1605-65-8

Basic information

• Product Name: BIS(DIMETHYLAMINO)PHOSPHORYL CHLORIDE
• Synonyms: Bis(diMethylaMino)phosphoryl chloride, 90%, tech.;Bis(diMethylaMino)phosphoryl chloride, tech.;Bis(N,N-diMethylaMino)phosphinic chloride SynonyMs Bis(diMethylaMino)chlorophosphine oxide;N,N,N',N'-Tetramethylphosphorodiamidic chloride technical grade, 90%;bis-(N,N-dimethylamino)-phosphorylchloride;Phosphorodiamidic chloride, N,N,N',N'-tetramethyl-;Phosphorodiamidic chloride, tetramethyl-;Phosphorodiamidicchloride,tetramethyl-
• CAS NO: 1605-65-8
• Molecular Formula: C₄H₁₂ClN₂OP
• Molecular Weight: 170.58
• EINECS: 216-517-1
• Product Categories: organophosphorus compound
• Mol File: 1605-65-8.mol

Chemical Properties

• Boiling Point: 246-247 °C
• Flash Point: >230 °F
• Appearance: Colorless/Liquid
• Density: 1.152 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.644mmHg at 25°C
• Refractive Index: n20/D 1.466(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• PKA: -0.04±0.70(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 471430
• CAS DataBase Reference: BIS(DIMETHYLAMINO)PHOSPHORYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(DIMETHYLAMINO)PHOSPHORYL CHLORIDE(1605-65-8)
• EPA Substance Registry System: BIS(DIMETHYLAMINO)PHOSPHORYL CHLORIDE(1605-65-8)

Safety Data

• Hazard Codes: C
• Statements: 34-37-20/21/22
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1605-65-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bis(dimethylamino)phosphoryl chloride is used as a synthetic reagent for the production of various pharmaceutical compounds. Its application is primarily due to its ability to facilitate the formation of complex organic molecules, which are essential in the development of new drugs and therapies.
Used in Chemical Synthesis:
In the field of chemical synthesis, Bis(dimethylamino)phosphoryl chloride is used as a key intermediate for the synthesis of a wide range of organic compounds. Its utility stems from its ability to participate in various chemical reactions, leading to the formation of diverse products with potential applications in different industries.
Used in Total Synthesis:
Bis(dimethylamino)phosphoryl chloride is used as a crucial component in the total synthesis of complex organic molecules, such as (-)-allohedycaryol and C2-symmetric binaphthyl phosphortriamide. Its role in these syntheses is to provide a stable and reactive platform for the construction of the target molecules.
Used in Research and Development:
In the research and development sector, Bis(dimethylamino)phosphoryl chloride is employed as a valuable tool for exploring new chemical reactions and pathways. Its unique properties make it an attractive candidate for studying the mechanisms of various organic transformations and for developing new synthetic methodologies.

InChI:InChI=1/C4H12ClN2OP/c1-6(2)9(5,8)7(3)4/h1-4H3

Upstream product

• 856612-19-6 {(CH₃)2N}3PO*ClB(C₆H₅)2 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 64991-65-7 C₇H₁₈ClN₃O₂P⁽¹⁺⁾*Cl^(1-) 
• 22949-94-6 C₆H₁₈Cl₂N₃O₂P₂⁽¹⁺⁾*Cl^(1-) 
• 102269-11-4 N,N-dibenzyl-O-diphenylphosphinylhydroxylamine 
• 3348-44-5 bis(N,N-dimethylamino)chlorophosphine 
• 15743-13-2 tetrachloro-cyclopent-4-ene-1,3-dione 
• 677-43-0 N,N-dimethylphosphoroamidic dichloride 
• 124-40-3 dimethyl amine 

Downstream Products

• 64394-07-6 C₁₂H₂₁N₂OP 
• 64394-08-7 Bis-dimethylamin-diphenylmethyl-phosphonat 
• 59740-64-6 ethyl-μ-imido-diphosphoric acid-1,1-diethyl ester-2,2-bis-dimethylamide 
• 67886-50-4 C₂₅H₄₅N₂O₄PS 
• 67886-49-1 C₂₅H₄₅N₂O₄PS 
• 30645-29-5 C₁₂H₂₁N₄O₃P 
• 30645-30-8 C₁₂H₁₉Cl₂N₄O₃P 
• 13012-98-1 2--1,1,3,3-tetramethylguanidine 
• 14655-73-3 N,N,N',N'-tetramethyldiamide of phenylmethanephosphonic acid 
• 59950-71-9 N,N tetramethyl, N'benzylphosphotriamide 
• 870138-49-1 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl N,N,N',N'-tetramethylphosphorodiamidate 
• 556062-75-0 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl N,N,N',N'-tetramethylphosphoroamidate 
• 21554-47-2 Benzyl-tetramethylphosphordiamidat 
• 59617-89-9 Bis-(dimethylamino)-α-phenylcyanomethylphosphonat 

Relevant articles and documents

SYNTHESE DE COMPOSES BIPHOSPHPORYLES UTILISES COMME AGENTS COMPLEXANTS

Summary: N-alkylated derivatives of nonamethylimidodiphosphoramide (NIPA) (Me2N)2P(O)N(R)P(O)(NMe2)2 with R = n-C6H13 and n-C12H25 have been synthesized to obtain powerful neutral chelating reagents much more hydrophobic than NIPA itself.

Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides: Useful synthons for the stereoselective synthesis of 9-oxo- and 10-hydroxy-2(E)-decenoic acids, important components of queen substance and royal jelly of honeybee Apis mellifera

Lithiated anions derived from (alkenyl)pentamethyl phosphoric triamides as homoenolate equivalents are used in the reaction with halogenated acetal and ketal giving regioselectively the γ-alkylation adducts. Chemoselective acidic hydrolysis of the enephosphoramide moiety in the presence of acetal or ketal groups leads to expected carbonyl products, key intermediates in the synthesis of natural compounds. The synthetic potential of the presented strategy is illustrated by stereoselective synthesis of two pheromones namely, 9-oxo-2(E)-decenoic acid 1 from queen substance and 10-hydroxy-2(E)-decenoic acid 2 from royal jelly of honeybee Apis mellifera.

Preparation of organohalosilanes

In an industrial process for preparing organohalosilanes by reacting metallic silicon particles with an organohalide in the presence of a copper catalyst, a contact mass composed of the metallic silicon and the catalyst further contains an effective amount of a phosphine chalcogenide compound. The invention drastically increases the silane formation rate and the utilization of silicon without lowering the selectivity of useful silane.

REACTIONS OF P(IV)-ACID DIMETHYLAMIDES WITH ACETYL CHLORIDE

Substitution of the dimethylamino group by chlorine in a series of P=O and P=S P(IV)-acid dimethylamides by means of acetyl chloride proceeds more readily for P=O amides.

Phosphorylation of cyclic amides

Compounds of the general formula STR1 are reacted with a strong base followed by a phosphorylating agent, such as dicyclicaminophosphinic halide or bis-di-lower alkylaminophosphinic halide to produce an imine of the formula STR2 wherein R is dicyclicaminophosphinyloxy or bis-di-lower alkylaminophosphinyloxy. R represents a leaving group which will undergo nucleophilic displacement with nitrogen, oxygen, sulfur and carbon containing nucleophiles, that is, nucleophiles which have, as a reactive site, a nitrogen, oxygen, sulfur or carbon atom, such that, when the cyclic imine undergoes nucleophilic displacement, there is formed C--N, C--O, C--S and C--C bonds between the carbon atom of the cyclic imine and the nucleophilic group. The end products may be utilized as intermediates in the production of pharmaceutically valuable compounds and, in some instances, are pharmaceutically valuable compounds per se.

Thermal Oxidative Deamination of Aliphatic Amines to Aldehydes with Bis(diphenylphosphinyl) Peroxide

Reaction of N-substituted alkylamines having pseudoacidic hydrogen at the 1-methylene group with bis(diphenylphosphinyl) peroxide yields the deaminated products by thermal elimination of diphenylphosphinic acid from the intermediate O-diphenylphosphinylhydroxylamines.

Ozonization: An Efficient Method for the Oxidation of Halophosphines

The ozonization of various halophosphines 1a-j leads with quantitative yields to the corresponding phosphine oxides 2a-j.Ozonization is a convenient method of oxidation, in particular of compounds with bulky ligands (1c, 1d, 1e).

Phosphoryl to carbonyl migration of amino groups in mixed anhydrides

Mixed anhydrides derived from carboxylic and aminophosphoric acids, (RO)(R'2N)P(O)OC(O)R'' (1), undergo unimolecular fragmentation yielding carboxyamides, R''C(O)NR'2, and metaphosphate esters, ROPO2.The mechanism of the amino group transfer was studied for substrate 1a (1, R = R' = Me; R'' = Ph); solvent as well as substituent effects indicate little (if any) charge development in the transition state.The effects of solvents and Lewis acids on the reaction rate and the activation parameters determined for 1a can be explained best in terms of stabilizing interactions with either carboxyamide or metaphosphate being formed in the course of reaction.The transfer of a functional group from one acyl center to another was investigated for other anhydride systems and the relative contributions of the fragmentation vs. disproportionation of substrates are discussed.

REACTIONS OF PERCHLOROCYCLOPENTENONES WITH ORGANIC OXIDES

The products from the reactions of perchloro-2-cyclopentene-1,4-dione and 2,3-dichloro-5-dichloromethylene-2-cyclopentene-1,4-dione with some N,N-disubstituted formamides, dimethyl sulfoxide, and hexamethylphosphorotriamide were identified by mass spectrometry and 13C NMR spectrometry.A reaction mechanism is proposed.