4441-12-7

Basic information

• Product Name: Trimorpholinophosphine oxide
• Synonyms: 4-dimorpholin-4-ylphosphorylmorpholine;4-dimorpholinophosphorylmorpholine;Phosphoric acid trimorpholide, 4,4',4''-Phosphoryltrimorpholine;Tris(morpholin-4-yl)phosphine oxide 98%;4,4',4''-phosphoryltriMorpholine;TMPO Tris-(Morpholino)-phosphine oxide;Trimorpholinophosphine oxide≥ 99%(HPLC);TRI(4-MORPHOLINO)PHOSPHINE OXIDE
• CAS NO: 4441-12-7
• Molecular Formula: C₁₂H₂₄N₃O₄P
• Molecular Weight: 305.31
• EINECS: 224-662-7
• Product Categories: Building Blocks;C11 to C20+;Chemical Synthesis;Heterocyclic Building Blocks;Morpholines/Thiomorpholines
• Mol File: 4441-12-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 188-190°C
• Boiling Point: 476.4 °C at 760 mmHg
• Flash Point: 241.9 °C
• Appearance: /
• Density: 1.3000 (rough estimate)
• Vapor Pressure: 0-0Pa at 20-50℃
• Refractive Index: 1.5540 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 1.61±0.20(Predicted)
• Water Solubility: 607.20g/L(25 oC)
• BRN: 280155
• CAS DataBase Reference: Trimorpholinophosphine oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Trimorpholinophosphine oxide(4441-12-7)
• EPA Substance Registry System: Trimorpholinophosphine oxide(4441-12-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 1
• Hazardous Substances Data: 4441-12-7(Hazardous Substances Data)

Usage

Chemical Properties

White to Light yellow powder to crystal.

Uses

Trimorpholinophosphine oxide (morPO) is used a coordination chemistry of phosphoryl compounds. It forms the complexes [Fe(morPO)nX2](n =1/2-4,X=BF4，NO3, NCS,Cl, Br, or I) in which the ligand morPO is co-ordinated by the oxygen atom.

Application

Tri(4-morpholinyl)phosphine Oxide can be used to manufacture lined three-layer PVA chemical resistant gloves.

Synthetic route

trimorpholylmethane (22630-09-7) + di-morpholin-4-yl-phosphinic acid chloride (7264-90-6) → tris(morpholino)phenylphosphine oxide (4441-12-7)

Conditions	Yield
In benzene at 60℃; for 1h;	60%

trimorpholylmethane (22630-09-7) → tris(morpholino)phenylphosphine oxide (4441-12-7)

Conditions	Yield
With trichlorophosphate In benzene for 1h;	50%

morpholine (110-91-8) → tris(morpholino)phenylphosphine oxide (4441-12-7)

Conditions	Yield
With trichlorophosphate
With trichlorophosphate In acetonitrile at -0.16℃; for 4h;
With trichlorophosphate In acetonitrile at -0.16℃; for 4h;
With trichlorophosphate

morpholine (110-91-8) + P,P-dichlorophenylphosphine oxide (824-72-6) → tris(morpholino)phenylphosphine oxide (4441-12-7)

Conditions	Yield
With triethylamine In hexane; toluene for 39h; Cooling with ice;

Benzylidenemalononitrile (2700-22-3) + tris(morpholino)phenylphosphine oxide (4441-12-7) → ((4-(dimorpholin-4-ylphosphoryl)morpholin-3-yl)(phenyl)methyl)propanedinitrile

Conditions	Yield
With eosin y In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation;	88%

thorium(IV) nitrate pentahydrate + tris(morpholino)phenylphosphine oxide (4441-12-7) → Th(NO3)4(tris(morpholino)phenylphosphine oxide)2

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;	82.5%

La(NO3)3.7H2O + tris(morpholino)phenylphosphine oxide (4441-12-7) → La(3+)*3NO3(1-)*3C12H24N3O4P

Conditions	Yield
In ethanol; dichloromethane for 24h;	80.2%

lanthanide(III)chloride heptahydrate + tris(morpholino)phenylphosphine oxide (4441-12-7) → LaCl3(tris(morpholino)phenylphosphine oxide)3 (26380-28-9)

Conditions	Yield
In chloroform at 20℃; Inert atmosphere; Schlenk technique;	78.3%

uranyl nirate hexahydrate + tris(morpholino)phenylphosphine oxide (4441-12-7) → O2U(2+)*2NO3(1-)*2C12H24N3O4P

Conditions	Yield
In ethanol; dichloromethane for 24h;	76.6%

1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + tris(morpholino)phenylphosphine oxide (4441-12-7) + neodymium(III) acetate (6192-13-8) → [neodymium(III)(hexafluoroacetylacetonate)3(tri(4-morpholino) phosphine oxide)2]

Conditions	Yield
Stage #1: 1,1,1,5,5,5-hexafluoroacetylacetone; neodymium(III) acetate In ethanol; water at 20℃; for 4h; Stage #2: tris(morpholino)phenylphosphine oxide In ethanol; water	70.2%

Upstream product

• 22630-09-7 trimorpholylmethane 
• 110-91-8 morpholine 
• 824-72-6 P,P-dichlorophenylphosphine oxide 
• 7264-90-6 di-morpholin-4-yl-phosphinic acid chloride 

Relevant articles and documents

The first coordination compounds of OP[NC4H8O]3 phosphoric triamide ligand: structural study and Hirshfeld surface analysis of SnIV and MnII complexes

The first X-ray crystal structures of coordination compounds of OP[NC4H8O]3 phosphoric triamide (L) are investigated in Cl2(CH3)2Sn(trans-L)2 (1) and [Mn(H2O)4(trans-L)2]Cl2·2H2O (2) as models of molecular and salt complexes for Hirshfeld surface (HS)-based analysis. The crystal packing of 1 includes weak interactions, while in the salt complex 2, a 2-D aggregate, along the (001) plane, is mediated by normal O–H?Cl and O–H?O hydrogen bonds. In the Hirshfeld study, the crystal cohesions of 1 and 2 are recognized via H?H, O?H/H?O, and Cl?H/H?Cl contacts. Among these interactions, hydrogen bonds O–H?Cl occur in the salt structure of 2, as well as some weaker hydrogen interactions as C–H?O (1 and 2), C–H?Cl (1), and O–H?O (2). The full fingerprint plots have nearly symmetric shapes for two independent molecules of 1, while an asymmetric shape appears for the cationic component of 2. To extract more detailed information on close intermolecular contacts, the molecular surface of the previously reported structure L was also mapped. The structure 2 is the first monomeric octahedral Mn(II)–phosphoric triamide complex reported so far. Furthermore, the HS analysis of 2 is the first such study on a cation–anion complex structure including phosphoric triamide ligand.

Investigations on synthesis, thermolysis, and coordination chemistry of aminophosphine oxides

Some aminophosphine oxides (AmPOs), (R1)(R2)(R 3)P=O [R1=R2=R3= HNCH 2CH=CH2; R1= R2=Ph, R 3=HNCH2CH=CH2; R