4090-51-1

Basic information

• Product Name: 2,2'-oxybis[5,5-dimethyl-1,3,2-dioxaphosphorinane] 2,2'-disulphide
• Synonyms: 2,2'-oxybis[5,5-dimethyl-1,3,2-dioxaphosphorinane] 2,2'-disulphide;1,3,2-Dioxaphosphorinane, 2,2-oxybis5,5-dimethyl-, 2,2-disulfide;SANDOFLAM;22OXYBIS55DIMETHYL132DIOXAPHOSPHORINANE22DISULFIDE;2,2'-Oxybis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane);Sandoflam 5060
• CAS NO: 4090-51-1
• Molecular Formula: C₁₀H₂₀O₅P₂S₂
• Molecular Weight: 346.340322
• EINECS: 223-829-1
• Mol File: 4090-51-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 233 °C
• Boiling Point: 342.6°Cat760mmHg
• Flash Point: 161°C
• Appearance: /
• Density: 1.35g/cm³
• Vapor Pressure: 0Pa at 25℃
• Water Solubility: 1.4mg/L at 20℃
• CAS DataBase Reference: 2,2'-oxybis[5,5-dimethyl-1,3,2-dioxaphosphorinane] 2,2'-disulphide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-oxybis[5,5-dimethyl-1,3,2-dioxaphosphorinane] 2,2'-disulphide(4090-51-1)
• EPA Substance Registry System: 2,2'-oxybis[5,5-dimethyl-1,3,2-dioxaphosphorinane] 2,2'-disulphide(4090-51-1)

Safety Data

• Hazardous Substances Data: 4090-51-1(Hazardous Substances Data)

Usage

Uses

Sandoflam 5060 is a flame retardant.

Flammability and Explosibility

Nonflammable

Synthetic route

2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-thione (873-98-3) → 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-disulfide (4090-51-1)

Conditions	Yield
With pyridine; water at 100℃; for 5h; Temperature; Reagent/catalyst;	90.2%

Bis<5,5-dimethyl-2-oxo-P(V)-1,3,2-dioxaphosphorinan-2-yl> disulphide (15995-44-5) → 5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl-oxide (15762-04-6) + 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-disulfide (4090-51-1)

Conditions	Yield
With triphenylphosphine In dichloromethane 1.) -70 deg C -> room temperature, 2.) room temperature, 30 min; Title compound not separated from byproducts;

3-Methylpyridine (108-99-6) + 2,2-Dimethyl-1,3-propanediol (126-30-7) → 5,5,5',5'-tetramethyl-2,2'-oxy-bis-[1,3,2]dioxaphosphinane 2,2'-disulfide (4090-51-1) + 3-methylpyridinium chloride (14401-92-4)

Conditions	Yield
With trichlorothiophosphine; water at 50 - 60℃; Product distribution / selectivity;

Upstream product

• 108-99-6 3-Methylpyridine 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 873-98-3 2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-thione 
• 15995-44-5 Bis<5,5-dimethyl-2-oxo-P(V)-1,3,2-dioxaphosphorinan-2-yl> disulphide 

Relevant articles and documents

Preparation method of special flame retardant for viscose fiber

The invention relates to the technical field of material chemical engineering, in particular to a preparation method of a special flame retardant for viscose fiber. The preparation method comprises the following steps: (1) putting thiophosphoryl chloride and neopentyl glycol into a reaction kettle at a mass ratio of 1:(4-8) for an acylation reaction to obtain a reaction liquid A, wherein the reaction temperature is 60-80 DEG C and the reaction time is 3-6h; (2) adding an acid binding agent and water into the reaction liquid A obtained in the step (1) for an esterification reaction, and adjusting the PH value of the liquid to 10 by adding a base after the reaction is finished to obtain a reaction liquid B, wherein the reaction temperature is 85-100 DEG C and the reaction time is 3-5h; and (3) performing suction filtration on the reaction liquid B obtained in the step (2), recrystallizing a filter cake obtained after suction filtration with anhydrous methanol to obtain a finished productof the special flame retardant for viscose fiber. The method provided by the invention has the advantages of short reaction time, low production cost, few three wastes, mild reaction conditions, no high-temperature and high-pressure reaction, and high safety. At the same time, the finished product prepared with the method has high purity and high total reaction yield.

Reaction of Three-coordinate Phosphorus Compounds with Organophosphorus Pseudohalogens. 3. Phosphonium and Phosphorane Intermediates in the Desulfurization and Dehalogenation of Bis(phosphinoyl) Disulfides. Influence of Lewis Acids on the Reaction Chemoselectivity

The reactions of bis(phosphinoyl) disulfides RR1P(O)S-S-P(O)RR1 1 with PIII compounds have been investigated and various mechanistic features have been elucidated by variable-temperature 31P NMR spectroscopy.These studies show that in most cases phosphonium intermediates 5 and 6 are involved.In cases were ligands on PIII increase the stability of the five coordinate structures phosphorane intermediates are observed.In the isomerization 5 -> 6, the mode of decomposition (desulfurization, deoxygenation or dealkylation) to give stable end products is influenced by electronic and steric factors.The presence of the Lewis acid BF3 influences considerably the stability of the transient species 5 and 6 and the chemoselectivity of the reaction.