873-97-2

Usage

Class

Organophosphorus compound

Common Uses

+ Flame retardant in polymers, resins, and textiles
+ Stabilizer in PVC formulations
+ Production of fire-resistant adhesives, sealants, and coatings

Physical Properties

+ Colorless to pale yellow liquid
+ Characteristic odor

Toxicity

Relatively low

Other Properties

+ High thermal stability
+ Excellent flame-retardant properties

InChI:InChI=1/C6H13O3P/c1-6(2)4-8-10(3,7)9-5-6/h4-5H2,1-3H3

Upstream product

• 1007-57-4 2-ethoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 74-88-4 methyl iodide 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 1005-69-2 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 598-31-2 1-bromoacetone 
• 2428-06-0 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane 
• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 1141898-73-8 CF₃O₃S^(1-)*C₉H₂₂O₃PSi⁽¹⁺⁾ 

Downstream Products

• 126741-56-8 ((1E,3E)-3-Methyl-hexa-1,3-dienyl)-diphenyl-phosphane 
• 126741-55-7 ((1E,3Z)-3-Bromo-4-phenyl-buta-1,3-dienyl)-diphenyl-phosphane 
• 126741-54-6 (E)-(trans)-crotonic butadienylphosphine 
• 1067197-74-3 (E)-1-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphorinan-2-yl)-6-phenylhex-3-en-2-one 

Relevant academic research and scientific papers

RESORCINOL DERIVATIVES FOR THEIR COSMETIC USE

The invention relates to resorcinol derivatives of formula (I) and also the salts thereof, the solvates thereof and the optical and/or geometrical isomers thereof, including enantiomers and diastereoisomers, and the racemic mixtures thereof, alone or as a mixture. The invention also relates to a cosmetic process for depigmenting, lightening and/or bleaching keratin materials, especially the skin, using these compounds (I).

Non-Halogen Flameproof Resin Composition

A non-halogen flameproof resin composition is disclosed. The resin composition includes a base resin including (A) about 80 to about 99% by weight of an aromatic vinyl resin and (B) about 1 to about 20% by weight of a polyphenylene ether; and (C) about 0.5 to about 30 parts by weight of a cyclic t-butyl phosphonate, based on about 100 parts by weight of the base resin comprising (A) and (B).

Studies on the efficient generation of phosphorus-carbon bonds via a rearrangement of PIII esters catalysed by trimethylhalosilanes

Halotrimethylsilanes Me3SiX (X = Br, I) catalyse rearrangements of tricoordinate phosphorus esters R′R″P-OR into the corresponding phosphoryl systems R′R″P(O)R. This provides a simple and efficient route to a variety of structures containing phosphorus-carbon bonds, under mild conditions and with good yields. The reaction mechanism was investigated in detail by 31P NMR spectroscopy and independent synthesis of the reaction intermediates. It has been demonstrated that the primary products of this catalytic reaction are halogeno PIII structures R′R″PX and silyl ethers ROSiMe3 and that they subsequently react to give the corresponding phosphorus silyl esters - Me 3SiOPR′R″-and alkyl halides RX. At higher temperatures these intermediates then react to form R′R″P(P)R compounds. This paper also features the surprising observation that when esters Ph 2POR and halotrimethylsilanes Me3SiX (X = Br, I) are used in 2:1 ratio, phosphonium salts Ph2R2P+X - and trimethylsilyl diphenylphosphinate - Ph2P(O) OSiMe3 - are formed as the major products. Experimental evidence indicates that the mechanisms of both reactions are fundamentally different from that of the Michaelis-Arbuzov reaction. Me3SiCl is not reactive and this paper explains why.

Enantioselective radical conjugate addition to α′-phosphoric enones

(Chemical Equation Presented) Catalytic enantioselective radical conjugate addition reactions using α′-phosphoric enone templates have been studied. The C2-symmetric bisoxazoline-zinc(ll) complex proves to be effective for high enantioselectivi

2-Alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones α-Lithiated Carbanions. Synthesis, Stability, and Conformation

The preparation and a conformational study of lithiated 2-alkyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-ones (2) in THF-hexane are described.These anions are present as two rapidly interconverting species with the P=O bond either axial (2a) or equatorial (2e).They are thermally unstable, but can be stabilised by the presence of one equivalent of LiBr or of lithium di-isopropylamide.A 31P NMR study of the self condensation of the carbanions (2) showed that the phosphorus atom in the axial conformation (2a) is more electrophilic than in the equatorial one (2e).An X-ray structural study of 2,5,5-trimethyl-1,3,2-dioxaphosphorinan-2-one is described.

A GENERAL ONE-POT SYNTHESIS OF 1,3-BUTADIENYL PHOSPHANES

The condensation of a six membered cyclic phosphonyl-phosphanyl anion with an α,β-unsaturated aldehyde leads to the direct generation of a 1,3-butadienyl phosphane according to a Wittig-Horner type elimination.

Reaction of Cyclic Phosphites with Haloacetones

Treatment of various cyclic phosphites (1), e.g.,2-methoxy-1,3,2-dioxaphosphorinane (1a), 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (1b) and 2-methoxy-1,3,2-dioxaphosphorane (1c), with haloacetones (2) gave cyclic Arbuzov products (3), cyclic Perkow products (4), cyclic methylphosphonates (5), and acyclic products (6-8).Compound 1a gave all of the products (3a,4a,5a,6ag,7ag,8ag).However, cyclic phosphites with substituents in the ring (1b,1d) gave only the cyclic products (3-5).The five -membered ring phosphite (1c) yielded only the acyclic products (6cg, 7cg).Treatment of 1a with chloroacetone gave only the Perkow products (4a,7ah).Cyclic phosphite (1f)with 2-benzyloxy substituenet afforded simply the cyclic products (3a, 4a, 9).A mechanistic interpretation of these reactions is presented. Keywords---cyclic phosphite; haloacetone; cyclic acetonylphosphonate; cyclic enol phosphate; Arbuzov reaction; Perkow reaction

CARBANIONS PHOSPHONATES α-LITHIES: SYNTHESE, BASICITE COMPAREE ET STABILITE A L'AUTOCONDENSATION

Non stabilized α-lithio-α-substituted alkanephosphonates (RO)2P(O)CHR1Li(R1 = H, alkyl, Cl) are commonly used as phosphonoalkylating agents.The strength of the conjugated acids (RO)2P(O)CH2R1 is estimated by concurrent metallation.The data checked range from phenylacetylene to toluene in relation with the inductive electronic effects of R and R1.Most of the α-phosphonyl carbanions give stable dimers via thermal self-condensation which is steric (R) and electronic (R1) effects dependent.In addition preparative conditions for some phosphonate precursors are reexamined.

ALKYLIDENEDIPHOSPHONATES ET VINYLPHOSPHONATES: UNE DEMARCHE SYNTHETIQUE SELECTIVE PAR VOIE CARBANIONIQUE

Phosphonoalkylation of acylchloro-phosphates or -phosphinates in the presence of excess lithium diisopropylamide leads to direct generation of lithiated methylenediphosphonate anions.This stable type of anion can be either protonated in acidic medium to provide tetrasubstituted methylenediphosphonate or alkylated.When aliphatic or aromatic aldehydes are added spontaneous formation of vinylphosphonates is observed.This process is a simple and convenient route to diphosphonic as well as to vinylphosphonic compounds.