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533-75-5

Basic Information
CAS No.: 533-75-5
Name: Tropolone
Article Data: 50
Molecular Structure:
Molecular Structure of 533-75-5 (Tropolone)
Formula: C7H6O2
Molecular Weight: 122.123
Synonyms: Tropolone(8CI);2-Hydroxy-2,4,6-cycloheptatrien-1-one;2-Hydroxytropone;NSC 89303;Purpurocatechol;a-Tropolone;
EINECS: 208-577-2
Density: 1.278 g/cm3
Melting Point: 50-52 °C(lit.)
Boiling Point: 290.109 °C at 760 mmHg
Flash Point: 121.974 °C
Solubility: Soluble in water.
Appearance: white to light yellow crystalline
Hazard Symbols: IrritantXi
Risk Codes: 22-36/37/38-41
Safety: 22-24/25-26-36/37/39
PSA: 37.30000
LogP: 0.75240
Synthetic route
50904-09-1

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

533-75-5

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

Conditions
ConditionsYield
In dimethyl sulfoxide at 180℃; for 0.5h;96%
87563-17-5

2-(cycloheptyloxy)tropone

A

628-92-2

Cycloheptene

B

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;
87563-18-6

2-(cyclooctyloxy)tropone

A

931-88-4, 931-87-3

(Z)-Cyclooctene

B

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.);
87563-19-7

2-(cyclododecyloxy)tropone

A

533-75-5

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

B

1501-82-2

cyclododecene

Conditions
ConditionsYield
In dimethylsulfoxide-d6 at 180℃; for 2h;A n/a
B 95%
5307-99-3

(+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-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%
77367-70-5

2-benzyloxycyclohepta-2,4,6-trienone

A

75-18-3

dimethylsulfide

B

533-75-5

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

C

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

533-75-5

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

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; triethylamine Elimination;75%
87563-16-4

2-(cyclopentyloxy)tropone

A

533-75-5

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

B

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;
77367-69-2

2-(p-tolylmethoxy)tropone

A

533-75-5

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

B

77367-83-0

5-(p-tolylmethyl)tropolone

C

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;
77367-72-7

2-(4-chlorophenylmethoxy)tropone

A

533-75-5

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

B

77367-86-3

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

C

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%
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    Tropolone Chemical Properties Melting point 50-52 °C (lit.) Boiling point 80-84 °C/0.1 mmHg (lit.) density 1.1483 (rough estimate) refractive index 1.5286 (estimate) Fp >230 °F storage temp. 2-8°C solubility

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Specification

The Tropolone, with its CAS registry number 533-75-5, has the IUPAC name of 2-hydroxycyclohepta-2,4,6-trien-1-one. For being a kind of white to light yellow crystalline, it is hygroscopic and it is usually applied as the pharmaceutic and dye intermediates. Besides, when store it, keep this chemical in the dry, cool and well-ventilated storeroom, away from the kindling, heat source and light.

The physical properties of this chemical are as below: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 19.482; (5)ACD/KOC (pH 7.4): 6.87; (6)#H bond acceptors: 2; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 1; (9)Polar Surface Area: 37.3; (10)Index of Refraction: 1.603; (11)Molar Refractivity: 32.81 cm3; (12)Molar Volume: 95.55 cm3; (13)Polarizability: 13.007×10-24 cm3; (14)Surface Tension: 56.55 dyne/cm; (15)Density: 1.278 g/cm3; (16)Flash Point: 121.974 °C; (17)Enthalpy of Vaporization: 61.435 kJ/mol; (18)Boiling Point: 290.109 °C at 760 mmHg; (19)Exact Mass: 122.036779; (20)MonoIsotopic Mass: 122.036779; (21)Topological Polar Surface Area: 37.3; (22)Heavy Atom Count: 9; (23)Complexity: 209.

Use of this chemical: Tropolone could react with diazomethane to produce 2-methoxy-cycloheptatrienone. This reaction could happen in the presence of the methanol and diethyl ether with its yield of 97%.

Production method of this chemical: 2-(3-Methylbut-2-enyloxy)tropon could react to produce tropolone. This reaction could happen in the presence of the solvent of dimethylsulfoxide, and it needs the reaction time of 30 mins and the reaction temperature of 180 ℃.

When you are dealing with this chemical, you should be cautious. This chemical is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. And it may have the risk of serious damage to eyes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and avoid contacting with skin and eyes. Besides, do not breathe dust and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C(=O)C=C1)O
(2)InChI: InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
(3)InChIKey: MDYOLVRUBBJPFM-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 212mg/kg (212mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY
Toxicology. Vol. 14, Pg. 217, 1979.
 
mouse LD50 intravenous 106mg/kg (106mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 92, Pg. 19, 1972.
 
mouse LD50 subcutaneous 233mg/kg (233mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ANALGESIA
Yakugaku Zasshi. Journal of Pharmacy. Vol. 91, Pg. 550, 1971.
 
rat LD50 intraperitoneal 190mg/kg (190mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY
Toxicology. Vol. 14, Pg. 217, 1979.