NORBORNANE-2-CARBOXALDEHYDE

Base Information

• Chemical Name: NORBORNANE-2-CARBOXALDEHYDE
• CAS No.: 3574-55-8
• Molecular Formula: C8H12 O
• Molecular Weight: 124.183
• Hs Code.: 2912299000
• Mol file: 3574-55-8.mol

Synonyms:2-Norbornanecarboxaldehyde,exo- (8CI); Bicyclo[2.2.1]heptane-2-carboxaldehyde, exo-;exo-Norbornane-2-carboxaldehyde; exo-Norbornylcarboxaldehyde

Chemical Property of NORBORNANE-2-CARBOXALDEHYDE

Chemical Property:

• PSA: 17.07000
• LogP: 1.62150

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of NORBORNANE-2-CARBOXALDEHYDE

There total 6 articles about NORBORNANE-2-CARBOXALDEHYDE 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: 73.0%

Bicyclo<2.2.1>heptan-1-oxiran-2-ylmethyltrimethylsilane (86553-92-6) → 3-formyl-bicyclo<2.2.1>heptane (3574-54-7,3574-55-8,19396-83-9,69769-91-1,69769-92-2,104418-69-1,110849-52-0,135818-35-8)

Guidance literature:

With tetrahydrofuran; perchloric acid; at 20 ℃; for 10h;

DOI:10.1016/S0040-4020(01)88585-9

Reference yield:

5-carboxybicyclo<2.2.1>hept-2-ene (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) → 2-exo-Bicyclo<2.2.1>heptanecarboxaldehyde (3574-55-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 2 h / 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 40 °C

3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 4.17 h / 20 °C

4.1: oxalyl dichloride / dimethyl sulfoxide; dichloromethane / 0.5 h / -75 - -70 °C

4.2: 0.33 h / -75 - -68 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1021/acs.jmedchem.0c00359

Reference yield:

carbon monoxide (201230-82-2) + norbornene (498-66-8) → 3-formyl-bicyclo<2.2.1>heptane (3574-54-7,3574-55-8,19396-83-9,69769-91-1,69769-92-2,104418-69-1,110849-52-0,135818-35-8)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; (acetylacetonato)dicarbonylrhodium (l); hydrogen; In tert-butyl alcohol; at 35 ℃; for 20h; under 2327.23 Torr; Inert atmosphere; Large scale reaction;

DOI:10.1021/op100284a

upstream raw materials:

5-carboxybicyclo<2.2.1>hept-2-ene

Bicyclo<2.2.1>heptan-1-oxiran-2-ylmethyltrimethylsilane

5-(hydroxymethyl)bicyclo[2.2.1]hept-2-ene

2-norbornanone