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2, 4, 6-tribromophenol

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2, 4, 6-tribromophenol
2, 4, 6-tribromophenol

Chemical names and formulas

formula | Br_3C_6H_2OH Hill formula | C_6H_3Br_3O name | 2, 4, 6-tribromophenol mass fractions | Br (bromine) 72.5% | C (carbon) 21.8% | H (hydrogen) 0.914% | O (oxygen) 4.84%
formula | Br_3C_6H_2OH Hill formula | C_6H_3Br_3O name | 2, 4, 6-tribromophenol mass fractions | Br (bromine) 72.5% | C (carbon) 21.8% | H (hydrogen) 0.914% | O (oxygen) 4.84%

Lewis structure

Draw the Lewis structure of 2, 4, 6-tribromophenol. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds:  Count the total valence electrons of the bromine (n_Br, val = 7), carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 3 n_Br, val + 6 n_C, val + 3 n_H, val + n_O, val = 54 Calculate the number of electrons needed to completely fill the valence shells for bromine (n_Br, full = 8), carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 3 n_Br, full + 6 n_C, full + 3 n_H, full + n_O, full = 86 Subtracting these two numbers shows that 86 - 54 = 32 bonding electrons are needed. Each bond has two electrons, so in addition to the 13 bonds already present in the diagram add 3 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom:  Fill in the 3 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom ring is aromatic, so that the single and double bonds may be rearranged: Answer: |   |
Draw the Lewis structure of 2, 4, 6-tribromophenol. Start by drawing the overall structure of the molecule, ignoring potential double and triple bonds: Count the total valence electrons of the bromine (n_Br, val = 7), carbon (n_C, val = 4), hydrogen (n_H, val = 1), and oxygen (n_O, val = 6) atoms: 3 n_Br, val + 6 n_C, val + 3 n_H, val + n_O, val = 54 Calculate the number of electrons needed to completely fill the valence shells for bromine (n_Br, full = 8), carbon (n_C, full = 8), hydrogen (n_H, full = 2), and oxygen (n_O, full = 8): 3 n_Br, full + 6 n_C, full + 3 n_H, full + n_O, full = 86 Subtracting these two numbers shows that 86 - 54 = 32 bonding electrons are needed. Each bond has two electrons, so in addition to the 13 bonds already present in the diagram add 3 bonds. To minimize formal charge carbon wants 4 bonds. Identify the atoms that want additional bonds and the number of electrons remaining on each atom: Fill in the 3 bonds by pairing electrons between adjacent highlighted atoms. Note that the six atom ring is aromatic, so that the single and double bonds may be rearranged: Answer: | |

3D structure

3D structure
3D structure

Basic properties

molar mass | 330.8 g/mol phase | solid (at STP) melting point | 92 °C boiling point | 286 °C (measured at 99442 Pa)
molar mass | 330.8 g/mol phase | solid (at STP) melting point | 92 °C boiling point | 286 °C (measured at 99442 Pa)

Units

Hydrophobicity and permeability properties

experimental LogP hydrophobicity | 4.13 predicted LogP hydrophobicity | 4.2 predicted LogS | -3.78
experimental LogP hydrophobicity | 4.13 predicted LogP hydrophobicity | 4.2 predicted LogS | -3.78

Basic drug properties

approval status | experimental | small molecule
approval status | experimental | small molecule

Thermodynamic properties

molar heat of vaporization | 54.7 kJ/mol specific heat of vaporization | 0.1654 kJ/g (at STP)
molar heat of vaporization | 54.7 kJ/mol specific heat of vaporization | 0.1654 kJ/g (at STP)

Chemical identifiers

CAS number | 118-79-6 Beilstein number | 776920 PubChem CID number | 1483 PubChem SID number | 24848344 SMILES identifier | C1=C(C=C(C(=C1Br)O)Br)Br InChI identifier | InChI=1/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2, 10H InChI key | BSWWXRFVMJHFBN-UHFFFAOYAF RTECS number | SN1225000 MDL number | MFCD00002150
CAS number | 118-79-6 Beilstein number | 776920 PubChem CID number | 1483 PubChem SID number | 24848344 SMILES identifier | C1=C(C=C(C(=C1Br)O)Br)Br InChI identifier | InChI=1/C6H3Br3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2, 10H InChI key | BSWWXRFVMJHFBN-UHFFFAOYAF RTECS number | SN1225000 MDL number | MFCD00002150