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M3933

Sigma-Aldrich

2-Methylisoborneol solution

~10 mg/mL in methanol, ≥98% (GC)

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Synonym(s):
(1R-exo)-1,2,7,7-Tetramethylbicyclo[2.2.1]heptan-2-ol
Empirical Formula (Hill Notation):
C11H20O
CAS Number:
2371-42-8
Molecular Weight:
168.28
EC Number:
200-659-6
MDL number:
MFCD00082463
UNSPSC Code:
12352001
PubChem Substance ID:
57654381
NACRES:
NA.22

Quality Level

200

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

WGK

WGK 2

Flash Point(F)

51.8 °F

Flash Point(C)

11 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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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 destruction of 2-methylisoborneol and geosmin using titanium dioxide photocatalysis.
Lawton LA, et al.
Applied Catalysis. B, Environmental, 44(1), 9-13 (2003)
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)
Reaktionen an Indolderivaten, LIII. Enantioselektive Totalsynthese von (+)-Geissoschizin und (-)-Geissoschizol
Bohlmann C, et al.
Liebigs Annalen der Chemie , 1985(9), 1752-1763 (1985)
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