10317-10-9

Usage

Uses

Used in Chemical Synthesis:
3-Chloro-2-methyl-1-propanol is used as a reagent for the oxidation of organoboranes with sodium percarbonate. This reaction is significant in the synthesis of various organic compounds, as it allows for the conversion of organoboranes into their corresponding alcohols or carbonyl compounds.
In the field of organic chemistry, 3-Chloro-2-methyl-1-propanol serves as a versatile intermediate for the preparation of a wide range of chemical products. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. By utilizing its chloro and hydroxyl functional groups, chemists can perform various transformations, such as nucleophilic substitution, elimination, and addition reactions, to construct complex molecular architectures.

Synthesis Reference(s)

Tetrahedron Letters, 30, p. 1483, 1989 DOI: 10.1016/S0040-4039(00)99497-8

Upstream product

• 616-19-3 1,3-dichloro-2-methylpropane 
• 2159-71-9 1-acetoxy-3-chloro-2-methyl-propane 
• 563-47-3 3-Chloro-2-methylpropene 
• 78-85-3 2-methylpropenal 

Relevant academic research and scientific papers

SODIUM PERBORATE: A MILD AND CONVENIENT REAGENT FOR EFFICIENTLY OXIDIZING TRIALKYLBORANES

Sodium perborate, a readily available and inexpensivereagent, efficiently oxidizes organoboranes.The reagent permits the oxidation of a wide variety of functionally substituted organoboranes.In nearly every instance, the product yields exceed those obtained using standard oxidation procedures.

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

Sequenced Reactions with Samarium(II) Iodide. Sequential Intermolecular Carbonyl Addition/Intramolecular Nucleophilic Acyl Substitution for the Preparation of Seven-, Eight-, and Nine-Membered Carbocycles

Samarium(II) iodide has been employed to promote a tandem intermolecular carbonyl addition/ intramolecular nucleophilic acyl substitution sequence, generating seven-through nine-membered monocyclic, bicyclic, and tricyclic ring systems with good yields an

Sodium Perborate: A Mild and Convenient Reagent for Efficiently Oxidizing Organoboranes

Sodium perborate, a readily available and inexpensive reagent, efficiently oxidizes organoboranes.The reagent permits the oxidation of a wide variety of functionally substituted organoboranes.In nearly every instance, the product yields exceed those obtained using standard oxidation procedures.

Anodic Oxidation of Organoboranes

Organoboranes are converted into more easily oxidizable borates by reaction with nucleophiles and the alkyl groups are dimerized by anodic oxidation.The oxidation potentials (Ep) of the borates depend strongly on the nature of the complexing nucleophile, for instance Ep = +0.37 V (vs.SCE) with OH- or +1.65 V with tetrahydrofuran.The dimer yields are optimized with trioctylborane (5) by variation of the electrode material and the elctrolyte.At the platinum anode in sodium hydroxide-methanol/tetrahydrofuran yields of 80percent are obtained for acyclic alkyl groups, and lo wer ones for cycloalkyl groups.They exceed those obtained by the Kolbe electrolysis or the oxidation with neutral hydrogen peroxide and they are comparable to those of the AgNO3 oxidation. - The selective preparation of unsymmetrical products from borates with different alkyl groups is not possible, the dimerization proceeds likely via free radicals that couple statistically.Good yields of unsymmetrical coupling products are achieved, when one olefin is used in excess.With choro-, ethoxy-, acetoxy-, and aryl-substituted alkyl groups the dimers are obtained in 21 - 66percent yield, with bromide the yield are lower and with nitriles the dimerization fails.

Hydroboration. 57. Hydroboration with 9-Borabicyclononane of Alkenes Containing Representative Functional Groups

The hydroboration of alkenes containing representative functional groups was examined with 9-borabicyclononane (9-BBN) in order to extend the hydroboration reaction for the preparation of functionally substituted organoboranes.Terminal alkenes containing a remote functional group are hydroborated with a remarkable regioselectivity (>=98percent terminal), producing the corresponding stable organoboranes. 9-BBN hydroborates the allylic derivatives so as to place boron essentially on the terminal carbon atom (>=97percent).The directive effect is further enhanced (>=99percent) in the case of β-methylallyl derivatives.The hydroboration of crotyl derivatives attaches boron predominantly at the 2-position, followed by an elimination-rehydroboration sequence.However, crotyl alcohol can be protected against elimination as the tert-butyl or tetrahydropyranyl ethers.The hydroboration-oxidation of ethyl crotonate involves a series of elimination, hydroboration, and condensation processes.In the vinyl, crotyl, and isobutenyl systems, the mesomeric effect of the substituent favors the placement of boron at the β-position, while the inductive effect favors the α-position, with the former effect predominating in most cases.Acyclic β-substituted organoboranes undergo rapid elimination.Nonpolar solvents and lower reaction temperatures decrease the rate of elimination.However, those derived from cyclic vinyl derivatives are relatively stable under neutral conditions, undergoing facile elimination in the presence of a base.