57609-64-0

Basic information

• Product Name: TRIMETHYLENE BIS(4-AMINOBENZOATE)
• Synonyms: CUA-4;1,3-PROPANEDIOL BIS(4-AMINOBENZOATE);1,3-BIS(4-AMINOBENZOYLOXY)PROPANE;propane-1,3-diyl bis(4-aminobenzoate);1,3-PROPANEDIOL BIS(4-AMINOBENZOATE), 98 %;PROPYLENE GLYCOL BIS (4-AMINOBENZOATE) [CUA-4];Trimethylene glycol di-p-aminobenzoate;BIS(4-AMINOBENZOATE)
• CAS NO: 57609-64-0
• Molecular Formula: C₁₇H₁₈N₂O₄
• Molecular Weight: 314.34
• EINECS: 260-847-9
• Product Categories: C12 to C63;Carbonyl Compounds;Esters
• Mol File: 57609-64-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 124-127 °C(lit.)
• Boiling Point: 454.02°C (rough estimate)
• Flash Point: 257.4 °C
• Appearance: /powder (Granular)
• Density: 1.14 g/mL at 140 °C (specific gravity)(lit
• Vapor Pressure: 5.11E-12mmHg at 25°C
• Refractive Index: 1.5486 (estimate)
• Solubility: almost transparency in Acetone
• PKA: 2.61±0.10(Predicted)
• Water Solubility: 4mg/L at 25℃
• CAS DataBase Reference: TRIMETHYLENE BIS(4-AMINOBENZOATE)(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLENE BIS(4-AMINOBENZOATE)(57609-64-0)
• EPA Substance Registry System: TRIMETHYLENE BIS(4-AMINOBENZOATE)(57609-64-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 57609-64-0(Hazardous Substances Data)

Usage

Description

TRIMETHYLENE BIS(4-AMINOBENZOATE) is a versatile chemical compound known for its high performance as a reactant with polyurethane and epoxide prepolymers. It is characterized by its non-hygroscopic properties and the ability to form urethanes with excellent hydrolytic stability, dry heat aging, and resistance to various chemicals and environmental factors.

Uses

Used in the Polymer Industry:
TRIMETHYLENE BIS(4-AMINOBENZOATE) is used as a high-performance reactant for the production of polyurethane and epoxide prepolymers. Its application is valued for enhancing the hydrolytic stability, dry heat aging, and chemical and environmental resistance of the resulting urethanes, making them suitable for a wide range of applications in the polymer industry.
Used in the Manufacturing of Urethane Products:
As a key component in the production of urethanes, TRIMETHYLENE BIS(4-AMINOBENZOATE) is used to improve the overall quality and performance of urethane products. Its contribution to the enhanced properties of urethanes makes it an essential ingredient in the manufacturing process, leading to the creation of durable and reliable urethane products for various industries.
Used in the Development of Coatings and Adhesives:
TRIMETHYLENE BIS(4-AMINOBENZOATE) is utilized as a reactant in the formulation of coatings and adhesives, providing them with improved hydrolytic stability and resistance to environmental factors. This results in coatings and adhesives with longer-lasting performance and durability, making them ideal for various applications in the construction, automotive, and industrial sectors.
Used in the Production of High-Performance Plastics:
TRIMETHYLENE BIS(4-AMINOBENZOATE) is also used in the production of high-performance plastics, where its properties contribute to the creation of materials with enhanced stability and resistance to various environmental factors. These plastics find applications in a wide range of industries, including electronics, automotive, and aerospace, where high-performance materials are crucial for the success and longevity of the products.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C17H18N2O4/c18-14-6-2-12(3-7-14)16(20)22-10-1-11-23-17(21)13-4-8-15(19)9-5-13/h2-9H,1,10-11,18-19H2

Synthetic route

sodium p-aminobenzoate (555-06-6) + 1,3-Dichloropropane (142-28-9) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
In N-methyl-acetamide; water	95%
With sodium carbonate; dimethyl sulfoxide; 1,2-dichloro-ethane In water	91.5%

potassium 4-aminobenzoate (138-84-1) + 1,3-chlorobromopropane (109-70-6) + 1,2-dichloro-benzene (95-50-1) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
With sodium carbonate In N-methyl-acetamide; water	90.8%

dibutyltin diacetate + p-aminoethylbenzoate (94-09-7) + trimethyleneglycol (504-63-2) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
In isopropyl alcohol	82.2%

1,3-bis(4-nitrobenzoyloxy)propane (57609-63-9) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In ethanol for 10.5h; Reflux;	76%
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 12h;	2265 mg

4-amino-benzoic acid (150-13-0) + trimethyleneglycol (504-63-2) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
With 1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium 4-methylbenzenesulfonate In 5,5-dimethyl-1,3-cyclohexadiene at 135 - 140℃; for 5h; Reagent/catalyst; Solvent; Temperature;	65.4%

4-nitro-benzoyl chloride (122-04-3) → propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / toluene / 3.25 h / 10 °C / Reflux 2: hydrazine hydrate; palladium 10% on activated carbon / ethanol / 10.5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / toluene / 4.25 h / 0 °C / Inert atmosphere; Schlenk technique; Reflux 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 12 h / 20 °C View Scheme

propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) + diethyl 2,2'-(sulfonylbis(4,1-phenylene)bis(oxy))diacetate (38775-52-9) → C66H56N4O20S2

Conditions	Yield
In ethanol at 80℃; Solvent;	90%

tert-butylisonitrile (119072-55-8, 7188-38-7) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) + o-carboxybenzaldehyde (119-67-5) → propane-1,3-diyl bis(4-((R)-1-(tert-butylcarbamoyl)-3-oxoisoindolin-2-yl)benzoate) + propane-1,3-diyl bis(4-(1-(tert-butylcarbamoyl)-3-oxoisoindolin-2-yl)benzoate)

Conditions	Yield
Stage #1: propane-1,3-diyl bis(4-aminobenzoate); o-carboxybenzaldehyde In dichloromethane at 20℃; Ugi Condensation; Inert atmosphere; Stage #2: tert-butylisonitrile With (S)-3,3'-bis(4-nitrophenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diylphosphoric acid In dichloromethane Ugi Condensation; Inert atmosphere; Molecular sieve; Reflux; enantioselective reaction;	A 73% B 15%

4-(decyloxy)benzaldehyde (24083-16-7) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C51H66N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

4-(hexyloxy)benzaldehyde (5736-94-7) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C43H50N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

4-(n-heptyloxy)benzaldehyde (27893-41-0) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C45H54N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

4-octyloxybenzaldehyde (24083-13-4) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C47H58N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

4-nonyloxy-benzaldehyde (50262-46-9) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C49H62N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

4-n-dodecyloxybenzaldehyde (24083-19-0) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) → C55H74N2O6

Conditions	Yield
With acetic acid In ethanol for 2h; Heating;

propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) + Tosyl isocyanate (4083-64-1) → 1,3-trimethylene bis(4-(p-toluenesulfonylaminocarbonylamino)benzoate)

Conditions	Yield
In acetonitrile at 20 - 70℃; for 5.08333h; white crystals;

tert-butylisonitrile (119072-55-8, 7188-38-7) + propane-1,3-diyl bis(4-aminobenzoate) (57609-64-0) + o-carboxybenzaldehyde (119-67-5) → propane-1,3-diyl bis(4-(1-(tert-butylcarbamoyl)-3-oxoisoindolin-2-yl)benzoate)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; Inert atmosphere;

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 504-63-2 trimethyleneglycol 
• 57609-63-9 1,3-bis(4-nitrobenzoyloxy)propane 
• 122-04-3 4-nitro-benzoyl chloride 
• 555-06-6 sodium p-aminobenzoate 
• 142-28-9 1,3-Dichloropropane 
• 138-84-1 potassium 4-aminobenzoate 
• 109-70-6 1.3-chlorobromopropane 
• 95-50-1 1,2-dichloro-benzene 
• 94-09-7 p-aminoethylbenzoate 

Relevant articles and documents

Organocatalytic Double Ugi Reaction with Statistical Amplification of Product Enantiopurity: A Linker Cleavage Approach to Access Highly Enantiopure Ugi Products

Here we report an organocatalytic double Ugi reaction combining the enantioselective process and ee enhancement in a single operation to afford the chiral Ugi products with very high ee values. Both bisisocyanides and bisanilines tethered by carbonate and diester, respectively, were designed to accomplish this double multicomponent reaction that formed 10 new chemical bonds (4 C-N, 2 C-C, 2 C-O, and 2 N-H bonds). The strategy was further applied for the fast construction of an enantiomerically enriched macrocycle.

Synthesis, characterization and morphological studies of some novel siloxane-based block copolymeric materials containing organometallic as well as organic polyesteramides

A series of semi-aromatic diamine monomers (1,m-bis (4-amino benzoyloxy) alkanes; m = 2-6) having in-built ester linkages with variable methylene spacers were synthesized in two steps from aliphatic diols and p-nitrobenzoyl chloride and characterized by their melting points, elemental analysis, FTIR, 1H and 13C NMR spectroscopic studies. The diamines were then polymerized in-situ with ferrocene-based organometallic and terephthaloyl- as well as isophthaloyl-based organic acyl chlorides along with telechelic polydimethylsiloxane oligomer to produce a novel set of ferrocene-containing siloxane-based block copolymers and their organic analogues. The corresponding polyesteramides of the synthesized copolymers, without siloxane segment, were also prepared for comparative studies. The structural features of the organometallic and organic block copolymers along with their respective polyesteramides were confirmed by their physical properties and spectroscopic studies. The molecular parameters of all these materials were determined by static laser light scattering (LLS) technique and glass transition temperatures (Tg) were obtained by differential scanning calorimetry (DSC). The materials were soluble in sulphuric acid and partially soluble in common organic solvents at room temperature, yet become readily soluble upon N-trifluoroacetylation. The morphological information of the synthesized materials was obtained by X-ray diffraction and surface studies (SEM and AFM).

Process for the preparation of 1,3-propanediol bis(p-aminobenzoate)

A process for the preparation of 1,3-propanediol bis(p-aminobenzoate) is described, comprising reacting a p-aminobenzoic acid alkali metal salt with dihalogenated propane in an aprotic polar solvent. In accordance with this process, diesterification proceeds under mild conditions without causing any undesirable side reactions and, therefore the desired 1,3-propanediol bis(p-aminobenzoate) can be obtained in high purity and high yield.