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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

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About This Item

Empirical Formula (Hill Notation):
C11H20O
CAS Number:
Molecular Weight:
168.28
EC Number:
MDL number:
UNSPSC Code:
12352001
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.

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

Target Organs

Eyes,Central nervous system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

51.8 °F

Flash Point(C)

11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)

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