1005-69-2

Basic information

• Product Name: 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane
• Synonyms: 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane
• CAS NO: 1005-69-2
• Molecular Formula: C₆H₁₃O₃P
• Molecular Weight: 164.139381
• EINECS: 213-739-0
• Mol File: 1005-69-2.mol

Chemical Properties

• Boiling Point: 140.7°Cat760mmHg
• Flash Point: 39.2°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 7.58mmHg at 25°C
• CAS DataBase Reference: 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane(1005-69-2)
• EPA Substance Registry System: 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane(1005-69-2)

Safety Data

• Hazardous Substances Data: 1005-69-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane is utilized as a solvent in organic synthesis for its capacity to dissolve a wide range of organic compounds, facilitating the progress of various chemical reactions.
Used in Pharmaceutical and Agrochemical Industries:
In the pharmaceutical and agrochemical sectors, 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane is employed as a reagent in chemical reactions, contributing to the development of new drugs and agrochemical products.
Used in Chemical Reactions:
2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane is used as a reagent in various chemical reactions, playing a crucial role in the synthesis of different compounds.
Safety Considerations:
It is imperative to handle 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane with caution due to its potential harmful effects if ingested or inhaled, and its ability to cause skin irritation upon contact. Proper safety measures should be implemented during its use to mitigate these risks.

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

Upstream product

• 67-56-1 methanol 
• 2428-06-0 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane 
• 21458-75-3 2-diethylamino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 3279-26-3 methyl dichlorophosphite 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 21458-74-2 1-fluoro-4,4-dimethyl-1-phospha-2,6-dioxacyclohexane 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 111830-18-3 5,5-dimethyl-2-(N-ethyl-N-phenyl)amino-1,3,2-dioxaphosphorinane 
• 139230-79-8 2-(1-ethyl-1,2-dihydropyridin-2-ylideneimino)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 139230-78-7 2-(N-ethyl-2-pyridylamino)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 139230-75-4 2-(2-pyridineamino)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 83444-09-1 2-(imidazol-1-yl)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 135474-14-5 2-(3,5-Dimethylpyrazol-1-yl)-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 121-45-9 phosphorous acid trimethyl ester 

Downstream Products

• 15761-95-2 2-Oxo-2-triphenylmethyl-5,5-dimethyl-1,3,2-dioxaphosphorinan 
• 15761-96-3 2-benzyl-5,5-dimethyl-1,3,2-dioxaphosphorinan-2-one 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 1005-96-5 2-methoxy-5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide 
• 102969-01-7 2-methoxy-2-N-phenylimino-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 873-97-2 2,5,5-trimethyl-1,3,2-dioxaphosphorinan-2-one 
• 116944-17-3 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane 
• 111011-80-4 2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane 
• 350589-61-6 2-((E)-1-Methoxy-3-phenyl-allyl)-5,5-dimethyl-[1,3,2]dioxaphosphinane 2-oxide 
• 111495-28-4 (R)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 
• 111495-26-2 (S)-5-(5,5-Dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid 
• 115578-90-0 (E)-2,2-dimethyl-1,3-propanediyl α-acetyl-2,3-dichlorostyrylphosphonate 
• 115578-86-4 (E)-2,2-dimethyl-1,3-propanediyl α-acetyl-3-nitrostyrylphosphonate 
• 102097-81-4 methyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate 

Relevant articles and documents

Photoinduced Cyclization of (o-Alkylbenzoyl)phosphonates to Benzocyclobutenols

(o-Alkylbenzoyl)phosphonates readily cyclize to highly strained benzocyclobutenols simply upon irradiation with UV light. The remarkable efficiency is ascribed to the electron-accepting character of the phosphonate substituent, which facilitates thermal ring closing of the o-quinodimethane intermediate and suppresses reversion to the starting carbonyl compound.

Synthesis and Utility of α-Methoxy Phosphonates with a 1,3,2-Dioxaphosphorinane Ring

Synthesis of several α-methoxy phosphonates with the phosphorus as a part of 1,3,2-dioxaphosphorinane ring by the simple reaction of (OCH 2CMe2CH2O)PCl with acetals is described. Analogous methoxy phosphonates using (±) (C20H 12O2)PCl were also synthesized using the same route. Utility of these phosphonates in the synthesis of vinyl ethers via the Horner-Wadsworth-Emmons [HWE] reaction is demonstrated.

Chemiluminescence in autoxidation of phosphonate carbanions. Phospha-1,2-dioxetanes as the most likely high-energy intermediates

Autoxidation of the phosphonate carbanions derived from 9-phosphono-10-hydroacridanes provided chemiluminescence ascribed to the excited acridone anion. The intramolecular CIEEL (chemically initiated electron exchange luminescence) mechanism can be applied to this chemiluminescence because of the much higher emission efficiency compared to that of 9-phosphono-10-methylacridanes. The effect of the phosphonate substituents on the emission efficiency and especially on the rates of the chemiluminescence decay can be interpreted to originate from the valence deviation of the phosphorus atoms, which is connected with the substituent effect on the geometrical selectivity in the olefination reaction of the phosphonate carbanions. The enhanced chemiluminescence in the presence of the fluorophores was also detected in autoxidation of the carbanions of diethyl diphenylmethylphosphonate and fluorenylphosphonate. Although the evidence is circumstantial, these results strongly support the belief that phospha-1,2-dioxetane is the most likely high-energy intermediate generating the excited molecules.

Catalytic activity of amine hydrochlorides in alcoholysis of 2-N-ethylaniline-5,5-dimethyl-1,3,2-dioxaphosphorinane

The effect of acid-base properties of amine hydrochlorides on their catalytic activity has been studied in methanolysis of 2-N-ethylaniline-5,5-dimethyl-1,3,2-dioxaphosphorinane.Analysis of the Broensted correlation indicates general acid catalysis of phosphorylation.The nature of the alcoholysis of P(III) amides in the presence of amine hydrochlorides is discussed in terms of the general theory of acid catalysis.

SYNTHESIS AND FEATURES OF CHEMICAL BEHAVIOR OF P(III)-PHOSPHORYLATED 2-AMINOPYRIDINES AND THEIR DERIVATIVES

A series of derivatives of 2-aminopyridine, 2-(ethylamino)pyridine, and 1-ethyl-2-imino-1,2-dihydropyridine formed with diisopropylphosphinous esters were obtained.The structure of the compounds was studied. (2-Pyridylamino)diisopropylphosphine was alkylated with triethyloxonium tetrafluoroborate to a quasiphosphonium salt and was protonated with hydrogen chloride at the endocyclic nitrogen atom to give a pyridinium salt.Protonation with fluoroboric acid results in a complex mixture of three products.The methanolysis of P(III)-phosphorylated 2-aminopyridines and their derivatives was studied.These investigations demonstrated that amides capable of prototropic transformations exhibit markedly enhanced phosphorylating activity.

COMPARISON OF THE PHOSPHORYLATING POWER OF 2-(N-AZOLYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANES

The methanolysis of phosphorous azolides was studied. Their reactivity as well as the effect of the solvent and the additives of amine and azole hydrochlorides on the rate of the reaction were discussed.

Synthesis of 1,4-dihydropyridine-5-phosphonates and their calcium-antagonistic and antihypertensive activities

The effect of the 3-carboxylic-ester variation in 2,2-dimethyltrimethylene 3-alkoxycarbonyl-4-aryl-1,4-dihydro-2,6-dimethyl-5-pyridinephosphonate s (1) was investigated with relation to the calcium-antagonistic and antihypertensive activities: the analogs containing the alkyl groups of not more than 12 carbons and an amino functionality in the carboxylic-ester moiety were synthesized to be examined for biological activities. Among them, 2-[benzyl(phenyl)amino]-ethyl 5-(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-di methyl-4-(3-nitrophenyl)-3-pyridine-carboxylate hydrochloride ethanol (NZ-105) showed particularly beneficial activities and was selected for further pharmacological studies and clinical development. Some aspects of the structure-activity relationships and solid-state structure of NZ-105 by X-ray crystallographic analysis were described.