Dibenzyl sulfide

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Dibenzyl sulfide
Dibenzyl sulfide.svg
Names
Preferred IUPAC name
1,1′-[Sulfanediylbis(methylene)]dibenzene
Other names
1,1′-[Thiobis(methylene)]dibenzene; Benzyl thioether; dibenzyl sulfide
Identifiers
3D model (JSmol)
1911157
ChEMBL
ChemSpider
ECHA InfoCard 100.007.913 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-703-6
PubChem CID
UNII
UN number 3335
  • InChI=1S/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2
    Key: LUFPJJNWMYZRQE-UHFFFAOYSA-N
  • C1=CC=C(C=C1)CSCC2=CC=CC=C2
Properties
C14H14S
Molar mass 214.33 g·mol−1
Melting point 49.5 °C (121.1 °F; 322.6 K)
Boiling point 322 °C (612 °F; 595 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dibenzyl sulfide is a symmetrical thioether. It contains two C6H5CH2- (benzyl) groups linked by a sulfide bridge. It is a colorless or white solid that is soluble in nonpolar solvents.

Contents

Crystallography

The crystal structure of the solid is of the orthorhombic system with space group Pbcn; number 60. The unit cell dimensions are a=13.991 Å b=11.3985 Å c 7.2081 Å. The molecules in the gas take the same form as in the solid with a C2 symmetry. [1]

Production

Benzyl sulfide is commercially manufactured by treating potassium sulfide with benzyl chloride, followed by distillation of the product. [2] It is also obtainable by desulfurization of dibenzyldisulfide with phosphine reagents. [3]

Related Research Articles

Thiol Any organic compound having a sulfanyl group

A thiol or thiol derivative is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The –SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol", where the first word deriving from Greek θεῖον (theion) meaning "sulfur".

Sulfide (organic)

An organic sulfide or thioether is a functional group in organosulfur chemistry with the connectivity C–S–C as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sulfide is similar to an ether except that it contains a sulfur atom in place of the oxygen. The grouping of oxygen and sulfur in the periodic table suggests that the chemical properties of ethers and sulfides are somewhat similar, though the extent to which this is true in practice varies depending on the application.

Benzyl alcohol Chemical compound

Benzyl alcohol is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

Benzyl group

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure C6H5CH2–. Benzyl features a benzene ring attached to a CH2 group.

Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfur is essential for life. Of the 20 common amino acids, two are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries.

Thioketone

Thioketones (also known as thiones or thiocarbonyls) are organosulfur compounds related to conventional ketones in which the oxygen has been replaced by a sulfur. Instead of a structure of R2C=O, thioketones have the structure R2C=S, which is reflected by the prefix "thio-" in the name of the functional group. Unhindered alkylthioketones typically tend to form polymers or rings.

Benzyl benzoate

Benzyl benzoate is an organic compound which is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.

Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.

Boron trichloride is the inorganic compound with the formula BCl3. This colorless gas is a reagent in organic synthesis. It is highly reactive toward water.

Indium(III) sulfide (Indium sesquisulfide, Indium sulfide (2:3), Indium (3+) sulfide) is the inorganic compound with the formula In2S3.

Benzylamine Chemical compound

Benzylamine is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). It consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. This colorless water-soluble liquid is a common precursor in organic chemistry and used in the industrial production of many pharmaceuticals. The hydrochloride salt was used to treat motion sickness on the Mercury-Atlas 6 mission in which NASA astronaut John Glenn became the first American to orbit the Earth.

Tetraphenylcyclopentadienone Chemical compound

Tetraphenylcyclopentadienone is an organic compound with the formula (C6H5)4C4CO. It is a dark purple to black crystalline solid that is soluble in organic solvents. It is an easily made building block for many organic and organometallic compounds.

Germanium disulfide Chemical compound

Germanium disulfide or Germanium(IV) sulfide is the inorganic compound with the formula GeS2. It is a white high-melting crystalline solid. The compound is a 3-dimensional polymer, in contrast to silicon disulfide, which is a one-dimensional polymer. The Ge-S distance is 2.19 Å.

Dibenzyl ketone Chemical compound

Dibenzyl ketone, or 1,3-diphenylacetone, is an organic compound composed of two benzyl groups attached to a central carbonyl group. This results in the central carbonyl carbon atom being electrophilic and the two adjacent carbon atoms slightly nucleophilic. For this reason, dibenzyl ketone is frequently used in an aldol condensation reaction with benzil and base to create tetraphenylcyclopentadienone. Vera Bogdanovskaia is credited with the classification of dibenzyl ketone.

Benzyl mercaptan Chemical compound

Benzyl mercaptan is an organosulfur compound with the formula C6H5CH2SH. It is a common laboratory alkylthiol that occurs in trace amounts naturally. It is a colorless, malodorous liquid.

Benzyl carbamate Chemical compound

Benzyl carbamate is the organic compound with the formula C6H5CH2OC(O)NH2. The compound can be viewed as the ester of carbamic acid (O=C(OH)(NH2)) and benzyl alcohol, although it is produced from benzyl chloroformate with ammonia. It is a white solid that is soluble in organic solvents and moderately soluble in water. Benzyl carbamate is used as a protected form of ammonia in the synthesis of primary amines. After N-alkylation, C6H5CH2OC(O) group is removable with Lewis acids.

Silver(I) hyponitrite is an ionic compound with formula Ag2N2O2 or (Ag+
)2[ON=NO]2−, containing monovalent silver cations and hyponitrite anions. It is a bright canary yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.

Sulfoxylic acid Chemical compound

Sulfoxylic acid (H2SO2) (also known as hyposulfurous acid or sulfur dihydroxide) is an unstable oxoacid of sulfur in an intermediate oxidation state between hydrogen sulfide and dithionous acid. It consists of two hydroxy groups attached to a sulfur atom. Sulfoxylic acid contains sulfur in an oxidation state of +2. Sulfur monoxide (SO) can be considered as a theoretical anhydride for sulfoxylic acid, but it is not actually known to react with water.

Tris(dimethylamino)phosphine Chemical compound

Tris(dimethylamino)phosphine is the organophosphorus compound with the formula P(NMe2)3 (Me = methyl). It is a colorless oil that is one of the most common aminophosphines. Its structure has been determined by X-ray crystallography.

Dibenzylaniline Chemical compound

Dibenzylaniline or N,N-Dibenzylaniline is a chemical compound consisting of aniline with two benzyl groups as substituents on the nitrogen.

References

  1. Hansson, Christian (19 May 2006). "Dibenzyl sulfide at 150 K". Acta Crystallographica Section E. 62 (6): o2377–o2379. doi:10.1107/S1600536806017491.
  2. Lewis, R.J. Sr, ed. (1993). Hawley's Condensed Chemical Dictionary (12 ed.). New York, NY: Van Nostrand Rheinhold Co. p. 137.
  3. Harpp, David N.; Smith, Roger A. (1978). "Sulfide Synthesis: Benzyl Sulfide". Org. Synth. 58: 138. doi:10.15227/orgsyn.058.0138.