(-)-Menthyl chloroformate

Base Information

• Chemical Name: (-)-Menthyl chloroformate
• CAS No.: 14602-86-9
• Molecular Formula: C11H19ClO2
• Molecular Weight: 218.724
• DSSTox Substance ID: DTXSID60932752
• Nikkaji Number: J23.486I,J345.764H,J1.762.953K
• Mol file: 14602-86-9.mol

Synonyms:menthyl chloroformate;S(-)-menthyl chloroformate

Chemical Property of (-)-Menthyl chloroformate

Chemical Property:

• Vapor Pressure: 0.01 psi ( 20 °C)
• Refractive Index: n20/D 1.459
• Boiling Point: 233.9 °C at 760 mmHg
• Flash Point: 70 °C
• PSA: 26.30000
• Density: 1.046 g/cm³
• LogP: 3.82260
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 218.1073575
• Heavy Atom Count: 14
• Complexity: 204

Purity/Quality:

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

(-)-(1R)-MenthylChloroformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 23-34-51/53
• Safety Statements: 26-36/37/39-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1CCC(C(C1)OC(=O)Cl)C(C)C
• Uses: Readily forms a chloroimidodicarbonate which asymmetrically chlorinates silyl enol ethers under mild conditions and in good yields.

Technology Process of (-)-Menthyl chloroformate

There total 4 articles about (-)-Menthyl chloroformate 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: 100.0%

bis(trichloromethyl) carbonate (32315-10-9) + (-)-menthol (2216-51-5) → (1R,2S,5R)-menthyl chloroformate (14602-86-9,7635-53-2)

Guidance literature:

With pyridine; In tetrachloromethane; at 55 - 60 ℃; for 6h;

DOI:10.1021/jo070614n

Reference yield: 82.0%

phosgene (75-44-5) + (-)-menthol (2216-51-5) → (1R,2S,5R)-menthyl chloroformate (14602-86-9,7635-53-2)

Guidance literature:

In toluene; at -10 ℃; for 5h;

DOI:10.1016/S0040-4020(98)00504-3

Reference yield:

(-)-menthol (2216-51-5) + trichloromethyl chloroformate (503-38-8) → (1R,2S,5R)-menthyl chloroformate (14602-86-9,7635-53-2)

Guidance literature:

In benzene; 1.) 100 deg C, 13 h, 2.) RT, 18 h;

upstream raw materials:

phosgene

(-)-menthol

bis(trichloromethyl) carbonate

trichloromethyl chloroformate

Downstream raw materials:

5-(-)-menthyloxycarbonyl-(6R)-tetrahydrofolic acid

5-(-)-menthyloxycarbonyl-(6S)-tetrahydrofolic acid

(2S,4R)-di-tert-butyl 4-{[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]carbonyloxy}pyrrolidine-1,2-dicarboxylate

Refernces

• 1、 Li, Bing,Zhang, Shengyong,Chen, Weiping. "An efficient and practical synthesis of BINAM derivatives by diastereoselective [3,3]-rearrangement". . p. 1002 - 1007. Retrieved 2014.
• 2、 Zou, Ying,Huang, Zhi-Cheng,Xiang, Min,Li, Chen-Yi,Li, Xia,Tian, Fang,Wang, Li-Xin. "Spiro Scaffold Chiral Organocatalyst of 3,2′-Pyrrolidinyl Spiro-oxindole Amine and Its Catalytic Evaluation in the Enantioselective Aldol Condensation between 3-(3-Hydroxy-1 H-pyrazol-1-yl)-Oxindole and Paraformaldehyde". . p. 17371 - 17379. Retrieved 2021/12/02.
• 3、 -. "A preparation method of lamivudine". Paragraph 0042; 0046-0048. . Retrieved 2019/04/02.