3-(Dimethylphosphono)-N-methylolpropionamide

• CAS: 20120-33-6
• Catalog Number: ACM20120336-2
• Category: Main Products
• Molecular Weight: 211.15
• Molecular Formula: C6H14NO5P
• Synonyms: Dimethyl (3-((hydroxymethyl)amino)-3-oxopropyl)phosphonate
• IUPAC Name: 3-Dimethoxyphosphoryl-N-(hydroxymethyl)propanamide
• SMILES: COP(=O)(CCC(=O)NCO)OC
• InChI: InChI=1S/C6H14NO5P/c1-11-13(10,12-2)4-3-6(9)7-5-8/h8H,3-5H2,1-2H3,(H,7,9)
• InChI Key: MCONGYNHPPCHSD-UHFFFAOYSA-N
• Boiling Point: 210.5 °C
• Density: 1.257 g/cm3
• Appearance: Colourless to Light Yellow Thick Oil
• Complexity: 199
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Exact Mass: 211.06095954
• Formal Charge: 0
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 2
• Isotope Atom Count: 0
• Monoisotopic Mass: 211.06095954
• Physical State: Solid
• Rotatable Bond Count: 6
• Topological Polar Surface Area: 84.9 Ų
• Undefined Atom Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0

Case Study

3-(Dimethylphosphono)-N-methylolpropionamide: A Durable Flame Retardant for Lyocell Fibers

Peng, Kang, et al. Fire and Materials 46.2 (2022): 487-495.

Providing durable flame retardancy to comfortable, bio-based cellulosic fibers like Lyocell is a significant technical challenge. This study demonstrates how 3-(Dimethylphosphono)-N-methylolpropionamide (MDPA), applied with a cross-linking agent, creates an effective and wash-resistant flame-retardant finish for Lyocell. In this application, MDPA was grafted onto Lyocell fibers using hexamethylolmelamine (HMM) as a cross-linker in a post-treatment process involving pad application, microwave treatment, and baking. The phosphorous-containing MDPA acts as the active flame-retardant agent, while HMM ensures its covalent fixation to the fiber to enhance durability.
Key Performance:
· Under optimal conditions (40% MDPA, 320W microwave for 3 min, baking at 160°C for 5 min), treated fibers achieved a high LOI of 34.6%, indicating excellent flame resistance. Thermogravimetric analysis showed the char residue increased from 4.7% to 21.5%, confirming a condensed-phase protective mechanism.
· Balanced Mechanical Properties: The treated fiber retained a breaking strength of 2.47 cN/dtex, meeting textile performance requirements despite some reduction from untreated levels. The finish showed good wash fastness, maintaining a LOI of 26.5% after 30 laundering cycles, which still signifies a good flame-retardant effect. The treatment also caused only minimal change to the fiber's hygroscopicity.

3-(Dimethylphosphono)-N-methylolpropionamide: A Key Component for Bifunctional Cotton Finishing

Sun, Ling, et al. Surfaces and Interfaces 38 (2023): 102771.

Meeting modern textile demands often requires fabrics with multiple high-performance properties, such as flame retardancy and water repellency. This study highlights how 3-(Dimethylphosphono)-N-methylolpropionamide (MDPA) serves as a critical raw material for synthesizing a novel, multifunctional polysiloxane-based polymer that efficiently imparts both properties to cotton fabric in a single treatment. In this application, MDPA was chemically introduced into the side chains of hydrogen-containing silicone oil to create a new polymeric textile modifier (HSCP). The phosphorous-containing MDPA moiety provides the essential flame-retardant function, while the silicone backbone delivers hydrophobicity. This hybrid polymer was then applied to cotton fabrics using an efficient pad-dry-cure process.
Key Performance:
· Dual Functionality from a Single Treatment: Fabrics treated with HSCP acquired significant water repellency, with water contact angles increasing to 140°, 150°, and 158° for concentrations of 250, 350, and 450 g/L, respectively. Simultaneously, the treated fabrics showed markedly improved flame resistance.
· The treatment significantly altered the fabric's thermal degradation and combustion pathway. All treated samples demonstrated increased Limiting Oxygen Index (LOI) values and reduced damage length in vertical burning tests. The finished fabrics maintained good washing durability, and the manufacturing process is noted for its short production steps and low energy consumption, offering a practical new strategy for advanced textile finishing.

Custom Q&A

What is the molecular formula of 3-(Dimethylphosphono)-N-methylolpropionamide?

The molecular formula is C6H14NO5P.

What are the synonyms for 3-(Dimethylphosphono)-N-methylolpropionamide?

The synonyms are 20120-33-6 and 3-dimethoxyphosphoryl-N-(hydroxymethyl)propanamide.

What is the molecular weight of 3-(Dimethylphosphono)-N-methylolpropionamide?

The molecular weight is 211.15 g/mol.

When was 3-(Dimethylphosphono)-N-methylolpropionamide created?

It was created on August 8, 2005.

What is the InChI of 3-(Dimethylphosphono)-N-methylolpropionamide?

The InChI is InChI=1S/C6H14NO5P/c1-11-13(10,12-2)4-3-6(9)7-5-8/h8H,3-5H2,1-2H3,(H,7,9).

What is the Canonical SMILES of 3-(Dimethylphosphono)-N-methylolpropionamide?

The Canonical SMILES is COP(=O)(CCC(=O)NCO)OC.

What is the CAS number of 3-(Dimethylphosphono)-N-methylolpropionamide?

The CAS number is 20120-33-6.

What is the XLogP3-AA value of 3-(Dimethylphosphono)-N-methylolpropionamide?

The XLogP3-AA value is -1.9.

What is the hydrogen bond donor count of 3-(Dimethylphosphono)-N-methylolpropionamide?

The hydrogen bond donor count is 2.

What is the topological polar surface area of 3-(Dimethylphosphono)-N-methylolpropionamide?

The topological polar surface area is 84.9Ų.