1026-92-2

Basic information

• Product Name: TEREPHTHALIC ACID DIALLYL ESTER
• Synonyms: TEREPHTHALIC ACID DIALLYL ESTER;Diallyl ester of terephthalic acid;DIALLYL TEREPHTHALATE;p-Phthalic acid, diallyl ester;1,4-Benzenedicarboxylic acid diallyl;Terephthalic acid bis(2-propenyl);Terephthalic acid diallyl;benzene-1,4-dicarboxylic acid diallyl ester
• CAS NO: 1026-92-2
• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26
• EINECS: 213-835-2
• Mol File: 1026-92-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 176-178°C 8mm
• Flash Point: 171°C
• Appearance: /
• Density: 1,121 g/cm3
• Vapor Pressure: 4.56E-05mmHg at 25°C
• Refractive Index: 1.5260 to 1.5280
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: TEREPHTHALIC ACID DIALLYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: TEREPHTHALIC ACID DIALLYL ESTER(1026-92-2)
• EPA Substance Registry System: TEREPHTHALIC ACID DIALLYL ESTER(1026-92-2)

Safety Data

• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1026-92-2(Hazardous Substances Data)

Usage

Uses

Diallyl Terephthalate is used as a plasticizer. Also used in the preparation of organotin polymers.

InChI:InChI=1/C14H14O4/c1-3-9-17-13(15)11-5-7-12(8-6-11)14(16)18-10-4-2/h3-8H,1-2,9-10H2

Synthetic route

allyl alcohol (107-18-6) + terephthaloyl chloride (100-20-9) → diallyl terephthalate (1026-92-2)

terephthalic acid (100-21-0) + allyl bromide (106-95-6) → diallyl terephthalate (1026-92-2)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide 1.) 60 deg C, 0.1 Torr, 6 h, 2.) 85 deg C, 60 h; Yield given. Multistep reaction;

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) → diallyl terephthalate (1026-92-2)

sodium tungstate (VI) dihydrate (10213-10-2) + diallyl terephthalate (1026-92-2) + Aliquat 336 (5137-55-3) → terephthalic acid diglycidyl ester (7195-44-0)

Conditions	Yield
With phosphoric acid; dihydrogen peroxide In water; toluene	85%

diallyl terephthalate (1026-92-2) → C36H30O12

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; for 22h;	60%

dimethylmonochlorosilane (1066-35-9) + diallyl terephthalate (1026-92-2) → Terephthalic acid 1-allyl ester 4-[3-(chloro-dimethyl-silanyl)-propyl] ester (20083-45-8)

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol

diallyl terephthalate (1026-92-2) → Terephthalic acid 1-allyl ester 4-[3-(methoxy-dimethyl-silanyl)-propyl] ester (20083-48-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2PtCl6 / propan-2-ol 2: urea / benzene View Scheme

Reaxys ID: 12665026 + dibenzyl maleate (622-06-0) + vinyl benzoate (769-78-8) + diallyl terephthalate (1026-92-2) → Reaxys ID: 12664759

Conditions	Yield
1,1,3,3-tetramethyl butyl-1-peroxy 2-ethylhexanoate at 50 - 90℃; for 24h; Product distribution / selectivity;

Reaxys ID: 12665026 + vinyl benzoate (769-78-8) + diallyl terephthalate (1026-92-2) → Reaxys ID: 12664754

Conditions	Yield
1,1,3,3-tetramethyl butyl-1-peroxy 2-ethylhexanoate at 50 - 90℃; for 24h; Product distribution / selectivity;

diallyl terephthalate (1026-92-2) + diethyltin dihydride (871-33-0) → {C6H4COO(CH2)3Sn(C2H5)2(CH2)3OCO}

2,2′-((propane-2,2-diylbis(2,6-dibromo-4,1-phenylene))bis(oxy)) bis(ethan-1-ol) (4162-45-2) + diallyl terephthalate (1026-92-2) → poly(2,2-bis[4-(2-hydroxyethoxy)-3,5-dibromophenyl]propane-co-diallyl terephthalate) + allyl alcohol (107-18-6)

Conditions	Yield
With dibutyltin oxide at 180℃; under 0.975098 - 9.976 Torr; for 1h;

Upstream product

• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 100-21-0 terephthalic acid 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 100-20-9 terephthaloyl chloride 

Downstream Products

• 107-18-6 allyl alcohol 
• 20083-48-1 Terephthalic acid 1-allyl ester 4-[3-(methoxy-dimethyl-silanyl)-propyl] ester 
• 20083-45-8 Terephthalic acid 1-allyl ester 4-[3-(chloro-dimethyl-silanyl)-propyl] ester 
• 7195-44-0 terephthalic acid diglycidyl ester 

Relevant articles and documents

Efficient synthesis of macrocyclic paracyclophanes by ring-closing metathesis dimerization and trimerization reactions

(Matrix presented) Ring-closing metathesis reactions of para-disubstituted aromatic substrates produced macrocyclic [n.n]-, and [n.n.n]paracyclophanes efficiently through dimerization and trimerization reactions. Sufficiently long alkyl chains allowed direct monocyclizations to yield [n]paracyclophanes. A small library of paracyclophanes were generated by the combinatorial cross-metathesis approach.

Solid-Liquid Phase-Transfer Catalysis without Added Solvent. A Simple, Efficient, and Inexpensive Synthesis of Aromatic Carboxylic Esters by Alkylation of Potassium Carboxylates

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