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

Used in Pharmaceutical Industry:
2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide is used as a key intermediate in the synthesis of 5,5-dimethyl-2-oxido-[1,3,2]-dioxaphosphorinane-2-yl-amino carboxylates. These carboxylates are important building blocks in the development of pharmaceutical compounds, particularly those with potential therapeutic applications.
Used in Biochemistry Research:
2-CHLORO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-ONE is also used in the synthesis of cyclic diguanosine monophosphate (c-di-GMP), a crucial second messenger molecule in bacteria that plays a significant role in regulating bacterial virulence, biofilm formation, and motility. The synthesis of c-di-GMP using 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide aids researchers in understanding the molecular mechanisms underlying these processes and developing potential therapeutic strategies to combat bacterial infections.

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

Upstream product

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

Downstream Products

• 4090-52-2 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-dioxide 
• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 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 
• 929616-77-3 5,5-dimethyl-2-(4'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide 
• 929616-75-1 5,5-dimethyl-2-(2'-phenylphenoxy)-1,3,2-dioxaphosphorinane-2-oxide 
• 1007-80-3 2-Oxo-2-ethoxy-5.5-dimethyl-1.3.2-dioxaphosphorinan 
• 873-99-4 5,5-dimethyl-2-hydroxy-2-oxo-1,3,2-dioxaphosphorinane 
• 1384985-11-8 (Z)-2-{[4-(methyldiphenylsilyl)but-3-en-2-yl]oxy}-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide 
• 1384985-12-9 (Z)-2-{[4-(benzyldimethylsilyl)but-3-en-2-yl]oxy}-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide 
• 1378249-61-6 2-{[(1Z,3S)-1-[dimethyl(phenyl)silyl]-4-methyl-1-penten-3-yl]oxy}-5,5-dimethyl-1,3,2-dioxaphosphinane-2-oxide 
• 1384985-10-7 (Z)-2-{[4-(dimethylphenylsilyl)but-3-en-2-yl]oxy}-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide 
• 1367356-69-1 C₁₃H₁₉O₄P 
• 1367356-71-5 C₁₃H₂₀NO₃P 

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.

Synthesis of novel phosphorus-based flame retardants containing 9,9-bis (4-hydroxyphenyl) fluorine and their reinforcements on the fire safety of polypropylene

Fabricating an effective synergism to improve the flame-retardant (FR) efficiency is recently considered to be a very promising way to prepare high-efficient FRs system. A novel FRs containing phosphorus and (4-hydroxyphenyl) fluorene have been synthesized and characterized by FTIR, 1H NMR and MS. The FRs were then incorporated into polypropylene (PP) in different ratios, and then, ammonium polyphosphate (APP) was added to the FRs/PP system, with subsequent investigation into the synergistic effects between FRs and APP. Limited oxygen index (LOI), UL-94 test and cone calorimeter test were adopted to investigate the FR properties of the flame-retardant PP composites. The LOI value is as high as 31.0%, when FRs/APP is 2/3. Moreover, due to the synergistic FR effects between FRs and APP, the pHRR of PP7 decreases from 783?kW?m?2 (PP0) to 110?kW?m?2 (PP7), which is 85% lower than those of PP. Meanwhile, thermogravimetric analysis (TG) was used to study the thermal degradation characteristics of the PP composites. The char residues increased from 0.02 mass% to 15.85 mass% at 650?°C when FRs/APP is 3:2, indicating that there are synergistic flame-retarding effects between FRs and APP. Generally, the stable char layers of FR/APP/PP composites are responsible for the improved FRs properties, and the char layers could not only effectively prevent the release of combustion gases from releasing but also hinder the propagation of oxygen and heat into the interior substrate.

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 antimicrobial activity of 5,5′-dimethyl-2-oxido-[1,2,3] -dioxaphosphorinane-2-yl-amino carboxylates

Synthesis of several 5,5-dimethyl-2-oxido-[1, 3,2]-dioxaphosphorinane-2-yl- amino car-boxylates (4a-j) was accomplished through a two-step process. This involves prior preparation of the intermediate monochloride (2), 2-chloro-5,5-dimethyl [1,3,2]dioxaphosphorinane-2-oxide and its subsequent reaction with various amino acid esters (3a-j) in dry tetrahydrofuran in the presence of triethyl amine at room temperature. They were characterized by elemental analysis, IR, 1H, 13C, 31P NMR, and mass spectral data. Their antifungal and antibacterial activity is also evaluated. Majority of these compounds exhibited moderate antimicrobial activity in the assay.

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.

Phosphorus-nitrogen type flame retardant as well as preparation method and application thereof

The invention discloses a novel phosphorus-nitrogen type flame retardant and a preparation method thereof, and relates to the technical field of flame retardants, and the structural formula of the phosphorus-nitrogen type flame retardant is as shown in the formula I. The preparation method of the phosphorus-nitrogen type flame retardant comprises the following steps: reacting an intermediate neopentyl glycol phosphoryl chloride with imidazole, cooling to room temperature after the reaction is completed, and carrying out suction filtration, water washing, reduced pressure rotary evaporation and drying to obtain the phosphorus-nitrogen type flame retardant; and blending the phosphorus-nitrogen flame retardant solution and the ripened viscose liquid to prepare a flame-retardant viscose spinning solution, forming in a coagulating bath, and drafting, washing and drying to obtain the phosphorus-nitrogen flame-retardant viscose fiber. The phosphorus-nitrogen type flame retardant prepared by the invention contains a nitrogen element, can play a flame retardant role when a condensed phase and a gas phase are used, and is simple in synthesis process, and is halogen-free, formaldehyde-free, environment-friendly and pollution-free; the prepared phosphorus-nitrogen type flame-retardant viscose fiber overcomes the defect that the existing viscose fiber is easy to burn, avoids the problems of poor durability, serious strength damage and the like, and improves the flame retardance of the viscose fiber.

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.

A phosphorus-nitrogen intumescent fire retardant and its preparation method

The invention relates to a phosphorus-nitrogen intumescent flame retardant and a preparation method thereof. The preparation method comprises the steps: mixing neopentyl glycol and a solvent, adding a catalyst, dissolving the catalyst, then, adding phosphorus oxychloride into a reaction solution under the condition of stirring at the temperature of 0-10 DEG C, reacting for 4-8 hours at the temperature of 20-50 DEG C after phosphorus oxychloride is added completely, removing the solvent through distilling after reacting ends, and washing and drying residues, so as to obtain cyclic phosphoryl chloride; adding the obtained cyclic phosphoryl chloride and an acid binding agent into a solvent, stirring to dissolve, adding diamine into a reaction solution under the condition of stirring at the temperature of 15-30 DEG C, then, reacting for 8-12 hours at the temperature of 50-110 DEG C, removing the solvent through distilling after reacting ends, and washing and drying residues, thereby obtaining the phosphorus-nitrogen intumescent flame retardant. The phosphorus-nitrogen intumescent flame retardant and the preparation method thereof have the advantages that the synthesis process is simple, the reaction time is short, the product has a melting point, the transparency is good when the flame retardant is added into materials, the flame-retardant effect is good, the influence on mechanical properties is low, and the like; and meanwhile, the disadvantage that intumescent flame retardants cannot be applied to the flame retardance of engineering plastics due to poor thermal stability is overcome.

Phosphaphenanthrene phosphate flame retardant with xenyl and preparation method and application thereof

The invention provides a phosphaphenanthrene phosphate flame retardant with xenyl and a preparation method. The preparation method comprises the steps that phenyl-P-benzoquinone and DOPO react to generate an intermediate I; neopentyl glycol and phosphorus oxychloride synthesize an intermediate II under the effect of chloroform; triethylamine is used as an acid-binding agent, N,N-dimethyl formamide (DMF) is used as a solvent, and the intermediate I and the intermediate II react to obtain the phosphaphenanthrene phosphate flame retardant with the xenyl. The appearance of the flame retardant is white powder, the initial decomposition temperature is about 315 DEG C, weightlessness reaches 10% at the temperature of 420 DEG C, and the carbon residue rate of the flame retardant reaches 39% at the temperature of 700 DEG C. The flame retardant has the good heat stability and high carbon residue rate, and can be used for ABS halogen-free flame retardance.

PROCESSES FOR PRODUCTION OF CYCLIC ALKYLENE PHOSPHOHALIDATE AND CYCLIC PHOSPHORIC ACID ESTER

A process for producing a cyclic alkylene phosphorohalidite, which comprises reacting a specific phosphorus trihalide with a specific alkylene glycol compound under conditions where the phosphorus trihalide is present in an excess amount relative to the amount of the alkylene glycol compound in the reaction system to order to obtain the cyclic alkylene phosphorohalidite by reacting the alkylene glycol compound with the phosphorus trihalide; and a process for producing a cyclic phosphoric acid ester by using the obtained cyclic alkylene phosphorohalidite as a raw material.