Tetrabromobisphenol A diglycidyl ether

Tetrabromobisphenol A diglycidyl ether is an epoxy resin consisting of tetrabromobisphenol A with ether linkages to two epichlorohydrin groups. An alternative structural comparison is as brominated form of bisphenol A diglycidyl ether. It is a brominated aromatic chemical used principally for giving flame retardant properties to materials.^[1] It is TSCA and REACH registered and has the molecular formula C₂₁H₂₀Br₄O₄. The IUPAC name is 2-{[2,6-dibromo-4-(2-{3,5-dibromo-4-[(oxiran-2-yl)methoxy]phenyl}propan-2-yl)phenoxy]methyl}oxirane.^[2][3]

Tetrabromobisphenol A diglycidyl ether

Names
IUPAC name 2-[[2,6-dibromo-4-[2-[3,5-dibromo-4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane
Identifiers
CAS Number	3072-84-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2392655
ChemSpider	56055
EC Number	221-346-0
PubChem CID	62250
CompTox Dashboard (EPA)	DTXSID0052700
InChI InChI=1S/C21H20Br4O4/c1-21(2,11-3-15(22)19(16(23)4-11)28-9-13-7-26-13)12-5-17(24)20(18(25)6-12)29-10-14-8-27-14/h3-6,13-14H,7-10H2,1-2H3 Key: ZJRAAAWYHORFHN-UHFFFAOYSA-N
SMILES CC(C)(C1=CC(=C(C(=C1)Br)OCC2CO2)Br)C3=CC(=C(C(=C3)Br)OCC4CO4)Br
Properties
Chemical formula	C21H20Br4O4
Molar mass	656.003 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

A method of synthesis is to take tetrabromobisphenol A and react with epichlorohydrin using a base to form the halohydrin.^[4] This species is then further reacted with sodium hydroxide to form the diglycidyl ether.^[5] Higher molecular weight epoxy resins with bromine atoms along the chain maybe synthesized by reacting standard epoxy resin with tetrabromobisphenol A in a technique called advancement.^[6]

Uses

Its primary use is as a flame retardant in various materials including composites.^[7][8] It finds extensive use in electronic applications including printed circuit boards and general packaging for electronic materials.^[9][10][11]

Toxicity

The toxicity has been studied extensively, and even dusts containing the material have been studied for safer reuse and recovery.^[12] The material and its analogs have likewise had their toxicological properties studied.^[13] It is used as a control in studies evaluating the use of non-halogenated flame retardants.^[14]

Further reading

• Bruins, Paul F. (1968). Epoxy resin technology. New York: Interscience Publishers. ISBN 0-470-11390-1. OCLC 182890.
• Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ: Elsevier Science. ISBN 978-0-8155-1708-5. OCLC 915134542.
• Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.