CAS 533-75-5 Tropolone (HCID 10789)

Names & identifiers

Preferred name: Tropolone
IUPAC: 2-hydroxycyclohepta-2,4,6-trien-1-one
English name: Tropolone
Molecular formula: C7H6O2
Molecular weight: 122.12

Names & synonyms

Tropolone533-75-52-Hydroxycyclohepta-2,4,6-trienonePurpurocatechol2-Hydroxytropone2,4,6-Cycloheptatrien-1-one, 2-hydroxy-DTXSID80494167L6DL16P1TNSC-89303DTXCID7029376CHEBI:79966RefChem:389350

Show more names

TropoLSKL248a-TropoloneTropolone 98%

208-577-22-hydroxycyclohepta-2,4,6-trien-1-one2-Hydroxy-2,4,6-cycloheptatrien-1-one2-Hydroxy-2,4,6-cycloheptatrienoneMFCD00004158CCRIS 6609NSC89303SCHEMBL42739

Database identifiers

CAS: 533-75-5
PubChem CID: 10789
DTXSID: DTXSID8049416
ChEMBL: CHEMBL121188
ChEBI: CHEBI:79966
UNII: 7L6DL16P1T
EC Number: 208-577-2
Nikkaji: J44.110D

Properties

Computed structural properties

XLogP: 0.5
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 9
Formal charge: 0
Complexity: 209

Experimental & physicochemical properties

Vapor Pressure0.000679 [mmHg]

Physical DescriptionColorless solid; [Merck Index] Light yellow to cream hygroscopic solid; [Acros Organics MSDS]

Kovats Retention Index2003

Physicochemical properties

Melting point: 50 · 50-52 °C (lit.)
Boiling point: 80 · 80-84 °C/0.1 mmHg (lit.)
Density: 1.1483 · 1.1483 (rough estimate)
vapor pressure: 3.4 Pa · 3.4Pa at 25℃
refractive index: 1.5286 · 1.5286 (estimate)
Flash point: 230 °F · >230 °F
storage temp.: 2 · 2-8°C
solubility: 40.9 g/l · 40.9g/l (experimental)
pka: 6.7 · 6.7(at 25℃)
form: Crystalline Powder
color: Off-white to cream-beige
Water Solubility: Soluble in water.
Sensitive: Hygroscopic
BRN: 1904978 · 1904978
Cosmetics Ingredients Functions: SKIN CONDITIONING
InChI: 1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
InChIKey: MDYOLVRUBBJPFM-UHFFFAOYSA-N
SMILES: OC1=CC=CC=CC1=O
LogP: 1.58 at · 1.58 at 23℃
CAS DataBase Reference: 533 · 533-75-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 7 L6DL16P1T · 7L6DL16P1T
NIST Chemistry Reference: 2 · 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-(533-75-5)
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 5 · GHS05,GHS07,GHS09
Signal word: Danger
Hazard statements: 314 · H314-H317-H410
Precautionary statements: 260 · P260-P272-P273-P280-P303+P361+P353-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 22 · 22-36/37/38-37/38-41
Safety Statements: 22 · 22-24/25-36/37/39-36-26
WGK Germany: 3 · 3
RTECS: 4075000 · GU4075000
F: 8 · 8-10-23
HS Code: 29144090 · 29144090
Storage Class: 8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSkin Sens. 1B
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 10% (2 of 20) of reports.

Danger

H314 (85%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H317 (85%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H318 (85%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H400 (85%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (85%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P260, P261, P264, P264+P265, P272, P273, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P333+P317, P362+P364, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 20 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 2 of 20 reports by companies.；There are 2 notifications provided by 18 of 20 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24770；Status: Active Update: 07-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21361

2,4,6-Cycloheptatrien-1-one, 2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses convulsions and rigidity (including catalepsy) in intraperitoneal lethal-dose studies of mice and rats; [RTECS] May cause irritation; [Acros Organics MSDS]

Hazard Classes and CategoriesSkin Corr. 1B (85%)；Skin Sens. 1B (85%)；Eye Dam. 1 (85%)；Aquatic Acute 1 (85%)；Aquatic Chronic 1 (85%)

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 18-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24770；Status: Active Update: 07-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21361

2,4,6-Cycloheptatrien-1-one, 2-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F: 8-10-23
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: GU4075000
hs_code: 29144090
risk_code: 22-36/37/38-37/38-41
Signal word: Danger
Symbol(GHS): GHS05,GHS07,GHS09
hazard_code: Xi
safety_code: 22-24/25-36/37/39-36-26
Storage Class: 8A - Combustible corrosive hazardous materials
Hazard statements: H314-H317-H410
REACH Registrations: Active
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1BSkin Sens. 1B
Precautionary statements: P260-P272-P273-P280-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

UsesA natural antibiotic; The seven-carbon ring structure is a prototype for a group of natural bioactive products known as tropolonoids; Used as a ligand for cell radiolabeling; [Merck Index]

Household ProductsInformation on 1 consumer products that contain Tropolone in the following categories is provided:；• Personal Care

Applications · 3 items

UsesKnown 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.

UsesTropolone 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).

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

Upstream & downstream products

Upstream raw materials

Bicyclo[3.2.0]hept-2-ene, 6,6,7,7-tetrafluoro-Cycloheptanone, 2-hydroxy-1,3-Cycloheptadiene, 5,5,6,6-tetrafluoro-1,4-Cycloheptadiene, 6,6,7,7-tetrafluoro-Cycloheptatriene 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one

Downstream products

Cycloheptene

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

郑州阿尔法化工有限公司+86-18530059196 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 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.