5-METHYL-1,3,4-THIADIAZOLE-2-THIOL

PRODUCT IDENTIFICATION
CAS NO. 29490-19-5

5-METHYL-1,3,4-THIADIAZOLE-2-THIOL

EINECS NO. 249-667-1
FORMULA C3H4N2S2
MOL WT. 132.21

H.S. CODE

 

TOXICITY

 
SYNONYMS 2-mercapto-5-methyl-1,3,4-thiadiazole; MMTD;
5-methyl-1,3,4-Thiadiazole-2(3H)-thione ; 2-Methyl-5-Mercapto-Thiadiazole-1,3,4; 甲基巯基噻二唑;
SMILES

 

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white powder
MELTING POINT 183 - 186
BOILING POINT

 

SPECIFIC GRAVITY

 

SOLUBILITY IN WATER  
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 

FLASH POINT

 

STABILITY

Stable under ordinary conditions

APPLICATIONS
Thiazole is a heterocyclic organic compound that has a five-member ring molecular structure, C3H3NS, containing three carbon atoms, one sulphur atom, and one nitrogen atom. It is a clear to yellowish liquid with a pyridine like odor. It is soluble in alcohol and ether and slightly soluble in water. It is parent material for numerous of chemical compounds including sulfur drugs, biocides, fungicides, dyes, chemical reaction accelerators. Thiazole dyes contain  the color radicals of =C=N- and -S-C= which decide colors to a compound . Azo dyes contain -N=N- radical. Thiazole dyes are useful in dying cotton. Benzothiazole is a thiazole fused to benzene ring. Benzothiazole derivatives are important in the industry of dyes, photographic chemicals, sulfa drugs and rubber. Thiabendazole, a substituted derivative of benzimidazole, is used as broad-spectrum anthelmintic and presevative. Some thiazole derivatives, belong to a class of cyclic sulfur organo products containing sulfur atom (S) and often oxygen (O), nitrogen (N), hydrogen (H), as well as other elements, can find application for making biological activitive agents such as antiviral, antibacterial, antifungal , antituberculous, antbody and antifungal agents. Thiazole and its derivatives are also used as thiol flavouring substances. Thiadiazole contains the five-membered diunsaturated ring structure composed of two nitrogen atoms and one sulfur atom. Thiadiazole and its derivatives are used for biological activities such as antiviral, antibacterial, antifungal and antituberculous. Benzothiadiazole, fused to benzene ring with two nitrogen atoms at 1,3 position and one sulfur atom at 2 position in the five-membered ring, is known as an inducer of systemic resistance to diseases rather than direct antifungal or antibacterial activities. 2-Mercapto-5-methyl-1,3,4-thiadiazole is used as an intermediate of Cephalosporin side chains. (Cefazolin, Cefamandole).

 

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

 white powder

ASSAY

98.0% min
MELTING POINT

183 - 186 C

MOISTURE

0.5% max
TRANSPORTATION
PACKING
25kgs in Drum
HAZARD CLASS  
UN NO.  
OTHER INFORMATION
Hazard Symbols: XI, Risk Phrases: 36/37/38, Safety Phrases: 24/25