39635-79-5

Basic information

• Product Name: 4,4'-Sulphonylbis(2,6-dibromophenol)
• Synonyms: 4,4'-sulphonylbis(2,6-dibromophenol);3,3,5,5-TetrabromobisphenolS;3,3,5,5-TetrabromoBisphenol-S;4,4''-SULFONYLBIS[2,6-DIBROMO-PHENO,95%;3,3',5,5'-Tetrabromo-4,4'-dihydroxydiphenylsulfone;4,4'-Sulphonylbis(2,6-dibromophenol)(Tetrabromobisphenol S);Bis(4-hydroxy-3,5-dibromophenyl) sulfone
• CAS NO: 39635-79-5
• Molecular Formula: C₁₂H₆Br₄O₄S
• Molecular Weight: 565.85
• EINECS: 254-551-9
• Mol File: 39635-79-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 539.4 °C at 760 mmHg
• Flash Point: 280 °C
• Appearance: white powder
• Density: 2.363 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 4,4'-Sulphonylbis(2,6-dibromophenol)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Sulphonylbis(2,6-dibromophenol)(39635-79-5)
• EPA Substance Registry System: 4,4'-Sulphonylbis(2,6-dibromophenol)(39635-79-5)

Safety Data

• RIDADR: 3152
• HazardClass: 9
• PackingGroup: II
• Hazardous Substances Data: 39635-79-5(Hazardous Substances Data)

Usage

Description

4,4'-Sulphonylbis(2,6-dibromophenol) is a chemical compound known for its reactive flame retardant properties. It is characterized by its high efficiency in flame retardancy and strong heat resistance, making it a valuable additive in various industries.

Uses

Used in Plastics and Resin Industry:
4,4'-Sulphonylbis(2,6-dibromophenol) is used as a flame retardant additive for epoxy resin, polycarbonate resin, polyester, phenolic resin, polysulfone, and polyether sulfone. Its application reason is to enhance the fire safety of these materials by reducing their flammability and improving their resistance to heat.
Used in ABS and HIPS Industry:
In the production of ABS (Acrylonitrile Butadiene Styrene) and HIPS (High Impact Polystyrene), 4,4'-Sulphonylbis(2,6-dibromophenol) is used as an additive to improve the flame retardancy and heat resistance of these materials, ensuring they meet safety standards and perform well under high-temperature conditions.
Used in Unsaturated Polyesters Industry:
4,4'-Sulphonylbis(2,6-dibromophenol) is utilized as a flame retardant in unsaturated polyesters, contributing to the enhancement of their fire safety and thermal stability.
Used in Adhesives and Coatings Industry:
4,4'-Sulphonylbis(2,6-dibromophenol) is also employed as an additive in the formulation of adhesives and coatings, where it serves to improve the flame retardancy and heat resistance of these products, making them suitable for use in various applications that require fire safety.
Used in Organic Synthesis:
4,4'-Sulphonylbis(2,6-dibromophenol) is used as an intermediate in organic synthesis, where it can be further reacted to produce other valuable compounds for various applications.

Synthetic route

4,4'-sulfonediphenol (80-09-1) → 2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5)

Conditions	Yield
With dihydrogen peroxide; bromine In dichloromethane; 2-methyl-propan-1-ol; water at 25 - 37℃; for 7.58333h; Temperature;	99.5%
With bromine; acetic acid at 85℃; for 2h;	72%
With bromine; iron Bromination;	45.7%
With bromine; acetic acid at 85℃;
With bromine

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + 1-bromo-3-propanol (627-18-9) → 2,6-dibromo-4-((3,5-dibromo-4-(3-hydroxypropoxy)phenyl)sulfonyl)phenol

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	65%

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + allyl bromide (106-95-6) → 4-((4-(allyloxy)-3,5-dibromophenyl)sulfonyl)-2,6-dibromophenol (122438-83-9)

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃; for 3h;	64%

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + 2-bromoethanol (540-51-2) → 2,6-dibromo-4-[3,5-dibromo-4-(2-hydroxyethoxy)benzene-1-sulfonyl]phenol

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	56%

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + allyl bromide (106-95-6) → TBBP-S-dially ether (42757-54-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Alkylation; Heating;	54%

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + chloroacetic acid (79-11-8) → [2,6-dibromo-4-(3,5-dibromo-4-carboxymethoxy-benzenesulfonyl)-phenoxy]-acetic acid

Conditions	Yield
With sodium hydroxide for 4h; Heating;

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) → tetrabromobisphenol-S-bis-(2,3-dibromopropyl ether)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / K2CO3 / dimethylformamide / Heating 2: 97 percent / bromine / CCl4; CH2Cl2 / 0 °C View Scheme

2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) + 3-chloroprop-1-ene (107-05-1) → TBBP-S-dially ether (42757-54-0)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; sodium bromide In water
With cetyltrimethylammonim bromide; sodium bromide; sodium hydroxide In 2-methyl-propan-1-ol; water at 65℃; for 9h; Temperature;

piperazine (110-85-0) + methanol (67-56-1) + 2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) → C4H10N2*C12H6Br4O4S (1297592-22-3) + C9H20N4*C12H6Br4O4S (1297592-20-1)

Conditions	Yield
at 130℃; for 72h;

piperazine (110-85-0) + 2,2-bis(3,5-dibromo-4-hydroxyphenyl)sulfone (39635-79-5) → C4H10N2*C12H6Br4O4S (1297592-22-3)

Conditions	Yield
In methanol Grinding/kneading;

Upstream product

• 80-09-1 4,4'-sulfonediphenol 

Downstream Products

• 122438-83-9 4-((4-(allyloxy)-3,5-dibromophenyl)sulfonyl)-2,6-dibromophenol 
• 42757-54-0 TBBP-S-dially ether 
• 42757-55-1 tetrabromobisphenol-S-bis-(2,3-dibromopropyl ether) 
• 1297592-22-3 C₄H₁₀N₂*C₁₂H₆Br₄O₄S 

Relevant articles and documents

Rare case of a triple-stranded molecular braid in an organic cocrystal

We describe the use of two "bent" molecules, tetrabromobisphenol- S (2) and 1,3-bis(4-pyridyl)-propane (3), to build an interesting organic cocrystal [(C6H2OHBr2)2SO 2]?[(C5H4N)2(CH 2)3]?MeOH (4). In the molecular structure of cocrystal 4, the cocrystallizing components (coformers) 2 and 3 assemble into a 1:1 supramolecular adduct featuring unprecedented triple-stranded molecular entanglement, called a "molecular braid", via O-H...N interactions, which is the first example of such one-dimensional entanglement in the realm of organic cocrystals.

Simple and sensitive synchronous- fluorescence method for the determination of trace bisphenol s based on its inhibitory effect on the fluorescence quenching reaction of rhodamine B

An inhibitory kinetic fluorimetric method is reported for the determination of trace bisphenol S (BPS). The proposed method is based on the inhibitory effect of BPS on the fluorescence quenching of rhodamine B (RhB) caused by potassium bromate in a dilute phosphoric acid medium. Under the optimal conditions of the experiment, the detection limit for BPS was 0.021 mg/L, and the linear range of determination was from 0.035 mg/L to 0.750 mg/L. The relative standard deviations of 11 measurements for 0.20 mg/L and 0.40 mg/L BPS solutions were 2.74 % and 1.87 %, respectively. The method was successfully applied to the determination of bisphenol S derived from commercially available plastic film samples in hot water. A possible reaction mechanism of the inhibitory effect of BPS on the fluorescence quenching of RhB was proposed.

Organic complexes built by halogenated molecules: Unexpected in situ C-N bond formation in metal-free solvothermal conditions

Reactions of two halogenated derivatives of bis(4-hydroxyphenyl)sulphone (BPS, 1), tetrabromobisphenol-S (TBBPS, 2), and tetrachlorobisphenol-S (TCBPS, 3), with piperazine (PZ, 4), were investigated by means of the combinational usage of solvothermal and mechanochemical methods. The resultant organic complexes, [(C6H2OBr2)2SO 2]?[(C4H10N2) 2CH2] (5), [(C6H2OBr 2)2SO2]2?(C4H 12N2)2?3(CH3OH) (6), [(C 6H2OCl2)2SO2] ?[(C4H10N2)2CH2] (7), and [(C6H2OCl2)2SO 2]2?(C4H12N2) 2?3(CH3OH) (8), were fully characterized by single crystal and powder X-ray diffractions. In the cases of complexes 5 and 7 that were prepared from solvothermal conditions, a rare metal-free in situ ligand formation has been observed, in which the new organic molecule 1,2-bispiperazinylmethane was presumably originated from the double C-N coupling of two piperazines on a carbon atom coming from methanol. In addition, the relevant concomitants 6 and 8 were also isolated from the solutions of 5 and 7, respectively. Complexes 6 and 8 contain 1:1 starting molecules of 2/3 with 4 assembled into helical structures.