Benzyl Sulfide

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Benzyl Sulfide are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Benzyl Sulfide?

The molecule Benzyl Sulfide presents a molecular formula of C14H14S and its IUPAC name is benzyl sulfide.

Benzyl sulfide is a molecule with the chemical formula C6H5CH2SH. It is a colorless liquid with a characteristic odor of rotten cabbage. It is insoluble in water but soluble in most organic solvents..

Benzyl sulfide is produced by the action of hydrogen sulfide on benzyl chloride in the presence of a catalyst:.

C6H5CH2Cl + H2S → C6H5CH2SH + HCl.

It is also produced by the action of thiophenol on benzyl chloride:.

C6H5CH2Cl + C6H5SH → C6H5CH2SH + C6H5Cl.

Benzyl sulfide is used as a starting material for the synthesis of other organic compounds. For example, it can be converted to thiophenol:.

C6H5CH2SH + Cl2 → C6H5CH2SCl + HCl.

C6H5CH2SCl + Zn → C6H5CH2SH + ZnCl2.

It can also be used to make the insecticide fenitrothion:.

C6H5CH2SH + O2 → C6H5CH2SOH.

C6H5CH2SOH + (CH3)3CCO2H → (CH3)3CCOF + H2O.

3D structure

Cartesian coordinates

Geometry of Benzyl Sulfide in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Benzyl Sulfide LUFPJJNWMYZRQE-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Benzyl Sulfide

 

Molecule descriptors

 
IUPAC namebenzyl sulfide
InChI codeInChI=1S/CH2BrCl/c2-1-3/h1H2
InChI KeyLUFPJJNWMYZRQE-UHFFFAOYSA-N
SMILESS(Cc1ccccc1)Cc1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

Physico-Chemical properties

IUPAC namebenzyl sulfide
Molecular formulaC14H14S
Molecular weight214.326
Melting point (ºC)49
Boiling point (ºC)-
Density (g/cm3)-
Molar refractivity68.29
LogP4.1
Topological polar surface area-

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.