Welcome to LookChem.com Sign In|Join Free

CAS

  • or

533-75-5

Post Buying Request

533-75-5 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

533-75-5 Usage

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: Hinokitiol, as a red iron complex, is found in cypress wood in Taiwan. 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 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. Purpurogallin, as glycoside, is found in the galls of mistletoe plants and can be used as a phenol oxidase test. 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

Different sources of media describe the Uses of 533-75-5 differently. You can refer to the following data:
1. 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.
2. Reagent for the preparation of fused heterocycles1 and complexes of Ga(III) and In(III).2 Used as medicine and dye intermediates.
3. 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).

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)

Flammability and Explosibility

Notclassified

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 533-75-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 533-75:
(5*5)+(4*3)+(3*3)+(2*7)+(1*5)=65
65 % 10 = 5
So 533-75-5 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

533-75-5 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A11299)  Tropolone, 98%   

  • 533-75-5

  • 1g

  • 385.0CNY

  • Detail
  • Alfa Aesar

  • (A11299)  Tropolone, 98%   

  • 533-75-5

  • 5g

  • 1409.0CNY

  • Detail
  • Alfa Aesar

  • (A11299)  Tropolone, 98%   

  • 533-75-5

  • 25g

  • 2918.0CNY

  • Detail

533-75-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Tropolone

1.2 Other means of identification

Product number -
Other names a-Tropolone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:533-75-5 SDS

533-75-5Synthetic route

2-<(-3-methyl-2-butenyl)oxy>tropone
50904-09-1

2-<(-3-methyl-2-butenyl)oxy>tropone

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
In dimethyl sulfoxide at 180℃; for 0.5h;96%
2-(cycloheptyloxy)tropone
87563-17-5

2-(cycloheptyloxy)tropone

A

Cycloheptene
628-92-2

Cycloheptene

B

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 180℃; for 2h;A 95%
B n/a
In decalin at 180℃; for 2h;
2-(cyclooctyloxy)tropone
87563-18-6

2-(cyclooctyloxy)tropone

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 180℃; for 2h;A 95%
B n/a
In decalin at 180℃; for 2h;
In dimethylsulfoxide-d6 at 180℃; Rate constant; Product distribution; Thermodynamic data; Ea, ΔS(excit.);
2-(cyclododecyloxy)tropone
87563-19-7

2-(cyclododecyloxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

cyclododecene
1501-82-2

cyclododecene

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 180℃; for 2h;A n/a
B 95%
(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
5307-99-3

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With acetic acid; sodium hydroxide95%
With sodium hydroxide; acetic acid at 130℃; for 7h; Rearrangement;87%
With hydrogenchloride; sodium hydroxide; acetic acid for 8h; pH=1; Heating;77%
With sodium hydroxide; acetic acid for 8h; Heating;77%
2-benzyloxycyclohepta-2,4,6-trienone
77367-70-5

2-benzyloxycyclohepta-2,4,6-trienone

A

dimethylsulfide
75-18-3

dimethylsulfide

B

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With dimethyl sulfoxide at 180℃; for 2h; other troponyl ethers;A n/a
B n/a
C 82%
4-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-3-one

4-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-3-one

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; triethylamine Elimination;75%
2-(cyclopentyloxy)tropone
87563-16-4

2-(cyclopentyloxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

cyclopentene
142-29-0

cyclopentene

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 180℃; for 2h;A n/a
B 70%
In dimethyl sulfoxide at 180℃; for 8h;
2-(p-tolylmethoxy)tropone
77367-69-2

2-(p-tolylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

5-(p-tolylmethyl)tropolone
77367-83-0

5-(p-tolylmethyl)tropolone

C

3-(p-tolylmethyl)tropolone
77367-76-1

3-(p-tolylmethyl)tropolone

Conditions
ConditionsYield
In decalin at 190℃; for 11h;A 10%
B 6.6%
C 60%
With dibenzoyl peroxide In decalin at 180.6℃; Rate constant; variation of the amounts of reagent and the time;
2-(4-chlorophenylmethoxy)tropone
77367-72-7

2-(4-chlorophenylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

5-(4-Chloro-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone
77367-86-3

5-(4-Chloro-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone

C

3-(4-Chloro-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone
77367-79-4

3-(4-Chloro-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
In decalin at 190℃; for 14h;A 15%
B 3.5%
C 59%
2-(1-naphthylmethoxy)tropolone
77367-74-9

2-(1-naphthylmethoxy)tropolone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

2-Hydroxy-5-naphthalen-1-ylmethyl-cyclohepta-2,4,6-trienone
77367-87-4

2-Hydroxy-5-naphthalen-1-ylmethyl-cyclohepta-2,4,6-trienone

C

2-Hydroxy-3-naphthalen-1-ylmethyl-cyclohepta-2,4,6-trienone
77367-81-8

2-Hydroxy-3-naphthalen-1-ylmethyl-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
In decalin at 190℃; for 7.5h;A 5%
B 20%
C 52%
In decalin at 190℃; for 7.5h;A 5%
B 20%
C 52%
In decalin at 153.1 - 180.1℃; for 7.5h; Kinetics;
2-benzyloxycyclohepta-2,4,6-trienone
77367-70-5

2-benzyloxycyclohepta-2,4,6-trienone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

3-benzyl-tropolone
77367-77-2

3-benzyl-tropolone

C

5-benzyltropolone
77367-84-1

5-benzyltropolone

Conditions
ConditionsYield
In decalin at 190℃; for 12h;A 10%
B 47%
C 3.1%
2-(4-bromophenylmethoxy)tropone
77367-71-6

2-(4-bromophenylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

5-(4-Bromo-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone
77367-85-2

5-(4-Bromo-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone

C

3-(4-Bromo-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone
77367-78-3

3-(4-Bromo-benzyl)-2-hydroxy-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
In decalin at 190℃; for 17h;A 11%
B 3.2%
C 46%
2-(4-methoxyphenylmethoxy)tropone
77367-73-8

2-(4-methoxyphenylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

2-Hydroxy-3-(4-methoxy-benzyl)-cyclohepta-2,4,6-trienone
77367-80-7

2-Hydroxy-3-(4-methoxy-benzyl)-cyclohepta-2,4,6-trienone

C

2-Hydroxy-5-(4-methoxy-benzyl)-cyclohepta-2,4,6-trienone
77401-26-4

2-Hydroxy-5-(4-methoxy-benzyl)-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
In decalin at 190℃; for 9h;A 20%
B 41%
C 6.1%
/PRWGD173-1520/

/PRWGD173-1520/

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

tropolonoboron difluoride, 3-bromotropolonoboron difluoride, 5-bromotropolonoboron difluoride

tropolonoboron difluoride, 3-bromotropolonoboron difluoride, 5-bromotropolonoboron difluoride

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 17h; Heating;A 40%
B n/a
2-(2-furylmethoxy)tropone

2-(2-furylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

3-(2-methyl-3-furyl)tropolone

3-(2-methyl-3-furyl)tropolone

C

5-(5-methyl-2-furyl)tropolone

5-(5-methyl-2-furyl)tropolone

D

5-(2-furylmethyl)tropolone

5-(2-furylmethyl)tropolone

E

3-(2-furylmethyl)tropolone

3-(2-furylmethyl)tropolone

Conditions
ConditionsYield
In 1,2-dichloro-benzene at 180℃; for 0.5h; Mechanism; other 2-(2-furylmethoxy)tropones;A n/a
B 3%
C 31%
D 19%
E 5%
/PRWGD173-1530/

/PRWGD173-1530/

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

tropolonoboron difluoride, 3-bromotropolonoboron difluoride, 5-bromotropolonoboron difluoride

tropolonoboron difluoride, 3-bromotropolonoboron difluoride, 5-bromotropolonoboron difluoride

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 17h; Heating;A 23%
B n/a
2-(3-pentyloxy)tropone
87563-21-1

2-(3-pentyloxy)tropone

A

(Z)-pent-2-ene
627-20-3

(Z)-pent-2-ene

B

(E)-pent-2-ene
646-04-8

(E)-pent-2-ene

C

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

D

butanone
78-93-3

butanone

Conditions
ConditionsYield
In dimethyl sulfoxide at 180℃; for 8h;A 4%
B 8%
C n/a
D 20%
In dimethyl sulfoxide at 180℃; for 8h;A n/a
B 4%
C n/a
D 20%
2-(2-butyloxy)tropone
87563-20-0

2-(2-butyloxy)tropone

A

(Z)-2-Butene
590-18-1

(Z)-2-Butene

B

trans-2-Butene
624-64-6

trans-2-Butene

C

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

D

acetone
67-64-1

acetone

Conditions
ConditionsYield
In dimethyl sulfoxide at 180℃; for 8h;A 7%
B n/a
C n/a
D 5%
In dimethyl sulfoxide at 180℃; for 8h;A 5%
B 7%
C n/a
D 7%
In dimethyl sulfoxide at 180℃; for 8h;
2-(2-Thienylmethoxy)tropone
108279-98-7

2-(2-Thienylmethoxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

5-(2-Thienylmethyl)tropolone
108280-07-5

5-(2-Thienylmethyl)tropolone

C

3-(2-Thienylmethyl)tropolone
108280-08-6

3-(2-Thienylmethyl)tropolone

D

5-(2-Thienylmethyl)-2-(2-thienylmethoxy)tropone
108280-00-8

5-(2-Thienylmethyl)-2-(2-thienylmethoxy)tropone

E

3,5-Bis(2-thienylmethyl)tropolone
108280-06-4

3,5-Bis(2-thienylmethyl)tropolone

Conditions
ConditionsYield
In 1,2-dichloro-benzene for 1.5h; Product distribution; Mechanism; Heating;A n/a
B n/a
C n/a
D 6%
E n/a
cycloheptane-1,2-dione
3008-39-7

cycloheptane-1,2-dione

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With N-Bromosuccinimide; chloroform und Erwaermen des Reaktionsprodukts auf 90-100grad;
2-hydroxycyloheptanone
4436-58-2

2-hydroxycyloheptanone

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With bromine; acetic acid und Erhitzen des Reaktionsprodukts unter vermindertem Druck;
5,5,6,6-tetrafluoro-cyclohepta-1,3-diene
2267-32-5

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

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With potassium acetate; acetic acid at 120 - 130℃;
3-carboxytropolone
33739-60-5

3-carboxytropolone

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
at 240 - 250℃;
With water at 160 - 170℃;
With pyridine at 135℃;
6-hydroxy-5-oxo-cyclohepta-1,3,6-trienecarboxylic acid
101011-99-8

6-hydroxy-5-oxo-cyclohepta-1,3,6-trienecarboxylic acid

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With quinoline; copper
6,6,7,7-tetrafluoro-cyclohepta-1,4-diene
2267-33-6

6,6,7,7-tetrafluoro-cyclohepta-1,4-diene

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With potassium acetate; acetic acid at 120 - 130℃;
Cyclohepta-1,3,5-triene
544-25-2

Cyclohepta-1,3,5-triene

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With potassium hydroxide; potassium permanganate
7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one
5307-99-3, 62182-64-3

7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Conditions
ConditionsYield
With sodium acetate In acetic acid
2-(cyclohexyloxy)tropone
61697-26-5

2-(cyclohexyloxy)tropone

A

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

B

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
In decalin at 180℃; for 4h;
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

benzyl bromide
100-39-0

benzyl bromide

2-benzyloxycyclohepta-2,4,6-trienone
77367-70-5

2-benzyloxycyclohepta-2,4,6-trienone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Williamson etherification reaction; Heating;100%
With tetra(n-butyl)ammonium hydroxide at 20℃;65%
With perhydrodibenzo-18-crown-6; potassium carbonate In acetonitrile for 10h; Heating;50%
With potassium carbonate In acetonitrile at 25℃; for 16h; Inert atmosphere; Reflux;
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-(tosyloxy)tropone
38768-08-0

2-(tosyloxy)tropone

Conditions
ConditionsYield
With pyridine at 20℃;100%
With triethylamine In dichloromethane at 21℃; for 38h;99%
In pyridine for 0.5h;98%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

2-(4-methoxyphenylmethoxy)tropone
77367-73-8

2-(4-methoxyphenylmethoxy)tropone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Williamson etherification reaction; Heating;100%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

Tosyl tropolone

Tosyl tropolone

Conditions
ConditionsYield
In pyridine99.5%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

triethylaluminum
97-93-8

triethylaluminum

Et2Al(tropolonato)
196198-25-1

Et2Al(tropolonato)

Conditions
ConditionsYield
In diethyl ether N2-atmosphere; -78°C to room temp.; evapn. (vac.); elem. anal.;99%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

3,5,7-tribromotropolone
363-67-7

3,5,7-tribromotropolone

Conditions
ConditionsYield
With benzyltrimethylammonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 24h; Bromination;98%
With bromine In methanol at 25℃; for 0.5h;95%
With bromine In methanol at 25℃; for 0.5h;95%
[(η-C5H5)W(μ-OH)2W(η-C5H5)](tosyl)2

[(η-C5H5)W(μ-OH)2W(η-C5H5)](tosyl)2

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

acetone
67-64-1

acetone

[(η-C5H5)2W(tropolonato)](tosyl)*0.5(acetone)

[(η-C5H5)2W(tropolonato)](tosyl)*0.5(acetone)

Conditions
ConditionsYield
In methanol byproducts: H2O; (Ar); std. Schlenk technique; tropolone was added to suspn. of W complexin MeOH; mixt. was heated at 50°C for 5 h; solvent removed (vac.); residie washed (hexane, ether); extd. (acetone);hexane added; kept at 0°C;98%
4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole
1078739-24-8

4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

N-[2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

N-[2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 3h; Inert atmosphere;98%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

2-methoxytropone
2161-40-2

2-methoxytropone

Conditions
ConditionsYield
In methanol; diethyl ether97%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

(R,R)-(-)-1,6-bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol
86436-19-3

(R,R)-(-)-1,6-bis(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol

(1R,6R)-1,6-Bis-(2-chloro-phenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol; compound with 2-hydroxy-cyclohepta-2,4,6-trienone
113397-22-1

(1R,6R)-1,6-Bis-(2-chloro-phenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol; compound with 2-hydroxy-cyclohepta-2,4,6-trienone

Conditions
ConditionsYield
In hexane; benzene for 12h; Ambient temperature;97%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

1-p-toluenesulfonyl-4-m-tolyl-1,2,3-triazole

1-p-toluenesulfonyl-4-m-tolyl-1,2,3-triazole

4-methyl-N-(2-oxo-2-(m-tolyl)ethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

4-methyl-N-(2-oxo-2-(m-tolyl)ethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 2h; Inert atmosphere;97%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

Zr(4+)*4C2O4(2-)*4K(1+)

Zr(4+)*4C2O4(2-)*4K(1+)

Zr(tropolonate)4

Zr(tropolonate)4

Conditions
ConditionsYield
Stage #1: Zr(4+)*4C2O4(2-)*4K(1+) With oxalic acid; sodium carbonate In chloroform
Stage #2: 2-hydroxy-2,4,6-cycloheptatrien-1-one In chloroform; water for 0.333333h;
97%
ytterbium trichloride hydrate

ytterbium trichloride hydrate

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

potassium tris(1-pyrazolyl)borate

potassium tris(1-pyrazolyl)borate

bis(hydrotris(pyrazol-1-yl)borato)tropolonatoytterbium(III)

bis(hydrotris(pyrazol-1-yl)borato)tropolonatoytterbium(III)

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water The boron compound, the organic compound, aqueous KOH and ethanol are mixed and added to a stirred solution of the Yb-salt in H2O, further stirring; filtn., drying in vac., recrystn. from methylene chloride/hexane mixture, elem. anal.;96%
tris(2-oxy-3,5-di-tert-butylbenzyl)amino titanium(IV) tert-butoxide
851636-66-3

tris(2-oxy-3,5-di-tert-butylbenzyl)amino titanium(IV) tert-butoxide

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

[nitrilotris(3,5-di-tert-butyl-2-cresolato)](tropolonato)titanium(IV)
851636-55-0

[nitrilotris(3,5-di-tert-butyl-2-cresolato)](tropolonato)titanium(IV)

Conditions
ConditionsYield
In benzene byproducts: t-butanol; ligand added to a soln. of Ti complex, stirred for 1 h; evapd. (vac.), dissolved in C6H6, MeCN added, mixed, crystd. for 24 h oncooling, filtered, washed (MeCN), dried (air); elem. anal.;96%
[(η-C5H5)Mo(μ-OH)2Mo(η-C5H5)](tosyl)2

[(η-C5H5)Mo(μ-OH)2Mo(η-C5H5)](tosyl)2

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

[(η-C5H5)2Mo(tropolonato)](tosyl)
876665-57-5

[(η-C5H5)2Mo(tropolonato)](tosyl)

Conditions
ConditionsYield
In methanol byproducts: H2O; (Ar); std. Schlenk technique; tropolone was added to suspn. of Mo complex in MeOH; mixt. was heated at 50°C for 5 h; solvent removed (vac.); residie washed (hexane, ether); extd. (acetone);hexane added; kept at 0°C; elem. anal.;96%
Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

pentanal
110-62-3

pentanal

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

benzylamine
100-46-9

benzylamine

2-[benzyl(7-oxo-1,3,5-cycloheptatrienyl)amino]-N1-cyclohexylhexanamide
1369591-76-3

2-[benzyl(7-oxo-1,3,5-cycloheptatrienyl)amino]-N1-cyclohexylhexanamide

Conditions
ConditionsYield
In methanol at 60℃; for 6h; Ugi-Smiles-type reaction;96%
1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

1-(4-methylbenzenesulfonyl)-4-(4-methylphenyl)-1,2,3-triazole

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

4-methyl-N-(2-oxo-2-(p-tolyl)ethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

4-methyl-N-(2-oxo-2-(p-tolyl)ethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 1h; Inert atmosphere;96%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

acetonitrile
75-05-8

acetonitrile

2-methoxytropone
2161-40-2

2-methoxytropone

Conditions
ConditionsYield
With 18-crown-6 ether; potassium carbonate at 90℃; for 4h;96%
lanthanumtrichloridehydrate

lanthanumtrichloridehydrate

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

potassium tris(1-pyrazolyl)borate

potassium tris(1-pyrazolyl)borate

La(hydrotrispyrazol-1-ylborate)2(tropolonate)

La(hydrotrispyrazol-1-ylborate)2(tropolonate)

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water The boron compound, the organic compound, aqueous KOH and ethanol are mixed and added to a stirred solution of the La-salt in H2O, further stirring; filtn., drying in vac., vac. sublimation at 250°C, elem. anal.;95%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

boron tribromide
10294-33-4

boron tribromide

{(C7H5O2)2B}(1+)*Br(1-)={(C7H5O2)2B}Br

{(C7H5O2)2B}(1+)*Br(1-)={(C7H5O2)2B}Br

Conditions
ConditionsYield
In chloroform95%
In chloroform
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

trimethyl gallium
1445-79-0

trimethyl gallium

dimethylgallium tropolonate

dimethylgallium tropolonate

Conditions
ConditionsYield
In not given byproducts: CH4; trimethyl metal deriv. reacts with an equimolr amt. of tropolone in ether, toluene or benzene at 25-40°C; purified by sublimation or recrystn. from toluene; identified by elem. anal., IR, NMR and mass spectra;95%
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

4-methyl-N-(2-oxo-2-phenylethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

4-methyl-N-(2-oxo-2-phenylethyl)-N-(7-oxocyclohepta-1,3,5-trienyl)benzenesulfonamide

Conditions
ConditionsYield
With dirhodium tetraacetate In 1,2-dichloro-ethane at 80℃; for 1h; Catalytic behavior; Solvent; Inert atmosphere;95%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

2-chlorotropone
3839-48-3

2-chlorotropone

Conditions
ConditionsYield
With thionyl chloride In benzene for 1.5h; Heating;94%
With thionyl chloride In benzene at 95℃; for 2.5h; Inert atmosphere;94%
With thionyl chloride In toluene at 120℃; for 1.5h;93%
2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

tris(tropolonato)bismuth(III)

tris(tropolonato)bismuth(III)

Conditions
ConditionsYield
In methanol; acetone for 3h; pH=Ca. 4; Reflux;93.2%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate

cis-bis-(2,2′-bipyridine) dichlororuthenium(II) dihydrate

2-hydroxy-2,4,6-cycloheptatrien-1-one
533-75-5

2-hydroxy-2,4,6-cycloheptatrien-1-one

cis-[(2,2'-bipyridine)2Ru(tropolonate)](PF6)
166268-22-0

cis-[(2,2'-bipyridine)2Ru(tropolonate)](PF6)

Conditions
ConditionsYield
In ethanol stirring and refluxing Ru-complex with 2 equiv. of tropolone for 2 h (N2-atmosphere), filtration, addn. of aq. NH4PF6; collection, washing (EtOH, ether), drying in air; elem. anal.;93%
In water stirring Ru-complex (75°C, 0.5 h), addn. of tropolone, stirring for 1 h, pptn. on addn. of NH4PF6; filtration, washing (H2O, Et2O), drying (vac.); elem. anal.;

533-75-5Relevant articles and documents

Plymale, D. L.,Smith, W. H.

, p. 2267 - 2269 (1968)

Chiroptical switching behavior of heteroleptic ruthenium complexes bearing acetylacetonato and tropolonato ligands

Sato, Hisako,Tateyama, Kazunori,Yamazaki, Kana,Yoshida, Jun,Yuge, Hidetaka

, p. 14611 - 14617 (2021/11/04)

Four types of tris-chelate ruthenium complexes bearing acetylacetonato (acac) and tropolonato (trop) ligands were synthesized and optically resolved into Δ and Λ isomers: [Ru(acac)3] (Ru-0), [Ru(acac)2(trop)] (Ru-1), [Ru(acac)(trop)2] (Ru-2), and [Ru(trop)3] (Ru-3). Chiral HPLC chromatograms, electronic circular dichroism (ECD), and vibrational circular dichroism (VCD) of the four ruthenium complexes were systematically investigated. As a result, the absolute configurations of the newly prepared enantiomeric complexes Ru-2 and Ru-3 were determined. For the case of Ru-2, its absolute configuration was also confirmed by single crystal X-ray diffraction analysis. The ECD changes upon chemical oxidation were further investigated for the four complexes. An ECD change in enantiomeric Ru-1 was observed upon oxidation, but the oxidized species soon returned to the neutral state within a few minutes. Enantiomers of Ru-3 also showed explicit ECD changes upon oxidation. Further, the lifetime of the oxidized state was the longest among the four investigated complexes, whereas they racemized in solution at room temperature. In contrast, the enantiomers of heteroleptic complexes (Ru-1 and Ru-2) concurrently exhibited ECD changes, relatively long lifetime of the oxidized state, and nil or quite slow racemization behavior. The coexistence of acac and trop ligands was key to making the competing factors compatible in the resultant ruthenium complexes.

Investigation of self-immolative linkers in the design of hydrogen peroxide activated metalloprotein inhibitors

Jourden, Jody L. Major,Daniel, Kevin B.,Cohen, Seth M.

supporting information; experimental part, p. 7968 - 7970 (2011/08/07)

A series of self-immolative boronic ester protected methyl salicylates and metal-binding groups with various linking strategies have been investigated for their use in the design of matrix metalloproteinase proinhibitors.

Evidence from mechanistic probes for distinct hydroperoxide rearrangement mechanisms in the intradiol and extradiol catechol dioxygenases

Xin, Meite,Bugg, Timothy D. H.

experimental part, p. 10422 - 10430 (2009/02/04)

Three mechanistic probes were used to investigate whether the Criegee rearrangement step of catechol 1,2-dioxygenase (CatA) from Acinetobacter sp. proceeds via a direct 1,2-acyl migration, via homolytic O-O cleavage, or via a benzene oxide-oxepin rearrangement. Incubation of CatA with 3- chloroperoxybenzoic acid led to the formation of a 9:1 mixture of 2-chlorophenol and 3-chlorophenol, via a mechanism involving O-O homolytic cleavage. Incubation of CatA with 2-hydroperoxy-2-methylcyclohexanone led to formation of 5,6-diketoheptan-1-ol, also consistent with an O-O homolytic cleavage mechanism, and not consistent with a direct 1,2-acyl migration. No reaction product was isolated from incubation of CatA with 6-hydroxymethyl-6-methylcyclohexa-2,4- dienone, an analogue that is able to undergo the benzene oxide-oxepin rearrangement, but not able to undergo O-O homolytic cleavage. In contrast, incubation of extradiol dioxygenase MhpB from Escherichia coli with 6-hydroxymethyl-6-methylcyclohexa2,4-dienone led to the formation of a 2-tropolone ring expansion product, consistent with a direct 1,2-alkenyl migration for extradiol cleavage. Taken together, the results imply different mechanisms for the Criegee rearrangement steps of intradiol and extradiol catechol dioxygenases: a direct 1,2-alkenyl migration for extradiol cleavage and an O-O homolytic cleavage mechanism for intradiol cleavage.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 533-75-5