2,3,5-Triiodobenzoic acid supplier

Name
2,3,5-Triiodobenzoic acid
EINECS 201-859-6
CAS No. 88-82-4
Article Data7
CAS DataBase
Density 2.971 g/cm³
Solubility Insoluble in water.
Melting Point 220-222 °C
Formula C₇H₃I₃O₂
Boiling Point 456.7 °C at 760 mmHg
Molecular Weight 499.813
Flash Point 230 °C
Transport Information
Appearance beige powder
Safety 22-26-36-24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 2,3,5-TIBA;A 20812;Floraltone;Johnkolor;NSC 2582;TIB;TIBA;Triiodobenzoic acid;
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

Conditions	Yield
With potassium iodide Diazotization;

: 37960-65-9
potassium anthranilate

: 88-82-4
2,3,5-triiodobenzoic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; potassium carbonate In ethyl acetate; N,N-dimethyl-formamide	11.4 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With thionyl chloride	85%
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

Conditions	Yield
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

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 88-82-4
2,3,5-triiodobenzoic acid

: 161234-25-9
2,5-dioxopyrrolidin-1-yl 2,3,5-triiodobenzoate

Conditions

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;	82%

: 88-82-4
2,3,5-triiodobenzoic acid

: 1743-36-8
1-phenylbut-3-yn-1-ol

: 3-(2-hydroxy-2-phenylethyl)-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: 1-phenylbut-3-yn-1-ol With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	81%

: 88-82-4
2,3,5-triiodobenzoic acid

: 87976-29-2
benzoic-2,3,5-d3 acid

Conditions

Conditions	Yield
With H2O(2)H2O2P(1-)Na(1+); α,α'-azodiizobutyramidine-dihydrochloride; sodium hydrogencarbonate In water at 80℃; for 8h; Inert atmosphere;	81%

: 88-82-4
2,3,5-triiodobenzoic acid

: 221147-26-8
1-amino-2,3,6,7,10,11-hexa(heptyloxy)triphenylene

: 1-(2,3,5-triiodobenzoylamino)-2,3,6,7,10,11-hexaheptyloxytriphenylene

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 9h;	80%

: 88-82-4
2,3,5-triiodobenzoic acid

: 627-41-8
propargyl alcohol methyl ether

: 3-methoxymethyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: propargyl alcohol methyl ether With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	77%

: 59-02-9
vitamin E

: 88-82-4
2,3,5-triiodobenzoic acid

: α-tocopheryl 2,3,5-triiodobenzoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 22h;	75%

: 45985-24-8, 2226-96-2
TEMPOL

: 88-82-4
2,3,5-triiodobenzoic acid

: 2,2,6,6-tetramethylpiperidine-1-oxyl-4-yl 2,3,5-triiodobenzoate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 26h; Inert atmosphere;	75%

: 88-82-4
2,3,5-triiodobenzoic acid

: 1204-55-3
thioacetic acid S-(2-acetylamino-phenyl)ester

: 3-iodo-10H-phenothiazine-1-carboxylic acid

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Inert atmosphere;	75%

: 88-82-4
2,3,5-triiodobenzoic acid

: C7H7ClF5O5S(1-)*C9H14N(1+)

: C14H9F5I3O7S(1-)*C9H14N(1+)

Conditions

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 90℃;	71%

: 88-82-4
2,3,5-triiodobenzoic acid

: 145-13-1
Pregnenolone

: 97545-42-1
pregnenolone 2,3,5-triiodobenzoat

Conditions

Conditions	Yield
With dmap; 2`,3`-dideoxycytidine In dichloromethane for 24h; Ambient temperature;	69%

: 88-82-4
2,3,5-triiodobenzoic acid

: 536-74-3
phenylacetylene

A: 886-66-8
1,4-diphenyl-1,3-butadiyne

B: 3-phenyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 50℃; Inert atmosphere; Schlenk technique;	A 19% B 68%

...Expand

: 88-82-4
2,3,5-triiodobenzoic acid

: 94612-95-0
1-(p-bromophenyl)-but-3-yn-1-ol

: 3-[2-(4-bromophenyl)-2-hydroxyethyl]-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: 1-(p-bromophenyl)-but-3-yn-1-ol With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	68%

: 88-82-4
2,3,5-triiodobenzoic acid

: 123563-83-7
8-bromooctyl acrylate

: 2,3,5-triiodobenzoic acid 8-acryloyloxyoctyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 2.5h; Inert atmosphere; Sealed tube;	66%

: 88-82-4
2,3,5-triiodobenzoic acid

: 693-02-7
hex-1-yne

: 3-butyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: hex-1-yne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	60%

: 75-09-2
dichloromethane

: 88-82-4
2,3,5-triiodobenzoic acid

: 6,8-diiodo-4H-benzo[d][1,3]dioxin-4-one

Conditions

Conditions	Yield
With 8-quinolinol; copper diacetate; sodium hydrogencarbonate; potassium hydroxide In N,N-dimethyl-formamide at 110℃; for 12h;	60%

: 88-82-4
2,3,5-triiodobenzoic acid

: 107-19-7
propargyl alcohol

: 3-(hydroxymethyl)-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: propargyl alcohol With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	59%

: 88-82-4
2,3,5-triiodobenzoic acid

: 563-63-3
silver(I) acetate

: 271790-47-7
Ag(1+)*C6H2I3COO(1-)=C6H2I3COOAg

Conditions

Conditions	Yield
In methanol; water aq. soln. AgCH3COO was layered with methanolic soln. triiodobenzoic acid and was alloweed to stand at room temp. for 1 day; elem. anal.;	57%

: 629-05-0
n-octyne

: 88-82-4
2,3,5-triiodobenzoic acid

: 3-hexyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: n-octyne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	53%

: 871-84-1
1,7-Octadiyne

: 88-82-4
2,3,5-triiodobenzoic acid

: 3-(hex-5-ynyl)-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: 1,7-Octadiyne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	38%

: 88-82-4
2,3,5-triiodobenzoic acid

: C30H56NO12S(1-)*Na(1+)

: C37H57I3NO13S(1-)*Na(1+)

Conditions

Conditions	Yield
With pyridine; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	36.3%

: 88-82-4
2,3,5-triiodobenzoic acid

: 6-(aminooxy)-N-(triphenylmethoxy)hexanamide

: 2,3,5-triiodo-N-((6-oxo-6-((trityloxy)amino)hexyl)oxy)benzamide

Conditions

Conditions	Yield
Stage #1: 2,3,5-triiodobenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.25h; Stage #2: 6-(aminooxy)-N-(triphenylmethoxy)hexanamide In N,N-dimethyl-formamide at 20℃; for 16h;	35%

: 88-82-4
2,3,5-triiodobenzoic acid

: 1234307-18-6
C47H96O9SSi3

: 1234307-24-4
C54H97I3O10SSi3

Conditions

Conditions	Yield
With dmap; 2,2'-dipyridyl carbonate In dichloromethane at 20℃; for 48h;	34.4%

: 10160-87-9
Propiolaldehyde diethyl acetal

: 88-82-4
2,3,5-triiodobenzoic acid

: 3-diethoxymethyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: Propiolaldehyde diethyl acetal With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	32%

: 13397-78-9
4,4-diethoxybut-1-yne

: 88-82-4
2,3,5-triiodobenzoic acid

: 3-(2,2-diethoxyethyl)-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: 4,4-diethoxybut-1-yne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	31%

: 2243-98-3
1-undecyne

: 88-82-4
2,3,5-triiodobenzoic acid

: 3-nonyl-5,7-diiodoisocoumarin

Conditions

Conditions	Yield
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: 1-undecyne With copper(l) iodide In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; Schlenk technique; regioselective reaction;	30%

2,3,5-Triiodobenzoic acid Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

2,3,5-Triiodobenzoic acid 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.

Product Name

2,3,5-Triiodobenzoic acid

Synthetic route

2,3,5-Triiodobenzoic acid Consensus Reports

2,3,5-Triiodobenzoic acid Specification

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