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

Uses

4,4'-sulphonylbis(2,6-dibromophenol) is reactive flame retardant, used in epoxy resin, polycarbonate resin, polyester, phenolic resin, polysulfone, polyether sulfone, can also be used as additive of ABS. HIPS unsaturated polyesters, adhesives, coatings, etc., also used as the intermediate of organic synthesis. Characteristics are high efficient flame retardant, and strong heat resistance .

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

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

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.

COLOR DEVELOPING COMPOSITION CONTAINING MOLECULAR COMPOUND, AND RECORDING MATERIAL

Provided is a color-developing composition containing a molecular compound which has as a component compound a compound represented by formula (I) [wherein Y represents a C1-C12 hydrocarbon group which is chained or branched and saturated or unsaturated, or a C1-C8 hydrocarbon group which is chained or branched, saturated or unsaturated and has an ether or thioether bond; R1, R2, R3 and R4 each independently represent a C1-C6 alkyl group or C2-C6 alkenyl group; n, p, q and r each represents any integer of 0 to 4; and m represents any integer of 0 to 2]. Also provided is a recording material with a sufficient color-forming sensitivity, superior storage stability, and especially with an extremely little background fogging in a heat resistance test.