103128-76-3

Basic information

• Product Name: (+)-CHLOROMETHYL MENTHYL ETHER
• Synonyms: (1R,2S,4S)-2-(CHLOROMETHYLOXY)-1-ISOPROPYL-4-METHYLCYCLOHEXANE;(+)-CHLOROMETHYL MENTHYL ETHER;(+)-Chloromethyl menthyl ether, 97% ee
• CAS NO: 103128-76-3
• Molecular Formula: C₁₁H₂₁ClO
• Molecular Weight: 204.74
• Product Categories: Chiral Building Blocks;Ethers;Organic Building Blocks
• Mol File: 103128-76-3.mol

Chemical Properties

• Boiling Point: 72 °C0.4 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: WHITE TO TAN SOLID, POWDER, CRYSTALS,
• Density: 0.994 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.467(lit.)
• Storage Temp.: -20°C
• CAS DataBase Reference: (+)-CHLOROMETHYL MENTHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CHLOROMETHYL MENTHYL ETHER(103128-76-3)
• EPA Substance Registry System: (+)-CHLOROMETHYL MENTHYL ETHER(103128-76-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 103128-76-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(+)-Chloromethyl menthyl ether is used as a starting material for the synthesis of 1-methyl-3-(+)-methylmenthoxide imidazolium chloride, which is a key intermediate for the preparation of Ag(I) N-heterocyclic carbene. This carbene is applicable as a catalyst in the diboration of alkenes, a significant reaction in organic chemistry for the formation of vicinal diols.
Used in Pharmaceutical Industry:
(+)-Chloromethyl menthyl ether serves as a substrate in the synthesis of commercially important O-substituted α-methoxymethylketones. These compounds are valuable in the development of pharmaceuticals and other bioactive molecules due to their unique structural features and potential for further functionalization.
Used in Analytical Chemistry:
(+)-Chloromethyl menthyl ether is utilized to determine the enantiomeric excess (ee) of an iron chiral auxiliary named [Fe(CO)(η;5-C2H5)(PPh3)COCH3]. This application is crucial in the field of asymmetric catalysis and enantioselective synthesis, where the ability to accurately measure ee is essential for assessing the success of a reaction and the quality of the resulting chiral products.

InChI:InChI=1/C11H21ClO/c1-8(2)10-5-4-9(3)6-11(10)13-7-12/h8-11H,4-7H2,1-3H3/t9-,10+,11-/m0/s1

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 15356-60-2 (1S,2R,5S)-(+)-menthol 

Downstream Products

• 1228173-17-8 C₄₀H₅₁NO₁₀S₂ 
• 89398-74-3 5',12'-Bis-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxymethoxy)-[11,11']bi[naphtho[2,3-a]azulenyl]-5,12-dione 
• 89398-69-6 5,12-Bis-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxymethoxy)-naphtho[2,3-a]azulene 
• 132339-28-7 (1S,1'R,2R,2'S,5S,5'R)-1,1'-methylenedioxybis(2-isopropyl-5-methylcyclohexane) 

Relevant articles and documents

Supramolecular interaction of non-racemic benzimidazolium based ion pairs with chiral substrates

A series of novel benzimidazolium-based non-racemic ionic liquids (ILs) was synthesized from low-cost chiral terpenoid alcohols and fully characterized by the use of a wide variety of techniques, such as DSC, ESI-MS, ATR FT-IR, polarimetry as well as 1H and 13C NMR spectroscopy. The ILs were investigated as chiral shift agents for the chiral recognition of racemic mixtures of Mosher's acid potassium salt by 19F NMR spectroscopy, leading to high splitting values of the CF3 signal. Supramolecular interactions between salt and H-C2 of chiral benzimidazolium cation are responsible for the chiral recognition, as was demonstrated by experimental evidences. Indeed, the enantiomeric excess value of enantioenriched substrates depends mainly on the strength of the contact ion pairs.

Preparation and Use of Chloromethyl (-)-Menthyl Ether in the Synthesis of Optically Pure α-Branched α-Amino Nitriles

The synthesis of optically pure chloromethyl (-)-menthyl ether (2b) and its use in the synthesis of di-(-)-menthyl acetal (-)-menthyl (+)-menthyl acetals are described.The diastereomeric mixed acetals 7a,b and 8a,b are easily obtainable from the nitrones 5 and 6, KCN and 2b.The mixture of diastereomers are separated into the pure components 7a, 7b and 8a, 8b by simple silica gel column chromatography.Hydrolysis of these products (H2O2/Na2CO3, ultrasound) followed by N-O cleavage affords the heterocyclic α-methyl-α-amino amides 11a, 11b and 12a, 12b.These are subsequently hydrolyzed to give the corresponding α-methyl-α-amino acids with S and R configuration, respectively.