Bicyclo[2.2.1]hept-5-en-2-ol

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-en-2-ol
• CAS No.: 13080-90-5
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.156
• Hs Code.: 2906199090
• European Community (EC) Number: 235-987-9
• NSC Number: 110578,108290,50234
• DSSTox Substance ID: DTXSID40871953
• Nikkaji Number: J110.391A
• Mol file: 13080-90-5.mol

Synonyms:Bicyclo[2.2.1]hept-5-en-2-ol;13080-90-5;5-Norbornene-2-ol;5-Norbornen-2-ol;5-Norbornen-2-ol, exo-;exo-2-Norbornenol;Bicyclo(2.2.1)hept-5-en-2-ol;EINECS 235-987-9;Bicyclo[2.2.1]hept-5-en-2-ol, exo-;bicyclo[2.2.1)hept-5-en-2-ol;Bicyclo(2.2.1)hept-5-en-2-ol, exo-;bicyclo[2.2.1]hept-2-en-5-ol;norbornene-5-ol;Norbornen-5-ol;5-exo-norbornenol;2890-98-4;endo-2-Norbornenol;NSC50234;exo-Dehydronorborneol;endo-Dehydronorborneol;5-Norbornen-2-ol, endo-;ghl.PD_Mitscher_leg0.740;SCHEMBL278517;DTXSID40871953;5-bicyclo[2.2.1]hept-2-enol;MFCD00167566;NSC 50234;NSC-50234;NSC108290;NSC110578;AKOS015917582;Bicyclo[2.2.1]hept-5-en-2-ol #;CS-W008466;FD14040;NSC-108290;NSC-110578;DS-13830;Bicyclo[2.2.1]hept-5-en-2-ol, endo-;FT-0689543;EN300-110065;A806152;A905540;694-97-3

Chemical Property of Bicyclo[2.2.1]hept-5-en-2-ol

Chemical Property:

• Vapor Pressure: 0.218mmHg at 25°C
• Melting Point: 104-106 °C(lit.)
• Refractive Index: 1.574
• Boiling Point: 183.7 °C at 760 mmHg
• PKA: 14.85±0.20(Predicted)
• Flash Point: 62 °C
• PSA: 20.23000
• Density: 1.153 g/cm³
• LogP: 0.94330
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.073164938
• Heavy Atom Count: 8
• Complexity: 128

Purity/Quality:

98% ^*data from raw suppliers

5-Norbornen-2-ol, mixture of endo and exo 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-27-33-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)O
• Uses: It is applied in High Performance Liquid Chromatography. (HPLC) and Nuclear Magnetic Resonance (NMR).

Technology Process of Bicyclo[2.2.1]hept-5-en-2-ol

There total 61 articles about Bicyclo[2.2.1]hept-5-en-2-ol 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: 91.0%

(1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate (5257-37-4) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

With sodium hydroxide; In methanol; for 4h; Heating;

DOI:10.1002/hlca.19800630409

Reference yield: 85.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

bicyclo[2.2.1]hepta-2,5-diene; With [(S,S)-MeDuphos]Rh(NBD)OTf; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 20 ℃; for 3h;

With dihydrogen peroxide; sodium hydroxide; In water; optical yield given as %de; Inert atmosphere;

DOI:10.1002/adsc.200900013

Reference yield: 75.0%

(2-acetoxy-cis-exo-bicyclo[2.2.1]hept-5-en-3-yl)mercuric chloride (1077-98-1) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

With sodium hydroxide; sodium amalgam; at 20 ℃; for 18h;

DOI:10.1016/S0040-4020(02)01276-0

upstream raw materials:

vinyl acetate

endo-5-norbornen-2-ol

(-)-<1S,4S>bicyclo<2.2.1>heptene-5 one-2

5-norbornenyl-2-acetate

Downstream raw materials:

5-endo-Bromo-6-exo-(phenylselenyl)bicyclo<2.2.1>heptan-2-exo-ol

6-endo-Bromo-5-exo-(phenylselenyl)bicyclo<2.2.1>heptan-2-exo-ol

Norbornan-2-on

Norborneol

Refernces

• 1、 Pisano, Pablo L.,Pellegrinet, Silvina C.. "Alkylhalovinylboranes: a new class of Diels-Alder dienophiles". . p. 33864 - 33871. Retrieved 2018/10/20.
• 2、 Vallejos, Margarita M.,Grimblat, Nicolas,Pellegrinet, Silvina C.. "Diels-Alder reactions of pinacol alkenylboronates: An experimental and theoretical study". . p. 36385 - 36400. Retrieved 2014/12/09.