10059-13-9

Basic information

• Product Name: 2-methylundecane-2-thiol
• Synonyms: 2-methylundecane-2-thiol;1,1-Dimethyldecane-1-thiol;2-Methyl-2-undecanethiol;2-Nonyl-2-propanethiol;Einecs 233-191-6
• CAS NO: 10059-13-9
• Molecular Formula: C₁₂H₂₆S
• Molecular Weight: 202.39984
• EINECS: 233-191-6
• Mol File: 10059-13-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: -10.8°C (estimate)
• Boiling Point: 270.55°C (estimate)
• Flash Point: 93.9°C
• Appearance: /
• Density: 0.8429 (estimate)
• Vapor Pressure: 0.0234mmHg at 25°C
• Refractive Index: 1.4503 (estimate)
• PKA: 11.38±0.10(Predicted)
• CAS DataBase Reference: 2-methylundecane-2-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methylundecane-2-thiol(10059-13-9)
• EPA Substance Registry System: 2-methylundecane-2-thiol(10059-13-9)

Safety Data

• Hazardous Substances Data: 10059-13-9(Hazardous Substances Data)

Usage

General Description

2-methylundecane-2-thiol is a chemical compound with the molecular formula C12H26S. It is a sulfur-containing compound and belongs to the class of organic compounds known as thioethers. This chemical is used in various industrial applications, including as a flavoring agent in the food and beverage industry, and as an odorant in the gas industry to give a distinctive smell to odorless gases, such as natural gas. Additionally, it is also used in the production of perfumes and fragrances due to its strong, unpleasant odor, which can serve as a masking agent for other odors.

InChI:InChI=1/C12H26S/c1-4-5-6-7-8-9-10-11-12(2,3)13/h13H,4-11H2,1-3H3

Upstream product

• 18516-37-5 2-methyl-undec-1-ene 
• 7783-06-4 hydrogen sulfide 

Relevant articles and documents

Hydropersulfides: H-Atom Transfer Agents Par Excellence

Hydropersulfides (RSSH) are formed endogenously via the reaction of the gaseous biotransmitter hydrogen sulfide (H2S) and disulfides (RSSR) and/or sulfenic acids (RSOH). RSSH have been investigated for their ability to store H2S in vivo and as a line of defense against oxidative stress, from which it is clear that RSSH are much more reactive to two-electron oxidants than thiols. Herein we describe the results of our investigations into the H-atom transfer chemistry of RSSH, contrasting it with the well-known H-atom transfer chemistry of thiols. In fact, RSSH are excellent H-atom donors to alkyl (k ～ 5 × 108 M-1 s-1), alkoxyl (k ～ 1 × 109 M-1 s-1), peroxyl (k ～ 2 × 106 M-1 s-1), and thiyl (k > 1 × 1010 M-1 s-1) radicals, besting thiols by as little as 1 order and as much as 4 orders of magnitude. The inherently high reactivity of RSSH to H-atom transfer is based largely on thermodynamic factors; the weak RSS-H bond dissociation enthalpy (～70 kcal/mol) and the associated high stability of the perthiyl radical make the foregoing reactions exothermic by 15-34 kcal/mol. Of particular relevance in the context of oxidative stress is the reactivity of RSSH to peroxyl radicals, where favorable thermodynamics are bolstered by a secondary orbital interaction in the transition state of the formal H-atom transfer that drives the inherent reactivity of RSSH to match that of α-tocopherol (α-TOH), nature's premier radical-trapping antioxidant. Significantly, the reactivity of RSSH eclipses that of α-TOH in H-bond-accepting media because of their low H-bond acidity (α2H ～ 0.1). This affords RSSH a unique versatility compared to other highly reactive radical-trapping antioxidants (e.g., phenols, diarylamines, hydroxylamines, sulfenic acids), which tend to have high H-bond acidities. Moreover, the perthiyl radicals that result are highly persistent under autoxidation conditions and undergo very rapid dimerization (k = 5 × 109 M-1 s-1) in lieu of reacting with O2 or autoxidizable substrates.