3,5-Diiodosalicylic acid supplier

Name
3,5-Diiodosalicylic acid
EINECS 205-124-0
CAS No. 133-91-5
Article Data33
CAS DataBase
Density 2.697 g/cm³
Solubility 0.02 g/100mL (25 °C) in water
Melting Point 220-230 °C (dec.)(lit.)
Formula C₇H₄I₂O₃
Boiling Point 380.8 °C at 760 mmHg
Molecular Weight 389.916
Flash Point 184.1 °C
Transport Information
Appearance Off-white to beige or grey powder
Safety 26-36-37/39
Risk Codes 20/21/22-36/37/38-22
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms Salicylicacid, 3,5-diiodo- (6CI,7CI,8CI);2-Hydroxy-3,5-diiodobenzenecarboxylic acid;2-Hydroxy-3,5-diiodobenzoic acid;3,5-Diiodo-2-hydroxybenzoic acid;NSC 6303;Benzoicacid, 2-hydroxy-3,5-diiodo-;
PSA 57.53000
LogP 2.29960

Synthetic route

: 69-72-7
salicylic acid

: 133-91-5
3,5-diiodosalicylic acid

Conditions

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%

: 2631-77-8
3,5-diodosalicylaldehyde

: 133-91-5
3,5-diiodosalicylic acid

Conditions

Conditions	Yield
With permanganate(VII) ion; acetone

: 119-30-2
2-hydroxy-5-iodobenzoic acid

: 133-91-5
3,5-diiodosalicylic acid

: 520-79-6
2-hydroxy-3-iodobenzoic acid

: 133-91-5
3,5-diiodosalicylic acid

: 528-93-8, 14800-64-7
silver salicylate

: 133-91-5
3,5-diiodosalicylic acid

Conditions

Conditions	Yield
With iodine

: 69-72-7
salicylic acid

A: 119-30-2
2-hydroxy-5-iodobenzoic acid

B: 133-91-5
3,5-diiodosalicylic acid

Conditions

Conditions	Yield
With ethanol; iodine

: 3-acetyl-6,8-diiodo-chroman-2,4-dione

KOH-solution: KOH-solution

: 133-91-5
3,5-diiodosalicylic acid

: 6,8-diiodo-2,4-dioxo-chroman-3-carbonitrile

KOH-solution: KOH-solution

: 133-91-5
3,5-diiodosalicylic acid

: 6,8-diiodo-2,4-dioxo-chroman-3-carboxylic acid ethyl ester

KOH-solution: KOH-solution

: 133-91-5
3,5-diiodosalicylic acid

: 64-17-5
ethanol

: 7553-56-2
iodine

: 69-72-7
salicylic acid

A: 119-30-2
2-hydroxy-5-iodobenzoic acid

B: 520-79-6
2-hydroxy-3-iodobenzoic acid

C: 133-91-5
3,5-diiodosalicylic acid

...Expand

: 2631-77-8
3,5-diodosalicylaldehyde

: 67-64-1
acetone

permanganate: permanganate

: 133-91-5
3,5-diiodosalicylic acid

...Expand

: 64-17-5
ethanol

: 119-30-2
2-hydroxy-5-iodobenzoic acid

: 7553-56-2
iodine

yellow mercury oxide: yellow mercury oxide

: 133-91-5
3,5-diiodosalicylic acid

...Expand

: 64-17-5
ethanol

: 520-79-6
2-hydroxy-3-iodobenzoic acid

: 7553-56-2
iodine

yellow mercury oxide: yellow mercury oxide

: 133-91-5
3,5-diiodosalicylic acid

...Expand

: 42016-91-1
2-hydroxy-3,5-diiodobenzoyl chloride

: 7732-18-5
water

: 133-91-5
3,5-diiodosalicylic acid

alkaline aqueous sodium salicylate: alkaline aqueous sodium salicylate

: 133-91-5
3,5-diiodosalicylic acid

Conditions

Conditions	Yield
With iodine

mercury (II)-salicylate: mercury (II)-salicylate

: 133-91-5
3,5-diiodosalicylic acid

Conditions

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

: 69-72-7
salicylic acid

A: 133-91-5
3,5-diiodosalicylic acid

B iodosalicylic acid: iodosalicylic acid

Conditions

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

: dichlorophosphoric acid-(2,4-diiodo-6-trichloromethyl-phenyl ester)

: 7732-18-5
water

: 133-91-5
3,5-diiodosalicylic acid

: 7553-56-2
iodine

: 54-21-7
sodium salicylate

alkaline aqueous solution: alkaline aqueous solution

: 133-91-5
3,5-diiodosalicylic acid

Conditions

Conditions	Yield
anschliessendes Erhitzen;

...Expand

: 100-97-0
hexamethylenetetramine

: 119-30-2
2-hydroxy-5-iodobenzoic acid

A: 133-91-5
3,5-diiodosalicylic acid

B: 685870-21-7
3-formyl-2-hydroxy-5-iodobenzoic acid

Conditions

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;

...Expand

: 89-57-6
5-Aminosalicylic Acid

: 133-91-5
3,5-diiodosalicylic acid

Conditions

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

: 570-23-0
3-aminosalicylic acid

: 133-91-5
3,5-diiodosalicylic acid

Conditions

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

: 69-72-7
salicylic acid

A: 119-30-2
2-hydroxy-5-iodobenzoic acid

B: 520-79-6
2-hydroxy-3-iodobenzoic acid

C: 133-91-5
3,5-diiodosalicylic acid

Conditions

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;

...Expand

: 133-91-5
3,5-diiodosalicylic acid

: 77-78-1
dimethyl sulfate

: 121789-21-7
methyl 3,5-diiodo-2-methoxybenzoate

Conditions

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;

: 13194-68-8
4-iodo-2-methylaniline

: 133-91-5
3,5-diiodosalicylic acid

: 90426-00-9
2-Hydroxy-3,5-diiodo-N-(4-iodo-2-methyl-phenyl)-benzamide

Conditions

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

: 133-91-5
3,5-diiodosalicylic acid

: 137-07-5
2-amino-benzenethiol

: 90481-45-1
2-Benzothiazol-2-yl-4,6-diiodo-phenol

Conditions

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

: 133-91-5
3,5-diiodosalicylic acid

: 100-01-6
4-nitro-aniline

: 19503-66-3
2-Hydroxy-3,5-diiodo-N-(4-nitro-phenyl)-benzamide

Conditions

Conditions	Yield
With trichlorophosphate In toluene	88%

: 583-58-4
3,4-Lutidin

: zinc(II) nitrate hexahydrate

: 133-91-5
3,5-diiodosalicylic acid

: [(3,4-dimethylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions

Conditions	Yield
In ethanol	87%

...Expand

: 626-55-1
3-Bromopyridine

: zinc(II) nitrate hexahydrate

: 133-91-5
3,5-diiodosalicylic acid

: [(3-bromopyridine)2Zn(3,5-iodosalicylate)2]

Conditions

Conditions	Yield
In ethanol	87%

...Expand

: 133-91-5
3,5-diiodosalicylic acid

: 367-25-9
2,4-difluorophenylamine

: 79402-06-5
N-(2,4-Difluoro-phenyl)-2-hydroxy-3,5-diiodo-benzamide

Conditions

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

: 133-91-5
3,5-diiodosalicylic acid

: 22706-11-2
3-phenyl-4-amino-5-mercapto-1,2,4-triazole

: 2-hydroxy-3,5-diiodo-N-(3-phenyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl)benzamide

Conditions

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%

: 635-22-3
4-Chloro-3-nitroaniline

: 133-91-5
3,5-diiodosalicylic acid

: 128126-92-1
3,5-Diiodo-4'-chloro-3'-nitrosalicylanilide

Conditions

Conditions	Yield
With trichlorophosphate In toluene	83%

: 108-89-4
picoline

: zinc(II) nitrate hexahydrate

: 133-91-5
3,5-diiodosalicylic acid

: [(4-methylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions

Conditions	Yield
In ethanol	83%

...Expand

: 591-22-0
3,5-Lutidine

: zinc(II) nitrate hexahydrate

: 133-91-5
3,5-diiodosalicylic acid

: [(3,5-dimethylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions

Conditions	Yield
In ethanol	83%

...Expand

: 108-99-6
3-Methylpyridine

: zinc(II) nitrate hexahydrate

: 133-91-5
3,5-diiodosalicylic acid

: [(3-methylpyridine)2Zn(3,5-iodosalicylate)2]

Conditions

Conditions	Yield
In ethanol	79%

...Expand

: 5307-14-2
2-nitro-1,4-phenylenediamine

: 133-91-5
3,5-diiodosalicylic acid

: 128126-84-1
3,5-Diiodo-4'-amino-3'-nitrosalicylanilide

Conditions

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

: 133-91-5
3,5-diiodosalicylic acid

: 94-09-7
p-aminoethylbenzoate

: 128126-93-2
4-(2-Hydroxy-3,5-diiodo-benzoylamino)-benzoic acid ethyl ester

Conditions

Conditions	Yield
With trichlorophosphate In toluene	75%

: 1635-31-0
aminocoumarine

: 133-91-5
3,5-diiodosalicylic acid

: 2-hydroxy-3,5-diiodo-N-(2-oxo-2H-chromen-3-yl)benzamide

Conditions

Conditions	Yield
With phosphorus trichloride In acetonitrile Reflux;	75%

: 133-91-5
3,5-diiodosalicylic acid

: 53065-28-4
5-(phenylthio)-1H-benzo[d]imidazol-2-amine

: 128126-87-4
2-(3,5-Diiodosalicyloyl)amino-5-phenylthio-benzimidazole

Conditions

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

: 66-71-7
1,10-Phenanthroline

: tetrakis(acetato)diaquadicopper(II)

: 133-91-5
3,5-diiodosalicylic acid

: Cu(3,5-C6H2I2(O)(COO))(1,10-phenanthroline)*2H2O

Conditions

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%

...Expand

: 1135-14-4
4-aminophenyl phenyl sulfide

: 133-91-5
3,5-diiodosalicylic acid

: 128126-94-3
2-Hydroxy-3,5-diiodo-N-(4-phenylsulfanyl-phenyl)-benzamide

Conditions

Conditions	Yield
With trichlorophosphate In toluene	65%

: 22865-52-7
4-amino-4'-methyldiphenylsulphide

: 133-91-5
3,5-diiodosalicylic acid

: 128126-95-4
2-Hydroxy-3,5-diiodo-N-(4-p-tolylsulfanyl-phenyl)-benzamide

Conditions

Conditions	Yield
With trichlorophosphate In toluene	62%

: 133-91-5
3,5-diiodosalicylic acid

: copper(II) nitrate

: 123-54-6
acetylacetone

: (2,4-pentanediono)(3,5-diiodosalicylato)copper(II)

Conditions

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%

...Expand

: 833-63-6
5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine

: 133-91-5
3,5-diiodosalicylic acid

: 128127-05-9
2-(3,5-Diiodosalicyloyl)amino-5-(4-nitrophenyl)-1,3,4-thiadiazole

Conditions

Conditions	Yield
With trichlorophosphate In toluene	60%

: 133-91-5
3,5-diiodosalicylic acid

: 101-79-1
4-amino-4'-chlorodiphenyl ether

: 128126-96-5
N-(4-(4-chlorophenoxy)phenyl)-2-hydroxy-3,5-diiodobenzamide

Conditions

Conditions	Yield
With trichlorophosphate In toluene	60%

: 133-91-5
3,5-diiodosalicylic acid

: 52329-60-9
(2-amino-1H-benzimidazol-5-yl)(phenyl)methanone

: 128126-88-5
2-(3,5-Diiodosalicyloyl)amino-5-benzoyl-benzimidazole

Conditions

Conditions	Yield
With trichlorophosphate In toluene	58%

: 504-15-4
orcinol

: 133-91-5
3,5-diiodosalicylic acid

: 39156-34-8
1-hydroxy-3-methyl-9H-xanthen-9-one

Conditions

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

: 4894-26-2
3,4-dihydro-β-carboline

: 133-91-5
3,5-diiodosalicylic acid

: 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

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

: [Na4(cucurbituril)2(H2O)16]Cl4/water (1/6)

: 84-88-8
8-quinolinol-5-sulfonic acid

: 133-91-5
3,5-diiodosalicylic acid

: 7647-14-5
sodium chloride

: copper dichloride

: [Na2(cucurbituril)(H2O)2][copper(II)(3,5-diiodosalicylate)(8-hydroxyquinoline-5-sulfonate)]/water (1/6.5)

Conditions

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%

...Expand

3,5-Diiodosalicylic acid Chemical Properties

Molecular Structure of 3,5-Diiodosalicylic acid (CAS NO.133-91-5):

IUPAC Name: 2-Hydroxy-3,5-diiodobenzoic acid
Canonical SMILES: C1=C(C=C(C(=C1I)O)C(=O)O)I
InChI: InChI=1S/C7H4I2O3/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2,10H,(H,11,12)
InChIKey: DHZVWQPHNWDCFS-UHFFFAOYSA-N
Molecular Weight: 389.9138 [g/mol]
Molecular Formula: C₇H₄I₂O₃
XLogP3: 4.6
H-Bond Donor: 2
H-Bond Acceptor: 3
EINECS: 205-124-0
Index of Refraction: 1.784
Molar Refractivity: 60.87 cm³
Molar Volume: 144.5 cm³
Surface Tension: 82.5 dyne/cm
Density: 2.697 g/cm³
Flash Point: 184.1 °C
Enthalpy of Vaporization: 66.35 kJ/mol
Boiling Point: 380.8 °C at 760 mmHg
Vapour Pressure: 1.77E-06 mmHg at 25 °C
Appearance: Off-white to beige or grey powder
Melting Point: 220-230 °C (dec.)(lit.)
Water Solubility: 0.02 g/100mL (25 °C)
Sensitive: Light Sensitive
Classification Code: Agricultural Chemical; Drug / Therapeutic Agent; Experimental pesticide; Unspecified / Unclassified pesticide
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic acids

3,5-Diiodosalicylic acid Uses

3,5-Diiodosalicylic acid (CAS NO.133-91-5) is used as an intermediate for veterinary anthelmintic agents (closentel and rafoxanide). It is also used as food source of iodine.

3,5-Diiodosalicylic acid Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	450mg/kg (450mg/kg)		Quarterly Journal of Pharmacy & Pharmacology. Vol. 19, Pg. 483, 1946.
rat	LDLo	oral	500mg/kg (500mg/kg)		National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 8, 1953.

3,5-Diiodosalicylic acid Consensus Reports

Reported in EPA TSCA Inventory.

3,5-Diiodosalicylic acid Safety Profile

Safety Information of 3,5-Diiodosalicylic acid (CAS NO.133-91-5):
Hazard Codes : Harmful Xn, Irritant Xi
Risk Statements : 20/21/22-36/37/38-22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R22:Harmful if swallowed.
Safety Statements : 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany : 3
RTECS : VO2800000
F : 8 (Photosensitive)
Moderately toxic by ingestion. A trace mineral added to animal feeds. When heated to decomposition it emits toxic fumes of I⁻.

3,5-Diiodosalicylic acid Standards and Recommendations

ASSAY: 99.0% min
MOISTURE: 0.5% max
ASH: 0.5% max

3,5-Diiodosalicylic acid Specification

3,5-Diiodosalicylic acid (CAS NO.133-91-5), its Synonyms are 2-Hydroxy-3,5-diiodobenzenecarboxylic acid ; 2-Hydroxy-3,5-diiodobenzoate ; 2-Hydroxy-3,5-diiodobenzoic acid ; 3,5-Diiodo-2-hydroxybenzoic acid ; 3,5-Diiodosalicylate ; Benzoic acid, 3,5-diiodo-2-hydroxy- ; Salicylic acid, 3,5-diiodo- .

Product Name

3,5-Diiodosalicylic acid

Synthetic route

3,5-Diiodosalicylic acid Chemical Properties

3,5-Diiodosalicylic acid Uses

3,5-Diiodosalicylic acid Toxicity Data With Reference

3,5-Diiodosalicylic acid Consensus Reports

3,5-Diiodosalicylic acid Safety Profile

3,5-Diiodosalicylic acid Standards and Recommendations

3,5-Diiodosalicylic acid Specification

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