4090-60-2

Basic information

• Product Name: 5 5-DIMETHYL-1 3 2-DIOXAPHOSPHORINAN-2-&
• Synonyms: 5 5-DIMETHYL-1 3 2-DIOXAPHOSPHORINAN-2-&;3,2-dioxaphosphorinane,5,5-dimethyl-2-oxide;5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide;5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINAN-2-O;1,3,2-Dioxaphosphorinane, 5,5-diMethyl-, 2-oxide;2,2-Dimethylpropane-1,3-diol cyclic phosphonate;Cyclic 2,2-dimethyltrimethylene phosphonate;Neopentylene phosphite
• CAS NO: 4090-60-2
• Molecular Formula: C₅H₁₁O₃P
• Molecular Weight: 150.112801
• EINECS: 223-832-8
• Product Categories: Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors
• Mol File: 4090-60-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 51-56 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: 229 °F
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.043mmHg at 25°C
• CAS DataBase Reference: 5 5-DIMETHYL-1 3 2-DIOXAPHOSPHORINAN-2-&(CAS DataBase Reference)
• NIST Chemistry Reference: 5 5-DIMETHYL-1 3 2-DIOXAPHOSPHORINAN-2-&(4090-60-2)
• EPA Substance Registry System: 5 5-DIMETHYL-1 3 2-DIOXAPHOSPHORINAN-2-&(4090-60-2)

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: 4090-60-2(Hazardous Substances Data)

Usage

Uses

Reactant for:Palladium(I) catalyzed addition of P(O)-H bondsHighly regioselective modified Pudovik addition reactionRadical reactions mediated by manganese(III) acetateStable cyclic DEPMPO derivatives as mechanistic markers of stereoselective hydroxyl radical adduct formation in biological systemsCopper-catalyzed aerobic oxidative dehydrogenative coupling reactionsBisphosphonates/phosphanamidates as anticancer agents

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 
• 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 
• 119713-39-2 5,5-dimethyl-2-oxo-2-(propa-1',2'-diene)-1,3,2-dioxaphosphorinane 
• 56465-64-6 2-(dimethylamino)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 5843-26-5 tetramethylphosphorodiamidous acid 
• 108-90-7 chlorobenzene 
• 4090-55-5 2-chloro-5,5-dimethyl[1,3,2]dioxaphosphinane 2-oxide 
• 3057-08-7 5,5-dimethyl-2-phenoxy-[1,3,2]dioxaphosphinane 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 
• 25236-29-7 5,5-dimethyl-2-H-1,3,2-dioxaphosphorinane 
• 25236-26-4 phosphinic acid 3-hydroxy-2,2-dimethyl-propyl ester 

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 
• 67-64-1 acetone 
• 108-95-2 phenol 
• 110907-85-2 5,5-dimethyl-2-trimethylsilyloxy-1,3,2-dioxaphosphorinane 
• 108483-22-3 (4-Chloro-phenyl)-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-methanol 
• 186968-55-8 (5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-m-tolyl-methanol 
• 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 articles and documents

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.

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.

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.