ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Cyclic hydrocarbons 5-Norbornene-2-methanol

5-Norbornene-2-methanol

Product Name5-Norbornene-2-methanol
CAS95-12-5
MFC8H12O
MW124.18
EINECS202-392-0
MOL File95-12-5.mol

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
pka	14.92±0.10(Predicted)
form	clear liquid
color	Colorless to Almost colorless
optical activity	Consistent with structure
InChI	1S/C8H12O/c9-5-8-4-6-1-2-7(8)3-6/h1-2,6-9H,3-5H2/t6-,7+,8/m0/s1
InChIKey	LUMNWCHHXDUKFI-KJFJCRTCSA-N
SMILES	OCC1C[C@@H]2C[C@H]1C=C2
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
TSCA	TSCA listed
HS Code	2906190090
Storage Class	10 - Combustible liquids
Hazard Classifications	Acute Tox. 4 Oral

MSDS

Provider	Language
SigmaAldrich	English

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

542-92-7

107-18-6

95-12-5

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 cm1 (OH stretching vibration), 2930-2895 cm1 and 2880-2830 cm1 (C-H stretching vibration), 1200 -1100 cm1 (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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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