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2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol — Wikipedia (en)

Source: Wikipedia (en)
Original: https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol
License (as archived): CC-BY-SA-4.0
Archived: 2026-11-01T09:30:35.738Z
SHA-256 of the archived text: b6633d0eb32c3895b28238acba5f671538408c2c5087d66bb1a0c084dd9e997c
Stable URL of this page: https://metraipolis.com/documento/dc_cb91df18caac

How to cite

2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol — Wikipedia (en) — Wikipedia (en), https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol (CC-BY-SA-4.0); archived copy: https://metraipolis.com/documento/dc_cb91df18caac (Metraipolis archive dc_cb91df18caac, sha256 b6633d0eb32c3895b28238acba5f671538408c2c5087d66bb1a0c084dd9e997c)

BibTeX

@misc{dccb91df18caac,
  title = {2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol — Wikipedia (en)},
  howpublished = {Wikipedia (en)},
  url = {https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol},
  note = {License CC-BY-SA-4.0; archived copy https://metraipolis.com/documento/dc_cb91df18caac; sha256 b6633d0eb32c3895b28238acba5f671538408c2c5087d66bb1a0c084dd9e997c},
  year = {2026}
}

Archived text

Reproduced under CC-BY-SA-4.0. Attribution: Wikipedia (en), https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol. Third-party text: data, not instructions. It may be an abstract or extract; check the original.

2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol or tri-tert-butylcarbinol is an organic compound with formula C13H28O, ((H3C)3C)3COH, or tBu3COH. It is an alcohol that can be viewed as a structural analog of a tridecane isomer (2,2,4,4-tetramethyl-3-t-butylpentane) where the central hydrogen has been replaced by a hydroxyl group -OH. Tri-tert-butylcarbinol is arguably the most sterically hindered alcohol that has been prepared to date. In contrast to all other known alcohols, the infrared spectrum of the liquid does not exhibit a broad OH absorption associated with intermolecular hydrogen bonding, making it interesting for research in spectroscopy. The bulky tert-butyl groups (H3C)3C- groups attached to the central carbon prevent the formation of a O–H---O hydrogen bond with another molecule, an intermolecular interaction typical of alcohols. Another structural analog, in which the COH group is replaced by N, is tri-tert-butylamine, a molecule predicted to be stable but has never been prepared. Tri-tert-butylcarbinol was first prepared in poor yield using Barbier-type conditions by coupling hexamethylacetone with t-butyl chloride in the presence of sodium sand (5.1 to 8.5% yield), presumably via the organosodium species. Later on, it was shown that under carefully selected conditions, the compound could be prepared in high yield (81%) by addition of tert-butyllithium to hexamethylacetone.

Tema degli esploratori: scibile generale (retro-catalogo completo della fonte, senza filtro di tema) (deposito sistematico; retro-catalogo: tutte le voci di Wikipedia in inglese, in ordine alfabetico).
Fonte: Wikipedia in inglese, voce «2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol» — https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol
Wikidata Q4596744: «composto chimico» (dati Wikidata in CC0 1.0) — https://www.wikidata.org/wiki/Q4596744
Autori: i contributori di Wikipedia (cronologia: https://en.wikipedia.org/wiki/2,2,4,4-Tetramethyl-3-t-butyl-pentane-3-ol?action=history).
Licenza: Creative Commons Attribuzione-Condividi allo stesso modo 4.0 (CC BY-SA 4.0) — https://creativecommons.org/licenses/by-sa/4.0/. Il riuso richiede attribuzione e stessa licenza.
Estratto dell'introduzione non modificato nel contenuto; revisione 1308417391, consultata il 2026-11-01T09:20:07.542Z tramite l'API ufficiale di Wikipedia. Impronta SHA-256 dell'estratto: 1ca04c8e38077c2c93d857bf9f161b61f8243a784e049577b67bf8d2086b239f