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131-17-9

Basic Information
CAS No.: 131-17-9
Name: Diallyl phthalate
Article Data: 29
Molecular Structure:
Molecular Structure of 131-17-9 (Diallyl phthalate)
Formula: C14H14O4
Molecular Weight: 246.263
Synonyms: 1,2-Benzenedicarboxylic acid, di-2-propenyl ester;1,2-Benzenedicarboxylic acid,esters,di-2-propenyl ester;o-Phthalic acid, diallyl ester;DAP monomer (Diallyl Phthalate monomer) manufacturer;Phthalic acid, diallyl ester;
EINECS: 205-016-3
Density: 1.112 g/cm3
Melting Point: -70 °C
Boiling Point: 329.066 °C at 760 mmHg
Flash Point: 164.836 °C
Solubility: Insoluble in water, slightly soluble in petroleum ether and glycerol
Appearance: clear colourless to light yellow liquid
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 22-50/53
Safety: 24/25-60-61
Transport Information: UN 3082 9/PG 3
PSA: 52.60000
LogP: 2.37220
Synthetic route
85-44-9

phthalic anhydride

107-18-6

allyl alcohol

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With 3,3′-(2,2-bis(hydroxymethyl)propane-1,3-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate for 2h; Dean-Stark; Reflux;100%
With diacidic ionic liquid supported on magnetic-silica nanoparticles In neat (no solvent) at 97℃; for 5h; Dean-Stark;95%
With phosphoric acid
182342-88-7

Phthalic acid 1-allyl ester 2-prop-2-ynyl ester

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With indium In ethanol for 40h; Heating;95%
88-99-3

benzene-1,2-dicarboxylic acid

107-05-1

3-chloroprop-1-ene

131-17-9

diallyl phthalate

Conditions
ConditionsYield
Stage #1: benzene-1,2-dicarboxylic acid With copper; sodium iodide In water under 760.051 Torr; for 1h; Green chemistry;
Stage #2: 3-chloroprop-1-ene In water under 760.051 Torr; for 6h; Concentration; Time; Temperature; Reflux; Green chemistry;
91.7%
106-95-6

allyl bromide

88-99-3

benzene-1,2-dicarboxylic acid

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;91%
Stage #1: benzene-1,2-dicarboxylic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: allyl bromide With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;
91%
With potassium hydroxide; Aliquat 336 1.) 60 deg C, 0.1 Torr, 6 h, 2.) 60 deg C, 16 h; Yield given. Multistep reaction;
85-44-9

phthalic anhydride

106-95-6

allyl bromide

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With potassium carbonate; Katamin AB at 55 - 60℃; for 3h; Product distribution; or DMF, KOH powder; other catalysts;58.4%
With potassium carbonate; Katamin AB at 55 - 60℃; for 3h;58.4%
allyl chloride vapour

allyl chloride vapour

sodium-salt of phthalic acid monoallyl ester

sodium-salt of phthalic acid monoallyl ester

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With netting agent; water at 100℃;
591-87-7

Allyl acetate

88-99-3

benzene-1,2-dicarboxylic acid

131-17-9

diallyl phthalate

Conditions
ConditionsYield
tin(IV) chloride
63770-79-6

C11H10O4*C9H16N2

106-95-6

allyl bromide

131-17-9

diallyl phthalate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; chemoselective reaction;
85-44-9

phthalic anhydride

131-17-9

diallyl phthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.17 h / 20 °C
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 20 °C
View Scheme
827-27-0, 10197-71-4, 15968-01-1

sodium 1,2-benzenedicarboxylate

107-05-1

3-chloroprop-1-ene

131-17-9

diallyl phthalate

Conditions
ConditionsYield
at 40 - 60℃;
at 65℃; for 3h;
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Consensus Reports

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.

Specification

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%.

Diallyl phthalate can be prepared by phthalic acid anhydride and 3-bromo-propene at the temperature of 55 - 60 °C

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%.

Diallyl phthalate can be used to produce but-3-enyl-benzene at the temperature of 60 °C

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:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 800mg/kg (800mg/kg)   National Technical Information Service. Vol. OTS0521092,
mouse LDLo oral 681mg/kg (681mg/kg)   National Toxicology Program Technical Report Series. Vol. NTP-TR-242, Pg. 1983,
rabbit LD50 oral 1700mg/kg (1700mg/kg)   "Industrial Hygiene and Toxicology," 2nd ed., Patty, F.A., ed., New York, John Wiley & Sons, Inc., 1958-63Vol. 2, Pg. 1904, 1963.
rabbit LD50 skin 3300mg/kg (3300mg/kg)   National Technical Information Service. Vol. OTS0521092,
rabbit LDLo subcutaneous 1gm/kg (1000mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 5, Pg. 191, 1946.
rat LC50 inhalation 5200mg/m3/1H (5200mg/m3) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
National Technical Information Service. Vol. OTS0521092,
rat LD50 oral 656mg/kg (656mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Toxicology Program Technical Report Series. Vol. NTP-TR-284, Pg. 1985,