Diphenylmethane
Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH
2Ph
2). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid.
 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
1,1'-Methylenedibenzene | |
| Other names
Diphenylmethane Benzylbenzene | |
| Identifiers | |
3D model (JSmol) |
|
| Abbreviations | BnPh, Ph2CH2 |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.002.708 |
| MeSH | Diphenylmethane |
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C13H12 | |
| Molar mass | 168.234 |
| Appearance | colourless oil |
| Density | 1.006 g/mL |
| Melting point | 22 to 24 °C (72 to 75 °F; 295 to 297 K) |
| Boiling point | 264 °C (507 °F; 537 K) |
| 14 mg/L | |
| Acidity (pKa) | 33 |
| -115.7·10−6 cm3/mol | |
| Hazards | |
| Main hazards | flammable |
| Flash point | > 110 °C; 230 °F; 383 K |
| Related compounds | |
Related compounds |
Diphenylmethanol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
  | |
| Infobox references | |
Diphenylmethane is a common skeleton in organic chemistry. The diphenylmethyl group is also known as benzhydryl.
Synthesis and reactions
It is prepared by the Friedel–Crafts alkylation of benzyl chloride with benzene in the presence of a Lewis acid such as aluminium chloride:[1]
- C6H5CH2Cl + C6H6 → (C6H5)2CH2 + HCl
The methylene group in diphenylmethane is mildly acidic. The resulting carbanion can be alkylated:[2]
- (C6H5)2CH2 + NaNH2 → (C6H5)2CHNa + NH3
- (C6H5)2CHNa + RBr → (C6H5)2CHR + NaBr
gollark: See, when I believe things, I believe them properly, by storing them in the belief hashset on my secondary server.
gollark: What? You said I was Host! Repeatedly! Was that just signalling?
gollark: Say, do you have any secret scrypt ASICs?
gollark: Under heavy load.
gollark: Plus the GPU power supply seems to be broken a bit because it buzzes unpleasantly.
References
- W. W. Hartman and Ross Phillips (1934). "Diphenylmethane". Organic Syntheses. 14: 34. doi:10.15227/orgsyn.014.0034.
- Murphy, William S.; Hamrick, Phillip J.; Hauser, Charles R. (1968). "1,1-Diphenylpentane". Organic Syntheses. 48: 80. doi:10.15227/orgsyn.048.0080.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.