5-Dibenzosuberenone Chemical Properties

Melting point:

87-88 °C (lit.)

Boiling point:

210 °C / 3mmHg

Density 

1.0701 (rough estimate)

vapor pressure 

0.006Pa at 25℃

refractive index 

1.6324 (estimate)

Flash point:

>110℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Crystalline Powder

Specific Gravity

1.156

color 

White to pale yellow or beige

Water Solubility 

Soluble in chloroform, ethyl acetate. Insoluble in water.

BRN 

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 25℃

CAS DataBase Reference

2222-33-5(CAS DataBase Reference)

NIST Chemistry Reference

5H-Dibenzo[a,d]cyclohepten-5-one(2222-33-5)

EPA Substance Registry System

5H-Dibenzo[a,d]cyclohepten-5-one (2222-33-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

RIDADR 

3077

WGK Germany 

3

RTECS 

HP1147500

Hazard Note 

Irritant

TSCA 

TSCA listed

HazardClass 

9

PackingGroup 

III

HS Code 

29143990

Storage Class

11 - Combustible Solids

Toxicity

mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02244,

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Dibenzosuberenone Usage And Synthesis

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。

Chemical Properties

5-Dibenzosuberenone is white to pale yellow or beige crystalline powder

Uses

5-Dibenzosuberenone Can be used in the synthesis of a series of potent antidepressants.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 8, p. 886, 1965 DOI: 10.1021/jm00330a044

Synthesis

Method 1: Dibenzo[a,d]cycloheptan-5-one was used as the starting material, and the target product was prepared by bromine bromination reflux reaction in CCl4 for 18h, followed by addition of triethylamine and then continued reflux for another 16h, and then after post-treatment. This method uses more toxic raw materials and the preparation reaction period is also longer.

Method 2: Using trans-dibromo-substitute as the substrate, the target product was prepared by reacting under light radiation via a Schlenk tube device under the action of argon protection and ??-selenothiophene and tetramethylethylenediamine. The preparation of the target product of this method is in milligram scale and requires column chromatography for purification, which is difficult for mass production.

Method 3: The target product 5-dibenzocycloheptenone was prepared by intramolecular decarboxylation coupling of 3-(2-benzoylphenyl)acrylic acid as starting material under the effect of silver catalyst and oxidizing agent.

5-Dibenzosuberenone(2222-33-5)Related Product Information

• Oxybenzone
• CYCLOBENZAPRINE HCL
• 2-Phenylacetophenone
• Benzophenone hydrazone
• Benzophenone
• DIETHYLPROPION
• TROPONE
• CYCLOHEPTENE
• Cycloheptatriene
• Dibenzosuberone
• DIBENZOSUBERYL CHLORIDE
• CIS-STILBENE
• 2-METHYLSTYRENE
• 5H-dibenzo[a,d]cycloheptene
• 1-ETHYL-2-VINYL-BENZENE
• 5-Dibenzosuberenone
• 2,3:6,7-DIBENZOSUBERENONE
• CYPROHEPTADINE HYDROCHLORIDE IMP. B (EP): 5H-DIBENZO[A,D]CYCLOHEPTEN-5-ONE (DIBENZOSUBERENONE)