THIOANISOLE

PRODUCT IDENTIFICATION

CAS NO. 100-68-5

THIOANISOLE

EINECS NO. 202-878-2
FORMULA C6H5SCH3
MOL WT. 124.20
H.S. CODE

2930.90.2900

TOXICITY

Rat LD50 (Oral): 891mg/kg
SYNONYMS Methyl phenyl sulfide; (Methylthio)benzene;
Methyl phenyl sulphide; Sulfuro de fenilo y metilo; Sulfure de méthyle et de phényle;

SMILES

c1(ccccc1)SC

CLASSIFICATION

Thioether, Flavor and Fragrance agent, Sulfide

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to yellowish liquid
MELTING POINT -15 C
BOILING POINT 188 C
SPECIFIC GRAVITY 1.05
SOLUBILITY IN WATER 506 mg/l at 25 C
SOLVENT SOLUBILITY soluble in most common organic solvents
pH

 

VAPOR DENSITY

 

log Pow 2.74 (Octanol-water)
HENRY'S LAW 1.57E-04 (atm-m3/mole at 25 C)
OH RATE 1.36E-11 (cm3/molecule-sec at 25 C Atmospheric)
AUTOIGNITION

 

NFPA RATINGS  

REFRACTIVE INDEX

1.585 - 1.587
FLASH POINT 57 C
STABILITY Stable under ordinary conditions.

APPLICATIONS

Sulfoxide (R2SO) is any of various organic sulfur compounds having the group -SO (sulfinyl group) whereas sulfone (RSOOR) with the group -SO2 (sulfonyl group). They are derived from oxidation of sulfides ((R-S-R). Thioethers (organic sulfides) can be oxidized either to oxidation state -1 disulfides (R-S-S-R) or to oxidation state 0 sulfoxides (R-S(=O)-R) which can be further oxidized to the corresponding oxidation state +2 sulfones (R-S(=O)2-R) depending on the structure of the thioether. They are widely used as solvent of both extraction and reaction as well as intermediates for the synthesis of textile chemicals and pharmaceuticals and agrochemicals.

Thioether is the sulfur analog of the ether (R-O-R), which sulfur atom replaces the oxygen. Sulfur and oxygen belong to the same group in the periodic table share similar chemical properties. The functional groups of sulfur and oxygen share similar chemical bonds and properties. Ethers can only be oxidized to peroxides (R-O-O-R). But thioethers (R-S-R) can be oxidized either to disulfides (R-S-S-R) or to sulfoxides (R-S(=O)-R) which can be further oxidized to the corresponding sulfones (R-S(=O)2-R) depending on the structure of the thioether.

Dimethyl Sulfide is the simplest thioether. The compound is a clear, flammable liquid; insoluble in water; boiling point 37C; with a distinctive garlic-like odor. It is used as a flavor component to enhance corn-related flavors. It is used as a presulfiding agent in the refinery and petrochemical production. The catalysts in hydrocracking, hydrodenitrification, hydrodesulfurization and reforming processes are used in oxide forms, which must be converted to the active sulfide form during the start-up to prevent the reduction of the catalysts to their base material by heat. The sulfur sources include alkyl mercaptans (methyl mercaptan, ethyl mercaptan, butyl mercaptan), dimethyl sulfide, dimethyl sulfoxide, dimethyl disulfide, and tert-nolyl polysulfide. They are used to modify the reactivity of catalysts to use in high temperature process furnaces. Dimethyl Sulfide is used to prevent the coke deposits which acts as a thermal insulator in the tube as it accumulates in pyrolysis furnaces. It is also used in steel mill furnaces to control dusting. Dimethyl Sulfide is included as a component of dangerous gases to detect the leaks by smell.

Thioethers have applications in organic synthesis as solvents as well as reagents. Acyclic thioethers with oxidized branches such as alcohol, aldehyde, ester, acid, beta-ketone, phenol demonstrate centres of greater polarity and additional functional sites for the additional uses. Cyclic sulfides containing oxidized carbon atoms would involve extensive S-oxidation. Thioethers are involved in versatile in the synthesis of specific compound classes include agricultural chemical, property-enhancing additives, pharmacological drugs, chemical resistant polymers, detergents, and rubber antioxidants. Some examples of aliphatic and aromatic thioethers found in flavouring agents include:

Thioethers

CAS RN

Methyl sulfide

75-18-3

Methyl phenyl sulfide

100-68-5

Diethyl sulfide

352-93-2

Butyl sulfide

544-40-1

Allyl sulfide

592-88-1

Methyl ethyl sulfide

624-89-5

Benzyl methyl sulfide

766-92-7

Bis(methylthio)methane

1618-26-4

(1-Butenyl-1) methyl sulfide

32951-19-2

Thioethers with oxidized branches

CAS RN

o-(Methylthio)phenol

1073-29-

Ethyl 3-methylthiopropionate

133327-56-5

Methyl 3-methylthiopropionate

13532-18-8

1-(Methylthio)-2-butanone

13678-58-5

1-Methylthio-2-propanone

14109-72-9

3-(Methylthio)butanal

16630-52-7

3-(Methylthio)propyl acetate

16630-55-0

4-(Methylthio)butanol

20582-85-8

Ethyl 4-(methylthio)butyrate

22014-48-8

2-Methylthioacetaldehyde

23328-62-3

4-(Methylthio)-4-methyl-2-pentanone

23550-40-5

3-(Methylthio)

3268-49-3

4-(Methylthio)-2-butanone

34047-39-7

3-Methylthiohexanal

38433-74-8

Di(butan-3-one-1-yl) sulfide

40790-04-3

2-(Methylthio)

40878-72-6

4-(Methylthio)butanal

42919-64-2

Ethyl 2-(methylthio)acetate

4455-13-4

3-(Methylthio)propanol

505-10-2

3-(Methylthio)-1-hexanol

51755-66-9

3-(Methylthio)hexyl acetate

51755-85-2

4-(Methylthio)-2-oxobutanoic acid sodium salt

51828-97-8

Methyl 4-(methylthio)butyrate

53053-51-3

2,8-Dithianon-4-ene-4-carboxaldehyde

59902-01-1

2-(Methylthiomethyl)-3-phenyl-propenal

65887-08-3

Methylthiomethyl hexanoate

74758-91-1

Methylthiomethyl butyrate

74758-93-3

Cyclic Thioethers

CAS RN

1,4-Dithiane

505-29-3

Trithioacetone

828-26-2

4,5-Dihydro-3-(2H)-thiophenone

1003-04-9

2-Methyl-1,3-dithiolane

5616-51-3

2-Methyltetrahydrothiophen-3-one

13679-85-1

2,5-Dihydroxy-1,4-dithiane

40018-26-6

2,5-Dimethyl-2,5-dihydroxy-1,4-dithiane

55704-78-4

2-Methyl-4-propyl-1,3-oxathiane

67715-80-4

SALES SPECIFICATION

APPEARANCE

clear to yellowish liquid

ASSAY

99.0% min

WATER

0.5% max
TRANSPORTATION
PACKING

 

HAZARD CLASS 3 (Packing Group: III)
UN NO. 1993
SAFETY INFORMATION
Hazard Symbols: XN, Risk Phrases: , Safety Phrases: 24/25