Bisphenol A diglycidyl ether (HCID 2286)

Names & identifiers

Preferred name: Bisphenol A diglycidyl ether
IUPAC: 2-[[4-[2-[4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane
English name: BISPHENOL A DIGLYCIDYL ETHER RESIN
Molecular formula: C21H24O4
Molecular weight: 340.41

Names & synonyms

BISPHENOL A DIGLYCIDYL ETHER1675-54-3BADGE2,2-Bis(4-glycidyloxyphenyl)propaneEpoxide ADiglycidyl bisphenol AEpophen EL 5DGEBADGEBPADian diglycidyl etherDiglycidyl bisphenol A etherDiomethane diglycidyl ether

Show more names

Epon 828der332E-44DER 332 RESINEPON(R) RESIN 828Bisphenol-A epoxy resin E512,2'-(((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(Methylene))bis(oxirane)

Bpdgeepi-Rez 5102,2-Bis(4'-glycidyloxyphenyl)propaneDiglycidyl ether of bisphenol A2,2-Bis(p-glycidyloxyphenyl)propaneDiglycidyl diphenylolpropane ether4,4'-Isopropylidenediphenol diglycidyl etherBis(4-glycidyloxyphenyl)dimethylmethane

Database identifiers

CAS: 1675-54-3、25085-99-8
PubChem CID: 2286
DTXSID: DTXSID6024624
ChEMBL: CHEMBL258558
ChEBI: CHEBI:34578
UNII: F3XRM1NX4H
EC Number: 216-823-5
Nikkaji: J14.164J

Properties

Computed structural properties

XLogP: 4
Topological polar surface area: 43.5 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 8
Heavy atoms: 25
Formal charge: 0
Complexity: 384

Physicochemical properties

Melting point: 40 · 40-44 °C
Boiling point: 210 °C · 210 °C / 1mmHg
Density: 1 · 1,17 g/cm3
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 1.5735 · 1.5735
Flash point: 264 · 264-268°
storage temp.: 2 · Inert atmosphere,2-8°C
solubility: Soluble in DMSO (up to 30 mg/ml) or in Ethanol (up to 15 mg/ml)
form: viscous liquid
color: White
optical activity: 0.1375 ° · 0.1375°(C=1g/100ml MEOH)
Water Solubility: 100 % · Soluble in 100% ethanol, dimethyl sulfoxide (100 mM), dimethyl formamide, chloroform, methanol, and ethanol (50 mM). Insoluble in water.
BRN: 299026 · 299026
Henry's Law Constant: 2.2 · 2.2×105 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
Major Application: cleaning productscosmeticsfood and beveragespersonal care
InChI: 1S/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3
InChIKey: LCFVJGUPQDGYKZ-UHFFFAOYSA-N
SMILES: CC(C)(c1ccc(OCC2CO2)cc1)c3ccc(OCC4CO4)cc3
LogP: 3.242 at · 3.242 at 25℃
CAS DataBase Reference: 1675 · 1675-54-3(CAS DataBase Reference)
EWG's Food Scores: 6 · 6
FDA UNII: 3 XRM1NX4H · F3XRM1NX4H
IARC: 3 · 3 (Vol. 47, 71) 1999
EPA Substance Registry System: Bisphenol A diglycidyl ether (1675-54-3)
UNSPSC Code: 85151701 · 85151701
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H317-H319
Precautionary statements: 261 · P261-P264-P272-P280-P302+P352-P305+P351+P338
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi
Risk Statements: 36 · 36/38-43
Safety Statements: 28 · 28-37/39
WGK Germany: 1 · 1
RTECS: 3800000 · TX3800000
TSCA: TSCA listed
HS Code: 2910900090 · 2910900090
Storage Class: 10 · 10 - Combustible liquids
Hazard Classifications: 2 Eye · Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
Hazardous Substances Data: 1675 · 1675-54-3(Hazardous Substances Data)
Toxicity: 50 oral · LD50 oral in rabbit: 1980mg/kg
REACH Registrations: Active

Safety & regulation

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 1
tsca: TSCA listed
rtecs: TX3800000
hs_code: 2910900090
Toxicity: LD50 oral in rabbit: 1980mg/kg
risk_code: 36/38-43
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 28-37/39
Storage Class: 10 - Combustible liquids
Hazard statements: H315-H317-H319
REACH Registrations: Active
Hazard Classifications: Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
Precautionary statements: P261-P264-P272-P280-P302+P352-P305+P351+P338
Hazardous Substances Data: 1675-54-3(Hazardous Substances Data)

Chemistry & industry

Applications · 6 items

DescriptionMost epoxy resins result from polymerization of bisphenol A diglycidyl ether (BADGE). Delayed hypersensitivity is caused by the low-molecular-weight monomer BADGE (MW 340 g/mol), the dimer having a much lower sensitization power. This allergen caused contact dermatitis in six workers in a plant producing printed circuits boards made of copper sheets and fiberglass fabric impregnated with a brominated epoxy resin. It can also be contained in adhesives.

DescriptionPPARγ is a ligand-activated transcription factor involved in the regulation of lipid homeostasis and may function as a master regulator of adipogenesis. Ligands for PPARγ include antidiabetic drugs of the thiazolidinedione structural class, 15-deoxy-Δ12,14-prostaglandin J2 , and NSAIDS. BADGE is a synthetic compound used in the production of polycarbonate and industrial plastics. This compound was recently identified as an antagonist of PPARγ. BADGE binds to PPARγ with an apparent Kd of 100 μM and interferes with the ability of 3T3-L1 and 3T3-F442A cells to undergo hormone-mediated cell differentiation.

UsesBisphenol A derivative. A PPARγ antagonist; exhibits estrogenic activity; An inhibitor of PPARγ and suppressor of TNFα.

UsesIn the manufacture of epoxy resins and polycarbonates for food packaging.

UsesThe uniqueness of D.E.R. 332 epoxy resin is reflected in its maximum epoxide equivalent weight of 178. Because of its high purity and lack of polymer factions, samples embedded using D.E.R. 322 have uniform performance, exceptionally low viscosity and color; and improved elevated temperature properties.

General DescriptionOdorless yellowish brown liquid. Sinks in water.