52420-88-9

Basic information

• Product Name: TRIMETHYLPHOSPHORAMIDE
• Synonyms: DIMETHYL METHYLPHOSPHORAMIDATE
• CAS NO: 52420-88-9
• Molecular Formula: C₃H₁₀NO₃P
• Molecular Weight: 139.09
• Mol File: 52420-88-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 136.1°Cat760mmHg
• Flash Point: 36.1°C
• Appearance: /
• Density: 1.124g/cm³
• Vapor Pressure: 7.5mmHg at 25°C
• Refractive Index: 1.398
• CAS DataBase Reference: TRIMETHYLPHOSPHORAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLPHOSPHORAMIDE(52420-88-9)
• EPA Substance Registry System: TRIMETHYLPHOSPHORAMIDE(52420-88-9)

Safety Data

• Hazardous Substances Data: 52420-88-9(Hazardous Substances Data)

Usage

General Description

Trimethylphosphoramide (TMPA) is a colorless liquid with a slightly ammonia-like odor that is commonly used as a solvent in organic synthesis. This chemical is highly polar and has a high boiling point, making it useful for reactions that require high temperatures. TMPA is also a strong Lewis base, capable of coordinating with a wide range of metal ions. It has been utilized in various applications, such as in the production of pharmaceuticals, dyes, and pesticides. However, TMPA is considered to be a hazardous chemical, as exposure to it can cause skin and eye irritation, and prolonged or high-level exposure can lead to more serious health effects. Therefore, proper safety precautions should be taken when handling and using trimethylphosphoramide in laboratory settings.

InChI:InChI=1/C3H10NO3P/c1-4-8(5,6-2)7-3/h1-3H3,(H,4,5)

Upstream product

• 67-56-1 methanol 
• 2014-79-1 diphenyl methylphosphoramidate 
• 82134-80-3 N-methyl-N-acetyldimethylphosphoramidate 
• 102146-42-9 1,3-dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione 
• 917-64-6 methyl magnesium iodide 
• 64-17-5 ethanol 

Downstream Products

• 1455-13-6 deuteromethanol 
• 813-78-5 dimethylphosphoric acid 
• 74-89-5 methylamine 

Relevant articles and documents

Phosphoric Carboxylic Imides. Part 6. Structure and Reactivity of 1,3,2-Diazaphospholidine-4,5-diones; Crystal Structure of 1,3-Dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione

1,3-Dimethyl-2-methylamino-1,3,2-diazaphospholidine-2,4,5-trione (1b) has been synthesized, and its solvolytic behaviour and X-ray crystal structure determined.Methanolysis of (1b) gives products of the cleavage of both imide P-N bonds, indicating that the ring opening in (1b) is much slower than the second P-N cleavage in the ring-opened intermediate.The low reactivity of (1b) is correlated with the small size (92.3 deg) of the endocyclic N-P-N angle, which suggests that not much energy is released upon the formation of the PV trigonal bipyramidal adduct.The molecular structure of (1b) reveals a high degree of coplanarity of the phospholidine ring with both imide N-methyl groups and both carbonyl oxygen atoms.The geometry indicates that the endocyclic nitrogen atoms in (1b) are involved in the resonance interactions not only with the adjacent carbonyl groups, but also with the phosphoryl centre. 1,3-Dimethyl-2-phenoxy-1,3,2-diazaphospholidine-2,4,5-trione (1a) has been found to react with p-anisidine or ammonia exclusively at the phosphorus atom.In the reaction with p-anisidine both P-O bond cleavage (displacement of phenol) and ring P-N bond cleavage products were obtained; this is interpreted in terms of pseudorotation of the initially formed PV intermediate.Ammonia reacts with (1a) giving exclusively the ring-retained, P-OPh bond cleavage products.Our aminolysis results for (1a) contrast with those reported in the literature.

Phosphoric-Carboxylic Imides. 2. Solvolytic Cleavage of the Nitrogen-Carbonyl and Nitrogen-Phosphoryl Bonds

The neutral and acid-catalyzed solvolysis (hydrolysis and alcoholysis) of mixed phosphoric-carboxylic imides (1), X2P(O)-NR-C(O)R'(X = EtO, MeO, CH2O, Et; R = H, Me; R'= Me, Ph) has been studied and compared with the solvolytic behavior of parent phosphoric and carboxylic amides and symmetrical imides.The neutral cleavage of the P-N bond is believed to involve an oxyphosphorane intermediate.The ionization of 1 follows the amide acidity function, with half-protonation at the carbonyl oxygen atom occuring at ca. 70percent D2SO4.The remarkable stability of the P-N bond in acidic solutions, together with the susceptibility of the N-C(O)solvolysis toward acid catalysis, is consistent with the exclusion of the N-protonation of 1 and is in accordance with carbonyl oxygen protonation and the significant electron-withdrawing effect of the N-phosphinyl substituent.The hydration parameter treatment was applied to the acid-catalyzed N-C(O) hydrolysis of 1d (1, X = EtO; R = R'= Me), and the results are compared with those obtained for the acid-catalyzed hydrolysis of N-methylacetamide.The acidic solvolysis of 1, with respect to both the P(O)-N and N-C(O) cleavage, lies between the extremes characterized by the respective parent amides and symmetrical imides.