Prenyl acetate

Reported in EPA TSCA Inventory.

The IUPAC name of 3,3-Dimethylallyl acetate is 3-methylbut-2-enyl acetate. With the CAS registry number 1191-16-8, it is also named as 2-Buten-1-ol, 3-methyl-, acetate. The classification codes are Natural Product and Skin / Eye Irritant. It is colorless liquid with fruity odor. Additionally, this chemical should be sealed in the container and stored in the cool, ventilate and dry place. Besides, it is flammable, so people should keep it away from sources of ignition.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.07; (4)ACD/LogD (pH 7.4): 2.07; (5)ACD/BCF (pH 5.5): 22.01; (6)ACD/BCF (pH 7.4): 22.01; (7)ACD/KOC (pH 5.5): 318.19; (8)ACD/KOC (pH 7.4): 318.19; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.426; (13)Molar Refractivity: 36.15 cm³; (14)Molar Volume: 140.9 cm³; (15)Polarizability: 14.33×10^-24 cm³; (16)Surface Tension: 26.1 dyne/cm; (17)Enthalpy of Vaporization: 38.66 kJ/mol; (18)Vapour Pressure: 3.99 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 128.08373; (21)MonoIsotopic Mass: 128.08373; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 9; (24)Complexity: 121.

Preparation of 3,3-Dimethylallyl acetate: It can be obtained by acetic acid and 2-methyl-but-3-en-2-ol. This reaction needs reagent sulfuric acid and copper (II)-sulfate.
 

Uses of 3,3-Dimethylallyl acetate: It can react with 5-bromo-1H-pyrimidin-2-one to get 5-bromo-1-(3-methyl-2-butenyl)-2(1H)-pyrimidinone. This reaction needs reagent triethylamine, palladium(II) acetate and triisopropyl phosphite and solvent CH₂Cl₂ at ambient temperature. The reaction time is 16 hours. The yield is 46%.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(OC\C=C(/C)C)C
2. InChI:InChI=1/C7H12O2/c1-6(2)4-5-9-7(3)8/h4H,5H2,1-3H3 
3. InChIKey:XXIKYCPRDXIMQM-UHFFFAOYAR

The following are the toxicity data which has been tested.