133-91-5

Basic information

• Product Name: 3,5-Diiodosalicylic acid
• Synonyms: 2-HYDROXY-3,5-DIIODOBENZOIC ACID;3,5-DIIODOSALICYLIC ACID;3,5-DIIODO-2-BENZOXYBENZOIC ACID;3,5-DIIODO-2-HYDROXYBENZOIC ACID;RARECHEM AL BE 0656;2-Hydroxy-3,5-diiodobenzenecarboxylic acid;2-Hydroxy-3,5-diiodobenzoate;2-hydroxy-3,5-diiodo-benzoicaci
• CAS NO: 133-91-5
• Molecular Formula: C7H4I2O3
• Molecular Weight: 389.91
• EINECS: 205-124-0
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids
• Mol File: 133-91-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 220-230 °C (dec.)(lit.)
• Boiling Point: 260°C (rough estimate)
• Flash Point: 184.1 °C
• Appearance: Off-white to beige or grey powder
• Density: 2.4343 (estimate)
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Storage Temp.: -20°C
• Solubility: 0.192g/l
• PKA: 2.07±0.14(Predicted)
• Water Solubility: 0.02 g/100mL (25 ºC)
• Sensitive: Light Sensitive
• Merck: 14,3190
• BRN: 2615358
• CAS DataBase Reference: 3,5-Diiodosalicylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diiodosalicylic acid(133-91-5)
• EPA Substance Registry System: 3,5-Diiodosalicylic acid(133-91-5)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: VO2800000
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 133-91-5(Hazardous Substances Data)

Usage

Chemical Properties

OFF-WHITE TO BEIGE OR GREY POWDER

Uses

Different sources of media describe the Uses of 133-91-5 differently. You can refer to the following data:
1. 3,5-Diiodosalicylic Acid is an metabolite of Aspirin (A187780), an anti-inflammatory, anti-platelet and cancer-preventive agent. 3,5-Diiodosalicylic Acid was shown to exhibit agonist activity at GPR35 , a orphan G protein coupled receptor.
2. 3,5-Diiodosalicylic Acid is an metabolite of Aspirin (A187780), an anti-inflammatory, anti-platelet and cancer-preventive agent. 3,5-Diiodosalicylic Acid was shown to exhibit agonist activity at GPR35, a orphan G protein coupled receptor.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C7H4I2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)/p-1

Synthetic route

salicylic acid (69-72-7) → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With dihydrogen peroxide; iodine; trichloroacetic acid In methanol at 45 - 66℃; for 6h;	95.9%
With N-iodo-succinimide In water; acetonitrile at 25 - 30℃; for 0.333333h;	95%
With sodium hydrogencarbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate In methanol; dichloromethane for 7h; Ambient temperature;	91%

3,5-diodosalicylaldehyde (2631-77-8) → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With permanganate(VII) ion; acetone

2-hydroxy-5-iodobenzoic acid (119-30-2) → 3,5-diiodosalicylic acid (133-91-5)

2-hydroxy-3-iodobenzoic acid (520-79-6) → 3,5-diiodosalicylic acid (133-91-5)

silver salicylate (528-93-8, 14800-64-7) → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With iodine

salicylic acid (69-72-7) → 2-hydroxy-5-iodobenzoic acid (119-30-2) + 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With ethanol; iodine

3-acetyl-6,8-diiodo-chroman-2,4-dione + KOH-solution → 3,5-diiodosalicylic acid (133-91-5)

6,8-diiodo-2,4-dioxo-chroman-3-carbonitrile + KOH-solution → 3,5-diiodosalicylic acid (133-91-5)

6,8-diiodo-2,4-dioxo-chroman-3-carboxylic acid ethyl ester + KOH-solution → 3,5-diiodosalicylic acid (133-91-5)

ethanol (64-17-5) + iodine (7553-56-2) + salicylic acid (69-72-7) → 2-hydroxy-5-iodobenzoic acid (119-30-2) + 2-hydroxy-3-iodobenzoic acid (520-79-6) + 3,5-diiodosalicylic acid (133-91-5)

3,5-diodosalicylaldehyde (2631-77-8) + acetone (67-64-1) + permanganate → 3,5-diiodosalicylic acid (133-91-5)

ethanol (64-17-5) + 2-hydroxy-5-iodobenzoic acid (119-30-2) + iodine (7553-56-2) + yellow mercury oxide → 3,5-diiodosalicylic acid (133-91-5)

ethanol (64-17-5) + 2-hydroxy-3-iodobenzoic acid (520-79-6) + iodine (7553-56-2) + yellow mercury oxide → 3,5-diiodosalicylic acid (133-91-5)

2-hydroxy-3,5-diiodobenzoyl chloride (42016-91-1) + water (7732-18-5) → 3,5-diiodosalicylic acid (133-91-5)

alkaline aqueous sodium salicylate → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With iodine

mercury (II)-salicylate → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
With sodium chloride Erwaermen des Reaktionsprodukts mit Jod in Methanol;

salicylic acid (69-72-7) → 3,5-diiodosalicylic acid (133-91-5) + iodosalicylic acid

Conditions	Yield
With ethanol; iodine; mercury(II) oxide

dichlorophosphoric acid-(2,4-diiodo-6-trichloromethyl-phenyl ester) + water (7732-18-5) → 3,5-diiodosalicylic acid (133-91-5)

iodine (7553-56-2) + sodium salicylate (54-21-7) + alkaline aqueous solution → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
anschliessendes Erhitzen;

hexamethylenetetramine (100-97-0) + 2-hydroxy-5-iodobenzoic acid (119-30-2) → 3,5-diiodosalicylic acid (133-91-5) + 3-formyl-2-hydroxy-5-iodobenzoic acid (685870-21-7)

Conditions	Yield
Stage #1: hexamethylenetetramine; 2-hydroxy-5-iodobenzoic acid With trifluoroacetic acid at 90℃; Duff reaction; Stage #2: With hydrogenchloride for 5h; Title compound not separated from byproducts;

5-Aminosalicylic Acid (89-57-6) → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / Diazotization.Eintragen der Diazoloesung in konzentrierte Jodwasserstoffsaeure und nachfolgendes Erwaermen auf 80-90grad View Scheme

3-aminosalicylic acid (570-23-0) → 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: Behandeln des Sulfats mit Natriumnitrit in Wasser und Erwaermen der Diazoloesung mit konz. Jodwasserstoffsaeure auf 80-90grad View Scheme

salicylic acid (69-72-7) → 2-hydroxy-5-iodobenzoic acid (119-30-2) + 2-hydroxy-3-iodobenzoic acid (520-79-6) + 3,5-diiodosalicylic acid (133-91-5)

Conditions	Yield
Stage #1: salicylic acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-iodo-succinimide In acetonitrile at 20℃; for 48h;

3,5-diiodosalicylic acid (133-91-5) + dimethyl sulfate (77-78-1) → methyl 3,5-diiodo-2-methoxybenzoate (121789-21-7)

Conditions	Yield
With potassium carbonate In acetone for 16h; Heating / reflux;	100%
With potassium carbonate In acetone for 6h; Methylation; Heating;	96%
With potassium carbonate Inert atmosphere;	95%
With potassium carbonate In acetone for 12h; Heating;	93%
With potassium carbonate In acetone Heating; Yield given;

4-iodo-2-methylaniline (13194-68-8) + 3,5-diiodosalicylic acid (133-91-5) → 2-Hydroxy-3,5-diiodo-N-(4-iodo-2-methyl-phenyl)-benzamide (90426-00-9)

Conditions	Yield
With phosphorus trichloride In xylene at 140℃; for 4h;	91%

3,5-diiodosalicylic acid (133-91-5) + 2-amino-benzenethiol (137-07-5) → 2-Benzothiazol-2-yl-4,6-diiodo-phenol (90481-45-1)

Conditions	Yield
With phosphorus trichloride In toluene for 4h; Heating;	90%

3,5-diiodosalicylic acid (133-91-5) + 4-nitro-aniline (100-01-6) → 2-Hydroxy-3,5-diiodo-N-(4-nitro-phenyl)-benzamide (19503-66-3)

Conditions	Yield
With trichlorophosphate In toluene	88%

3,4-Lutidin (583-58-4) + zinc(II) nitrate hexahydrate + 3,5-diiodosalicylic acid (133-91-5) → [(3,4-dimethylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions	Yield
In ethanol	87%

3-Bromopyridine (626-55-1) + zinc(II) nitrate hexahydrate + 3,5-diiodosalicylic acid (133-91-5) → [(3-bromopyridine)2Zn(3,5-iodosalicylate)2]

Conditions	Yield
In ethanol	87%

3,5-diiodosalicylic acid (133-91-5) + 2,4-difluorophenylamine (367-25-9) → N-(2,4-Difluoro-phenyl)-2-hydroxy-3,5-diiodo-benzamide (79402-06-5)

Conditions	Yield
With phosphorus trichloride In xylene at 140℃; for 4h;	84%

3,5-diiodosalicylic acid (133-91-5) + 3-phenyl-4-amino-5-mercapto-1,2,4-triazole (22706-11-2) → 2-hydroxy-3,5-diiodo-N-(3-phenyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl)benzamide

Conditions	Yield
Stage #1: 3,5-diiodosalicylic acid With benzotriazol-1-ol; 1,2-dichloro-ethane In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 3-phenyl-4-amino-5-mercapto-1,2,4-triazole In N,N-dimethyl-formamide for 2h;	84%

4-Chloro-3-nitroaniline (635-22-3) + 3,5-diiodosalicylic acid (133-91-5) → 3,5-Diiodo-4'-chloro-3'-nitrosalicylanilide (128126-92-1)

Conditions	Yield
With trichlorophosphate In toluene	83%

picoline (108-89-4) + zinc(II) nitrate hexahydrate + 3,5-diiodosalicylic acid (133-91-5) → [(4-methylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions	Yield
In ethanol	83%

3,5-Lutidine (591-22-0) + zinc(II) nitrate hexahydrate + 3,5-diiodosalicylic acid (133-91-5) → [(3,5-dimethylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions	Yield
In ethanol	83%

3-Methylpyridine (108-99-6) + zinc(II) nitrate hexahydrate + 3,5-diiodosalicylic acid (133-91-5) → [(3-methylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions	Yield
In ethanol	79%

2-nitro-1,4-phenylenediamine (5307-14-2) + 3,5-diiodosalicylic acid (133-91-5) → 3,5-Diiodo-4'-amino-3'-nitrosalicylanilide (128126-84-1)

Conditions	Yield
With trichlorophosphate In toluene at 140℃; for 8h;	75%

3,5-diiodosalicylic acid (133-91-5) + p-aminoethylbenzoate (94-09-7) → 4-(2-Hydroxy-3,5-diiodo-benzoylamino)-benzoic acid ethyl ester (128126-93-2)

Conditions	Yield
With trichlorophosphate In toluene	75%

aminocoumarine (1635-31-0) + 3,5-diiodosalicylic acid (133-91-5) → 2-hydroxy-3,5-diiodo-N-(2-oxo-2H-chromen-3-yl)benzamide

Conditions	Yield
With phosphorus trichloride In acetonitrile Reflux;	75%

3,5-diiodosalicylic acid (133-91-5) + 5-(phenylthio)-1H-benzo[d]imidazol-2-amine (53065-28-4) → 2-(3,5-Diiodosalicyloyl)amino-5-phenylthio-benzimidazole (128126-87-4)

Conditions	Yield
With trichlorophosphate In toluene at 140℃;	70%

1,10-Phenanthroline (66-71-7) + tetrakis(acetato)diaquadicopper(II) + 3,5-diiodosalicylic acid (133-91-5) → Cu(3,5-C6H2I2(O)(COO))(1,10-phenanthroline)*2H2O

Conditions	Yield
In ethanol addn. of filtered soln. of acid to soln. of Cu-compound and 1,10-phenanthroline; heating;; filtration; washing (EtOH); elem. anal.;	70%

4-aminophenyl phenyl sulfide (1135-14-4) + 3,5-diiodosalicylic acid (133-91-5) → 2-Hydroxy-3,5-diiodo-N-(4-phenylsulfanyl-phenyl)-benzamide (128126-94-3)

Conditions	Yield
With trichlorophosphate In toluene	65%

4-amino-4'-methyldiphenylsulphide (22865-52-7) + 3,5-diiodosalicylic acid (133-91-5) → 2-Hydroxy-3,5-diiodo-N-(4-p-tolylsulfanyl-phenyl)-benzamide (128126-95-4)

Conditions	Yield
With trichlorophosphate In toluene	62%

3,5-diiodosalicylic acid (133-91-5) + copper(II) nitrate + acetylacetone (123-54-6) → (2,4-pentanediono)(3,5-diiodosalicylato)copper(II)

Conditions	Yield
In ethanol to Cu(NO3)2 an EtOH soln. of acetylacetone and 3,5-diiodosalicylic acid were added, pH was 8.5 by addn. of KOH, the soln. was refluxed for 2 h; concd., cooled to room temp., sepd., filtered, washed with aq. EtOH, recrystd. from EtOH, dried at 110°C for 2 h; elem. anal.;	62%

5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (833-63-6) + 3,5-diiodosalicylic acid (133-91-5) → 2-(3,5-Diiodosalicyloyl)amino-5-(4-nitrophenyl)-1,3,4-thiadiazole (128127-05-9)

Conditions	Yield
With trichlorophosphate In toluene	60%

3,5-diiodosalicylic acid (133-91-5) + 4-amino-4'-chlorodiphenyl ether (101-79-1) → N-(4-(4-chlorophenoxy)phenyl)-2-hydroxy-3,5-diiodobenzamide (128126-96-5)

Conditions	Yield
With trichlorophosphate In toluene	60%

3,5-diiodosalicylic acid (133-91-5) + (2-amino-1H-benzimidazol-5-yl)(phenyl)methanone (52329-60-9) → 2-(3,5-Diiodosalicyloyl)amino-5-benzoyl-benzimidazole (128126-88-5)

Conditions	Yield
With trichlorophosphate In toluene	58%

orcinol (504-15-4) + 3,5-diiodosalicylic acid (133-91-5) → 1-hydroxy-3-methyl-9H-xanthen-9-one (39156-34-8)

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide at 90℃;	55%

3,4-dihydro-β-carboline (4894-26-2) + 3,5-diiodosalicylic acid (133-91-5) → 1,3-diiodo-7,8,13,13b-tetrahydro-5H-benzo[5',6'][1,3]oxazino[3',2':1,2]pyrido[3,4-b]indol-5-one

Conditions	Yield
In dichloromethane at 20℃; for 12h;	52%

[Na4(cucurbituril)2(H2O)16]Cl4/water (1/6) + 8-quinolinol-5-sulfonic acid (84-88-8) + 3,5-diiodosalicylic acid (133-91-5) + sodium chloride (7647-14-5) + copper dichloride → [Na2(cucurbituril)(H2O)2][copper(II)(3,5-diiodosalicylate)(8-hydroxyquinoline-5-sulfonate)]/water (1/6.5)

Conditions	Yield
In water (C72H104N48Na4O40)Cl4*6H2O dissolved in aq. soln. of NaCl; added dropwise to aq. mixt. of CuCl2, I2C6H2(OH)CO2H, and C9H5N(OH)(SO3H) at pH 6 under stirring; further educt: H2O; filtered, slowly evapd. over 2 wk; elem. anal.;	40%

Upstream product

• 2631-77-8 3,5-diodosalicylaldehyde 
• 119-30-2 2-hydroxy-5-iodobenzoic acid 
• 528-93-8 silver salicylate 
• 64-17-5 ethanol 
• 7553-56-2 iodine 
• 69-72-7 salicylic acid 
• 67-64-1 acetone 
• 520-79-6 2-hydroxy-3-iodobenzoic acid 
• 42016-91-1 2-hydroxy-3,5-diiodobenzoyl chloride 
• 7732-18-5 water 
• 570-23-0 3-aminosalicylic acid 
• 89-57-6 5-Aminosalicylic Acid 
• 100-97-0 hexamethylenetetramine 
• 54-21-7 sodium salicylate 

Downstream Products

• 528-15-4 2-hydroxy-3,5-diiodobenzoic acid ethyl ester 
• 609-23-4 2,4,6-Triiodophenol 
• 119185-68-1 2-hydroxy-3,5-diiodo-benzoic acid-(1H-tetrazol-5-ylamide) 
• 42016-91-1 2-hydroxy-3,5-diiodobenzoyl chloride 
• 36415-60-8 2-acetoxy-3,5-diiodo-benzoic acid 
• 19503-64-1 2-hydroxy-3,5-diiodo-N-phenyl-benzamide 
• 128127-05-9 2-(3,5-Diiodosalicyloyl)amino-5-(4-nitrophenyl)-1,3,4-thiadiazole 
• 128126-95-4 2-Hydroxy-3,5-diiodo-N-(4-p-tolylsulfanyl-phenyl)-benzamide 
• 90481-45-1 2-Benzothiazol-2-yl-4,6-diiodo-phenol 
• 51327-02-7 N-(3-chlorophenyl)-2-hydroxy-3,5-diiodobenzamide 

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