16958-20-6

Basic information

• Product Name: (Z)-2-Methyl-2-penten-1-ol
• Synonyms: (Z)-2-Methyl-2-penten-1-ol
• CAS NO: 16958-20-6
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• Mol File: 16958-20-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 65 °C(Press: 25 Torr)
• Appearance: /
• Density: 0.845±0.06 g/cm3(Predicted)
• PKA: 14.86±0.10(Predicted)
• CAS DataBase Reference: (Z)-2-Methyl-2-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-Methyl-2-penten-1-ol(16958-20-6)
• EPA Substance Registry System: (Z)-2-Methyl-2-penten-1-ol(16958-20-6)

Safety Data

• Hazardous Substances Data: 16958-20-6(Hazardous Substances Data)

Upstream product

• 763-29-1 2-Methyl-1-pentene 
• 36219-40-6 1-bromo-2-hydroxy-2-methyl-3-butene 
• 917-54-4 methyllithium 
• 1268237-40-6 C₈H₁₂O₂ 
• 1268237-41-7 C₈H₁₄O₂ 
• 623-36-9 (E)-2-methylpent-2-enal 

Downstream Products

• 76639-80-0 (+/-)-(2S^*,3R^*)-2,3-Epoxy-2-methyl-pentan-1-ol 
• 339994-61-5 C₁₁H₂₂O 

Relevant articles and documents

The synthesis of (Z)-trisubstituted allylic alcohols by the selective 1,4-hydrogenation of dienol esters: Improved synthesis of (-)-β-santalol

(E)-Trisubstituted allylic alcohols are commonly prepared from the corresponding (E)-enals, themselves readily accessible by a simple aldol condensation reaction. We demonstrate that these very same (E)-enals can be converted into (Z)-trisubstituted allylic acetates (and thus alcohols) by a ruthenium-catalyzed 1,4-hydrogenation of the corresponding dienol acetates. This simple solution to a long-lasting problem was applied to an industrially feasible synthesis of (-)-β-santalol.

COPPER(I)-CATALYZED REACTION OF ISOPRENE BROMOHYDRIN WITH ORGANOLITHIUM REAGENT

The reaction of isoprene bromohydrin (1-bromo-2-methyl-3-buten-2-ol) (1) with ethyl-, propyl- and butyllithium in the presence of copper(I) iodide leads to the exclusive formation of the vinyl group migrated 2-alkyl-4-penten-2-ols (3d-3f), in contrast to