Tropolone

Base Information

• Chemical Name: Tropolone
• CAS No.: 533-75-5
• Molecular Formula: C7H6O2
• Molecular Weight: 122.123
• Hs Code.: 29144090
• European Community (EC) Number: 208-577-2
• NSC Number: 89303
• UNII: 7L6DL16P1T
• DSSTox Substance ID: DTXSID8049416
• Nikkaji Number: J44.110D
• Wikipedia: Tropolone
• Wikidata: Q19952843
• RXCUI: 1368873
• Metabolomics Workbench ID: 144677
• ChEMBL ID: CHEMBL121188
• Mol file: 533-75-5.mol

Synonyms:Tropolone(8CI);2-Hydroxy-2,4,6-cycloheptatrien-1-one;2-Hydroxytropone;NSC 89303;Purpurocatechol;a-Tropolone;

Chemical Property of Tropolone

Chemical Property:

• Appearance/Colour: white to light yellow crystalline
• Vapor Pressure: 0.000231mmHg at 25°C
• Melting Point: 50-52 °C(lit.)
• Refractive Index: 1.602
• Boiling Point: 290.109 °C at 760 mmHg
• PKA: 6.7(at 25℃)
• Flash Point: 121.974 °C
• PSA: 37.30000
• Density: 1.278 g/cm³
• LogP: 0.75240
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: 40.9g/l (experimental)
• Water Solubility.: Soluble in water.
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 122.036779430
• Heavy Atom Count: 9
• Complexity: 209

Purity/Quality:

99% ^*data from raw suppliers

Tropolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38-37/38-41
• Safety Statements: 22-24/25-36/37/39-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1=CC=C(C(=O)C=C1)O
• Uses: Known as pyrrole pesticide, acaricide with new structure, it has been proved to have good biological control effect on boring, piercing-sucking and chewing insects and mites, better than cypermethrin and cypermethrin. Also its acaricidal activity is stronger than dicofol and tricyclic tin. This agent is characterized with the following: broad-spectrum pesticide and acaricide; both stomach poisoning and contact toxicity; no mutual resistance with other pesticides; moderate residual activity in crops; selective and systemic activity in nutrient solution absorbed by root system; moderate oral toxicity and lower dermal toxicity to mammalian life; low effective spray rate (100g active ingredient / hm2). Its significant insecticidal, acaricidal activity and unique chemical structure has received widespread attention and attention. Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates. Tropolone is a sensitive reagent for reducing sugars. A non-benzenoid aromatic compound, Reagent for the preparation of fused heterocycles and complexes of Ga(III) and In(III).

Technology Process of Tropolone

There total 56 articles about Tropolone 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: 96.0%

2-<(-3-methyl-2-butenyl)oxy>tropone (50904-09-1) → 2-hydroxy-2,4,6-cycloheptatrien-1-one (533-75-5)

Guidance literature:

In dimethyl sulfoxide; at 180 ℃; for 0.5h;

DOI:10.1246/bcsj.55.1137

Reference yield: 95.0%

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (5307-99-3) → 2-hydroxy-2,4,6-cycloheptatrien-1-one (533-75-5)

Guidance literature:

With acetic acid; sodium hydroxide;

DOI:10.1016/j.bmc.2017.12.017

Reference yield: 95.0%

2-(cycloheptyloxy)tropone (87563-17-5) → Cycloheptene (628-92-2,45509-99-7) + 2-hydroxy-2,4,6-cycloheptatrien-1-one (533-75-5)

Guidance literature:

In dimethylsulfoxide-d6; at 180 ℃; for 2h;

DOI:10.1039/c39830000483

upstream raw materials:

cycloheptane-1,2-dione

2-hydroxycyloheptanone

5,5,6,6-tetrafluoro-cyclohepta-1,3-diene

3-carboxytropolone

Downstream raw materials:

3,5,7-tris(morpholinomethyl)tropolone

5-phenylazo-tropolone

5-formyltroponolate

3-iodo-tropolone

Refernces

• 1、 Biggi et al.. "". . p. 183. Retrieved 1973.
• 2、 Sato, Daisuke,Kisen, Takuya,Kumagai, Mina,Ohta, Kiminori. "Synthesis, structure-activity relationships, and mechanistic studies of 5-arylazo-tropolone derivatives as novel xanthine oxidase (XO) inhibitors". . p. 536 - 542. Retrieved 2017/12/29.
• 3、 -. "STIMULUS-TRIGGERED PRODRUGS". Page/Page column 54-56. . Retrieved 2012/01/13.