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88-82-4

Basic Information
CAS No.: 88-82-4
Name: 2,3,5-Triiodobenzoic acid
Article Data: 7
Molecular Structure:
Molecular Structure of 88-82-4 (2,3,5-Triiodobenzoic acid)
Formula: C7H3I3O2
Molecular Weight: 499.813
Synonyms: 2,3,5-TIBA;A 20812;Floraltone;Johnkolor;NSC 2582;TIB;TIBA;Triiodobenzoic acid;
EINECS: 201-859-6
Density: 2.971 g/cm3
Melting Point: 220-222 °C
Boiling Point: 456.7 °C at 760 mmHg
Flash Point: 230 °C
Solubility: Insoluble in water.
Appearance: beige powder
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 22-26-36-24/25
PSA: 37.30000
LogP: 3.19860
Synthetic route
609-86-9

2-amino-3,5-diiodobenzoic acid

88-82-4

2,3,5-triiodobenzoic acid

Conditions
ConditionsYield
With potassium iodide Diazotization;
37960-65-9

potassium anthranilate

88-82-4

2,3,5-triiodobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; iodine
2: diluted hydrochloric acid; iodine monochloride
3: potassium iodide / Diazotization
View Scheme
118-92-3

anthranilic acid

88-82-4

2,3,5-triiodobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diluted hydrochloric acid; iodine monochloride
2: potassium iodide / Diazotization
View Scheme
5326-47-6

2-amino-5-iodobenzoic acid

88-82-4

2,3,5-triiodobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diluted hydrochloric acid; iodine monochloride
2: potassium iodide / Diazotization
View Scheme
2-octylmethanesulfonate

2-octylmethanesulfonate

98589-35-6

3-hydroxy-2,4,6-triiodo-benzoic acid ethyl ester

88-82-4

2,3,5-triiodobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride; potassium carbonate In ethyl acetate; N,N-dimethyl-formamide11.4 g (94%)
64-17-5

ethanol

88-82-4

2,3,5-triiodobenzoic acid

25546-12-7

2,3,5-triiodobenzoic acid ethyl ester

Conditions
ConditionsYield
With sulfuric acid Heating;95%
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

88-82-4

2,3,5-triiodobenzoic acid

3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-5,7-diiodoisocoumarin

Conditions
ConditionsYield
Stage #1: 2,3,5-triiodobenzoic acid With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 3-(tetrahydropyran-2'-yloxy)propyne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;
93%
88-82-4

2,3,5-triiodobenzoic acid

536-74-3

phenylacetylene

3-phenyl-5,7-diiodoisocoumarin

Conditions
ConditionsYield
Stage #1: 2,3,5-triiodobenzoic acid With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: phenylacetylene With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;
89%
88-82-4

2,3,5-triiodobenzoic acid

42860-33-3

2,3,5-triiodobenzoyl chloride

Conditions
ConditionsYield
With thionyl chloride85%
With thionyl chloride for 16h; Reflux;60%
With thionyl chloride In tetrahydrofuran for 0.666667h; Heating / reflux;49%
57260-73-8

N-BOC-1,2-diaminoethane

88-82-4

2,3,5-triiodobenzoic acid

819079-61-3

C14H17I3N2O3

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 13.5h; Inert atmosphere; Cooling with ice;82%
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane
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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The IUPAC name of this product is 2,3,5-triiodobenzoic acid. With the CAS registry number 88-82-4, it is also named as 2,3,5-TIBA; 4-09-00-01044 (Beilstein Handbook Reference); A 20812; AI3-27442; BRN 1955088; Caswell No. 890A; EPA Pesticide Chemical Code 009104; Floraltone; Johnkolor; Kyselina 2,3,5-trijodbenzoova; Benzoic acid, 2,3,5-triiodo-. The product's categories are aromatic carboxylic acids, amides, anilides, anhydrides & salts, benzoic acid, acids & esters, iodine compounds, auxins, biochemistry and plant growth regulators.

The 2,3,5-Triiodobenzoic acid is beige powder which is sensitive to light. It is toxic. When heated to decomposition it emits toxic fumes of I-. So the storage environment should be ventilate, low-temperature and dry. Keep 2,3,5-Triiodobenzoic acid separate from raw materials of food. It could be used as the plant growth regulator.

The 2,3,5-Triiodobenzoic acid is harmful if swallowed. So people should not breathe dust and must avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.87; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.94; (4)ACD/LogD (pH 7.4): 0.72; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 3.54; (8)ACD/KOC (pH 7.4): 2.17; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.8; (13)Molar Refractivity: 71.9 cm3; (14)Molar Volume: 168.1 cm3; (15)Polarizability: 28.5×10-24 cm3; (16)Surface Tension: 75.7 dyne/cm; (17)Enthalpy of Vaporization: 75.52 kJ/mol; (18)Vapour Pressure: 3.92E-09 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)MonoIsotopic Mass: 499.726708; (21)Topological Polar Surface Area: 37.3; (22)Heavy Atom Count: 12.

People can use the following data to convert to the molecule structure. SMILES: Ic1c(C(=O)O)cc(I)cc1I; InChI: InChI=1/C7H3I3O2/c8-3-1-4(7(11)12)6(10)5(9)2-3/h1-2H,(H,11,12); InChIKey: ZMZGFLUUZLELNE-UHFFFAOYAP. 2,3,5-Triiodobenzoic acid has many suppliers, such as Chemik Co., Ltd., BORI International Enterprises (Nanjing) Co., Ltd., BenzChem Co., Ltd., Byelen Chemicals Co., Ltd., Changzhou Ilhang Fine Chemical Co., Ltd. and Changzhou Suntton Co., Ltd..

The following is the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 562mg/kg (562mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.
mouse LD50 intravenous > 200mg/kg (200mg/kg)   Journal of Organic Chemistry. Vol. 22, Pg. 1686, 1957.
mouse LD50 oral 700mg/kg (700mg/kg)   Quarterly Journal of Pharmacy & Pharmacology. Vol. 19, Pg. 483, 1946.
rat LD50 oral 813mg/kg (813mg/kg)   Guide to the Chemicals Used in Crop Protection. Vol. 6, Pg. 504, 1973.