479029-86-2

Basic information

• Product Name: 2-([2H₃]methyl)-4-methyl-4-phenyl[1,1,1-2H₃]pentan-3-ol
• Synonyms: 2-([2H₃]methyl)-4-methyl-4-phenyl[1,1,1-2H₃]pentan-3-ol
• CAS NO: 479029-86-2
• Molecular Weight: 198.254
• Mol File: 479029-86-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-([2H₃]methyl)-4-methyl-4-phenyl[1,1,1-2H₃]pentan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-([2H₃]methyl)-4-methyl-4-phenyl[1,1,1-2H₃]pentan-3-ol(479029-86-2)
• EPA Substance Registry System: 2-([2H₃]methyl)-4-methyl-4-phenyl[1,1,1-2H₃]pentan-3-ol(479029-86-2)

Safety Data

• Hazardous Substances Data: 479029-86-2(Hazardous Substances Data)

Upstream product

• 1195-98-8 2-methyl-2-phenylpropionitrile 
• 23197-02-6 2-chloro[1,1,1,3,3,3-2H₆]propane 
• 3805-10-5 2,2-(dimethyl)-2-phenylacetaldehyde 

Downstream Products

• 31952-55-3 α,α-dimethyl-2-carboxyphenylacetic anhydride 

Relevant articles and documents

On rearrangements by cyclialkylations of arylpentanols to 2,3-dihydro-1H-indene derivatives. Part 2. An unexpected rearrangement by the acid-catalyzed cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol under formation of trans-2,3-dihydro-1,1,2,3-tetramethyl-1H-indene

The acid catalyzed-cyclialkylation of 4-(2-chloro-phenyl)-2,4-dimethylpentan-2-ol (1) gave two products: 4-chloro-2,3-dihydro-1,1,3,3-tetramethyl-1H-indene (2) and also trans-4-chloro-2,3-dihydro-1,1,2,3-tetramethyl-1H-indene (3). A mechanism was proposed in Part 1 (cf. Scheme 1) for this unexpected rearrangement. This mechanism would mainly be supported by the result of the cyclialkylation of 2,4-dimethyl-2-phenylpentan-3-ol (4), which, with respect to the similarity of ion II in Scheme I and ion V in Scheme 2, should give only product 5. This was indeed the experimental result of this cyclialkylation. But the result of the cyclialkylation of 1,1,1,2′,2′,2′-hexadeuterated isomer [2H6]-4 of 4 (cf. Scheme 3) requires a different mechanism as for the cyclialkylation of 1. Such a mechanism is proposed in Schemes 5 and 6. It gives a satisfactory explanation of the experimental results and is supported by the result of the cyclialkylation of 2,4-dimethyl-3-phenylpentan-3-ol (9; Scheme 7). The alternative migration of a Ph or of an i-Pr group (cf. Scheme 6) is under further investigation.