o-THIOANISIDINE

PRODUCT IDENTIFICATION

CAS NO. 2987-53-3

O-THIOANISIDINE

EINECS NO. 221-055-9
FORMULA CH3SC6H4NH2
MOL WT. 139.22
H.S. CODE

TOXICITY

SYNONYMS o-Methioaniline; 2-Methylmercaptoaniline; 2-Aminothioanisole;
2-(Methylthio)aniline; 2-(Metiltio)anilina; 2-(Méthylthio)aniline; 2-(Methylthio)benzenamine; 2-(Methylsulfanyl)aniline;

DERIVATION

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE yellowish liquid
MELTING POINT
BOILING POINT 234 C
SPECIFIC GRAVITY 1.11 - 1.12
SOLUBILITY IN WATER  
pH

VAPOR DENSITY
AUTOIGNITION

NFPA RATINGS

REFRACTIVE INDEX

FLASH POINT
STABILITY Stable under ordinary conditions.

APPLICATIONS

Ether is any of a number of organic compounds characterized by an oxygen atom joined with single bonds by two carbon atoms that are part of hydrocarbon groups. The general formula is R-O-R', where R and R' are alkyl or aromatic groups. Ethers are formed by the condensation of two alcohols by heating with sulfuric acid; the reaction is one of dehydration. Ethers can be prepared from alkyl halide reacted with metallic alkoxide (called Williamson synthesis). Ethers are similar to alcohols but are generally less dense, less soluble in water, and have lower boiling points. They are relatively unreactive, which makes them valuable solvents. But ethers will be cleaved at high temperatures by concentrated hydrogen halides. Ethers have relatively low boiling point compare to alkanes as they don't form hydrogen bonds each other. Ethers are more lipophilic than esters [R-C(=O)-O-R']or amides [RCO-NH2]. Ethers are widely used as solvents for various organic reactions because they are relatively the least reactive among common organic compounds except alkanes and fluorocarbons. The common reaction of ethers is cleavage of the C–O bond by strong acids either in linear chain or cyclic structure. Ethers in which oxygen is bonded to primary and secondary alkyl groups can form peroxide compounds in the presence of gaseous oxygen due to two unpaired electrons in oxygen. Ethers can act as Lewis bases in chemical reactions. Commonly, ethers are named simply in listing the alkyl groups in alphabetical order or alkane order such as ethyl methyl ether or methyl ethyl ether, which is methoxyethane in IUPAC nomenclature ( the formula of "alkoxyalkane" ). When ether is a parts of complex molecule or aromatic derivatives, it is described as an alkoxy substituent such as methoxybenzene ( trivial name is anisole). The methoxy prefix indicates the function methyl group joined by single bonds to an oxygen atom, with the general formula  -O-CH3. Cyclic ethers have ring structure where the oxygen has become part of the ring. The term of epoxide indicate three membered cyclic ether (also called oxirane) in which an oxygen atom is joined to each of two carbon atoms that are already bonded to each other; four membered cyclic ether is called oxetane; five membered cyclic ether, furan (or oxolane); six membered cyclic ether, pyran (also called oxane) respectively. Their unhindered oxygen atom carries two unshared pairs of electrons - a structure which favors the formation of coordination complexes and the solvation of cations. Cyclic ethers are used as important solvents, as chemical intermediate and as monomer for ring-opening polymerization. Crown Ether is a macrocyclic polyether whose structure contains hydrogen, carbon and oxygen atoms. Each oxygen atoms are confined between two carbon atoms and exhibits a conformation with a hole (accordingly called "crown").  Anisole is one of the simplest aromatic compound to which ether group is linked. But it is different with aromatic compounds like furan where the oxygen is a part of the ring.  Anisole, C6H5OCH3 (methyl phenyl ether), is a clear liquid that is soluble in ether and alcohol; insoluble in water; boiling point 155 C. Anisole and its derivatives are used as solvents and in perfumery. Anisole can be obtained from anise seed. Anisic acid, p-methoxybenzoic acid, is a part of cresol class antiseptic compounds. It is also used as an insect repellent and ovicide. Anisole, anisic acid, and their derivatives are also widely used in chemical reaction as intermediates to obtain target materials such as dyes, pharmaceuticals, perfumes, photoinitiators and agrochemicals. Anisidines, methoxyanilines, are used as intermediates for the synthesis of azo dyes, pigments and other chemical compounds.

Mercaptan: any of a class of organosulfur compounds is similar to the alcohol and phenol but containing a sulfur atom in place of the oxygen atom. Compounds containing -SH as the principal group directly attached to carbon are named 'thiols'. In substitutive nomenclature their names are formed by adding '-thiol' as a suffix to the name of the parent compound. When -SH is not the principal group, the prefix 'mercapto-' is placed before the name of the parent compound to denote an unsubstituted -SH group. 'thio'  is a chemical prefix indicates the replacement of an oxygen in an acid radical by sulfur with a negative valence of 2. Sulfur analog of alcohol is called thiol (or mercaptan), and ether analog is called sulfide.

The first chemical contrast of thiols and sulfides with alcohols and ethers is acidity which is important in organic reactions. Thiols are stronger acids than relevant alcohols and phenols. Thiolate conjugate bases are easily formed, and are excellent nucleophiles in SN2 reactions of alkyl halides and tosylates. The nucleophilicity of sulfur is much greater than that of oxygen, resulting in a number of useful electrophilic substitution reaction that are rare by oxygen. For example, sulfides form (with alkyl halides) ternary sulfonium salts, in the same alkylattion of tert-amines quaternary ammonium salts, whereas ternary oxonium salts are prepared only under extream conditions. Without exception, sulfoxides, sulfinate salts and sulfite anion also alkylate on sulfur, despite of the partial negative formal charge on oxygen and partial positive charge on sulfur. The second character is the oxidation states of sulfur. Oxygen has only two oxidation states, whereas sulfur covers from –2 to +6 as follows:

  • -2: Hydrogen Sulfide (H2S), sulfides, sulfonium ions
  • -1: disulfides
  • 0: S elemental, sulfoxides, sulfenic acids
  • +2: sulfones, sulfinic acids
  • +4: sulfonic acids, sulfite esters
  • +6: sulfate esters

One more sulfur compound's contrast with oxygen analog is in oxidation chemistry. Oxidation of sulfur compounds changes the oxidation state of sulfur rather than carbon, whereas, oxidation of  alcohols to aldehydes and ketones changes the oxidation state of carbon not oxygen. Thiols is oxidized to S-S single bond (disufide) which is stronger than O–O bond in peroxide. Disufide forms sulfenyl chlorides (with chlorine in mild condition) or sulfonic acids under harder condition. Oxidation of sulfides with hydrogen peroxide (or peracids) yields sulfoxides and then to sulfones. A certain sulfoxide compound such as dimethyl sulfoxide can be used as an effective oxygen source in the oxidation reaction of primary and secondary alcohols to aldehydes and ketones. DMSO easily is reduced to dimethyl sulfide and water is taken up by the electrophile. oxidation procedure is very mild and tolerates a variety of other functional groups, including those having oxidizable nitrogen and sulfur atoms.

SALES SPECIFICATION

APPEARANCE

yellowish liquid

ASSAY

98.0% min

WATER

0.5% max
TRANSPORTATION
PACKING

HAZARD CLASS 6.1 (Packing Group: III)
UN NO. 2810
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases: 36/37/38, Safety Phrases: 26-37/39