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2-Bornanol, 2-methyl-

HCID 16913
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Basic information

CAS
2371-42-8
Standard SMILES
CC1(O)CC2CCC1(C)C2(C)C
InChIKey
LFYXNXGVLGKVCJ-UHFFFAOYSA-N
Molecular formula
C11H20O
Average molar mass
168.28 g/mol
Monoisotopic mass
168.15141526

Overview

2-Methylisoborneol has been reported in Phormidium tenue, Streptomyces albidoflavus, and other organisms with data available.

Names & identifiers

Preferred name
2-Bornanol, 2-methyl-
IUPAC
1,2,7,7-tetramethylbicyclo[2.2.1]heptan-2-ol
English name
2-Methylisoborneol
Molecular formula
C11H20O
Molecular weight
168.28

Names & synonyms

2-Bornanol, 2-methyl-68330-43-818680-50-7CCRIS 65932-Methylborneolstarbld0001530UNII-D43XMP4DNW3,4,7,7-tetramethylbicyclo[2.2.1]heptan-3-olSCHEMBL50282LFYXNXGVLGKVCJ-UHFFFAOYSA-N2-Norbornanol, 1,2,7,7-tetramethyl-1,2,7,7-Tetramethylbicyclo[2.2.1]heptan-2-ol #
Show more names
47523-uGeosmin&2-Methylisoborneol2-Methylisoboreneol2-METHYLISOBORNEOLE2-methylisoborneol solution2-Methylisoborneol Standard(R)-(+)-EXO-2-METHYLISOBORNEOL2-Methylisoborneol in Methanol2-Methylisoborneol >=98.0% (GC)
Q1082826(1R,2R)-1,2,7,7-Tetramethylbicyclo[2.2.1]heptan-2-olBicyclo[2.2.1]heptan-2-ol, 1,2,7,7-tetramethyl-, (1R-exo)-

Database identifiers

CAS
2371-42-8
PubChem CID
16913
Nikkaji
J1.020.578F

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
20.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
12
Formal charge
0
Complexity
221

Experimental & physicochemical properties

Melting Point170 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
168 °C · 168 °C
Boiling point
208.7 · 208.7±8.0 °C(Predicted)
Density
0.968 · 0.968±0.06 g/cm3(Predicted)
Flash point
9 ℃ · 9℃
storage temp.
-20 °C · -20°C
solubility
Chloroform (Slightly), Ethanol (Slightly)
form
Solid
pka
15.43 · 15.43±0.60(Predicted)
color
White to Off-White Waxy
Odor
100 % · at 100.00 %. earthy musty
Odor Type
earthy
Henry's Law Constant
8.9 · 8.9×10-2 mol/(m3Pa) at 25℃, \"Omür-\"Ozbek and Dietrich (2005)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
ridadr
UN 1230 3/PG 2
risk_code
11-23/24/25-39/23/24/25
Signal word
Danger
Symbol(GHS)
GHS02,GHS07
hazard_code
F,T
safety_code
7-16-36/37-45
Storage Class
3 - Flammable liquids
target organs
Eyes,Central nervous system
Hazard statements
H228-H315
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Precautionary statements
P210-P240-P241-P264-P280-P302+P352

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular
Applications · 2 items

Uses2-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.

General Description2-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.

Preparation methods · 1 item

Preparation1) Add 197 g of D-camphor to a four-necked flask, then add 500 g of diethyl ether, 63 g of magnesium shavings, and 1 mg of elemental iodine sequentially at room temperature to obtain mixed system A;2) Slowly add 295 g of iodomethane dropwise to mixed system A at room temperature, keeping the reaction temperature below 20°C during the dropwise addition. After the dropwise addition is complete, stir the above reaction solution at room temperature for 2 hours, then heat and reflux for 7 hours. After gas chromatography shows that the raw materials have reacted completely, cool and filter. The solid obtained after filtration was discarded. The solution was diluted with 150 mL of petroleum ether, washed with 150 mL of 2M hydrochloric acid solution, and allowed to stand for separation. The organic and aqueous phases were then separated, and the aqueous phase was discarded. The organic phase was washed with 150 mL of saturated brine, and the organic and aqueous phases were then separated, and the aqueous phase was discarded. The organic phase was mixed with 150 mL of a solution containing 30 g of hydroxylamine hydrochloride and 30 g of sodium hydroxide, stirred at room temperature for 30 hours, separated, and the aqueous phase was discarded. The organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain 216 g of crude product. 3) The above crude product was recrystallized with a mixed solvent of 500 g of water and 1200 g of ethanol to obtain 178 g of product 2-methylisoborneol, with a yield of 82% and a purity >98%.

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Compound notes

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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
InChIKey
LFYXNXGVLGKVCJ-FBIMIBRVSA-N
SMILES
CC1(C)[C@@H]2CC[C@@]1(C)[C@](C)(O)C2
LogP
2.931 · 2.931 (est)
FDA UNII
43 XMP4DNW · D43XMP4DNW
EPA Substance Registry System
2.2 · Bicyclo[2.2.1]heptan-2-ol, 1,2,7,7-tetramethyl-, (1R,2R,4R)-rel- (2371-42-8)
UNSPSC Code
77101502 · 77101502
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS07
Signal word
Danger
Hazard statements
228 · H228-H315
Precautionary statements
210 · P210-P240-P241-P264-P280-P302+P352
target organs
Eyes,Central nervous system
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
F,T
Risk Statements
11 · 11-23/24/25-39/23/24/25
Safety Statements
7 · 7-16-36/37-45
RIDADR
1230 · UN 1230 3/PG 2
WGK Germany
2 · 2
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1

Additional notes

DefinitionChEBI: An bornane monoterpenoid comprising isoborneol carrying a 2-methyl substituent (the 1R,2R,4R-diastereomer).