4090-55-5

Basic information

• Product Name: 2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE
• Synonyms: 2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE;3,2-dioxaphosphorinane,2-chloro-5,5-dimethyl-2-oxide;2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide;5,5-Dimethyl-2-chloro-1,3,2-dioxaphosphorinane 2-oxide;1,3,2-Dioxaphosphorinane, 2-chloro-5,5-dimethyl-, 2-oxide;Einecs 223-831-2;Phosphorochloridic acid, cyclic (2,2-dimethyltrimethylene) ester;2-Chloro-5,5-diMethyl-1,3,2-dioxaphosphorinane 2-oxide 95%
• CAS NO: 4090-55-5
• Molecular Formula: C₅H₁₀ClO₃P
• Molecular Weight: 184.56
• EINECS: 223-831-2
• Product Categories: Organic Building Blocks;Phosphorus Compounds;Phosphorus Halides
• Mol File: 4090-55-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 97-102 °C(lit.)
• Boiling Point: 152.1°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.28g/cm³
• Vapor Pressure: 4.54mmHg at 25°C
• Refractive Index: 1.445
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE(4090-55-5)
• EPA Substance Registry System: 2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE(4090-55-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 1759 8/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 4090-55-5(Hazardous Substances Data)

Usage

Uses

2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide may be used in the synthesis of 5,5-dimethyl-2-oxido-[1,3,2]-dioxaphosphorinane-2-yl-amino carboxylates and cyclic diguanosine monophosphate (c-di-GMP).

General Description

2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide is also referred to as 5,5-dimethyl-2-oxo-2-chloro-1,3,2-dioxaphosphinane (DMOCP). It can be prepared by reacting phosphorous oxychloride (in dry toluene) with 2,2-dimethyl-1,3-propane diol and triethyl amine.

InChI:InChI=1/C5H10ClO3P/c1-5(2)3-8-10(6,7)9-4-5/h3-4H2,1-2H3

Upstream product

• 68305-69-1 5,5-dimethyl-2-(trimethylsiloxy)-1,3,2-dioxaphosphorinane 2-selenide 
• 506-77-4 cyanogen chloride 
• 97533-81-8 (5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-hydrazine 
• 75-65-0 tert-butyl alcohol 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 68305-67-9 2-hydroxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-selenide tetramethylammonium salt 
• 52912-91-1 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-selenide 
• 67-56-1 methanol 

Downstream Products

• 884-89-9 5,5-dimethyl-2-oxo-2-phenoxy-1,3,2-dioxaphosporinane 
• 4090-52-2 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-dioxide 
• 1007-80-3 2-Oxo-2-ethoxy-5.5-dimethyl-1.3.2-dioxaphosphorinan 
• 406225-93-2 (1R,2R)-N,N'-bis(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)cyclohexane-1,2-diamine 
• 922183-05-9 phenyl 3-O-benzyl-4,6-O-benzylidene-3-2-O-(2,2-dimethyltrimethylene phosphornoyl)-α-D-thiomannopyranoside 
• 873-99-4 5,5-dimethyl-2-hydroxy-2-oxo-1,3,2-dioxaphosphorinane 
• 1261216-57-2 C₁₃H₁₉O₃P 
• 1261216-55-0 C₁₃H₁₅O₃P 
• 1261216-56-1 C₁₄H₁₇O₃P 
• 1332480-42-8 C₂₀H₃₀NO₃P 
• 1332480-54-2 C₂₂H₂₆NO₃P 
• 1332480-52-0 C₁₆H₂₀NO₃P 
• 827348-43-6 2-(benzylamino)-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide 
• 1365566-16-0 C₁₈H₂₈NO₄P 

Relevant articles and documents

(Solid?+?Liquid) Phase Equilibria of 1,2-Bis(2-oxo-5,5-dimethyl-1,3,2-dioxyphosphacyclohexyl-2-imino)ethane in Nine Pure Solvents

1,2-Bis(2-oxo-5,5-dimethyl-1,3,2-dioxyphosphacyclohexyl-2-imino)ethane (BODIE) was synthesized and characterized by elemental analysis, mass spectra, infrared spectroscopy and nuclear magnetic resonance. The thermostability of BODIE was measured by thermogravimetric analysis and the melting temperature and the fusion enthalpy of BODIE were determined by using a differential scanning calorimeter. A gravimetric method was applied to measure the solubilities of BODIE in the selected solvents. The solubility data of BODIE in selected organic solvents are well fitted by the modified Apelblat model. Also, the solubility parameter of BODIE was estimated by the Scatchard–Hildebrand model. The results show that these models can satisfactorily reproduce the experimental data.

Waterborne polyurethane conjugated with novel diol chain-extender bearing cyclic phosphoramidate lateral group: Synthesis, flammability and thermal degradation mechanism

A diol bearing a cyclic phosphoramidate pendant group, namely 2-(5,5-dimethyl-2-oxo-2λ5-1,3,2-dioxaphosphinan-2-ylamino)-2-methyl-propane-1,3-diol (PNMPD) was synthesized and characterized by FTIR and NMR. Subsequently, PNMPD was applied as a flame-retardant chain extender to prepare phosphorus-nitrogen containing waterborne polyurethane (PNWPU), and the influence of PNMPD on the hydrolysis, thermal and flame-retardant properties of PNWPU was investigated. The fabricated PNMPD-based PNWPU shows controllable mechanical properties and maintains the good hydrolysis-resistance property of polyurethane. Thermal stability and flammability analysis demonstrate that though the covalent conjugation of PNMPD induces a slight thermal destabilization effect, it efficiently promotes char formation in PNWPU, as a result, a 27.2% limiting oxygen index (LOI) value and a UL-94 V-0 rating can be achieved with only 12 wt% PNMPD incorporated. Compared with WPU, the peak heat release rate (PHRR), total heat release (THR), peak smoke production rate (PSPR) and total smoke release (TSR) of PNWPU-12, evaluated with cone calorimetry, are decreased by 44.7%, 39.0%, 42.9% and 36.1%, respectively. In addition, the flame retarding mechanism of PNWPU was comprehensively investigated by SEM microscopy, EDX analysis, real time FTIR and TG-FTIR, and results elucidate that these notable reductions in fire hazards are probably attributed to the formation of polyphosphoric acid-rich rugged and intumescent char in the condensed phase, which behaves as a "labyrinth effect" to effectively inhibit the transmission of heat, oxygen and volatile fragments from entering into the flame zone and shield the underlying PNWPU matrix against flame.

Synthesis and thermal properties of two novel P-N compounds

Two novel P-N compounds were synthesized through a two-step reaction including the synthesis of 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide (M) and its reaction with 2,2,6,6-tetramethylpiperidine-4-amine and N-butyl-2,2,6,6-tetramethylpiperidin-4-amine. The structures were confirmed by NMR (1H, 13C, 31P), FT-IR and MS. Their thermal properties were also evaluated by thermogravimetric analysis (TGA). The TG curves showed that the two compounds have residues of 4.9 and 1.1 wt % at 600 °C and the temperature of maximum weight loss rate (Tmax) was 292 and 255 °C, respectively.

Regio- And Stereoselective Addition of Bronsted Acids to Yndiamides: Synthesis of N, O, N - And N, S, N -Trisubstituted Ketene Acetals

Yndiamides, N,N-disubstituted alkynes, are versatile building blocks for the synthesis of nitrogen-containing organic molecules. Unlike ynamides, relatives that are inherently polarized by a single nitrogen substituent, their pseudo-symmetric nature renders regioselective reactions challenging. Here we report investigations into the regioselective addition of Br nsted acids to non-symmetric yndiamides, a reaction that delivers N,O,N- and N,S,N-trisubstituted ketene acetals with excellent regio- and stereoselectivity.