Isobornyl acetate

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Structural formula
Structural formula of isobornyl acetate
General
Surname Isobornyl acetate
other names
  • Isobornyl acetate
  • exo-2 bornyl acetate
  • exo-1,7,7-trimethylbicyclo [2.2.1] hept-2-yl acetate
  • 2-acetoxy-1,7,7-trimethyl-bicyclo [2.2.1] heptane
Molecular formula C 12 H 20 O 2
Brief description

colorless liquid with a characteristic odor

External identifiers / databases
CAS number
  • 125-12-2 (±) -isobornyl acetate
  • 28974-17-6 (1R, 2R, 4R) -Isobornyl acetate
  • 71424-71-0 (1S, 2S, 4S) -Isobornyl acetate
EC number 204-727-6
ECHA InfoCard 100.004.298
PubChem 637531
Wikidata Q425010
properties
Molar mass 196.29 g mol −1
Physical state

liquid

density

0.98 g cm −3

boiling point

215 ° C

Vapor pressure

0.13 mbar (20 ° C)

solubility
  • very sparingly soluble in water (approx. 0.16 g l −1 at 20 ° C)
  • easily soluble in most organic solvents
Refractive index

1.4635 (20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315
P: 302 + 352
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Isobornyl acetate is a chemical compound from the group of carboxylic acid esters and is isomeric to boronyl acetate . It is the ethyl ester of the terpene isoborneol .

Isomers

Isobornyl acetate is always exo -configured, the endo -configuration is called bornyl acetate or boronyl acetate . There are two isomeric forms, (-) - and (+) - isobornyl acetate [synonyms: (1 S , 2 S , 4 S ) - or (1 R , 2 R , 4 R ) -boronyl acetate], which are often referred to as 1 : 1 mixture ( racemate ) occur.

Extraction and presentation

Isobornyl acetate is made from camphene , producing more than 1000 tons per year.

properties

Isobornyl acetate is a colorless to yellowish liquid with a characteristic odor, which is very poorly soluble in water. It has a dynamic viscosity of 8.5 mPa · s at 20 ° C.

use

Isobornyl acetate is contained in odoriferous compositions (bath preparations, soap perfumes, sprays) and is used as an intermediate in the production of camphor .

α- pinene is protonated; through Wagner-Meerwein rearrangement it is rearranged to the carbonium ion. This reacts with sodium acetate to form isobornyl acetate, which is then hydrolyzed to isoborneol and finally oxidized to camphor.

safety instructions

The vapors of isobornyl acetate can form an explosive mixture with air ( flash point 88 ° C, ignition temperature 430 ° C).

Individual evidence

  1. ↑ a b c d e f g h i j k Entry on isobornyl acetate in the GESTIS substance database of the IFA , accessed on February 8, 2017(JavaScript required) .
  2. ↑ a b Toxicological evaluation of isobornyl acetate (PDF) at the professional association raw materials and chemical industry (BG RCI), accessed on August 26, 2010.
  3. ↑ Isobornyl acetate data sheet from Sigma-Aldrich , accessed on August 26, 2010 ( PDF ).
  4. ↑ Isobornyl acetate data sheet (PDF) from Merck , accessed on April 6, 2011.