Product Name

  • Name

    3,3',5-TRIIODOTHYROACETIC ACID

  • EINECS 200-086-1
  • CAS No. 51-24-1
  • Article Data4
  • CAS DataBase
  • Density 2.467 g/cm3
  • Solubility
  • Melting Point 181.5 °C
  • Formula C14H9I3O4
  • Boiling Point 531.6 °C at 760 mmHg
  • Molecular Weight 621.937
  • Flash Point 275.3 °C
  • Transport Information
  • Appearance
  • Safety 36
  • Risk Codes 20/21/22
  • Molecular Structure Molecular Structure of 51-24-1 (3,3',5-TRIIODOTHYROACETIC ACID)
  • Hazard Symbols HarmfulXn
  • Synonyms Aceticacid, [4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]- (8CI);Thyroacetic acid,3,3',5-triiodo- (6CI);3,3',5-Triiodothyroacetic acid;Nidolin;Triac;[(4-Hydroxy-3-iodo-4-phenoxy)-3,5-diiodophenyl]acetic acid;
  • PSA 66.76000
  • LogP 4.62540

Synthetic route

2-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)acetic acid
1155-40-4

2-(4-(4-hydroxyphenoxy)-3,5-diiodophenyl)acetic acid

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

Conditions
ConditionsYield
With ammonia anschliessendes Behandeln mit wss. Jod-KI-Loesung;
3,3',5-triiodothyroacetic acid ethyl ester
41628-06-2

3,3',5-triiodothyroacetic acid ethyl ester

A

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

B

[4-(4-Hydroxy-3-iodo-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid

[4-(4-Hydroxy-3-iodo-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid

C

[4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3,5-diiodo-phenyl]-acetic acid

[4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3,5-diiodo-phenyl]-acetic acid

D

[4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid

[4-(4-Hydroxy-3-trifluoromethyl-phenoxy)-3-iodo-5-trifluoromethyl-phenyl]-acetic acid

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; dibromodifluoromethane; copper(I) bromide; cadmium Multistep reaction. Further byproducts given. Title compound not separated from byproducts;
...Expand
[3,5-diiodo-4-(4-methoxy-phenoxy)-phenyl]-acetic acid ethyl ester
85828-82-6

[3,5-diiodo-4-(4-methoxy-phenoxy)-phenyl]-acetic acid ethyl ester

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous HI; red phosphorus; acetic acid
2: aqueous methanol. NH3 / anschliessendes Behandeln mit wss. Jod-KI-Loesung
View Scheme
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

methylamine
74-89-5

methylamine

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-methylacetamide
1417653-47-4

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-methylacetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 2h; Sealed tube; Inert atmosphere;
Stage #2: methylamine In tetrahydrofuran at 20 - 50℃; for 16h; Inert atmosphere;		87%
Stage #1: 3,3',5-triiodothyroacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Sealed tube;
Stage #2: methylamine In tetrahydrofuran at 20 - 50℃; for 16h; Inert atmosphere;		87%
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: methylamine In N,N-dimethyl-formamide		40%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

dimethyl amine
124-40-3

dimethyl amine

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N,N-dimethylacetamide
1417653-48-5

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N,N-dimethylacetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: dimethyl amine In N,N-dimethyl-formamide		60%
morpholine
110-91-8

morpholine

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-1-morpholinoethanone
1417653-54-3

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-1-morpholinoethanone

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: morpholine In N,N-dimethyl-formamide		43%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetamide
92905-78-7

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With thionyl chloride for 2h; Reflux;
Stage #2: With ammonium hydroxide In water; toluene for 0.0833333h;		40%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

1-pentanamine
110-58-7

1-pentanamine

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-pentylacetamide
1417653-46-3

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-pentylacetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: n-Pentylamine In N,N-dimethyl-formamide		36%
piperidine
110-89-4

piperidine

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-1-(piperidin-1-yl)ethanone
1417653-45-2

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-1-(piperidin-1-yl)ethanone

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: piperidine In N,N-dimethyl-formamide		31%
methanesulfonamide
3144-09-0

methanesulfonamide

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-(methylsulfonyl)acetamide
1417653-49-6

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-(methylsulfonyl)acetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 1h;
Stage #2: methanesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane		21%
benzenesulfonamide
98-10-2

benzenesulfonamide

3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-(phenylsulfonyl)acetamide
1417653-50-9

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-(phenylsulfonyl)acetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃;
Stage #2: benzenesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane		16%
Stage #1: 3,3',5-triiodothyroacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 1h;
Stage #2: benzenesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane		16%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

aniline
62-53-3

aniline

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-phenylacetamide
1417653-39-4

2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-N-phenylacetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: aniline In N,N-dimethyl-formamide		16%
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: aniline In N,N-dimethyl-formamide		16%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

diethylamine
109-89-7

diethylamine

N,N-diethyl-2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetamide
1417653-43-0

N,N-diethyl-2-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetamide

Conditions
ConditionsYield
Stage #1: 3,3',5-triiodothyroacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h;
Stage #2: diethylamine In N,N-dimethyl-formamide		8%
3,3',5-triiodothyroacetic acid
51-24-1

3,3',5-triiodothyroacetic acid

4-(4-Hydroxy-3-iod-phenoxy)-3,5-diiod-phenethylalkohol
736-05-0

4-(4-Hydroxy-3-iod-phenoxy)-3,5-diiod-phenethylalkohol

Conditions
ConditionsYield
With diborane In tetrahydrofuran

Tiratricol Specification

The IUPAC name of Tiratricol is 2-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]acetic acid. With the CAS registry number 51-24-1, it is also named as (4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl)acetic acid. The product's category is Aromatic Phenylacetic Acids and Derivatives. Besides, it should be stored at -20 °C. In addition, its molecular formula is C14H9I3O4 and molecular weight is 621.93.

The other characteristics of Tiratricol can be summarized as: (1)EINECS: 200-086-1; (2)ACD/LogP: 5.47; (3)# of Rule of 5 Violations: 2; (4)ACD/LogD (pH 5.5): 3.97; (5)ACD/LogD (pH 7.4): 2.2; (6)ACD/BCF (pH 5.5): 269.08; (7)ACD/BCF (pH 7.4): 4.55; (8)ACD/KOC (pH 5.5): 715.31; (9)ACD/KOC (pH 7.4): 12.09; (10)#H bond acceptors: 4; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 5; (13)Index of Refraction: 1.766; (14)Molar Refractivity: 104.41 cm3; (15)Molar Volume: 252.1 cm3; (16)Surface Tension: 73.6 dyne/cm; (17)Density: 2.466 g/cm3; (18)Flash Point: 275.3 °C; (19)Melting Point: 181.5 °C; (20)Enthalpy of Vaporization: 84.97 kJ/mol; (21)Boiling Point: 531.6 °C at 760 mmHg; (22)Vapour Pressure: 3.92E-12 mmHg at 25 °C.

Uses of Tiratricol: this chemical is a thyroid hormone analogue. Moreover, it is indicated in the management of thyroid hormone resistance syndrome and is used, in combination with levothyroxine, to suppress thyroid-stimulating hormone production in patients with thyroid cancer.

When you are using this chemical, please be cautious about it as the following: it is harmful by inhalation, in contact with skin and if swallowed. You should wear suitable protective clothing when use it.

People can use the following data to convert to the molecule structure.
(1)SMILES: Ic2cc(Oc1c(I)cc(cc1I)CC(=O)O)ccc2O
(2)InChI: InChI=1/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
(3)InChIKey: UOWZUVNAGUAEQC-UHFFFAOYAM
(4)Std. InChI: InChI=1S/C14H9I3O4/c15-9-6-8(1-2-12(9)18)21-14-10(16)3-7(4-11(14)17)5-13(19)20/h1-4,6,18H,5H2,(H,19,20)
(5)Std. InChIKey: UOWZUVNAGUAEQC-UHFFFAOYSA-N

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View