Diallyl phthalate

NTP Carcinogenesis Studies (gavage); Equivocal Evidence: rat NTPTR*    National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No. NTP-TR-284 ,1985. . Reported in EPA TSCA Inventory.

Diallyl phthalate is an organic compound with the formula C₁₄H₁₄O₄, and its systematic name is the same with the product name. With the CAS registry number 131-17-9, it is also named as 1,2-Benzenedicarboxylic acid, di-2-propenyl ester. It belongs to the product categories of C12 to C63; Carbonyl Compounds; Esters; Alpha Sort; Analytical Standards; AromaticsVolatiles/ Semivolatiles; Chemical Class; Esters Analytical Standards; Plasticizers; Ester series. Its EINECS number is 205-016-3. In addition, the molecular weight is 246.26. Its classification codes are: (1)Mutation data; (2)Skin / Eye Irritant; (3)Tumor data. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from oxides, heat and fire. It is used to produced DAP polymerization fluid and DAP resin, and it is also used as crosslinking agent.

Physical properties of Diallyl phthalate are: (1)ACD/LogP: 3.228; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.23; (4)ACD/LogD (pH 7.4): 3.23; (5)ACD/BCF (pH 5.5): 167.36; (6)ACD/BCF (pH 7.4): 167.36; (7)ACD/KOC (pH 5.5): 1359.23; (8)ACD/KOC (pH 7.4): 1359.23; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 52.6 Å²; (13)Index of Refraction: 1.524; (14)Molar Refractivity: 67.781 cm³; (15)Molar Volume: 221.433 cm³; (16)Polarizability: 26.871×10^-24cm³; (17)Surface Tension: 39.21 dyne/cm; (18)Density: 1.112 g/cm³; (19)Flash Point: 164.836 °C; (20)Enthalpy of Vaporization: 57.152 kJ/mol; (21)Boiling Point: 329.066 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by phthalic acid anhydride and 3-bromo-propene at the temperature of 55 - 60 °C. This reaction will need reagent aqueous potash with the reaction time of 3 hours. This reaction will also need catalyst Katamin AB. The yield is about 58.4%.

Uses of Diallyl phthalate: it can be used to produce but-3-enyl-benzene at the temperature of 60 °C. It will need reagents Zn, triphenylphosphine, Pd(acac)₂ and solvent tetrahydrofuran with the reaction time of 5 hours. The yield is about 54%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. When using it, you must avoid contact with eyes. This material and its container must be disposed of as hazardous waste. You should avoid releasing it to the environment, and you need to refer to special instructions/safety data sheet.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC\C=C)c1ccccc1C(=O)OC\C=C
(2)Std. InChI: InChI=1S/C14H14O4/c1-3-9-17-13(15)11-7-5-6-8-12(11)14(16)18-10-4-2/h3-8H,1-2,9-10H2
(3)Std. InChIKey: QUDWYFHPNIMBFC-UHFFFAOYSA-N

The toxicity data is as follows: