(-)-Chloromethyl menthyl ether

Base Information

• Chemical Name: (-)-Chloromethyl menthyl ether
• CAS No.: 103128-76-3
• Molecular Formula: C11H21 Cl O
• Molecular Weight: 204.74
• European Community (EC) Number: 621-309-2,622-811-4,626-455-0
• DSSTox Substance ID: DTXSID90908208
• Nikkaji Number: J3.414.089H
• Wikidata: Q76145961
• Mol file: 103128-76-3.mol

Synonyms:(-)-Chloromethyl menthyl ether;26127-08-2;(1S,2R,4R)-2-(chloromethoxy)-4-methyl-1-propan-2-ylcyclohexane;(+)-Chloromethyl isomenthyl ether;DTXSID90908208;103128-76-3;(-)-Chloromethyl menthyl ether, 97%;2-(chloromethoxy)-4-methyl-1-(propan-2-yl)cyclohexane;(1S,2R,4R)-2-(CHLOROMETHOXY)-1-ISOPROPYL-4-METHYLCYCLOHEXANE

Chemical Property of (-)-Chloromethyl menthyl ether

Chemical Property:

• Appearance/Colour: WHITE TO TAN SOLID, POWDER, CRYSTALS,
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 249.1 °C at 760 mmHg 72 °C0.4 mm Hg(lit.)
• Flash Point: 108.6 °C
• PSA: 9.23000
• Density: 0.96 g/cm³
• LogP: 3.66010
• Storage Temp.: -20°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 204.1280930
• Heavy Atom Count: 13
• Complexity: 147

Purity/Quality:

98%,99%, ^*data from raw suppliers

(+)-Chloromethyl menthyl ether 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(C(C1)OCCl)C(C)C
• Isomeric SMILES: C[C@@H]1CC[C@H]([C@@H](C1)OCCl)C(C)C
• Uses: (+)-Chloromethyl menthyl ether can be used:As a starting material for the synthesis of 1-methyl-3-(+)-methylmenthoxide imidazolium chloride, a key intermediate for the preparation of Ag(I) N-heterocyclic carbene, applicable as a catalyst in the diboration of alkenes.As a substrate in the synthesis of commercially important O-substituted α-methoxymethylketones.To determine enantiomeric excess (ee) of an iron chiral auxiliary named [Fe(CO)(η;5- C2H5)(PPh3)COCH3].

Technology Process of (-)-Chloromethyl menthyl ether

There total 2 articles about (-)-Chloromethyl menthyl ether which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1,3,5-Trioxan (110-88-3) + (1S,2R,5S)-(+)-menthol (15356-60-2) → (1S,2R,4S)-2-(chloromethyloxy)-1-isopropyl-4-methylcyclohexane (103128-76-3,144177-48-0)

Guidance literature:

With hydrogenchloride; In pentane; at -4 ℃; for 0.5h;

Reference yield:

C21H40O2 → (1S,2R,4S)-2-(chloromethyloxy)-1-isopropyl-4-methylcyclohexane (103128-76-3,144177-48-0)

Guidance literature:

With acetyl chloride; at 20 ℃; for 36h;

DOI:10.1039/c8cp03881c

Reference yield: 97.0%

1-Methylbenzimidazole (1632-83-3) + (1S,2R,4S)-2-(chloromethyloxy)-1-isopropyl-4-methylcyclohexane (103128-76-3,144177-48-0) → C19H29N2O(1+)*Cl(1-)

Guidance literature:

In neat (no solvent); at 20 ℃; for 0.5h;

DOI:10.1039/c8cp03881c

upstream raw materials:

1,3,5-Trioxan

(1S,2R,5S)-(+)-menthol

Downstream raw materials:

(1S,1'R,2R,2'S,5S,5'R)-1,1'-methylenedioxybis(2-isopropyl-5-methylcyclohexane)

5,12-Bis-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxymethoxy)-naphtho[2,3-a]azulene

5',12'-Bis-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxymethoxy)-[11,11']bi[naphtho[2,3-a]azulenyl]-5,12-dione

C₄₀H₅₁NO₁₀S₂

Refernces

• 1、 Shatzmiller, Shimon,Dolithzky, Ben-Zion,Bahar, Eliezer. "Preparation and Use of Chloromethyl (-)-Menthyl Ether in the Synthesis of Optically Pure α-Branched α-Amino Nitriles". . p. 375 - 379. Retrieved 2007/10/02.