7774-74-5 Usage
Description
Thiophenethiol, also known as 2-thienyl mercaptan, is an organic compound with a distinctive chemical structure that features a thiophene ring and a mercapto group. It possesses a very unpleasant, burnt caramellic, and sulfuraceous odor, along with a similar flavor. This unique combination of properties makes it a versatile chemical with various applications across different industries.
Uses
Used in Chemical Synthesis:
Thiophenethiol is used as a key intermediate in the synthesis of various organic compounds, particularly those containing thiophene rings. Its reactivity and functional groups make it a valuable building block for the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Flavor and Fragrance Industry:
Due to its distinct burnt caramellic and sulfuraceous odor, Thiophenethiol is used as a flavoring agent and a fragrance ingredient in the food and cosmetics industries. It can be employed to create unique scents or enhance existing ones, adding depth and complexity to the final product.
Used in Analytical Chemistry:
Thiophenethiol's characteristic properties make it useful in analytical chemistry as a reagent or a derivatizing agent. It can be employed in techniques such as gas chromatography and mass spectrometry to improve the detection and analysis of various compounds.
Used in Material Science:
Thiophenethiol's ability to form self-assembled monolayers (SAMs) on gold and other metal surfaces makes it an important component in the development of sensors, electronic devices, and nanotechnology applications. Its use in material science allows for the creation of novel materials with tailored properties and functions.
Preparation
By heating sodium sulfosuccinate with phosphorous trichloride; also by reduction of thiophene-2-sulfonyl chloride.
Synthesis Reference(s)
Journal of the American Chemical Society, 75, p. 6316, 1953 DOI: 10.1021/ja01120a518
Check Digit Verification of cas no
The CAS Registry Mumber 7774-74-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,7,7 and 4 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 7774-74:
(6*7)+(5*7)+(4*7)+(3*4)+(2*7)+(1*4)=135
135 % 10 = 5
So 7774-74-5 is a valid CAS Registry Number.
InChI:InChI=1/C4H4S2/c5-4-2-1-3-6-4/h1-3,5H
7774-74-5Relevant articles and documents
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Voronkov et al.
, (1974)
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Preparation of oligo(thio-2,5-thienylenes)
Nakayama, Juzo,Katano, Naoki,Shimura, Yoshiaki,Sugihara, Yoshiaki,Ishii, Akihiko
, p. 7608 - 7610 (1996)
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Investigation of the aroma-active compounds formed in the maillard reaction between glutathione and reducing sugars
Lee, Sang Mi,Jo, Ye-Jin,Kim, Young-Suk
experimental part, p. 3116 - 3124 (2011/08/05)
Aroma-active compounds formed during the thermal reaction between glutathione (GSH) and reducing sugars were analyzed by gas chromatography-mass spectrometry (GC-MS) and GC-olfactometry (GC-O) with aroma extract dilution analysis (AEDA). Application of AEDA to glutathione Maillard reaction products (GSH MRPs) led to the identification of 19 aroma-active compounds in the thermal reaction of glutathione with glucose or fructose. In addition, the carbohydrate module labeling (CAMOLA) approach was also employed to elucidate the formation pathways for selected target sulfur aroma compounds, such as 5-methylthiophene-2-carbaldehyde and 3-methylthiophene-2-carbaldehyde, which have not been reported previously. The intact carbon skeleton of glucose via 3-deoxyhexosone is incorporated into 5-methylthiophene-2-carbaldehyde with the hydrogen sulfide of GSH. On the other hand, the formation of 3-methylthiophene2-carbaldehyde may occur via the recombination of a C-4 sugar fragment and mercaptoacetaldehyde.
A simple, fast and chemoselective method for the preparation of arylthiols
Bellale, Eknath V.,Chaudhari, Mahesh K.,Akamanchi, Krishnacharya G.
experimental part, p. 3211 - 3213 (2010/03/01)
An efficient and convenient method for the synthesis of arylthiols by reaction of sulfonyl chlorides with triphenylphosphine in toluene is reported.