NP-MRD: Showing NP-Card for 2,2',4,4',5,5'-Hexabromodiphenyl ether (NP0336596)

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Record Information

Version

2.0

Created at

2024-09-11 07:01:01 UTC

Updated at

2024-09-11 07:01:01 UTC

NP-MRD ID

NP0336596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2',4,4',5,5'-Hexabromodiphenyl ether

Description

2,2',4,4',5,5'-Hexabromodiphenyl ether, also known as BDE 153 or 1,1'-oxybis(2,4,5-tribromo-benzene, 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. 2,2',4,4',5,5'-Hexabromodiphenyl ether is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241214322D          

 19 20  0  0  0  0            999 V2000
   -1.2309    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2309   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583   -0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4678    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0583    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    0.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    1.4280    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.8281    1.4280    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2925    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2925    0.0000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -1.4280    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.4678   -1.4280    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 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 16  1  0  0  0  0
  4  5  1  0  0  0  0
  4 18  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
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  2  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
BrC1=CC(Br)=C(Br)C=C1OC1=CC(Br)=C(Br)C=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C12H4Br6O/c13-5-1-9(17)11(3-7(5)15)19-12-4-8(16)6(14)2-10(12)18/h1-4H

> <INCHI_KEY>
RZXIRSKYBISPGF-UHFFFAOYSA-N

> <FORMULA>
C12H4Br6O

> <MOLECULAR_WEIGHT>
643.584

> <EXACT_MASS>
637.536240632

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
38.56033776915717

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,2,4-tribromo-5-(2,4,5-tribromophenoxy)benzene

> <ALOGPS_LOGP>
6.96

> <JCHEM_LOGP>
8.086048751

> <ALOGPS_LOGS>
-6.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.149837776721133

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
98.03560000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.39e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2,4-tribromo-5-(2,4,5-tribromophenoxy)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      -2.298   1.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.837   1.337   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.607   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.837  -1.337   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.298  -1.337   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.533   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.007   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.546   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310  -1.337   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.842  -1.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.607   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.842   1.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   1.337   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0      -1.533   2.666   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0       1.546   2.666   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0      -6.146   0.000   0.000  0.00  0.00          Br+0
HETATM   17 Br   UNK     0       6.146   0.000   0.000  0.00  0.00          Br+0
HETATM   18 Br   UNK     0      -4.607  -2.666   0.000  0.00  0.00          Br+0
HETATM   19 Br   UNK     0       4.607  -2.666   0.000  0.00  0.00          Br+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   18                                                  
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   19                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12   15                                                  
CONECT   14    1                                                            
CONECT   15   13                                                            
CONECT   16    3                                                            
CONECT   17   11                                                            
CONECT   18    4                                                            
CONECT   19   10                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
BDE 153	Kegg
1,1'-Oxybis(2,4,5-tribromo-benzene	HMDB
1,1'-Oxybis(2,4,5-tribromobenzene)	HMDB
1,1'-Oxybis[2,4,5-tribromo]benzene, 9ci	HMDB
PBDE 153	HMDB
2,2',4,4',5,5'-Brominated diphenyl ether	HMDB
BDE-153	HMDB
Hexabrominated diphenyl ether 153	HMDB
2,2',4,4',5,5'-HexaBDE	MeSH
2,2',4,4',5,5'-Hexabrominated diphenyl ether	MeSH

Chemical Formula

C₁₂H₄Br₆O

Average Mass

643.5840 Da

Monoisotopic Mass

637.53624 Da

IUPAC Name

1,2,4-tribromo-5-(2,4,5-tribromophenoxy)benzene

Traditional Name

1,2,4-tribromo-5-(2,4,5-tribromophenoxy)benzene

CAS Registry Number

Not Available

SMILES

BrC1=CC(Br)=C(Br)C=C1OC1=CC(Br)=C(Br)C=C1Br

InChI Identifier

InChI=1S/C12H4Br6O/c13-5-1-9(17)11(3-7(5)15)19-12-4-8(16)6(14)2-10(12)18/h1-4H

InChI Key

RZXIRSKYBISPGF-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:81534 )
aromatic ether (CHEBI:81534 )

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	6.96	ALOGPS
logP	8.09	ChemAxon
logS	-6.9	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	98.04 m³·mol⁻¹	ChemAxon
Polarizability	38.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037525

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016606

KNApSAcK ID

Not Available

Chemspider ID

136695

KEGG Compound ID

C18137

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,2',4,4',5,5'-Hexabromodiphenyl ether (NP0336596)

MOL for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

3D MOL for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

3D SDF for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

3D-SDF for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

PDB for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

3D PDB for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

SMILES for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

INCHI for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

Structure for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)

3D Structure for NP0336596 (2,2',4,4',5,5'-Hexabromodiphenyl ether)