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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2023-03-30 20:45:18 UTC

Update Date

2023-03-30 20:45:18 UTC

HMDB ID

HMDB0341506

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,3’,4,4’-Tetrabromodiphenyl ether

Description

2,4-dibromophenyl 3,4-dibromophenyl ether, also known as BDE 66 or 2,3',4,4'-tetra-bde, belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group. A polybromodiphenyl ether that is diphenyl ether in which the hydrogens at the 2, 4, 3', and 4' positions have been replaced by bromines. 2,4-dibromophenyl 3,4-dibromophenyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1572011241503082D          

 17 18  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
  9 15  1  0  0  0  0
  4 16  1  0  0  0  0
  3 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341506

> <DATABASE_NAME>
hmdb

> <SMILES>
BrC1=CC(Br)=C(OC2=CC(Br)=C(Br)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H6Br4O/c13-7-1-4-12(11(16)5-7)17-8-2-3-9(14)10(15)6-8/h1-6H

> <INCHI_KEY>
DHUMTYRHKMCVAG-UHFFFAOYSA-N

> <FORMULA>
C12H6Br4O

> <MOLECULAR_WEIGHT>
485.795

> <EXACT_MASS>
481.715217

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
31.842935991521575

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2-dibromo-4-(2,4-dibromophenoxy)benzene

> <ALOGPS_LOGP>
6.37

> <JCHEM_LOGP>
6.5485435003333325

> <ALOGPS_LOGS>
-6.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7233904377506444

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
82.79

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dibromo-4-(2,4-dibromophenoxy)benzene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-NOV-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-NOV-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0      -6.668   2.310   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0      -4.001  -2.310   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0      -4.001  -5.390   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0      -1.334  -6.930   0.000  0.00  0.00          Br+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11                                                            
CONECT   15    9                                                            
CONECT   16    4                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3',4,4'-Tetra-bde	ChEBI
2,3',4,4'-Tetrabromodiphenyl ether	ChEBI
2,4,3',4`-tetrabromodiphenyl ether	ChEBI
2,4-Dibromo-1-(3,4-dibromophenoxy)benzene	ChEBI
BDE 66	ChEBI
BDE-66	ChEBI
PBDE 66	ChEBI
PBDE-66	ChEBI

Chemical Formula

C₁₂H₆Br₄O

Average Molecular Weight

485.795

Monoisotopic Molecular Weight

481.715217

IUPAC Name

1,2-dibromo-4-(2,4-dibromophenoxy)benzene

Traditional Name

1,2-dibromo-4-(2,4-dibromophenoxy)benzene

CAS Registry Number

Not Available

SMILES

BrC1=CC(Br)=C(OC2=CC(Br)=C(Br)C=C2)C=C1

InChI Identifier

InChI=1S/C12H6Br4O/c13-7-1-4-12(11(16)5-7)17-8-2-3-9(14)10(15)6-8/h1-6H

InChI Key

DHUMTYRHKMCVAG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bromodiphenyl ethers. Bromodiphenyl ethers are compounds that contain two benzene groups linked to each other via an ether bond, and where at least one ring is substituted with a bromo group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Bromodiphenyl ethers

Alternative Parents

Substituents

Bromodiphenyl ether
Diaryl ether
Phenoxy compound
Phenol ether
Halobenzene
Bromobenzene
Aryl halide
Aryl bromide
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	6.37	ALOGPS
logP	6.55	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.79 m³·mol⁻¹	ChemAxon
Polarizability	31.84 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 10V, Positive-QTOF	splash10-001i-0000900000-23b57fa9f430ce33802f	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 20V, Positive-QTOF	splash10-001i-0000900000-88adb3860eb53ffc3c61	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 40V, Positive-QTOF	splash10-0gc0-0891800000-0d772593b104249addab	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 10V, Negative-QTOF	splash10-001i-0000900000-2b3b13dd7679601c580f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 20V, Negative-QTOF	splash10-001i-0000900000-45c6e22ee29a8d1d5616	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3’,4,4’-Tetrabromodiphenyl ether 40V, Negative-QTOF	splash10-00rt-0094400000-2ccf730cbcc0e4e95166	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15509893

PDB ID

Not Available

ChEBI ID

138038

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2,3’,4,4’-Tetrabromodiphenyl ether (HMDB0341506)

MOL for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

3D MOL for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

3D SDF for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

3D-SDF for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

PDB for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

3D PDB for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

SMILES for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

INCHI for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

Structure for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

3D Structure for HMDB0341506 (2,3’,4,4’-Tetrabromodiphenyl ether)

Predicted Kovats Retention Indices

MS/MS Spectra