NP-MRD: Showing NP-Card for 1,1'-Oxybis[2,4-dibromobenzene] (NP0337586)

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Record Information

Version

2.0

Created at

2024-09-11 11:29:57 UTC

Updated at

2024-09-11 11:29:57 UTC

NP-MRD ID

NP0337586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,1'-Oxybis[2,4-dibromobenzene]

Description

1,1'-Oxybis[2,4-dibromobenzene], also known as PBDE 47 or 2,2',4,4'-tetrabromodiphenyl ether, 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. 1,1'-Oxybis[2,4-dibromobenzene] was first documented in 2011 (PMID: 21237513). 1,1'-Oxybis[2,4-dibromobenzene] is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217562D          

 17 18  0  0  0  0            999 V2000
   -1.2376    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4745   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0622   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2376   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0007   -0.3566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622   -1.0712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4745   -0.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0622    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2361    0.3580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8239    1.0712    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8253    1.0712    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2991   -0.3566    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2991   -0.3566    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
  8 13  1  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
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1

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

> <INCHI_KEY>
XYBSIYMGXVUVGY-UHFFFAOYSA-N

> <FORMULA>
C12H6Br4O

> <MOLECULAR_WEIGHT>
485.791

> <EXACT_MASS>
481.715215402

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
32.03758066988883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
6.37

> <JCHEM_LOGP>
6.5485435003333325

> <ALOGPS_LOGS>
-6.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.087832657574749

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
82.79000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.70e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.310   0.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.849   0.668   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.619  -0.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.849  -2.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310  -2.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.541  -0.666   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.001  -0.666   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.538  -0.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.307  -2.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.849  -2.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.619  -0.666   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.849   0.668   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.307   0.668   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.538   2.000   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0      -1.541   2.000   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0       6.158  -0.666   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0      -6.158  -0.666   0.000  0.00  0.00          Br+0
CONECT    1    2    6   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
CONECT   15    1                                                            
CONECT   16   11                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
PBDE 47	Kegg
BDE 47	Kegg
1,1'-Oxybis(2,4-dibromo-benzene	HMDB
1,1'-Oxybis(2,4-dibromobenzene)	HMDB
1,1'-Oxybis[2,4-dibromobenzene], 9ci	HMDB
2,2',4,4'-TetraBDE	HMDB
2,2',4,4'-Tetrabromodiphenyl ether	HMDB
2,2'4,4'-Tetrabromodiphenyl ether	HMDB
Dibromophenyl ether	HMDB
PBDE-47	HMDB
BDE-47	MeSH
2,2',4,4'-Tetrabromobiphenyl ether	MeSH
2,2,4,4-Tetrabromodiphenyl ether	MeSH
TBDP-Ether	MeSH
Tetrabrominated diphenyl ether 47	MeSH
2,2',4,4'-Brominated diphenyl ether	MeSH

Chemical Formula

C₁₂H₆Br₄O

Average Mass

485.7910 Da

Monoisotopic Mass

481.71522 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

BrC1=CC=C(OC2=CC=C(Br)C=C2Br)C(Br)=C1

InChI Identifier

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

InChI Key

XYBSIYMGXVUVGY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

organobromine compound (CHEBI:81584 )
aromatic ether (CHEBI:81584 )
PBDEs (C18205 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	6.37	ALOGPS
logP	6.55	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Basic)	-9.1	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	32.04 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

External Links

HMDB ID

HMDB0037547

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016629

KNApSAcK ID

Not Available

Chemspider ID

85876

KEGG Compound ID

C18205

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

95170

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gascon M, Vrijheid M, Martinez D, Forns J, Grimalt JO, Torrent M, Sunyer J: Effects of pre and postnatal exposure to low levels of polybromodiphenyl ethers on neurodevelopment and thyroid hormone levels at 4 years of age. Environ Int. 2011 Apr;37(3):605-11. doi: 10.1016/j.envint.2010.12.005. Epub 2011 Jan 14. [PubMed:21237513 ]

Showing NP-Card for 1,1'-Oxybis[2,4-dibromobenzene] (NP0337586)

MOL for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

3D MOL for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

3D SDF for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

3D-SDF for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

PDB for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

3D PDB for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

SMILES for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

INCHI for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

Structure for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])

3D Structure for NP0337586 (1,1'-Oxybis[2,4-dibromobenzene])