6964-04-1

Basic information

• Product Name: 3-METHYL-2,4-HEPTANEDIOL
• Synonyms: 3-METHYL-2,4-HEPTANEDIOL;3-methylheptane-2,4-diol;Nsc66399
• CAS NO: 6964-04-1
• Molecular Formula: C₈H₁₈O₂
• Molecular Weight: 146.23
• Mol File: 6964-04-1.mol

Chemical Properties

• Melting Point: 43.76°C (estimate)
• Boiling Point: 122-123℃ (15.5 Torr)
• Flash Point: 102.6°C
• Appearance: /
• Density: 0.9280
• Vapor Pressure: 0.0106mmHg at 25°C
• Refractive Index: 1.4459
• PKA: 14.92±0.20(Predicted)
• CAS DataBase Reference: 3-METHYL-2,4-HEPTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYL-2,4-HEPTANEDIOL(6964-04-1)
• EPA Substance Registry System: 3-METHYL-2,4-HEPTANEDIOL(6964-04-1)

Safety Data

• Hazardous Substances Data: 6964-04-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H18O2/c1-4-5-8(10)6(2)7(3)9/h6-10H,4-5H2,1-3H3

Upstream product

• 99506-67-9 3-hydroxy-2-methylbutanal 
• 927-77-5 n-propylmagnesium bromide 
• 56072-27-6 4-hydroxy-3-methyl-2-heptanone 

Downstream Products

• 15726-15-5 3-methyl-4-heptanone 

Relevant articles and documents

Diastereoselective nucleophilic substitution reactions of oxasilacyclopentane acetals: Application of the "inside attack" model for reactions of five-membered ring oxocarbenium ions

The additions of nucleophiles to oxocarbenium ions derived from oxasilacyclopentane acetates proceeded with high diastereoselectivity in most cases. Sterically demanding nucleophiles such as the silyl enol ether of diethyl ketone add to the face opposite the C-2 substituent. These reactions establish the syn stereochemistry about the newly formed carbon-carbon bond. Small nucleophiles such as allyltrimethylsilane do not show this same stereochemical preference: they add from the same face as the substituent in C-2-substituted oxocarbenium ions. The stereoselectivities exhibited by both small and large nucleophiles can be understood by application of the "inside attack" model for five-membered ring oxocarbenium ions developed previously for tetrahydrofuran-derived cations. This stereoelectronic model requires attack of the nucleophile from the face of the cation that provides the products in their lower energy staggered conformations. Small nucleophiles add to the "inside" of the lower energy ground-state conformer of the oxocarbenium ion. In contrast sterically demanding nucleophiles add to the inside of the envelope conformer where approach is anti to the C-2 substituent of the oxocarbenium ion, regardless of the ground-state conformer population.

REGIOSELECTIVITY OF ALDOL CONDENSATION AND THE STEREOCHEMISTRY OF THE PRODUCTS FROM THE REDUCTION OF β-HYDROXY KETONES

The thermodynamically controlled β-hydroxy ketones are mostly formed during the aldol condensation of ketones with aldehydes in the presence of alkali.The importance of considering the intramolecular hydrogen bonds was confirmed during conformational analysis of the isomeric mixtures of β-diols produced by the reduction of the β-hydroxy ketones.