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M3933

Sigma-Aldrich

2-Methylisoborneol solution

~10 mg/mL in methanol, ≥98% (GC)

Synonym(s):
(1R-exo)-1,2,7,7-Tetramethylbicyclo[2.2.1]heptan-2-ol
Empirical Formula (Hill Notation):
C11H20O
CAS Number:
Molecular Weight:
168.28
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥98% (GC)

concentration

~10 mg/mL in methanol

storage temp.

−20°C

SMILES string

CC1(C)[C@@H]2CC[C@@]1(C)[C@](C)(O)C2

InChI

1S/C11H20O/c1-9(2)8-5-6-10(9,3)11(4,12)7-8/h8,12H,5-7H2,1-4H3/t8-,10-,11-/m1/s1

InChI key

LFYXNXGVLGKVCJ-FBIMIBRVSA-N

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General description

2-Methylisoborneol (2-MIB) is a semi-volatile compound, responsible for the undesirable earthy-musty odor in surface water. It can be efficiently degraded by TiO2 photocatalysis. 2-MIB can also be easily adsorbed on granular activated carbon.

Application

2-Methylisoborneol can be used as a reactant:
  • To prepare N-[(1R,2R,4R)-1,4,7,7-tetramethylbicyclo[2.2.1]hept-2-yl]acetamide by reacting with acetonitrile in the presence of boron trifluoride etherate.
  • In the enantioselective total synthesis of geissoschizine as well as geissoschizol.

Packaging

1 mL in glass ampule

Other Notes

Fungal metabolite which contributes to the earthy odor in public water supplies.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Flam. Liq. 2 - STOT SE 1

Storage Class Code

3 - Flammable liquids

WGK Germany

WGK 2

Flash Point(F)

51.8 °F

Flash Point(C)

11 °C

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Ultrasonically induced degradation of 2-methylisoborneol and geosmin.
Song W and O'Shea KE.
Water Research, 41(12), 2672-2678 (2007)
The Reactions of Selected Terpene Alcohols with Acetonitrile in the Presence of Boron Trifluoride Etherate
Welniak M
Polish Journal of Chemistry, 76(10), 1405-1411 (2002)
The destruction of 2-methylisoborneol and geosmin using titanium dioxide photocatalysis.
Lawton LA, et al.
Applied Catalysis. B, Environmental, 44(1), 9-13 (2003)
Reaktionen an Indolderivaten, LIII. Enantioselektive Totalsynthese von (+)-Geissoschizin und (-)-Geissoschizol
Bohlmann C, et al.
Liebigs Annalen der Chemie , 1985(9), 1752-1763 (1985)
Activated carbon adsorption of the odorous compounds 2-methylisoborneol and geosmin.
J. Amer. Water Works Assoc., 223-228 (1977)

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