4090-60-2

Usage

Uses

Used in Organic Synthesis:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used as a reducing agent for various organic reactions, including the reduction of carbonyl compounds, nitro compounds, and imines. Its high reactivity and selectivity make it a preferred choice for chemists working in the field of organic synthesis.
Used in Palladium(I) Catalyzed Addition of P(O)-H Bonds:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used as a reagent in palladium(I) catalyzed addition reactions involving P(O)-H bonds. This allows for the formation of new chemical bonds and the synthesis of complex organic molecules.
Used in Highly Regioselective Modified Pudovik Addition Reaction:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used as a reagent in highly regioselective modified Pudovik addition reactions. This enables chemists to selectively form specific products, which is crucial for the synthesis of complex organic molecules.
Used in Radical Reactions Mediated by Manganese(III) Acetate:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used as a reagent in radical reactions mediated by manganese(III) acetate. This allows for the formation of new chemical bonds and the synthesis of complex organic molecules through radical mechanisms.
Used in Stable Cyclic DEPMPO Derivatives as Mechanistic Markers:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used in the synthesis of stable cyclic DEPMPO derivatives, which serve as mechanistic markers of stereoselective hydroxyl radical adduct formation in biological systems. This helps researchers understand the mechanisms of various chemical reactions in biological systems.
Used in Copper-Catalyzed Aerobic Oxidative Dehydrogenative Coupling Reactions:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used as a reagent in copper-catalyzed aerobic oxidative dehydrogenative coupling reactions. This allows for the formation of new chemical bonds and the synthesis of complex organic molecules through oxidative coupling mechanisms.
Used in Bisphosphonates/Phosphanamidates as Anticancer Agents:
5,5-Dimethyl-1,3,2-dioxaphosphorinan-2-& is used in the synthesis of bisphosphonates and phosphanamidates, which are potential anticancer agents. These compounds have shown promise in targeting cancer cells and inhibiting their growth, making them valuable tools in the development of new cancer therapies.

InChI:InChI=1/C5H11O3P/c1-5(2)3-7-9(6)8-4-5/h9H,3-4H2,1-2H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 762-04-9 phosphonic acid diethyl ester 
• 25236-26-4 phosphinic acid 3-hydroxy-2,2-dimethyl-propyl ester 
• 25236-29-7 5,5-dimethyl-2-H-1,3,2-dioxaphosphorinane 
• 2428-06-0 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane 
• 21458-75-3 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 1009-82-1 2-isopropoxy-5,5-dimethyl-1,3,2-dioxaphosphinane 
• 4090-55-5 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide 
• 56465-64-6 2-(dimethylamino)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 119713-39-2 5,5-dimethyl-2-oxo-2-(propa-1',2'-diene)-1,3,2-dioxaphosphorinane 
• 5843-26-5 tetramethylphosphorodiamidous acid 
• 108-90-7 chlorobenzene 
• 3057-08-7 5,5-dimethyl-2-phenoxy-[1,3,2]dioxaphosphinane 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 

Downstream Products

• 20615-06-9 2-Oxo-2-(α-propylamino-benzyl)-5,5-dimethyl-PV-1,3,2-dioxaphosphorinan 
• 57078-64-5 N-[1-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-cyclohexyl]-N'-[1-phenyl-meth-(Z)-ylidene]-hydrazine 
• 55015-18-4 N-[(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-phenyl-methyl]-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 
• 128766-97-2 2-[4-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylmethyl)-phenyl]-benzothiazole 
• 67-64-1 acetone 
• 108-95-2 phenol 
• 110907-85-2 5,5-dimethyl-2-trimethylsilyloxy-1,3,2-dioxaphosphorinane 
• 136001-43-9 5,5-dimethyl-2-(1-morpholino-1-phenylethyl)-2-oxo-1,3,2-dioxaphosphorinane 
• 108483-22-3 (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol 
• 4090-52-2 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-dioxide 
• 873-99-4 5,5-dimethyl-2-hydroxy-2-oxo-1,3,2-dioxaphosphorinane 
• 1128246-39-8 C₂₄H₂₃N₂O₅P 
• 934182-09-9 2-methyl-2-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphinan-2-yl)-3,4-dihydro-2H-pyrrole 1-oxide 

Relevant academic research and scientific papers

CyDEPMPOs: A class of stable cyclic DEPMPO derivatives with improved properties as mechanistic markers of stereoselective hydroxyl radical adduct formation in biological systems

The cis/trans diastereoisomeric composition of hydroxyl radical adducts to chiral cyclic nitrones can be used to approach mechanisms of free radical formation in biological systems. Such determination is greatly simplified when both diastereoisomers have ESR spectra with at least two non-overlapping lines. To achieve this prerequisite, a series of DEPMPO-derived spin traps bearing one unsubstituted or alkyl-substituted 2-oxo-1,3,2-dioxaphosphorinane ring were synthesized and their structures were confirmed by X-ray diffraction, 1H, 13C and 31P NMR. These CyDEPMPOs nitrones showed variable lipophilicities and LD50 values on murine fibroblasts compatible with a safe use in biological spin trapping. All CyDEPMPOs formed persistent spin adducts with a series of free radicals, including superoxide and hydroxyl (i.e., CyDEPMPOs-OH) and the in vitro half-life times of these two latter were at least as extended as those of parent DEPMPO. Using four methods of CyDEPMPOs-OH formation, the cis-CyDEPMPOs-OH percentage was found significantly varied with substitution on the P-containing ring and, more interestingly, with the generating system.

Phosphorus-nitrogen-containing polyether polyol compound as well as preparation method and application thereof

The invention discloses a phosphorus-nitrogen-containing polyether polyol compound as well as a preparation method and application thereof. The phosphorus-nitrogen-containing polyether polyol compound is selected from any one of substances with a structural formula shown in a formula I in the specification. The compound is used as a phosphorus-nitrogen-containing polyether polyol synergistic flame retardant, the compound is used as a reactive phosphorus-nitrogen-containing polyether polyol and can chemically react with isocyanate to generate a carbamate group, flame-retardant elements phosphorus and nitrogen are introduced into a polyurethane network in the form of covalent bonds, and the phosphorus-nitrogen-containing polyether polyol with excellent flame-retardant performance is prepared. The problem that an additive flame retardant is easy to separate out and migrate in the prior art is solved, and excellent flame resistance is achieved.

Herbicidal activity and application cyclic of phosphonates

Among alkylphosphonates Io,O,O-dimethyl 1-(2,4-dichlorophenoxyacetoxy) ethylphosphonate (clacyfos) was found to be an effective inhibitor against dicotyledons PHDc and exhibited excellent herbicidal activity in our previous work. According to our study on the alkylphosphonates Io, both R1 and R2 groups in the structural unit of phosphorus-containing played a very important role in herbicidal activity. Therefore, a series of 2-[1-(substituted phenoxycarboxy)alkyl]-5,5-dimethyl-1,3,2-dioxaphosphinane-2-one containing fluorine II was obtained by the modification of alkylphosphonates Io. The bioassay results showed that cyclic phosphonate II-6 with CH3 as R, 2-Cl,4-F as Yn exhibited promising herbicidal activity. Its herbicidal activity, weed-controlling spectrum, selectivity between crops and weeds were further evaluated in greenhouse and field.

Design, synthesis and herbicidal activity of novel cyclic phosphonates with diaryl ethers containing pyrimidine

Thirteen novel cyclic phosphates were rationally designed and synthesized by introducing diary ethers containing pyrimidine. All the target compounds were characterized by 1H, 13C, 31P NMR and HRMS. The test of herbicidal activity indicated that most of the compounds showed good herbicidal activities against Amaranthus retroflexus. The compounds IA-2 (1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)propyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) and IA-3 ((5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)(phenyl)methyl-2-((4,6-dimethoxypyrimidin-2-yl)oxy)benzoate) exhibited remarkable post-emergency herbicidal activity against the tested monocotyledonous weed at the dosage of 112.5 g ai/ha.

Reaction of allenylphosphonates/allenylphosphine oxides with thiocyanates/isothiocyanates or oxalyl chloride/AgNO3

In this paper, we describe thiocyanation as well as chlorination of selected allenylphosphonates/allenyl phosphine oxide, using ammonium thiocaynate or (OCH2CMe2CH2O)PNCS (for thiocyanation) or oxalyl chloride/AgNO3/

Synthesis and herbicidal activity of α-[(substituted phenoxybutyryloxy or valeryoxy)]alkylphosphonates and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine

Based on our previous work on the structural modification of the lead compound I, three series of novel fluorine-containing phosphonates derivatives (II, III and IV) were designed and synthesized. Their post-emergence herbicidal activities against some species of weeds were evaluated in a green house. The compounds II were synthesized by introducing of two methylene into the structure I. Compared with the commercial herbicidal clacyfos, compounds II showed moderate herbicidal activity with 60–85% inhibition effect against chingma abutilon (Abutilon theophrasti), common amaranth (Amaranthus retroflexus) and white eclipta (Eclipta prostrate) at a rate of 150 g ai/ha. The compounds III were designed by introducing open-chain phosphonates, which displayed notable herbicidal activity. Especially, the compounds III-1–III-4, III-6, III-8, III-11 and III-12 exhibited significant herbicidal activity (80–100%) comparing to the clacyfos against all tested broadleaf weeds, while compounds IV with five carbon atoms in the carboxylic acid chain were inactive against all of the tested weeds. Structure-activity relationship analyses indicated that the length of the carbon chain had a great effect on the herbicidal activity. Furthermore, a broad spectrum test confirmed that compounds III-4 and III-8 were comparable with glyphosate against all of the tested weeds at a rate of 75 g ai/ha.

Synthesis and Solubility of 5,5-Dimethyl-2-(phenyl(phenylamino)methyl)-1,3,2-dioxaphosphinane 2-oxide in Selected Solvents between 278.15 K and 347.15 K

A flame retardant with enhanced phosphorus-nitrogen content, 5,5-dimethyl-2-(phenyl(phenylamino)methyl)-1,3,2-dioxaphosphinane 2-oxide (DPPO), was synthesized by the reaction of 5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (DDPO) with N-benzylideneaniline. The structure of DPPO was characterized by nuclear magnetic resonance (1H NMR and 31P NMR) and Fourier transform infrared (FT-IR) spectroscopy. The thermal stability of DPPO was characterized by thermogravimetric analysis (TGA). The solubilities of DPPO were measured in different solvents including ethyl acetate, methanol, chloroform, acetonitrile, acetone, 1,2-dichloroethane, 1,4-dioxane, dichloromethane, tetrachloromethane, benzene, tetrahydrofuran, and isopropanol at temperature ranging from 278.15 to 347.15 K by the gravimetrical method. The mole fraction solubilities of DPPO in the above-mentioned organic solvents were correlated as the Apelblat equation, and the calculated values with equations shows good consistency with the experimental values. The root-mean-square deviation was less than 0.1%, and the average relative error was less than 0.04 in all of the experiments.

METHOD FOR THE SYNTHESIS OF HETEROCYCLIC HYDROGEN PHOSPHINE OXIDE

The present invention is related to a method for the synthesis of a heterocyclic hydrogen phosphine oxide, having the general formula (I), wherein: - R is a aliphatic or aromatic divalent group optionally comprising one or more heteroatoms and optionally comprising one or more substituents and - X and Y are independently selected from -O-, -C(O)O- and -NR'- wherein R' is a monovalent group optionally comprising one or more heteroatoms comprising the steps of: a) forming a reaction mixture by mixing a compound having the general formula HX-R-YH and tetraphosphorus hexaoxide; b) recovering the resulting compound comprising the heterocyclic hydrogen phosphine oxide.

Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one

On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.

PROCESS OF PREPARING CYCLIC PHOSPHONATE ESTER, CYCLIC PHOSPHONATE ESTER PREPARED THEREFROM AND INDUSTRIAL APPLICATIONS CONTAINING THE SAME

There is provided herein a process for preparing cyclic phosphonate ester comprising reacting a glycol with at least one of phosphonic acid and phosphinic acid in the presence of a solvent. There is also provided a flame retardant comprising the cyclic phosphonate ester and industrial applications containing a flame retardant effective amount of the cyclic phosphonate ester.