heating;	80%

ethylenediaminetetraacetic dianhydride (23911-25-3) + sodium p-aminosalicylate (133-10-8) → C24H24N4O12(2-)*2Na(1+)

Conditions	Yield
With magnesium sulfate In dimethyl sulfoxide at 70℃; for 18h; Inert atmosphere;	80%

copper(II) chloride monohydrate + sodium p-aminosalicylate (133-10-8) + ethylenediamine (107-15-3) → [Cu(p-aminosalicylato)2(ethylenediamine)2] (70459-99-3, 1277176-66-5)

Conditions	Yield
In ethanol a soln. of Cu salt added to a soln. of Na salt, (CH2NH2)2 added after 0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	78%

sodium p-aminosalicylate (133-10-8) + Methacryloyl chloride (920-46-7) → N-methacryloyl-p-aminosalicylic acid (50512-48-6)

Conditions	Yield
With sodium hydroxide In water at 0℃; for 5h; pH 9-10;	77%

morpholine (110-91-8) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) + disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid (7336-20-1) + sodium p-aminosalicylate (133-10-8) → C42H36N12O14S2(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; disodium salt of 4,4'-diaminostilbene-2,2'-disulfonic acid In water; acetone at 0℃; for 1h; pH=6 - 7; Stage #2: sodium p-aminosalicylate at 40 - 50℃; for 0.5h; pH=10 - 11; Stage #3: morpholine	74%

copper(II) chloride monohydrate + N,N,N,N,-tetramethylethylenediamine (110-18-9) + sodium p-aminosalicylate (133-10-8) → [Cu(p-aminosalicylato)2(N,N,N',N'-tetramethylethylenediamine)2] (1277176-69-8)

Conditions	Yield
In ethanol a soln. of Cu salt added to a soln. of Na salt, (CH2N(CH3)2)2 added after 0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	72%

copper(II) chloride monohydrate + sodium p-aminosalicylate (133-10-8) + N,N`-dimethylethylenediamine (110-70-3) → [Cu(p-aminosalicylato)2(N,N'-dimethylethylenediamine)2] (1277176-68-7)

Conditions	Yield
In ethanol a soln. of Cu salt added to a soln. of Na salt, (CH2NHCH3)2 added after 0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	70%

sodium p-aminosalicylate (133-10-8) + benzyl chloroformate (501-53-1) → 4‐{[(benzyloxy)carbonyl]amino}‐2‐hydroxybenzoic acid (6935-15-5)

Conditions	Yield
Stage #1: sodium p-aminosalicylate; benzyl chloroformate With sodium hydroxide In water; toluene at 0 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene at 0℃;	68%
Stage #1: sodium p-aminosalicylate; benzyl chloroformate With sodium hydroxide In water; toluene at 0 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene at 0℃;	68%
Stage #1: sodium p-aminosalicylate; benzyl chloroformate With sodium hydroxide In water; toluene at 0 - 20℃; for 48h; Stage #2: With hydrogenchloride In water; toluene at 0℃;	68%

copper(II) chloride monohydrate + sodium p-aminosalicylate (133-10-8) + N,N-dimethylethylenediamine (108-00-9) → [Cu(p-aminosalicylato)2(N,N-dimethylethylenediamine)2] (1277176-67-6)

Conditions	Yield
In ethanol a soln. of Cu salt added to a soln. of Na salt, (CH3)2NC2H4NH2 added after 0.5 h; H2O added slowly, filtered, rinsed with H2O and cold EtOH; elem. anal.;	65%

sodium p-aminosalicylate (133-10-8) + acryloyl chloride (814-68-6) → 4-(acrylamido)-2-hydroxybenzoic acid (24599-26-6)

Conditions	Yield
In diethyl ether for 2h; Acylation;	57%
In water	57%
In water at 5 - 20℃; for 2h;

sodium p-aminosalicylate (133-10-8) → 4-acetamidosalicylic acid (50-86-2)

Conditions	Yield
With hydrogenchloride; acetic anhydride In water	56%

1,10-Phenanthroline (66-71-7) + cadmium(II) nitrate tetrhydrate + ethanol (64-17-5) + sodium p-aminosalicylate (133-10-8) → [Cd(AS)2(1,10-phenanthroline)2]EtOH

Conditions	Yield
In water at 20℃; for 96h; Sealed tube;	28%

phosgene (75-44-5) + sodium p-aminosalicylate (133-10-8) → 2,2'-dihydroxy-4,4'-ureylene-di-benzoic acid (109411-59-8)

Conditions	Yield
With sodium hydroxide; acetone

2-bromoacetyl chloride (22118-09-8) + sodium p-aminosalicylate (133-10-8) → 4-(2-bromo-acetylamino)-2-hydroxy-benzoic acid

1-Iodooctane (629-27-6) + sodium p-aminosalicylate (133-10-8) → 2-hydroxy-4-octylamino-benzoic acid (101108-65-0)

Conditions	Yield
With ethanol

diethyl phosphorisothiocyanatidate (6374-26-1) + sodium p-aminosalicylate (133-10-8) → 4-(N'-diethoxyphosphoryl-thioureido)-2-hydroxy-benzoic acid

Conditions	Yield
With diethyl ether

L-arabinose (5328-37-0) + sodium p-aminosalicylate (133-10-8) → 4-L-arabitol-1-ylidenamino-2-hydroxy-benzoic acid

Conditions	Yield
With water

D-glucose (50-99-7) + sodium p-aminosalicylate (133-10-8) → 4-D-glucitol-1-ylidenamino-2-hydroxy-benzoic acid

Conditions	Yield
With formic acid

2-iodoacetyl chloride (38020-81-4) + sodium p-aminosalicylate (133-10-8) → 2-hydroxy-4-(2-iodo-acetylamino)-benzoic acid (4323-00-6)

Conditions	Yield
With water

1-iodohexadecane (544-77-4) + sodium p-aminosalicylate (133-10-8) → 4-(hexadecylamino)-2-hydroxybenzoic acid (86410-31-3)

Conditions	Yield
With ethanol

pentyl chloroformate (638-41-5) + sodium p-aminosalicylate (133-10-8) → 2-hydroxy-4-pentyloxycarbonylamino-benzoic acid (107416-66-0)

Conditions	Yield
With water

2-chlorophenylisothiocyanate (2740-81-0) + sodium p-aminosalicylate (133-10-8) → 4-[N'-(2-chloro-phenyl)-thioureido]-2-hydroxy-benzoic acid

Conditions	Yield
With methanol
With methanol

2-[2-(N-acetyl-anilino)-vinyl]-3,4-dimethyl-thiazolium; iodide + sodium p-aminosalicylate (133-10-8) → 4-[(3,4-dimethyl-3H-thiazol-2-yliden)-ethylidenamino]-2-hydroxy-benzoic acid ; 4-amino-2-hydroxy benzoate

Conditions	Yield
With ethanol

4-[2-(N-acetyl-anilino)-vinyl]-1-ethyl-quinolinium; iodide (56278-25-2) + sodium p-aminosalicylate (133-10-8) → 4-[2-(1-ethyl-1H-[4]quinolyliden)-ethylidenamino]-2-hydroxy-benzoic acid ; 4-amino-2-hydroxy benzoate

Conditions	Yield
With ethanol

Upstream product

• 65-49-6 4-Aminosalicylic acid 
• 65944-71-0 cytosinium 4-aminosalicylate 

Downstream Products

• 109411-59-8 2,2'-dihydroxy-4,4'-ureylene-di-benzoic acid 
• 101108-65-0 2-hydroxy-4-octylamino-benzoic acid 
• 86410-31-3 4-(hexadecylamino)-2-hydroxybenzoic acid 
• 107416-66-0 2-hydroxy-4-pentyloxycarbonylamino-benzoic acid 
• 24718-70-5 2-hydroxy-4-(N'-methyl-thioureido)-benzoic acid 
• 109337-88-4 2-hydroxy-4-(3-(4-methoxyphenyl)thioureido)benzoic acid 
• 26416-41-1 4-[N'-(4-ethoxy-phenyl)-thioureido]-2-hydroxy-benzoic acid 
• 14463-22-0 4-(2-chloro-acetylamino)-2-hydroxy-benzoic acid 
• 81059-99-6 2-(4-carboxy-3-hydroxyphenyl)amino-Δ²-thiazolin-4-one 
• 50512-48-6 N-methacryloyl-p-aminosalicylic acid 
• 66761-27-1 4-carboxy-3-hydroxyphenyl azide 
• 70459-99-3 [Cu(p-aminosalicylato)2(ethylenediamine)2] 
• 1277176-70-1 [Cu(p-aminosalicylato)2(1,3-propanediamine)2] 
• 1277176-68-7 [Cu(p-aminosalicylato)2(N,N'-dimethylethylenediamine)2] 

Relevant academic research and scientific papers

An interesting pseudo-honeycomb supramolecular arrangement obtained from the interaction between 4-aminosalicylic acid, trans-1,2-bis(4-pyridyl)ethylene and transition metal ions

In this work, three new compounds containing coordination polymers named [Co(bpe)(H2O)4]AS2·4H2O (1), [Ni(bpe)(H2O)4]AS2·4H2O (2) and [Zn(bpe)(H2O)4/s

4-aminosalicylic acid adducts

4-Aminosalicylic acid (p-aminosalicylic acid, PAS), an antituberculosis drug, is a model active pharmaceutical ingredient to study salt and cocrystal formation in a multiple hydrogen-bonding functionality molecule with carboxylic acid, amine, and phenol groups. A cytosine salt CYT+-PAS-, salt cocrystal hydrate CYT+-PAS--CYT-H2O, and nicotinamide cocrystal hydrate PAS-NAM-H2O, are described in this article. Furthermore, X-ray crystal structures of PAS sodium dihydrate, sulfate, and mesylate salts and dehydration/rehydration behavior of the sodium salt by powder X-ray diffraction are discussed.

Water soluble thymidine derivative

Thymidine may have its solubility in water increased by as much as 10 times or even more by combining the thymidine with a solubilizing agent, such as a salicylate derivative selected from salicylic acid, amino and methyleneamino substituted salicylic aci