25144-05-2

Basic information

• Product Name: Cyclopentanol,2-methyl-, (1R,2S)-rel-
• Synonyms: Cyclopentanol,2-methyl-, cis- (8CI); (?à)-cis-2-Methylcyclopentanol; cis-2-Methylcyclopentanol
• CAS NO: 25144-05-2
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.1589
• Mol File: 25144-05-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 17.63°C (estimate)
• Boiling Point: 146.9°Cat760mmHg
• Flash Point: 47.2°C
• Density: 0.947g/cm³
• Refractive Index: 1.4504
• PKA: 15.33±0.40(Predicted)
• CAS DataBase Reference: Cyclopentanol,2-methyl-, (1R,2S)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopentanol,2-methyl-, (1R,2S)-rel-(25144-05-2)
• EPA Substance Registry System: Cyclopentanol,2-methyl-, (1R,2S)-rel-(25144-05-2)

Safety Data

• Hazardous Substances Data: 25144-05-2(Hazardous Substances Data)

Upstream product

• 40911-83-9 tris(trans-2-methylcyclopentyl)borane 
• 125364-79-6 2-(4-pentenyl)-5-oxo-1,3-oxathiolane 
• 764-59-0 hex-5-en-1-al 
• 1120-72-5 2-Methylcyclopentanone 
• 89155-67-9 tert-Butyl-dimethyl-(2-methyl-cyclopentyloxy)-silane 
• 63452-95-9 1,4-bis(bromomagnesio)pentane 
• 109-94-4 formic acid ethyl ester 
• 135879-52-6 Mercapto-acetic acid 2-methyl-cyclopentyl ester 
• 121108-79-0 cis-6-bromo-2,3-epoxyhexane 
• 693-89-0 1-methylcyclopent-1-ene 
• 2396-80-7 methyl 5-hexenoate 

Downstream Products

• 693-89-0 1-methylcyclopent-1-ene 
• 85982-46-3 1-fluoro-1-methylcyclopentane 
• 5857-77-2 cis-2-methylcyclopentyl p-toluenesulfonate 
• 1120-72-5 (S)-2-methylcyclopentanone 
• 1120-72-5 (R)-α-methylcyclopentanone 
• 110434-51-0 trans-1-methyl-2-(phenylthio)cyclopentane 
• 1120-72-5 2-Methylcyclopentanone 
• 36367-81-4 cis-2-methylcyclopentyl brosylate 

Relevant articles and documents

Al-isopropoxydiisobutylalane: A study of the effect of solvent on the rate and stereoselectivity of cyclic ketone reduction

The effect of solvent on the rate and stereoselectivity of cyclic ketone reduction by Al-isopropoxydiisobutylalane (DIBAiOPr) has been investigated. In dichloromethane, DIBAiOPr behaves as a bulky reducing agent, approaching the carbonyl group along an equatorial trajectory to produce the axial alcohol with > 10:1 stereoselectivity. In sharp contrast, reduction in toluene gives the complementary outcome, affording the thermodynamically more stable isomer with > 99:1 stereoselectivity.

Electroreductive intramolecular cyclization of olefinic esters and its application to the synthesis of muscone

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Preparation and use of sterically hindered organobis(2,4,6-triisopropylphenyl)hydroborates and their polystyrene derivatives for the diastereoselective reduction of ketones

Preparations of benzyl and phenylbis(2,4,6-triisopropylphenyl)hydroborates [organoditripylhydroborates] are outlined. The lithium and potassium benzylditripylhydroborates reduce substituted cyclohexanones with diastereoselectivities comparable to those obtained with the most selective reagents known (eg. 99% cis-4-methylcyclohexanol from 4-methylcyclohexanone). Lithium phenylditripylhydroborate also reduces ketones with significant selectivity. For example, 4-methylcyclohexanone is reduced to cis-4-methylcyclohexanol in 88% isomeric purity. Unlike with most other highly selective reagents the reactions take place at room temperature and have the additional advantage that the boron reagent can be recovered quantitatively. Coupling of Merrifield's resin with ditripylfluoroborane in the presence of lithium naphthalenide affords (ditripylborylmethyl)polystyrene. Similarly, coupling of bromopolystyrene with ditripylfluoroborane in the presence of n-BuLi affords (ditripylboryl)polystyrene. Reactions of these polymeric organoboranes with t-BuLi give the corresponding polymer-supported lithium hydroborates. Lithium ditripylhydroboratylmethylpolystyrene reduces cyclic ketones in identical fashion to its non-polymeric counterpart, giving the corresponding thermodynamically less stable alcohols in 99% or better isomeric purity. Similarly, lithium ditripylhydroboratylpolystyrene behaves like its non-polymeric counterpart and reduces 4-methylcyclohexanone to cis-4-methylcyclohexanol in 89% isomeric purity. Recovery and reuse of the organoboranes are even easier for the polymeric reagents. The Royal Society of Chemistry 1999.