3,3',5-Triiodothyronamine

Base Information

• Chemical Name: 3,3',5-Triiodothyronamine
• CAS No.: 4731-88-8
• Molecular Formula: C14H12 I3 N O2
• Molecular Weight: 606.96
• UNII: JFU2LL83MX
• DSSTox Substance ID: DTXSID40197100
• Nikkaji Number: J2.654.706G
• Wikipedia: 3,3%27,5-Triiodothyronamine,3'
• Wikidata: Q4634051
• ChEMBL ID: CHEMBL201885
• Mol file: 4731-88-8.mol

Synonyms:3,3',5-triiodothyronamine;triiodothyronamine

Chemical Property of 3,3',5-Triiodothyronamine

Chemical Property:

• Vapor Pressure: 3.2E-10mmHg at 25°C
• Boiling Point: 489.9°Cat760mmHg
• Flash Point: 250.1°C
• PSA: 55.48000
• Density: 2.324g/cm³
• LogP: 5.19980
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 606.8002
• Heavy Atom Count: 20
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1OC2=C(C=C(C=C2I)CCN)I)I)O

Technology Process of 3,3',5-Triiodothyronamine

There total 13 articles about 3,3',5-Triiodothyronamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

N-tert-butoxycarbonyl-3,3’,5’-triiodothyronamine (788824-62-4) → 3,5,3'-Triiodothyronamine (4731-88-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h;

DOI:10.1021/acs.cgd.6b00945

Reference yield:

C14H11I4NO2*C2HF3O2 → 3,3'-Diiodothyronamine + 3,3',5'-Triiodothyronamine + 3,5,3'-Triiodothyronamine (4731-88-8)

Guidance literature:

With sodium tetrahydroborate; DL-dithiothreitol; Naphthalene-1,8-diselenol; In aq. phosphate buffer; acetonitrile; at 37 ℃; pH=7; regioselective reaction;

DOI:10.1039/c6ob01375a

Reference yield:

tyrosamine (51-67-2) → 3,3'-Diiodothyronamine + 3,3',5'-Triiodothyronamine + 3,5,3'-Triiodothyronamine (4731-88-8)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydrogencarbonate / tetrahydrofuran; water / 24 h

2: Iodine monochloride; sodium methylate / N,N-dimethyl-formamide; dichloromethane / 3 h / -40 °C

3: copper diacetate; triethylamine; pyridine / dichloromethane / 12 h / Molecular sieve

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5: Iodine monochloride; N-butylamine / N,N-dimethyl-formamide; dichloromethane / 0.5 h / 0 °C

6: dichloromethane / 1 h / 20 °C

7: Naphthalene-1,8-diselenol; DL-dithiothreitol; sodium tetrahydroborate / aq. phosphate buffer; acetonitrile / 37 °C / pH 7

With pyridine; sodium tetrahydroborate; DL-dithiothreitol; tetrabutyl ammonium fluoride; sodium methylate; copper diacetate; Iodine monochloride; sodium hydrogencarbonate; N-butylamine; triethylamine; Naphthalene-1,8-diselenol; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c6ob01375a

upstream raw materials:

3,5-Diiodothyronamine

N-tert-butoxycarbonyl-3,3’,5,5’-tetraiodothyronamine

N-t-butoxycarbonyl-3,5-diiodothyronamine

tyrosamine

Refernces

• 1、 Mondal, Santanu,Mugesh, Govindasamy. "Conformational Flexibility and Halogen Bonding in Thyroid Hormones and Their Metabolites". . p. 5896 - 5906. Retrieved 2016/10/13.