Cas no 819050-88-9 (alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid)

Alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid is a substituted aromatic dicarboxylic acid featuring four methyl groups symmetrically positioned on the propionic acid side chains. This structural configuration enhances steric hindrance and influences its reactivity, making it a valuable intermediate in organic synthesis, particularly for constructing rigid or sterically demanding molecular frameworks. Its high purity and consistent quality ensure reliable performance in applications such as polymer chemistry, pharmaceutical research, and specialty material development. The compound's stability and defined symmetry also facilitate controlled modifications, offering precise functionalization in complex synthetic pathways. Suitable for research and industrial use, it meets stringent analytical standards.
alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid structure
819050-88-9 structure
Product Name:alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid
CAS No:819050-88-9
MF:C16H22O4
MW:278.343485355377
MDL:MFCD08276874
CID:2602493
PubChem ID:354335269
Update Time:2025-11-01

alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Chemical and Physical Properties

Names and Identifiers

    • ALPHA,ALPHA,ALPHA',ALPHA'-TETRAMETHYL-1,3-BENZENEDIPROPIONIC ACID
    • 3-[3-(2-carboxy-2-methylpropyl)phenyl]-2,2-dimethylpropanoic acid
    • &alpha
    • ',&alpha
    • 3,3'-(1,3-Phenylene)bis(2,2-dimethylpropanoic Acid)
    • SMR000639419
    • MLS001075446
    • MLS001075426
    • MLS001075233
    • MLS001075368
    • HMS2203O21
    • HMS3343N05
    • 3,3'-(m-Phenylene)bis(2,2-dimethylpropanoic acid)
    • alpha,alpha,alpha',alpha'-tetramethyl-m-benzenedipropionic acid
    • 3-[3-(2-CARBOXY-2,2-DI
    • 1,3-Benzenedipropanoic acid, α,α,α′,α′-tetramethyl- (9CI)
    • α1,α1,α3,α3-Tetramethyl-1,3-benzenedipropanoic acid (ACI)
    • 3,3′-(1,3-Phenylene)bis(2,2-dimethylpropanoic acid)
    • α,α,α′,α′-Tetramethyl-1,3-benzenedipropionic acid
    • α,α,α',α'-Tetramethyl-1,3-benzenedipropionic Acid
    • 819050-88-9
    • A inverted exclamation marka,
    • AKOS037643140
    • AM-1001
    • 3-[3-(2-CARBOXY-2,2-DIMETHYLETHYL)PHENYL]-2,2-DIMETHYLPROPANOIC ACID
    • T72967
    • A,
    • alpha , alpha , alpha ', alpha '-Tetramethyl-1,3-benzenedipropionic acid
    • A inverted exclamation marka-Tetramethyl-1,3-benzenedipropionic acid
    • T3420
    • EN300-6477015
    • CHEMBL1899631
    • DTXSID70458599
    • SCHEMBL14740848
    • Z4884310340
    • alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid, 97%
    • MFCD08276874
    • 3,3''-(1,3-Phenylene)bis(2,2-dimethylpropanoic Acid)
    • alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid
    • MDL: MFCD08276874
    • Inchi: 1S/C16H22O4/c1-15(2,13(17)18)9-11-6-5-7-12(8-11)10-16(3,4)14(19)20/h5-8H,9-10H2,1-4H3,(H,17,18)(H,19,20)
    • InChI Key: BZWQVGTVYGEXTE-UHFFFAOYSA-N
    • SMILES: OC(C(C)(C)CC1C=CC=C(C=1)CC(C(=O)O)(C)C)=O

Computed Properties

  • Exact Mass: 278.15180918g/mol
  • Monoisotopic Mass: 278.15180918g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 6
  • Complexity: 337
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 74.6
  • XLogP3: 3.3

Experimental Properties

  • Density: 1.1±0.1 g/cm3
  • Melting Point: 155°C(lit.)
  • Boiling Point: 437.0±25.0 °C at 760 mmHg
  • Flash Point: 232.2±19.7 °C
  • Vapor Pressure: 0.0±1.1 mmHg at 25°C

alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Security Information

alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Pricemore >>

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alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrogen peroxide Solvents: Methanol ,  Water ;  0 °C; 4 h, 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  16 h, pH 9 - 10, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C
Reference
Scalable Synthesis of Esp and Rhodium(II) Carboxylates from Acetylacetone and RhCl3·xH2O
Martinez-Castro, Elisa; et al, Organic Process Research & Development, 2020, 24(6), 1207-1212

Production Method 2

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  12 h, rt → 185 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
Reference
An efficient method for the synthesis of 2-methyl-1-substituted-phenyl-2-propylamines
Zhu, Lanping; et al, Youji Huaxue, 2018, 38(7), 1695-1702

Production Method 3

Reaction Conditions
1.1 Reagents: 1,3,5-Benzenetricarboxylic acid ,  Molybdenum(2+), bis[μ-(acetato-κO:κO′)]hexakis(acetonitrile)di-, (Mo-Mo), stereo… ,  Methanesulfonic acid, 1,1,1-trifluoro-, compd. with N,N-dimethylformamide (1:1) Solvents: Dimethylacetamide ;  overnight, 95 °C
Reference
Synthesis, characterization, and polymerization of capped paddlewheel porous cages
Deegan, Meaghan M.; et al, Dalton Transactions, 2021, 50(9), 3127-3131

Production Method 4

Reaction Conditions
1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → 23 °C; 10 h, 23 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  12 h, 180 °C
Reference
Observation of a Photogenerated Rh2 Nitrenoid Intermediate in C-H Amination
Das, Anuvab ; et al, Journal of the American Chemical Society, 2018, 140(33), 10412-10415

Production Method 5

Reaction Conditions
1.1 Reagents: Diisopropylamine ,  Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; 30 min, -78 °C
1.2 1 h, -78 °C
1.3 1 h
1.4 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  12 h, rt → 185 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
Reference
An efficient method for the synthesis of 2-methyl-1-substituted-phenyl-2-propylamines
Zhu, Lanping; et al, Youji Huaxue, 2018, 38(7), 1695-1702

Production Method 6

Reaction Conditions
1.1 Reagents: Diisopropylamine ,  Butyllithium Solvents: Tetrahydrofuran ,  Hexane ,  Water ;  -78 °C; 60 min, -78 °C
1.2 Solvents: Tetrahydrofuran ;  10 min, rt
1.3 Reagents: Water ;  rt
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  9 h, 180 °C; 180 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Cobalt complexes of the chelating dicarboxylate ligand "esp": a paddlewheel-type dimer and a heptanuclear coordination cluster
Pakula, Ryan J.; et al, Dalton Transactions, 2018, 47(39), 13887-13893

Production Method 7

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  9 h, 180 °C; 180 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Cobalt complexes of the chelating dicarboxylate ligand "esp": a paddlewheel-type dimer and a heptanuclear coordination cluster
Pakula, Ryan J.; et al, Dalton Transactions, 2018, 47(39), 13887-13893

Production Method 8

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  12 h, 180 °C
Reference
Observation of a Photogenerated Rh2 Nitrenoid Intermediate in C-H Amination
Das, Anuvab ; et al, Journal of the American Chemical Society, 2018, 140(33), 10412-10415

Production Method 9

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Methyl ethyl ketone ;  5 min, rt
1.2 6 h, 60 °C; 60 °C → rt
1.3 Reagents: Potassium carbonate Solvents: 1,2-Dimethoxyethane ;  rt → 85 °C; 17 h, 85 °C
2.1 Reagents: Hydrogen peroxide Solvents: Methanol ,  Water ;  0 °C; 4 h, 0 °C
2.2 Reagents: Sodium hydroxide Solvents: Water ;  16 h, pH 9 - 10, rt
2.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 1, 0 °C
Reference
Scalable Synthesis of Esp and Rhodium(II) Carboxylates from Acetylacetone and RhCl3·xH2O
Martinez-Castro, Elisa; et al, Organic Process Research & Development, 2020, 24(6), 1207-1212

Production Method 10

Reaction Conditions
1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  10 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  rt → 180 °C; 6 h, 180 °C; 180 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Chloroform ,  Water ;  pH 1, rt
Reference
Bimetallic reductive elimination from dinuclear Pd(III) complexes
Powers, David C.; et al, Journal of the American Chemical Society, 2010, 132(40), 14092-14103

Production Method 11

Reaction Conditions
1.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran ;  10 min, 0 °C
1.2 Solvents: Tetrahydrofuran ;  20 min, 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol ;  rt → 180 °C; 6 h, 180 °C; 180 °C → rt
2.2 Reagents: Hydrochloric acid Solvents: Chloroform ,  Water ;  pH 1, rt
Reference
Bimetallic Pd(III) complexes in palladium-catalysed carbon-heteroatom bond formation
Powers, David C.; et al, Nature Chemistry, 2009, 1(4), 302-309

Production Method 12

Reaction Conditions
1.1 Reagents: Lithium diisopropylamide
1.2 5 min
2.1 Reagents: Potassium hydroxide Solvents: Ethylene glycol
Reference
Introducing a mixed-valent dirhodium(II,III) catalyst with increased stability in C-H amination
Kornecki, Katherine P.; et al, Chemical Communications (Cambridge, 2012, 48(99), 12097-12099

alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Raw materials

alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid Preparation Products

Additional information on alpha,alpha,alpha',alpha'-Tetramethyl-1,3-benzenedipropionic acid

Alpha,Alpha,Alpha',Alpha'-Tetramethyl-1,3-Benzenedipropionic Acid: A Comprehensive Overview

Alpha,Alpha,Alpha',Alpha'-Tetramethyl-1,3-Benzenedipropionic Acid (CAS No. 819050-88-9) is a compound of significant interest in the fields of organic chemistry and materials science. This compound is characterized by its unique structure, which combines a benzene ring with two propionic acid groups and four methyl substituents. The benzenedipropionic acid framework provides a versatile platform for various chemical modifications, making it a valuable component in the synthesis of advanced materials and functional molecules.

Recent studies have highlighted the potential of alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid in the development of high-performance polymers. Researchers have explored its ability to form cross-linked networks with enhanced mechanical and thermal properties. These findings suggest that the compound could be utilized in applications such as lightweight composites for aerospace and automotive industries. The benzenedipropionic acid moiety plays a crucial role in these applications due to its ability to participate in both covalent and non-covalent interactions.

In addition to its role in polymer science, alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid has shown promise in the field of biochemistry. Its methyl-substituted structure enhances its lipophilicity, making it an attractive candidate for drug delivery systems. Recent experiments have demonstrated that derivatives of this compound can serve as effective carriers for hydrophobic drugs, improving their solubility and bioavailability. This property is particularly valuable in the development of targeted therapies for chronic diseases.

The synthesis of alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid involves a multi-step process that typically begins with the preparation of the benzene ring derivative. The introduction of the propionic acid groups is achieved through esterification or direct alkylation techniques. The methyl substituents are introduced at specific positions to ensure optimal chemical reactivity and stability. Advanced spectroscopic techniques such as NMR and IR are employed to confirm the structure and purity of the final product.

From an environmental perspective, the compound's stability and biodegradability are critical factors. Recent studies have investigated its environmental impact under various conditions, including aqueous solutions and soil environments. Results indicate that alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid exhibits moderate biodegradability under aerobic conditions, suggesting that it could be incorporated into sustainable chemical processes with proper waste management practices.

Looking ahead, the potential applications of alpha,alpha,alpha',alpha'-tetramethyl-1,3-benzenedipropionic acid are expected to expand further as researchers continue to explore its unique properties. Its ability to function as both a building block for advanced materials and a component in biochemical systems positions it as a versatile compound with wide-ranging utility. As industries increasingly prioritize innovation and sustainability, this compound is poised to play a pivotal role in shaping future technologies.

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