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131-17-9

Basic Information
CAS No.: 131-17-9
Name: Diallyl phthalate
Molecular Structure:
Molecular Structure of 131-17-9 (Diallyl phthalate)
Formula: C14H14O4
Molecular Weight: 246.26
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;
131-17-9

diallyl phthalate

60-24-2

2-hydroxyethanethiol

C18H26O6S2

Conditions
ConditionsYield
With phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide at 20℃; Reagent/catalyst; Temperature; UV-irradiation;99%
131-17-9

diallyl phthalate

406911-89-5

C12H10O4

Conditions
ConditionsYield
With C46H54Cl2FeN2O3Ru In dichloromethane at 35℃; for 8h;97%
With C34H50B10Cl2N2O2Ru In dichloromethane at 40℃; for 8h; Reagent/catalyst; Time; Inert atmosphere;96%
With C96H111Cl6N9O3Ru3 In dichloromethane at 35℃; for 12h; Schlenk technique; Inert atmosphere;96%
131-17-9

diallyl phthalate

(Z)-7,10-Dihydro-6,11-dioxa-benzocyclodecene-5,12-dione

Conditions
ConditionsYield
[2-((2,6-iPr2-Ph-imino)methyl)phenol][p-cymene][=CHPh]Ru2Cl3 In various solvent(s) at 70℃; for 4h; Product distribution; Further Variations:; Catalysts; Temperatures;96%
With diazomethyl-trimethyl-silane; ruthenium Schiff-base In toluene at 85℃; for 17h; ring-closing metathesis;94%
With diazomethyl-trimethyl-silane; ruthenium In toluene at 85℃; for 17h; Product distribution; Further Variations:; Catalysts;94%
hybrid N,O-bidentate Schiff base ruthenium complex In toluene at 85℃; for 17h;94%
Schiff base substituted ruthenium benzylidene; 1,3-bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene In benzene-d6 at 55℃; for 4h; ring-closing metathesis;87 % Spectr.

(triethylsilyl)cobalt tetracarbonyl

131-17-9

diallyl phthalate

(η-allyl)tricarbonylcobalt

Conditions
ConditionsYield
at -25 - 7℃; for 4.16h;94%
131-17-9

diallyl phthalate

1608129-88-9

C26H24O8

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV)isopropoxide In toluene at 80℃; for 0.75h; Inert atmosphere;91%
998-30-1

Triethoxysilane

131-17-9

diallyl phthalate

bis(3-(triethoxysilyl)propyl)phthalate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride In dichloromethane at 20℃; Glovebox;80%
131-17-9

diallyl phthalate

diethylamino magnesium bromide

5666-17-1

N,N-diethylallylamine

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenylphosphine In tetrahydrofuran at 50℃; for 5h;59%
131-17-9

diallyl phthalate

100-39-0

benzyl bromide

768-56-9

4-Phenyl-1-butene

Conditions
ConditionsYield
With palladium(II) acetylacetonate; triphenylphosphine; zinc In tetrahydrofuran at 60℃; for 5h;54%
131-17-9

diallyl phthalate

1147550-11-5

ammonium thiocyanate

369-57-3

benzenediazonium tetrafluoroborate

allyl [(2-thiocyanato-3-phenyl)propyl]phthalate

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone at -15 - -10℃; for 2.5h;48%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;48%
131-17-9

diallyl phthalate

459-64-3

4-methoxybenzenediazonium tetrafluoroborate

1147550-11-5

ammonium thiocyanate

phthalic acid 1-allyl ester 2-[3-(4-methoxy-phenyl)-2-thiocyanato-propyl] ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone44%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;44%
1797-75-7

diallyl malonate

131-17-9

diallyl phthalate

A

C14H16O8

B

C24H20O8

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate In toluene at 80℃; Inert atmosphere;A 42%
B 38%
131-17-9

diallyl phthalate

2093-46-1

2-methylphenyl diazonium tetrafluoroborate

1147550-11-5

ammonium thiocyanate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-o-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone41%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;41%
131-17-9

diallyl phthalate

1147550-11-5

ammonium thiocyanate

459-44-9

4-methylbenzenediazonium tetrafluoroborate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-p-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone40%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;40%
131-17-9

diallyl phthalate

1147550-11-5

ammonium thiocyanate

1422-76-0

3-methylbenzenediazonium tetrafluoroborate

phthalic acid 1-allyl ester 2-(2-thiocyanato-3-m-tolyl-propyl) ester

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) In water; acetone38%
With copper(II) bis(tetrafluoroborate) In water; acetone at -20 - -15℃; for 2.5h;38%
131-17-9

diallyl phthalate

6407-35-8

N-cyclohexylidenemethylamine

A

94-66-6

2-allylcyclohexan-1-one

B

115782-91-7

(Z)-2,6-diallyl-1-cyclohexanone

36040-02-5, 115782-91-7, 115782-92-8

(E)-2,6-diallyl-1-cyclohexanone

Conditions
ConditionsYield
With ethylmagnesium bromide; triphenylphosphine; palladium(II) acetylacetonate 1.) ether, 2.) 36-40 deg C, 5 h; Yield given. Multistep reaction;
131-17-9

diallyl phthalate

6407-36-9

N-isopropyliden-cyclohexyl amine

A

109-49-9

1-hexen-5-one

B

74912-33-7

nona-1,8-dien-5-one

Conditions
ConditionsYield
With ethylmagnesium bromide Multistep reaction;
131-17-9

diallyl phthalate

29246-20-6

3,4,5,6-tetrahydrobenzo[c][1,6]dioxecine-1,8-dione

Conditions
ConditionsYield
Grubbs catalyst first generation In 1,2-dichloro-ethane at 150℃; for 0.5h; MW irradiation;79 % Chromat.
131-17-9

diallyl phthalate

A

406911-89-5

C12H10O4

B

74-85-1

ethene

Conditions
ConditionsYield
With Grubbs catalyst first generation In dichloromethane
131-17-9

diallyl phthalate

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
Stage #1: diallyl phthalate With dimethylaluminum chloride In toluene at 110℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; toluene at 20℃;
Stage #1: diallyl phthalate With dimethylaluminum chloride In toluene at 110℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; toluene at 20℃;
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    Product Name: Diallyl phthalate Synonyms: o-Phthalic acid,diallyl ester;PHTHALIC ACID DIALLYL ESTER;PHTHALIC ACID, BIS-ALLYL ESTER;ALLYL PHTHALATE;1,2-BENZENEDICARBOXYLIC ACID DI-2-PROPENYL ESTER;Diallyl-o-

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    131-17-9

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    Diallyl phthalate quality& low price CAS No 131-17-9

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    Diallyl phthalate 131-17-9

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  • Diallyl Phthalate CAS NO.131-17-9

  • Casno:

    131-17-9

    Diallyl Phthalate CAS NO.131-17-9

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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,