5-Norbornene-2-methanol Chemical Properties

Boiling point:

97 °C/20 mmHg (lit.)

Density 

1.027 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.500(lit.)

Flash point:

188 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

pka

14.92±0.10(Predicted)

color 

Colorless to Almost colorless

optical activity

Consistent with structure

CAS DataBase Reference

95-12-5(CAS DataBase Reference)

NIST Chemistry Reference

5-Norbornene-2-methanol(95-12-5)

EPA Substance Registry System

Bicyclo[2.2.1]hept-5-ene-2-methanol (95-12-5)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22

Safety Statements 

36/37/39-45

WGK Germany 

3

HS Code 

2906190090

MSDS

• Language:English Provider:SigmaAldrich

5-Norbornene-2-methanol Usage And Synthesis

Uses

Monomer for the modification of condensation and addition polymers for coatings.

Uses

5-Norbornene-2-methanol has been used in the preparation of:

• 4-(norborn-2-ene-5-ylmethyleneoxy)-2,2′:6′,2′′-terpyridine
• 5- {[(3,5-di-t-butyl-4-hydroxy-benzoyl)oxy]methyl}-2-norbornene (BHBN)

Definition

Stable, colorless liquid. Miscible with most common organic solvents; slightly soluble in hot water. Combustible.

General Description

Co-polymerization of 5-norbornene-2-methanol with ethylene using heterogeneous silica supported catalysts has been reported.

Synthesis

Cyclopentadiene was mixed with acryl alcohol in a pressure reactor at a molar ratio of 1:2.4 and the reaction was carried out at 170-180 °C and a pressure of 4-5 atm to give 5-norbornene-2-methanol. The product had a yield of 74%, a boiling point of 82-83 °C (10 mmHg), a refractive index nD20 of 1.4970, and a density d420 of 1.027 g/cm3. IR spectra showed characteristic absorption peaks: 3500 cm?1 (OH stretching vibration), 2930-2895 cm?1 and 2880-2830 cm?1 (C-H stretching vibration), 1200 -1100 cm?1 (C-O stretching vibration).1H NMR spectral data (δ, ppm; J, Hz): 0.45 (1H, H6exo, dd, J = 4.1, 13.4), 1.19 (1H, H7anti, t, J = 7.9), 1.44 (1H, H6endo, t, J = 4.1), 1.68-1.72 (1H , H7syn, m), 2.86 (1H, H5, m), 3.29 (1H, H4, m), 3.36-3.46 (2H, C8H2, m), 3.46 (1H, H1, ddd, J = 4.4, 4.6, 4.8), 3.92 (1H, OH, br s), 6.00-6.08 (2H, H2, H3, m).13C NMR spectral data (δC, ppm): 28.8 (C6), 41.8 (C5), 42.3 (C1), 43.6 (C4), 49.4 (C7), 65.8 (C8), 132.3 (C3), 137.8 (C2).

References

[1] Petroleum Chemistry, 2000, vol. 40, # 4, p. 272 - 274
[2] Russian Journal of General Chemistry, 2018, vol. 88, # 10, p. 2204 - 2208
[3] Zh. Obshch. Khim., 2018, vol. 88, # 10, p. 1718 - 1722,5
[4] Russian Journal of Organic Chemistry, 2003, vol. 39, # 7, p. 947 - 951
[5] Russian Journal of Applied Chemistry, 2008, vol. 81, # 10, p. 1803 - 1807

5-Norbornene-2-methanol(95-12-5)Related Product Information

• Norbornene
• Methanol
• 5-ETHYLIDENE-2-NORBORNENE
• 2,5-Norbornadiene
• 5-Norbornene-2,3-dicarboxylic acid
• 5-NORBONENE-2-METHANAMINE
• DiMethyl bicyclo[2.2.1]heptane-1,4-carboxylate
• Bicyclo[2.2.1]heptane-2,5-dione
• Bicyclo[2.2.2]octane-1,4-dimethanol
• bicyclo[1.1.1]pentan-1-ylmethanol
• 2-NORBORNEN-2-YLBORONIC ACID
• DiMethyl bicyclo[1.1.1]pentane-1,3-dicarboxylate
• Bicyclo[1.1.1]pentane-1-carboxylic acid
• BICYCLO[3.3.1]NONANE-2,6-DIONE
• tert-Butyl 5-norbornene-2-carboxylate
• bicyclo[2.2.2]octane-1-carboxylic acid
• bicyclo[1.1.1]pentan-1-ylmethanamine hydrochloride
• 2-(Aminomethyl)norbornane