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Merck
CN

M3933

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:
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

Key Documents

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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

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
0000297983
0000297983
0000155116
0000155116
0000145481

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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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