Basic information
- Standard SMILES
O=c1c2ccccc2ccc2ccccc12- InChIKey
SNVTZAIYUGUKNI-UHFFFAOYSA-N- Molecular formula
- C15H10O
- Average molar mass
- 206.24 g/mol
- Monoisotopic mass
- 206.07316494
Names & identifiers
- Preferred name
- 5H-Dibenzo[a,d]cyclohepten-5-one
- IUPAC
- tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-one
- English name
- 5-Dibenzosuberenone
- Molecular formula
- C15H10O
- Molecular weight
- 206.24
Names & synonyms
Dibenzosuberenone2222-33-55-Dibenzosuberenone5H-Dibenzo[a,d]cyclohepten-5-oneDibenzo[a,d]cyclohepten-5-one2,3:6,7-Dibenzotropone2,3:6,7-Dibenzosuberen-4-on-15H-Dibenzo(a,d)cyclohepten-5-oneDibenzo(a,d)cyclohepten-5-oneNSC 86151EINECS 218-737-35H-Dibenzo(a,d)cycloheptenone
Show more names
DibenzosberenoneDIBENZOSUBERENONE-5Dibenzosuberenone>Dibenzosuberenone,97%2,3,6,7-Dibenzotropone
Dibenzo[b,f]cyclohepten-1-oneXQJHQ6T1YB5H-Dibenzo[a,d]cycloheptenoneBRN 0743171Dibenzo(b,f)cyclohepten-1-oneEC 218-737-3NSC-86151DIBENZOCYCLOHEPTENONE [USP IMPURITY]
Database identifiers
- CAS
2222-33-5- PubChem CID
- 16679
- DTXSID
DTXSID4062274- ChEMBL
CHEMBL1535826- UNII
- XQJHQ6T1YB
- EC Number
- 218-737-3
- Nikkaji
- J3.734.245I、J42.185E
Properties
Computed structural properties
- XLogP
- 4.2
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 277
Physicochemical properties
- Melting point
- 87 · 87-88 °C (lit.)
- Boiling point
- 210 °C · 210 °C / 3mmHg
- Density
- 1.0701 · 1.0701 (rough estimate)
- vapor pressure
- 0.006 Pa · 0.006Pa at 25℃
- refractive index
- 1.6324 · 1.6324 (estimate)
- Flash point
- 110 ℃ · >110℃
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- Crystalline Powder
- Specific Gravity
- 1.156 · 1.156
- color
- White to pale yellow or beige
- Water Solubility
- Soluble in chloroform, ethyl acetate. Insoluble in water.
- BRN
- 743171 · 743171
- InChI
- 1S/C15H10O/c16-15-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)15/h1-10H
- InChIKey
- SNVTZAIYUGUKNI-UHFFFAOYSA-N
- SMILES
- O=C1c2ccccc2C=Cc3ccccc13
- LogP
- 3.508 at · 3.508 at 25℃
- CAS DataBase Reference
- 2222 · 2222-33-5(CAS DataBase Reference)
- FDA UNII
- 6 T1YB · XQJHQ6T1YB
- NIST Chemistry Reference
- 5 H-Dibenzo[a,d]cyclohepten-5-one · 5H-Dibenzo[a,d]cyclohepten-5-one(2222-33-5)
- EPA Substance Registry System
- 5 H-Dibenzo[a,d]cyclohepten-5-one · 5H-Dibenzo[a,d]cyclohepten-5-one (2222-33-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Warning
- Hazard statements
- 410 · H410
- Precautionary statements
- 273 · P273-P391-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 24 · 24/25-36-26
- RIDADR
- 3077 · 3077
- WGK Germany
- 3 · 3
- RTECS
- 1147500 · HP1147500
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29143990 · 29143990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 · mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02244,
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 53.1% (26 of 49) of all reports.
Warning
H400 (18.4%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H411 (40.8%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 26 of 49 reports by companies.；There are 5 notifications provided by 23 of 49 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
Status: Active Update: 06-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19091；Status: Active Update: 07-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18969
5H-Dibenzoa,dcyclohepten-5-one: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAquatic Acute 1 (18.4%)；Aquatic Chronic 2 (40.8%)
Regulatory information
Regulatory Information
Status: Active Update: 06-10-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/19091；Status: Active Update: 07-12-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18969
5H-Dibenzoa,dcyclohepten-5-one: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- HP1147500
- ridadr
- 3077
- hs_code
- 29143990
- Toxicity
- mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02244,
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 24/25-36-26
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H410
- REACH Registrations
- Active
- Precautionary statements
- P273-P391-P501
Chemistry & industry
Uses & manufacturing
General Manufacturing Information5H-Dibenzo[a,d]cyclohepten-5-one: ACTIVE
Applications
Uses5-Dibenzosuberenone Can be used in the synthesis of a series of potent antidepressants.
Preparation methods
合成方法方法1：以二苯并[a,d]环庚-5-酮为起始物料，在CCl4中经溴素溴代回流反应18h，随后加入三乙胺再继续回流16h后经后处理制得目标产品。该方法用的毒性较大的原料，且制备反应周期也较长。方法2：以反式二溴代物为底物，在氩气保护及α-硒代噻吩、四甲基乙二胺作用下，经Schlenk管装置在光辐射下反应制得目标产物。该方法目标产品的制备在毫克级，并且需要柱层析提纯，难于量产。方法3：以3-(2-苯甲酰基苯基)丙烯酸为起始物料，在银系催化剂及氧化剂的作用下分子内脱羧偶联制得目标产品5-二苯并环庚烯酮。
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
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