5-Norbornene-2,3-dimethanol

Base Information

• Chemical Name: 5-Norbornene-2,3-dimethanol
• CAS No.: 85-39-2
• Molecular Formula: C9H14 O2
• Molecular Weight: 154.209
• Hs Code.: 2906199090
• European Community (EC) Number: 201-601-2,625-614-1
• NSC Number: 31985
• DSSTox Substance ID: DTXSID801005320
• Nikkaji Number: J192.629B
• Mol file: 85-39-2.mol

Synonyms:5-norbornene-2,3-dimethanol;Nb-MEOH

Chemical Property of 5-Norbornene-2,3-dimethanol

Chemical Property:

• Melting Point: 82 °C
• Boiling Point: 144-162 °C(Press: 6.5 Torr)
• PKA: 14.62±0.10(Predicted)
• PSA: 40.46000
• Density: 1.136±0.06 g/cm3(Predicted)
• LogP: 0.40930
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

98% ^*data from raw suppliers

5-Norbornene-2,3-dimethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC1C(C2CO)CO

Technology Process of 5-Norbornene-2,3-dimethanol

There total 8 articles about 5-Norbornene-2,3-dimethanol 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: 76.0%

5-norbornene-2,3-dicarboxylic anhydride (826-62-0,85081-15-8,85081-16-9) → 5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene (85-39-2,448922-61-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 48h; Heating;

DOI:10.1021/ja00404a028

Reference yield:

(1S,2S,3S,4R)-3-carboxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ester (3813-52-3) → 5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene (85-39-2,448922-61-0)

Guidance literature:

Multistep reaction; (i) MeOH, HCl, (ii) H₂, Cr₂O₃, CuO, dioxane;

DOI:10.1007/BF00924776

Reference yield:

dimethyl carbate (5826-73-3) → 5,6-bis(hydroxymethyl)bicyclo<2.2.1>hept-2-ene (85-39-2,448922-61-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 48h; Heating;

DOI:10.1021/ja00404a028

upstream raw materials:

5-norbornene-2,3-dicarboxylic anhydride

dimethyl carbate

(1S,2S,3S,4R)-3-carboxy-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid ester

cyclopenta-1,3-diene

Downstream raw materials:

C₂₃H₂₆O₆S₂

Methanesulfonic acid (2R,3R)-3-methanesulfonyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester

Refernces

• 1、 Gajewski, Joseph J.,Salazar, Jose Del C.. "Degenerate Thermal Rearrangement of 1,3-Dimethylenecyclopentane. Evidence for Partially Stereospecific Biradical Formation and Closure in 1,3 Shift". . p. 4145 - 4154. Retrieved 2007/10/02.