1608-26-0

Basic information

• Product Name: Trisdimethylaminophosphine
• Synonyms: Hexamethylphosphorous triamide ,98％;Tris(dimethylamino)phosphine,HMPT, Hexamethylphosphorous triamide;Hexamethylphosphorous triamide 5g [1608-26-0];HexaMethylphosphorous triaMide, 97% 10ML;N,N,N',N',N'',N''-HexaMethyl-phosphorous TriaMide;NSC 102707;HEXAMETHYLTRIAMINOPHOSPHINE FOR SYNTHESI;N,N,N',N',N'',N''-hexaMethylphosphinetriaMine
• CAS NO: 1608-26-0
• Molecular Formula: C₆H₁₈N₃P
• Molecular Weight: 163.2
• EINECS: 216-534-4
• Product Categories: organophosphorus ligand;Miscellaneous Reagents;Phosphorylating and Phosphitylating Agents
• Mol File: 1608-26-0.mol

Chemical Properties

• Melting Point: -44 °C
• Boiling Point: 48-50 °C12 mm Hg(lit.)
• Flash Point: 73 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.898 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.4mmHg at 25°C
• Refractive Index: n20/D 1.463(lit.)
• Storage Temp.: Store at RT.
• PKA: 8.03±0.70(Predicted)
• Water Solubility: REACTS
• Sensitive: Moisture Sensitive
• Stability: Stable. Highly flammable - note low flash point. Incompatible with oxidizing agents.
• BRN: 906778
• CAS DataBase Reference: Trisdimethylaminophosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Trisdimethylaminophosphine(1608-26-0)
• EPA Substance Registry System: Trisdimethylaminophosphine(1608-26-0)

Safety Data

• Hazard Codes: T,Xi,Xn,F
• Statements: 45-46-10-40-36/37/38
• Safety Statements: 53-45-36/37/39-26-16-37/39-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: TH3390000
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1608-26-0(Hazardous Substances Data)

Usage

Uses

Used in Building Materials Industry:
Hexamethylphosphorous triamide is used as a flame retardant for building materials to enhance their fire resistance and safety.
Used in Synthetic Chemistry:
Hexamethylphosphorous triamide is used as a phosphorylating agent in synthetic chemistry, facilitating various chemical reactions and syntheses.
Used in Suzuki Reaction:
In the field of organic chemistry, Hexamethylphosphorous triamide is used in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds.
Used in Organic Synthesis:
Hexamethylphosphorous triamide is used in combination with CCl4 for the conversion of hydroxyl groups to the corresponding chlorides, hydroxyl group activation, and dehydrations, which are essential steps in the synthesis of various organic compounds.

Purification Methods

It may contain more than 1% of phosphoric triamide. The yellow oil is first distilled at atmospheric pressure, then under reduced pressure and stored under N2. It is air sensitive, TOXIC, and should not be inhaled. It is absorbed through the skin. [Mark Org Synth Coll Vol V 602 1973, Beilstein 4 IV 274.]

InChI:InChI=1/C6H18N3P/c1-7(2)10(8(3)4)9(5)6/h1-6H3

Upstream product

• 124-40-3 dimethyl amine 
• 683-85-2 N,N-dimethylaminodichlorophosphane 
• 3348-44-5 bis(N,N-dimethylamino)chlorophosphine 
• 20727-59-7 tetrakis(dimethylamino)phosphonium iodide 
• 13754-82-0 N,N,N',N',N'',N''-hexamethylphosphorohydrazonic triamide 
• 2083-91-2 N,N-Dimethyltrimethylsilylamine 
• 26546-75-8 phenyl tetramethylphosphorodiamidite 
• 863650-20-8 C₁₈H₃₀N₄O₂P₂ 
• 863650-26-4 C₁₈H₃₀N₄O₂P₂ 
• 244775-40-4 naphthalene-1,5-diylbis(dimethylphosphoramidite) 
• 863650-34-4 C₁₈H₃₀N₄O₂P₂ 
• 53617-91-7 C₁₁H₁₉N₂OP 
• 5574-93-6 chlorotris(dimethylamino)phosphonium chloride 
• 49778-01-0 iminotris(dimethylamino)phosphorane 

Downstream Products

• 36636-04-1 benzyltris(dimethylamino)phosphonium chloride 
• 70794-36-4 (2-chloro-benzyl)-tris-dimethylamino-phosphonium; chloride 
• 2680-03-7 N,N-Dimethylacrylamide 
• 57389-77-2 tris-dimethylamino-[(2,4-dioxo-3-phenyl-thiazolidin-5-yl)-phenyl-methyl]-phosphonium betaine 
• 13815-46-8 N,N-dimethylcyclohex-1-enylamine 
• 14205-42-6 3-dimethylamino-crotonic acid ethyl ester 
• 33697-33-5 <(Dimethylamino)phenylmethyl>phosphonic Bis(dimethylamide) 
• 3441-77-8 4,6-Dimethyl-benzochinon-(1,2)- 
• 55635-22-8 (2-phenyl-[1,3,2]oxazaphosphinan-3-yl)-phosphonous acid bis-dimethylamide 
• 62419-12-9 Dimethylamino-dianilino-phosphan 
• 3028-59-9 Benzochinon-(1,2)- 
• 29166-07-2 Benzamidin 
• 7137-83-9 hexa-N-methyl-4,5-diphenyl-2λ⁵-[1,3,2]dioxaphosphole-2,2,2-triamine 
• 33564-09-9 Phenylmalonsaeure-di-(N,N-dimethylamid) 

Relevant articles and documents

Novel Di-isopropylamino Derivatives of Trivalent Phosphorus

Reduction of (iPr2N)2PCl with LiAlH4 in diethyl ether gives (iPr2N)2PH; reaction of iPr2NPCl2 with Mg in boiling tetrahydrofuran gives either the cyclotetraphosphine (iPr2N)4P4 or the 1,2-dichlorobiphosphine iPr2NP(Cl)-P(Cl)NiPr2 depending upon the Mg:iPr2NPCl2 mole ratio.

SYNTHESE UND SPEKTROSKOPISCHE CHARAKTERISIERUNG VON CYCLOPENTADIENYLEISEN-KOMPLEXEN MIT P-N-LIGANDEN DES TYPS (C6H5)3-nP(NR2)N (n = 0-3; R = CH3, C2H5)

The complex cations BF4 (L = (C6H5)3-nP(NR2)n; n = 0-3; R = CH3, C2H5) have been obtained from the reaction of BF4 (I) with L.The reaction of I with E(NR2)3 (E = As, Sb; R = CH3) is also described.Spectroscopic investigations (IR, 1H, 13C and 31P NMR) indicate an increase in electron density on the iron center through increase of the number of P-bound NR2 groups.

Cyclization of C-phosphorylated (PIII) arylformamidines to 3H-1,3-benzazaphospholes

A synthesis of 3H-1,3-benzazaphospholes starting from C-phosphorylated P(III) arylformamidines has been developed. Electron-donating substituents were found to enhance markedly the rate of the cyclization, with substituents at the meta position having the greatest effect. A plausible mechanism of the cyclization was proposed based on DFT calculations.

Dismutation of arylene phosphorodiamidites: Specific features and aspects of preparative use

The dismutation of arylene phosphorodiamidites derived from the simplest phenols and naphthols and of their dibasic analogs was studied. The main regular trends of this process and the limits of its synthetic applicability were determined. Pleiades Publishing, Inc., 2006.

Dismutation of diamidoarylphosphites

Some examples of spontaneous dismutation of diamidoarylphosphites in different solvents were studied, and features of the process were revealed.

Solid-phase chemical synthesis of phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides

Phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides were prepared via a solid-phase synthesis strategy. Under Reformatsky reaction conditions, novel esterified acetic acid phosphinodiamidites were synthesized and condensed with appropriately protected 5′-O-(4, 4′-dimethoxytrityl)-2′-deoxynucleosides to yield 3′-O-phosphinoamidite reactive monomers. These synthons when activated with tetrazole were used with an automated DNA synthesizer to prepare phosphonoacetic acid modified internucleotide linkages on controlled pore glass. The phosphinoacetate coupling products were quantitatively oxidized at each step with (1S)-(+)-(10-camphorsulfonyl)oxaziridine or 3H-1,2-benzodithiol-3-one-1,1-dioxide to produce mixed sequence phosphonoacetate and thiophosphonoacetate oligodeoxynucleotides with an average per cycle coupling efficiency of greater than 97%. Completely deprotected, modified oligodeoxynucleotides were purified by reverse-phase HPLC and characterized by ion exchange HPLC, 31P NMR, and MALDI/TOF mass spectroscopy. Both analogues were stable toward hydrolysis with snake venom phosphodiesterase and stimulated RNase H1 activity.

Reactions of N,N′-dialkylcyclohexane-1,2-diimines with trivalent phosphorus acid chlorides

N,N′-Dialkylcyclohexane-1,2-diimines react with trivalent phosphorus acid chlorides to give, depending on the structure of the organophosphorus reagent and reaction conditions, either 1,3,2-diazaphospholanes (three-coordinate phosphorus) containing the cy

Features of Chemical Behavior of Phosphenium Cations Stabilized by Two Intramolecular Donor-Acceptor N→P Bonds

Properties of a new class of organophosphorus compounds, chelated phosphenium cations containing two intramolecular donor-acceptor N→P bonds, were studied. These cations react with nucleophiles with cleavage of the N→P bonds to give neutral products. On the contrary, in reactions with electrophiles the cationic structure and the N→P bonds are preserved. First representatives of five-coordinate cations containing a phosphazo group were prepared, and their structure was studied by single crystal X-ray diffraction.

THIONO COMPOUNDS. 8. MUTAGENIC ACTIVITY OF REPRESENTATIVE AMIDES OF THIOPHOSPHORIC ACID

Amides of thiophosphoric acid were studied, in order to initiate correlations of mutagenicity with structure, by use of a modified Ames assay.Representative thiophosphoramides of the structure (XArNH)3PS were not mutagenic, irrespective of whether X was a reference hydrogen atom, an electron-withdrawing, or an electron-donating group.One phosphoramidothioate of the structure (2,4-X2ArNH)P(S)(OCH2CH3)2 effected base-pair mutation when X was F (but not when X was CH3), when S-9 liver homogenate with exogenous NADP was used; when X was H, only inconsistent mutagenic activity following metabolic activation was observed even at concentrations near those that produced acute cellular toxicity.Mutagenicity of these N-arylamides thus appears to follow guidelines concluded for esters, (RO)3PS, i.e. that mutagenesis is most probable when two groups are small enough to permit nucleophilic attack by a biomacromolecule on the electrophilic phosphorus atom.That the third group should be electron withdrawing again seems important although it need not be a good leaving group.An alkyl thionamide, 3PS, resembled the oxygen counterpart, 3PO, to which it probably is biotransformed, in being only marginally mutagenic.We conclude that the hazard of mutagenesis is likely to be less with amides than with esters of thiophosphoric acid and that most of the representative thioamides tested are unlikely to pose serious mutagenic hazards. - Key Words: Ames assay, base-pair mutation, mutagenesis, phosphoramidothioate, thionamide, thiophosphoramide