METHYL BICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE

Base Information

• Chemical Name: METHYL BICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE
• CAS No.: 35520-81-1
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Hs Code.: 2916209090
• Mol file: 35520-81-1.mol

Synonyms:2-methoxycarbonylnorbornane;Methyl bicyclo[2.2.1]heptane-2-carboxylate;Norborn-5-en-2-carbonsaeuremethylester;methyl norbornane monocarboxylate;Bicyclo[2.2.1]heptane-2-carboxylic acid, methyl ester;exo-2-Norbornyl-carbonsaeure-methylester;endo-2-Norbornyl-carbonsaeure-methylester;2-Carbomethoxynorbornan;Bicyclo[2.2.1]heptane-2-carboxylic acid,methyl ester;2-Carbomethoxy-bicyclo<2.2.1>heptan;

Chemical Property of METHYL BICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 0.315mmHg at 25°C
• Boiling Point: 201°C at 760 mmHg
• Flash Point: 69°C
• PSA: 26.30000
• Density: 1.079g/cm³
• LogP: 1.59560

Purity/Quality:

99% ^*data from raw suppliers

methylbicyclo[2.2.1]heptane-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL BICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE

There total 6 articles about METHYL BICYCLO[2.2.1]HEPTANE-2-CARBOXYLATE 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:

(-)-(1S,4S,5R)-bicyclo<2.2.1>hept-2-ene-5-carboxylic acid (120-74-1,934-30-5,1195-12-6,20507-53-3,58001-99-3,67999-50-2,67999-53-5,74645-32-2,108266-75-7) → exo-2-(methoxycarbonyl)norbornane (16646-41-6,23057-38-7,35520-81-1,61967-04-2,78392-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium/charcoal; ethyl acetate / Hydrogenation

With palladium on activated charcoal; ethyl acetate;

DOI:10.1021/ja01524a066

Reference yield:

norborn-2-ene (498-66-8) + carbon monoxide (201230-82-2) → methyl exo-2-norbornanecarboxylate (186182-40-1) + exo-2-(methoxycarbonyl)norbornane (16646-41-6,23057-38-7,35520-81-1,61967-04-2,78392-10-6)

Guidance literature:

With C₃₀H₂₅FeP; trifluoroacetic acid; palladium dichloride; In tetrahydrofuran; methanol; at 70 ℃; for 24h; under 22502.3 Torr; optical yield given as %ee; enantioselective reaction; Autoclave;

DOI:10.1002/adsc.200900025

Reference yield:

methanol (67-56-1) + carbon monoxide (201230-82-2) + norbornene (498-66-8) → methyl exo-2-norbornanecarboxylate (186182-40-1) + exo-2-(methoxycarbonyl)norbornane (16646-41-6,23057-38-7,35520-81-1,61967-04-2,78392-10-6)

Guidance literature:

With trifluoroacetic acid; palladium dichloride; at 70 ℃; for 24h; under 22502.3 Torr; stereoselective reaction;

DOI:10.1039/c2dt30267e

upstream raw materials:

diazomethane

carbon dioxide

exo-2-chloronorbornane

endo-2-chloronorbornane

Downstream raw materials:

norbornane-2-carboxylic acid

2-isopropylidenebicyclo<2.2.1>heptane

Refernces

• 1、 Blanco, Carolina,Godard, Cyril,Zangrando, Ennio,Ruiz, Aurora,Claver, Carmen. "Room temperature asymmetric Pd-catalyzed methoxycarbonylation of norbornene: Highly selective catalysis and HP-NMR studies". experimental part. p. 6980 - 6991. Retrieved 2012/07/14.
• 2、 Stapersma, J.,Kuipers, P.,Klumpp, G. W.. "The reaction of some polycyclic halides with lihium p,p'-di-tert-butylbiphenyl". . p. 213 - 218. Retrieved 2007/10/02.