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Dimethyl 4-methoxyisophthalate is a chemical compound that serves as a key component in the production of various polymers and resins. It is a dimethyl ester of 4-methoxyisophthalic acid, known for its capacity to improve the mechanical and thermal properties of polymeric materials. Its chemical structure and properties render it a valuable asset in the creation of high-performance materials.

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  • 22955-73-3 Structure
  • Basic information

    1. Product Name: Dimethyl 4-methoxyisophthalate
    2. 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
    3. CAS NO:22955-73-3
    4. Molecular Formula: C11H12O5
    5. Molecular Weight: 224.21
    6. EINECS: 245-350-7
    7. Product Categories: C10 to C11;Carbonyl Compounds;Esters
    8. Mol File: 22955-73-3.mol
  • Chemical Properties

    1. Melting Point: 93-97 °C(lit.)
    2. Boiling Point: 331.6 °C at 760 mmHg
    3. Flash Point: 146 °C
    4. Appearance: /
    5. Density: 1.184g/cm3
    6. Vapor Pressure: 0.000154mmHg at 25°C
    7. Refractive Index: 1.508
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: Dimethyl 4-methoxyisophthalate(CAS DataBase Reference)
    11. NIST Chemistry Reference: Dimethyl 4-methoxyisophthalate(22955-73-3)
    12. EPA Substance Registry System: Dimethyl 4-methoxyisophthalate(22955-73-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36
    3. Safety Statements: 26-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22955-73-3(Hazardous Substances Data)

22955-73-3 Usage

Uses

Used in Polymer and Resin Production:
Dimethyl 4-methoxyisophthalate is used as a monomer in the synthesis of polyesters for its ability to enhance the mechanical and thermal properties of these materials. This makes it suitable for applications in various industries.
Used in Textile Industry:
In the textile industry, dimethyl 4-methoxyisophthalate is used as a component in the production of textiles, where its properties contribute to the creation of durable and high-performance fabrics.
Used in Packaging Materials:
Dimethyl 4-methoxyisophthalate is used as a constituent in the manufacturing of packaging materials, where its role is to improve the strength and thermal stability of the packaging, ensuring the protection and preservation of the contents.
Used in Engineering Plastics:
In the production of engineering plastics, dimethyl 4-methoxyisophthalate is utilized to enhance the mechanical properties, making the plastics more suitable for demanding applications that require robust materials.
Used as a Cross-linking Agent in Thermosetting Resins:
Dimethyl 4-methoxyisophthalate is used as a cross-linking agent in the production of thermosetting resins, which are crucial in the formulation of adhesives, coatings, and composite materials. Its inclusion in these formulations improves the overall performance and durability of the end products.

Check Digit Verification of cas no

The CAS Registry Mumber 22955-73-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,9,5 and 5 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 22955-73:
(7*2)+(6*2)+(5*9)+(4*5)+(3*5)+(2*7)+(1*3)=123
123 % 10 = 3
So 22955-73-3 is a valid CAS Registry Number.
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

22955-73-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name dimethyl 4-methoxybenzene-1,3-dicarboxylate

1.2 Other means of identification

Product number -
Other names 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22955-73-3 SDS

22955-73-3Synthetic route

methanol
67-56-1

methanol

4-methoxy-1,3-benzenedicarbonyl dichloride
13235-60-4

4-methoxy-1,3-benzenedicarbonyl dichloride

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Ambient temperature;92%
dimethyl 4-hydroxyisophthalate
5985-24-0

dimethyl 4-hydroxyisophthalate

methyl iodide
74-88-4

methyl iodide

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;87%
methanol
67-56-1

methanol

methyl 2-methoxy-5-methylbenzoate
63113-79-1

methyl 2-methoxy-5-methylbenzoate

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With tetradecyl(tributyl)phosphonium methanesulfonate at 20℃; for 18h; Inert atmosphere; Electrolysis; Sealed tube; Green chemistry;71%
4-methoxyisophthalic acid
2206-43-1

4-methoxyisophthalic acid

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With diethyl ether
4-hydroxyisophthalic acid
636-46-4

4-hydroxyisophthalic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With sodium hydroxide Erwaermen des Reaktionsprodukts mit methanol. H2SO4;
tiliacorinine dimethiodide
27073-74-1, 27073-75-2

tiliacorinine dimethiodide

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With potassium permanganate 1.) H2O, 70-80 deg C, 5 h 2.) ether; Yield given. Multistep reaction;
(1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane
81784-13-6

(1S)-1,2,2-trimethyl-1-(2-methoxy-5-methyl)phenylcyclopentane

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With nitric acid 1.) 17 h, 165 deg C, in a sealed tube, 2.) ether; Yield given. Multistep reaction;
With nitric acid Multistep reaction;
4-hydroxyisophthalic acid
636-46-4

4-hydroxyisophthalic acid

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Dimethyl-2-brom-4-methoxy-isophthalat
23531-29-5

Dimethyl-2-brom-4-methoxy-isophthalat

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
With iodobenzene; copper at 202 - 208℃;
C40H40O8
22955-82-4

C40H40O8

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
(i) aq. KMnO4, NaOH, Py, (ii) /BRN= 102415/; Multistep reaction;
N,N-dimethylpachyovatamine
27073-72-9, 27073-73-0

N,N-dimethylpachyovatamine

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

nortiliacorinine A

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

2,4-dimethylanisole

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KMnO4
2: diethyl ether
View Scheme
dimethyl 4-hydroxyisophthalate
5985-24-0

dimethyl 4-hydroxyisophthalate

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

2,4-bis-hydroxymethyl-1-methoxy-benzene

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous KMnO4
2: diethyl ether
View Scheme
5-bromo-4-hydroxyisophthalic acid dimethyl ester
54176-51-1

5-bromo-4-hydroxyisophthalic acid dimethyl ester

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

4-methoxyisophthalic acid

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride
View Scheme
2,4-Xylenol
105-67-9

2,4-Xylenol

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) aq. NaOH, (ii) aq. KMnO4
View Scheme
3-Iodophenol
626-02-8

3-Iodophenol

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

2-bromo-4-methoxy-1,3-dimethylbenzene

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

4-Hydroxy-2-iod-isophthalaldehyd

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

2-Brom-4-hydroxy-isophthalsaeure

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Cu, PhI / 202 - 208 °C
View Scheme
4-Hydroxy-2-iod-isophthalsaeure
23453-94-3

4-Hydroxy-2-iod-isophthalsaeure

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. NaOH / Raney-Ni
View Scheme
2-Brom-4-methoxy-isophthalsaeure
23453-91-0

2-Brom-4-methoxy-isophthalsaeure

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: Cu, PhI / 202 - 208 °C
View Scheme
2-Brom-4-hydroxy-isophthalaldehyd

2-Brom-4-hydroxy-isophthalaldehyd

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
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

3-bromo-2,4-dimethylphenol

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
2: aq. KMnO4
4: Cu, PhI / 202 - 208 °C
View Scheme
sulfuric acid
7664-93-9

sulfuric acid

4-methoxyisophthalic acid
2206-43-1

4-methoxyisophthalic acid

A

methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate
479579-02-7

methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate

B

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

Conditions
ConditionsYield
In methanol; ice-waterA 52 g (91%)
B n/a
dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

4-methoxyisophthalic acid
2206-43-1

4-methoxyisophthalic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 80℃; for 2h;90%
3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

4-methoxy-1,3-bis(4,4-dimethyl-3-oxopentanoyl)benzene

4-methoxy-1,3-bis(4,4-dimethyl-3-oxopentanoyl)benzene

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; hexane66%
With hydrogenchloride In tetrahydrofuran; hexane66%
dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

4-methoxy-5-nitro-isophthalic acid dimethyl ester
99843-85-3

4-methoxy-5-nitro-isophthalic acid dimethyl ester

Conditions
ConditionsYield
With sulfuric acid; nitric acid; acetic acid
dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

5-amino-4-methoxy-isophthalic acid dimethyl ester
99856-47-0

5-amino-4-methoxy-isophthalic acid dimethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; HNO3; H2SO4
2: platinum; methanol / Hydrogenation
View Scheme
dimethyl 4-methoxyisophthalate
22955-73-3

dimethyl 4-methoxyisophthalate

4-methoxy-5-nitro-isophthalic acid
98589-65-2

4-methoxy-5-nitro-isophthalic acid

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

22955-73-3Relevant articles and documents

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

Yu, Congjun,?zkaya, Bünyamin,Patureau, Frederic W.

supporting information, p. 3682 - 3687 (2021/02/01)

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

Preparation method of picotamide

-

Paragraph 0027; 0031-0033, (2021/01/25)

The invention provides a method for preparing picotamide, which comprises the following steps: taking dimethyl 4-hydroxyl isophthalate as a raw material, carrying out methyl etherification reaction toobtain dimethyl 4-methoxy isophthalate; then, carrying out hydrolysis reaction to obtain 4-methoxy isophthalic acid; and finally, carrying out amidation reaction to obtain picotamide. Compared with atraditional method, the preparation method has the advantages of short synthesis steps, simplicity and convenience in operation, high reaction speed, high yield and the like. Besides, the raw materials required by the method are extracted from waste residues generated in industrial production, the extraction method is simple, the resource utilization rate is increased, the environmental pollutionis reduced, the production cost is reduced, and the method is suitable for large-scale industrial production.

"Compound for the treatment of atherosclerotic-thrombotic pathological conditions"

-

, (2008/06/13)

4-Methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide of following formula 1: and acid addition salts thereof with pharmaceutically acceptable organic and inorganic acids, and a pharmaceutical composition containing the same, for the treatment of vascular diseases involving atherosclerotic-thrombotic conditions and of other pathological conditions as shown in the description.

Alkyliron and Alkylcobalt Reagents, VIII. - Alkyl-Iron(II) Compounds as Reagents and Catalysts for the Transformation of Acyl Chlorides into Ketones

Kauffmann, Thomas,Voss, Karl-Uwe,Neiteler, Gabriele

, p. 1453 - 1460 (2007/10/02)

Me2Fe, Bu2Fe, Me3FeLi, or Bu3FeLi - prepared in situ by reduction of FeCl3 to FeCl2 and subsequent alkylation with MeLi, MeMgBr, BuLi, or BuMgBr - are useful reagents for the conversion of acyl chlorides into ketones.The system (RMgX + catalytic amount of FeCl3) react like the FeII reagents with acyl chlorides to give ketones even at -65 deg C.Competition experiments with benzoyl chloride/2-methoxybenzoyl chloride show that the selectivity increases (competition constants Kk = 9.9, 10.7, 10.9, 15.0, ca. 110) in the sequence MeFeCl, Me2Fe, Me3Fe(MgBr), Me4Fe(MgBr)2, and catalytic system (MeMgBr + 2.5 mol percent FeCl3) (= 2, 3, 4, 5, and 40MeMgBr per 1 FeCl3, respectively).A new hypothesis on the nature of the active catalyst is discussed. Key Words: Organoiron compounds / Iron catalysts / Ketone synthesis

Structures of ent-Herbertane Sesquiterpenoids displaying Antifungal Properties from the Liverwort Herberta adunca

Matsua, Akihiko,Yuki, Shunji,Nakayama, Mitsuru

, p. 701 - 710 (2007/10/02)

Several aromatic sesquiterpenoids displaying antifungal propaerties have been isolated from the liverwort Herberta adunca together with a mother hydrocarbon with a novel irregular sesquiterpene skeleton, ent-herbertane, and their structures and absolute configurations have been determined on the basis of extensive degradation reactions and spectroscopic evidence.The biological activity is also described.

THREE NEW SESQUITERPENE PHENOLS OF THE ENT-HERBERTANE CLASS FROM THE LIVERWORT HERBERTA ADUNCA

Matsuo, Akihiko,Yuki, Shunji,Nakayama, Mitsuru,Hayashi, Shuichi

, p. 463 - 466 (2007/10/02)

Three sesquiterpene phenols with an ent-herberatne skeleton have been isolated from the liverworth Herberta adunca, and the alucidation of their structures and absolue configurations has been achieved on the basis of the chemical and spectral evidence.

THE STRUCTURE, ABSOLUTE CONFIGURATION AND BIOSYNTHESIS OF NORTILIACORININE A

Bhakuni, Dewan S,Singh, Awadhesh,Jain, Sudha

, p. 2651 - 2655 (2007/10/02)

The incorporation of (+/-)-norcoclaurine, (+/-)-coclaurine, (+/-)-N-methylcoclaurine and dehydro-N-methylcoclaurine into nortiliacorinine A in Tilicora racemosa colebr has been studied and specific utilisation of the (+/-)-coclaurine demonstrated.The evidence supports oxidative dimerization of two coclaurine units to give nortiliacorinine A.Experiments with (+/-)-N-methylcoclaurine and (+/-)-N-methylcoclaurine established that only one N-methylcoclaurine unit is specifically utilised to constitute that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion into nortiliacorine A.Double labelling experiment with (+/-)-N-methylcoclaurine showed that O-Me function of the precursor is lost in the bioconversion into nortiliacorine A.Parallel feedings of (+)-(S)-, and (-)-(R)-N-methyl-coclaurines and (-)-(S)-, and (+)-(R)-coclaurines revealed that the stereo-specificity is maintained in the biosynthesis of nortiliacorinine A from 1-benzylisoquinoline precursors and established S,S'-configuration at the two asymmetric centres in nortiliacorinine A.

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