Seven-carbon ring compound Uses Toxicity
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Tropolone

Seven-carbon ring compound Uses Toxicity
Product Name
Tropolone
CAS No.
533-75-5
Chemical Name
Tropolone
Synonyms
2-Hydroxycyclohepta-2,4,6-trien-1-one;Purpurocatechol;2-hydroxytropone;TropoL;SKL248;TROPOLONE;a-Tropolone;Tropolone 98%;Tropolone,98%;Tropolone >
CBNumber
CB7686256
Molecular Formula
C7H6O2
Formula Weight
122.12
MOL File
533-75-5.mol
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Tropolone Property

Melting point:
50-52 °C (lit.)
Boiling point:
80-84 °C/0.1 mmHg (lit.)
Density 
1.1483 (rough estimate)
vapor pressure 
3.4Pa at 25℃
refractive index 
1.5286 (estimate)
Flash point:
>230 °F
storage temp. 
2-8°C
solubility 
40.9g/l (experimental)
pka
6.7(at 25℃)
form 
Crystalline Powder
color 
Off-white to cream-beige
Water Solubility 
Soluble in water.
Sensitive 
Hygroscopic
BRN 
1904978
LogP
1.58 at 23℃
CAS DataBase Reference
533-75-5(CAS DataBase Reference)
NIST Chemistry Reference
2,4,6-Cycloheptatrien-1-one, 2-hydroxy-(533-75-5)
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Safety

Hazard Codes 
Xi
Risk Statements 
22-36/37/38-37/38-41
Safety Statements 
22-24/25-36/37/39-36-26
WGK Germany 
3
RTECS 
GU4075000
F 
8-10-23
HS Code 
29144090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
108637
Product name
Tropolone
Purity
EMPROVE? EVOLVE
Packaging
5G
Price
$1413
Updated
2024/03/01
TCI Chemical
Product number
T0606
Product name
Tropolone
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$26
Updated
2024/03/01
TCI Chemical
Product number
T0606
Product name
Tropolone
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$86
Updated
2024/03/01
Alfa Aesar
Product number
A11299
Product name
Tropolone, 98%
Packaging
1g
Price
$41
Updated
2024/03/01
Alfa Aesar
Product number
A11299
Product name
Tropolone, 98%
Packaging
5g
Price
$137
Updated
2024/03/01
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Tropolone Chemical Properties,Usage,Production

Seven-carbon ring compound

Tropolone, also known as tohenone and 2-hydroxygenone, is a kind of seven-carbon ring compound, which is weakly acidic and has the properties of aromatic compounds, double bond and weak ketone. There are more than ten kinds of compounds known in nature containing seven-carbon rings:

  1. Hinokitiol, as a red iron complex, is found in cypress wood in Taiwan.
  2. Alpha- and gamma-thujapricin (β-body is the same as hinokitiol) are found in cypress and coniferous plants. It acts as an antibacterial agent to the wood for anticorrosion
  3. α- body and β-body also exist in the cypress essential oil. Stipitatic acid (6- hydroxyaryl heptanone-4-carboxylic acid) is the metabolite of penicillium, and has an antibacterial effect.
  4. Purpurogallin, as glycoside, is found in the galls of mistletoe plants and can be used as a phenol oxidase test.
  5. As nootkatin of the nootka heartwood and subalkaloids of colchicine and the like of colchicum used as inhibitor.
According to the properties of the compounds above, the scientists speculate that tocophenone plays an important role in the metabolic process of living components. It wss Japanese scientists Tetsuo Nozoe who first paid attention to tropolone in 1936 when he was researching hinokitiol, while the work in Europe and the United States started from the structure of stipitatic acid and colchicine, going further after 1950.

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.

Toxicity

The acute oral toxicity LD50 in rats was 459 mg / kg (female) , 223 mg / kg (male) and (662 mg / kg, rat). The acute dermal toxicity LD(50) in rabbit was no less than 2000mg/kg. There was mild irritation to the eye of rabbits. LC50 in Japanese carp is 0.5mg / L (48h) . An improved test and hamster ovary test, done by Ames, showed no mutations had been caused. Japanese carp LC50 is 0.5mg / L (48h)

Chemical Properties

White to light yellow crystalline

Uses

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).

Uses

Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates.

Definition

ChEBI: Tropolone is a cyclic ketone that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2. It is a toxin produced by the agricultural pathogen Burkholderia plantarii. It has a role as a bacterial metabolite, a toxin and a fungicide. It is a cyclic ketone, an enol and an alpha-hydroxy ketone. It derives from a hydride of a cyclohepta-1,3,5-triene.

Flammability and Explosibility

Not classified

Synthesis

To a mixture of sodium hydroxide (33 g) with glacial acetic acid (270 ml) was added dropwise via funnel 7,7-dichlorobicyclo[3,2,0]hepta-2-ene-6-ketone (33.5 g) under nitrogen, and the mixture was heated to reflux for 8 hours. After PH was adjusted to 1 with hydrochloric acid (50 ml), the mixture was filtered and extracted with benzene (3 × 90ml). The combined extracts were concentrated in vacuo to give brownish black oil.Fraction of reduced pressure distillation at 100 °C/67 Pa was collected to give gross product as a pale yellow solid. Recrystallization from mixture of dichloromethane and pentane (1/4, V/V) gave analytically pure product Tropolone(17.8 g,77%) as a white needle crystal, m.p. 50~51 °C.

Purification Methods

Crystallise tropolone from hexane or pet ether and sublime it at 40o/4mm. Also distil it at high vacuum. [Beilstein 8 IV 159.]

structure and hydrogen bonding

The tropolone has a simple structure consisting of a seven-membered carbon ring. The pi electrons present in the ring are delocalised. A ketone grouped to the first carbon, and an hydroxyl group attached to the second carbon. Tropolone, C7H6O2, crystallizes in space group P21/c, with a = 7.135, b = 12.178, c = 7.122Å, β = 99.63 ° and Z = 4. The molecule is essentially planar and exhibits slight bond alternation in the seven-membered ring. The hydroxyl group makes a bifurcated hydrogen bond with carbonyl oxygen atoms, of which one branch is intramolecular and the other intermolecular. The latter intermolecular branches form a hydrogen-bonded dimer. These characteristic hydrogen bonds seem to play a role in increasing the contribution from the dipolar ionic forms to the ground state of the tropolone molecule.

Tropolone Preparation Products And Raw materials

Raw materials

Preparation Products

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Tropolone Suppliers

Belgium 1 China 247 France 1 Germany 3 India 4 Japan 5 Poland 1 Switzerland 2 United Kingdom 8 United States 40 Global 312
TargetMol Chemicals Inc.
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View Lastest Price from Tropolone manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Tropolone 533-75-5
Price
US $60.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000kg/week
Release date
2024-05-23
Hebei Yanxi Chemical Co., Ltd.
Product
Tropolone 533-75-5
Price
US $50.00-3.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
30 tons
Release date
2023-09-13
Hebei Chuanghai Biotechnology Co,.LTD
Product
Tropolone 533-75-5
Price
US $5.00-2.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10000kg
Release date
2024-08-16

533-75-5, TropoloneRelated Search:

Cycloheptatriene Gestrinone CHLOROPHOSPHONAZO III Clethodim Zearalenone Androstenedione Methyl cyclopentenolone Quinocetone GLORIOSINE Colchicine Tropolone, 4-isopropyl- colchiceine DEMECOLCINE cornigerine TRIMETHYLCOLCHICINIC ACID desacetamidocolchicine trimethylcolchicinic acid methyl ether COLCHICINE, [RING C, METHOXY-3H]

  • 2-Hydroxycyclohepta-2,4,6-trien-1-one
  • a-Tropolone
  • 2-Hydroxycycloheptane-2,4,6-triene-1-one
  • Tropolone, 98% 1GR
  • Tropolone, 98% 5GR
  • TROPOLONE FOR SYNTHESIS 5 G
  • TROPOLONE FOR SYNTHESIS 1 G
  • TROPOLONE FOR SYNTHESIS 25 G
  • Tropolone 98%
  • Tropolone puruM, >=98.0% (GC)
  • Tropolone≥ 99% (Assay)
  • 2-Hydroxy-2,4,6-cycloheptatriene-1-one
  • 2-hydroxytropone
  • 6-cycloheptatrien-1-one,2-hydroxy-4
  • Purpurocatechol
  • TROPOLONE
  • 2-HYDROXY-2,4,6-CYCLOHEPTATRIEN-1-ONE
  • 2-HYDROXY-2,4,6-CYCLOHEPTATRIENONE
  • 2-Hydroxycyclohepta-2,4,6-trienone
  • TROPOLONE 99+%
  • Tropolone,98%
  • 2-Hydroxy-2,4,6-Cycloheptatrie
  • 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-
  • Tropolone(8CI)
  • TropoL
  • Tropolone &gt
  • SKL248
  • Tropolone 533-75-5
  • -aminoethylbenzene hydrochloride
  • -Phenylethylamine hydrochloride
  • 533-75-5
  • C7H6O2
  • C7 to C8
  • Carbonyl Compounds
  • Ketones
  • Organic Building Blocks
  • Tropolones & Azulenes
  • Tropolones
  • Building Blocks
  • Tropolones
  • Tropolones & Azulenes
  • Building Blocks
  • C7 to C8
  • Carbonyl Compounds
  • Chemical Synthesis
  • Ketones
  • Organic Building Blocks