DIPHENYLCYCLOPROPENONE

Base Information

• Chemical Name: DIPHENYLCYCLOPROPENONE
• CAS No.: 886-38-4
• Molecular Formula: C15H10O
• Molecular Weight: 206.244
• Hs Code.: 29142990
• European Community (EC) Number: 212-948-4
• NSC Number: 57541
• UNII: I7G14NW5EC
• DSSTox Substance ID: DTXSID2046545
• Nikkaji Number: J133.037C
• Wikipedia: Diphenylcyclopropenone
• Wikidata: Q5279743
• NCI Thesaurus Code: C28994
• Metabolomics Workbench ID: 58529
• ChEMBL ID: CHEMBL1373467
• Mol file: 886-38-4.mol

Synonyms:Cyclopropenone,diphenyl- (6CI,7CI,8CI);1,2-Diphenylcyclopropenone;2,3-Diphenyl-2-cyclopropen-1-one;2,3-Diphenylcyclopropenone;Diphencyclopropenone;Diphencyprone;Diphenylcyclopropenone;NSC 57541;

Chemical Property of DIPHENYLCYCLOPROPENONE

Chemical Property:

• Appearance/Colour: slightly pinkish-orange to beige crystalline
• Vapor Pressure: 7.66E-07mmHg at 25°C
• Melting Point: 118-122 °C(lit.)
• Refractive Index: 1.668
• Boiling Point: 407.2 °C at 760 mmHg
• Flash Point: 182.7 °C
• PSA: 17.07000
• Density: 1.232 g/cm³
• LogP: 3.18010
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 206.073164938
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

98%, ^*data from raw suppliers

2,3-Diphenylcycloprop-2-en-1-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38-43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=C(C2=O)C3=CC=CC=C3
• Recent ClinicalTrials: Diphenylcyclopropenone (DPCP) as a Depigmenting Therapy in Extensive Vitiligo
• Description: Diphencyprone is a potent contact allergen responsible for occupational contact dermatitis in chemists and dermatological staff. Diphencyprone (DCP) is a contact sensitizing agent. Pretreatment with DCP reduces symptom severity in a mouse model of experimental autoimmune encephalomyelitis (EAE) induced by myelin basic protein (1-10) (MBP1-10). It enhances IL-10 production and antigen-specific IgG2a antibody responses and reduces anaphylaxis and asthma induced by ovalbumin in mice when administered during ovalbumin immunization at a concentration of 1% v/v. Topical administration of DCP increases intrafollicular CD4+ and CD8+ T cells, reduces upper dermal inflammation, and stimulates hair growth in the C3H/HeJ mouse model of alopecia areta. Formulations containing DCP have been used in the treatment of alopecia areta.
• Uses: Diphenylcyclopropenone was used in topical immunotherapy.

Technology Process of DIPHENYLCYCLOPROPENONE

There total 34 articles about DIPHENYLCYCLOPROPENONE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

bis(2,3-diphenylcyclopropenyliun) ether ditriflate + diethylamine (109-89-7) → diethylammonium trifluoromethanesulfonate (60933-18-8) + C19H20N(1+)*CF3O3S(1-) + diphenylcyclopropenone (886-38-4)

Guidance literature:

In chloroform;

DOI:10.1021/ja00406a028

Reference yield: 95.0%

3-phenyl-2-propanol (698-87-3,14898-87-4) + 3,3-dichloro-1,2-diphenylcyclopropene (2570-00-5) → 1-phenyl-2-chloropropane (10304-81-1) + diphenylcyclopropenone (886-38-4)

Guidance literature:

In acetonitrile; at 80 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja906520p

Reference yield: 95.0%

3,3-dichloro-1,2-diphenylcyclopropene (2570-00-5) + geraniol (624-15-7) → geranyl chloride (4490-10-2) + diphenylcyclopropenone (886-38-4)

Guidance literature:

In dichloromethane; at 23 ℃; for 0.0833333h; Inert atmosphere;

DOI:10.1021/ja906520p

upstream raw materials:

benzylidene dichloride

1,1-dimethoxy-2-phenylethene

4-methyl-2H-chromen-2-one

C₁₆H₁₃O⁽¹⁺⁾*BF₄^(1-)

Downstream raw materials:

2-(t-Butylthio)-9,9a-tetramethylen-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin

2-Methoxy-9,9a-tetramethylen-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin

2-Ethoxy-9,9a-tetramethylen-3,4-diphenyl-7,8,9,9a-tetrahydro-2H,6H-pyrido<2.1-b><1.3>oxazin

5,6-Tetramethylen-2,3-diphenyl-1-azabicyclo<4.3.0>non-2-en-4-on

Refernces

• 1、 Breslow,Peterson. "-". . p. 4426. Retrieved 1960.
• 2、 Sánchez García, Jessica J.,Joo-Cisneros, Rene S.,García-Bassoco, David,Flores-Alamo, Marcos,Stivalet, José M. Méndez,García-Valdés, Jesús,Klimova, Elena I.. "Synthesis, characterization, and oxidation electrochemistry of some novel 1,2-dithiol-3-ones and 1,2-dithiol-3-thiones containing aryl and metallocenyl fragments". . . Retrieved 2021/05/17.
• 3、 Nanda, Tanmayee,Biswal, Pragati,Pati, Bedadyuti Vedvyas,Banjare, Shyam Kumar,Ravikumar, Ponneri Chandrababu. "Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides". . p. 2682 - 2695. Retrieved 2021/02/01.