NP-MRD: Showing NP-Card for 2,4-Dibromo-1-(4-bromophenoxy)benzene (NP0337247)

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Record Information

Version

2.0

Created at

2024-09-11 10:00:37 UTC

Updated at

2024-09-11 10:00:38 UTC

NP-MRD ID

NP0337247

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4-Dibromo-1-(4-bromophenoxy)benzene

Description

2,4-Dibromo-1-(4-bromophenoxy)benzene, also known as BDE-28 or 2,4,4'-tribrominated diphenyl 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. 2,4-Dibromo-1-(4-bromophenoxy)benzene is an extremely weak basic (essentially neutral) compound (based on its pKa). It was first documented in 2012 (PMID: 22266365). A polybromodiphenyl ether that is diphenyl ether in which the hydrogens at the 2, 4, and 4' positions have been replaced by bromines (PMID: 24191540) (PMID: 24191731) (PMID: 26743650) (PMID: 27573363).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216492D          

 16 17  0  0  0  0            999 V2000
   -1.2310    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4680   -0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0556   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2310   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213   -0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0035   -0.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282   -0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2378   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584   -1.0687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4680   -0.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0584    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2378    0.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8282    1.0687    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.3526    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2927   -0.3526    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
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 15  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>
NP0337247

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H7Br3O/c13-8-1-4-10(5-2-8)16-12-6-3-9(14)7-11(12)15/h1-7H

> <INCHI_KEY>
UPNBETHEXPIWQX-UHFFFAOYSA-N

> <FORMULA>
C12H7Br3O

> <MOLECULAR_WEIGHT>
406.895

> <EXACT_MASS>
403.804702787

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
28.705757850841735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.84

> <JCHEM_LOGP>
5.779790875

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-8.900888750445457

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
75.16720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,4'-tribromodiphenyl ether

> <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   0.679   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.837   0.679   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.607  -0.658   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.837  -1.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.298  -1.995   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.533  -0.658   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.007  -0.658   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.546  -0.658   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.311  -1.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.842  -1.995   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.607  -0.658   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.842   0.679   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.311   0.679   0.000  0.00  0.00           C+0
HETATM   14 Br   UNK     0       1.546   1.995   0.000  0.00  0.00          Br+0
HETATM   15 Br   UNK     0      -6.146  -0.658   0.000  0.00  0.00          Br+0
HETATM   16 Br   UNK     0       6.146  -0.658   0.000  0.00  0.00          Br+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
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    3                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,4,4'-TriBDE	ChEBI
2,4,4'-Tribrominated diphenyl ether	ChEBI
2,4,4'-Tribromodiphenyl ether	ChEBI
BDE-28	ChEBI
BDE28	ChEBI
PBDE 28	ChEBI
PBDE-28	ChEBI
Tribromodiphenyl ether 28	ChEBI
244'-Tribromodiphenylether	HMDB
2,4-Dibromo-1-(4-bromophenoxy)benzene, 9ci	HMDB
BDE 28	HMDB
2,2',4-Tribromodiphenyl ether	HMDB
2,4-Dibromo-1-(4-bromophenoxy)benzene	ChEBI

Chemical Formula

C₁₂H₇Br₃O

Average Mass

406.8950 Da

Monoisotopic Mass

403.80470 Da

IUPAC Name

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

Traditional Name

2,4,4'-tribromodiphenyl ether

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H7Br3O/c13-8-1-4-10(5-2-8)16-12-6-3-9(14)7-11(12)15/h1-7H

InChI Key

UPNBETHEXPIWQX-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

Not Available

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	5.84	ALOGPS
logP	5.78	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-8.9	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	75.17 m³·mol⁻¹	ChemAxon
Polarizability	28.71 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

HMDB0037545

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016627

KNApSAcK ID

Not Available

Chemspider ID

10239063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12110098

PDB ID

Not Available

ChEBI ID

138036

Good Scents ID

Not Available

References

General References

Liu W, Cheng F, Li W, Xing B, Tao S: Desorption behaviors of BDE-28 and BDE-47 from natural soils with different organic carbon contents. Environ Pollut. 2012 Apr;163:235-42. doi: 10.1016/j.envpol.2011.12.043. Epub 2012 Jan 20. [PubMed:22266365 ]
Wang F, Ge W, Chai C, Meng XX: [Effect of nitrogen and phosphorus concentrations on the adsorption of BDE28 and BDE47 by Prorocentrum donghaiense dominant population]. Huan Jing Ke Xue. 2013 Aug;34(8):2992-3001. [PubMed:24191540 ]
Yu M, Liu J, Wang T, Sun J, Liu R, Jiang G: Metabolites of 2,4,4'-tribrominated diphenyl ether (BDE-28) in pumpkin after in vivo and in vitro exposure. Environ Sci Technol. 2013;47(23):13494-501. doi: 10.1021/es404144p. Epub 2013 Nov 18. [PubMed:24191731 ]
Huang H, Wang S, Lv J, Xu X, Zhang S: Influences of artificial root exudate components on the behaviors of BDE-28 and BDE-47 in soils: desorption, availability, and biodegradation. Environ Sci Pollut Res Int. 2016 Apr;23(8):7702-11. doi: 10.1007/s11356-015-6025-y. Epub 2016 Jan 8. [PubMed:26743650 ]
Kang Y, Pan W, Liang S, Zeng L, Zhang Q, Luo J, Guo X: In vitro digestion and absorption of BDE-28, -47, -99 and -153 in indoor dust and its implication in risk assessment. Ecotoxicol Environ Saf. 2016 Dec;134P1:11-16. doi: 10.1016/j.ecoenv.2016.08.017. Epub 2016 Aug 27. [PubMed:27573363 ]

Showing NP-Card for 2,4-Dibromo-1-(4-bromophenoxy)benzene (NP0337247)

MOL for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

3D MOL for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

3D SDF for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

3D-SDF for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

PDB for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

3D PDB for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

SMILES for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

INCHI for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

Structure for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)

3D Structure for NP0337247 (2,4-Dibromo-1-(4-bromophenoxy)benzene)