22955-73-3

Basic information

• Product Name: Dimethyl 4-methoxyisophthalate
• Synonyms: RARECHEM AL BF 1167;DIMETHYL 4-METHOXYISOPHTHALATE;4-Methoxy-1,3-benzenedicarboxylic acid dimethyl ester;4-Methoxyisophthalic acid dimethyl ester;1,3-Benzenedicarboxylic acid, 4-methoxy-, dimethyl ester
• CAS NO: 22955-73-3
• Molecular Formula: C₁₁H₁₂O₅
• Molecular Weight: 224.21
• EINECS: 245-350-7
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 22955-73-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 93-97 °C(lit.)
• Boiling Point: 331.6 °C at 760 mmHg
• Flash Point: 146 °C
• Appearance: /
• Density: 1.184g/cm3
• Vapor Pressure: 0.000154mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: Dimethyl 4-methoxyisophthalate(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyl 4-methoxyisophthalate(22955-73-3)
• EPA Substance Registry System: Dimethyl 4-methoxyisophthalate(22955-73-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 22955-73-3(Hazardous Substances Data)

Usage

General Description

Dimethyl 4-methoxyisophthalate is a chemical compound commonly used in the production of various polymers and resins. It is a dimethyl ester of 4-methoxyisophthalic acid and is known for its ability to enhance the mechanical and thermal properties of polymeric materials. Its primary application is as a monomer in the synthesis of polyesters, which are widely used in the manufacturing of textiles, packaging materials, and engineering plastics. Additionally, dimethyl 4-methoxyisophthalate is utilized as a cross-linking agent in the production of thermosetting resins, which are essential in the formulation of adhesives, coatings, and composite materials. Its chemical structure and properties make it a valuable component in the creation of high-performance materials.

InChI:InChI=1/C11H12O5/c1-14-9-5-4-7(10(12)15-2)6-8(9)11(13)16-3/h4-6H,1-3H3

Synthetic route

methanol (67-56-1) + 4-methoxy-1,3-benzenedicarbonyl dichloride (13235-60-4) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Ambient temperature;	92%

dimethyl 4-hydroxyisophthalate (5985-24-0) + methyl iodide (74-88-4) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	87%

methanol (67-56-1) + methyl 2-methoxy-5-methylbenzoate (63113-79-1) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With tetradecyl(tributyl)phosphonium methanesulfonate at 20℃; for 18h; Inert atmosphere; Electrolysis; Sealed tube; Green chemistry;	71%

diazomethane (186581-53-3, 908094-01-9) + 4-methoxyisophthalic acid (2206-43-1) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With diethyl ether

4-hydroxyisophthalic acid (636-46-4) + dimethyl sulfate (77-78-1) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With sodium hydroxide Erwaermen des Reaktionsprodukts mit methanol. H2SO4;

diazomethane (186581-53-3, 908094-01-9) + tiliacorinine dimethiodide (27073-74-1, 27073-75-2) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With potassium permanganate 1.) H2O, 70-80 deg C, 5 h 2.) ether; Yield given. Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + (1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane (81784-13-6) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With nitric acid 1.) 17 h, 165 deg C, in a sealed tube, 2.) ether; Yield given. Multistep reaction;
With nitric acid Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + 4-hydroxyisophthalic acid (636-46-4) → dimethyl 4-methoxyisophthalate (22955-73-3)

Dimethyl-2-brom-4-methoxy-isophthalat (23531-29-5) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
With iodobenzene; copper at 202 - 208℃;

diazomethane (186581-53-3, 908094-01-9) + C40H40O8 (22955-82-4) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
(i) aq. KMnO4, NaOH, Py, (ii) /BRN= 102415/; Multistep reaction;

N,N-dimethylpachyovatamine (27073-72-9, 27073-73-0) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 370 mg / 0.5 h / Ambient temperature 2: 1.) KMnO4 / 1.) H2O, 70-80 deg C, 5 h 2.) ether View Scheme

nortiliacorinine A → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 258 mg / formaldehyde, formic acid 2: 370 mg / 0.5 h / Ambient temperature 3: 1.) KMnO4 / 1.) H2O, 70-80 deg C, 5 h 2.) ether View Scheme

2,4-dimethylanisole (6738-23-4) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KMnO4 2: diethyl ether View Scheme

dimethyl 4-hydroxyisophthalate (5985-24-0) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol; bromine; H2O 2: aqueous KOH; copper-powder 3: aqueous NaOH / Erwaermen des Reaktionsprodukts mit methanol. H2SO4 View Scheme

2,4-bis-hydroxymethyl-1-methoxy-benzene (15471-26-8) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KMnO4 2: diethyl ether View Scheme

5-bromo-4-hydroxyisophthalic acid dimethyl ester (54176-51-1) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous KOH; copper-powder 2: aqueous NaOH / Erwaermen des Reaktionsprodukts mit methanol. H2SO4 View Scheme

4-methoxyisophthalic acid (2206-43-1) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride View Scheme

2,4-Xylenol (105-67-9) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. NaOH, (ii) aq. KMnO4 View Scheme

3-Iodophenol (626-02-8) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaOH 2: Ag2O, aq. NaOH 3: aq. NaOH / Raney-Ni View Scheme

2-bromo-4-methoxy-1,3-dimethylbenzene (23453-90-9) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq. KMnO4 3: Cu, PhI / 202 - 208 °C View Scheme

4-Hydroxy-2-iod-isophthalaldehyd (23454-14-0) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: Ag2O, aq. NaOH 2: aq. NaOH / Raney-Ni View Scheme

2-Brom-4-hydroxy-isophthalsaeure (23453-86-3) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: Cu, PhI / 202 - 208 °C View Scheme

4-Hydroxy-2-iod-isophthalsaeure (23453-94-3) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aq. NaOH / Raney-Ni View Scheme

2-Brom-4-methoxy-isophthalsaeure (23453-91-0) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: Cu, PhI / 202 - 208 °C View Scheme

2-Brom-4-hydroxy-isophthalaldehyd → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: Ag2O, aq. NaOH 3: Cu, PhI / 202 - 208 °C View Scheme

3-bromo-2,4-dimethylphenol (74571-81-6) → dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
Multi-step reaction with 4 steps 2: aq. KMnO4 4: Cu, PhI / 202 - 208 °C View Scheme

sulfuric acid (7664-93-9) + 4-methoxyisophthalic acid (2206-43-1) → methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (479579-02-7) + dimethyl 4-methoxyisophthalate (22955-73-3)

Conditions	Yield
In methanol; ice-water	A 52 g (91%) B n/a

dimethyl 4-methoxyisophthalate (22955-73-3) → 4-methoxyisophthalic acid (2206-43-1)

Conditions	Yield
With water; sodium hydroxide at 80℃; for 2h;	90%

3,3-dimethyl-butan-2-one (75-97-8) + dimethyl 4-methoxyisophthalate (22955-73-3) → 4-methoxy-1,3-bis(4,4-dimethyl-3-oxopentanoyl)benzene

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; hexane	66%
With hydrogenchloride In tetrahydrofuran; hexane	66%

dimethyl 4-methoxyisophthalate (22955-73-3) → 4-methoxy-5-nitro-isophthalic acid dimethyl ester (99843-85-3)

Conditions	Yield
With sulfuric acid; nitric acid; acetic acid

dimethyl 4-methoxyisophthalate (22955-73-3) → 5-amino-4-methoxy-isophthalic acid dimethyl ester (99856-47-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; HNO3; H2SO4 2: platinum; methanol / Hydrogenation View Scheme

dimethyl 4-methoxyisophthalate (22955-73-3) → 4-methoxy-5-nitro-isophthalic acid (98589-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; HNO3; H2SO4 2: Hydrolysis View Scheme

Upstream product

• 186581-53-3 diazomethane 
• 636-46-4 4-hydroxyisophthalic acid 
• 2206-43-1 4-methoxyisophthalic acid 
• 67-56-1 methanol 
• 63113-79-1 methyl 2-methoxy-5-methylbenzoate 
• 5985-24-0 dimethyl 4-hydroxyisophthalate 
• 74-88-4 methyl iodide 
• 7664-93-9 sulfuric acid 
• 74571-81-6 3-bromo-2,4-dimethylphenol 
• 23453-91-0 2-Brom-4-methoxy-isophthalsaeure 
• 23453-94-3 4-Hydroxy-2-iod-isophthalsaeure 
• 23453-86-3 2-Brom-4-hydroxy-isophthalsaeure 
• 23454-14-0 4-Hydroxy-2-iod-isophthalaldehyd 
• 23453-90-9 2-bromo-4-methoxy-1,3-dimethylbenzene 

Downstream Products

• 13235-60-4 4-methoxy-1,3-benzenedicarbonyl dichloride 
• 2206-43-1 4-methoxyisophthalic acid 
• 32828-81-2 Picotamide 
• 98589-65-2 4-methoxy-5-nitro-isophthalic acid 
• 99856-47-0 5-amino-4-methoxy-isophthalic acid dimethyl ester 
• 99843-85-3 4-methoxy-5-nitro-isophthalic acid dimethyl ester 

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