1,6-Hexanedithiol Structure, Synthesis, Properties, Uses, And Toxicity

1,6-Hexanedithiol is an organic compound. It belongs to the main alkane group of organic compounds.

It is the substituted product of 6 carbon molecule Hexane in which two Hydrogens at Carbon 1 and six are replaced by mercapto or –SH group.

This is the reason that most often they are also pronounced 1,6-Dimercaptohexaneor1,6-Hexanedimercapta and Hexamethylenedimercaptan. It can also be called  Alkanethiol.

Structure

1,6-Hexanedithiol (HDT) is a long-chained, bifunctional molecule that is structured in a criss-cross manner.

 It can be written as Hexan-1,6-dithiol instead. Its molecular weight is 150.31. Its structural condensed formula can be as SHCH2(CH2)4CH2SH but actually, it is arranged in zig-zag.

It is composed of the 6C long Hexane chain in which the last two Hydrogens from both ends are replaced by thiol or mercapto –SH group. Have a look at the 2D structure of 1,6-Hexanedithiol.

General Properties Of 1,6-Hexanedithiol

It is available in a liquid state. It can be observed as a colorless to slightly yellow liquid. It is not soluble in water as being immiscible in water being non-polar like many other organic compounds.

It is miscible and soluble in fats. Its observed density is 0.983 g/mL at 25°(lit.).Its boiling point is 118-119 °C/15 mmHg (lit.)

 Its melting point is −21 °C (lit.).Its refractive index value is 1.511-1.5140.  Its vapor pressure is about 1 mm Hg (20 °C). Its flash point is 195.00 °F or TCC (90.56 °C).

6-Hexanedithiol

Synthesis of 1,6-Hexanedithiol

One-Pot Synthesis Of 1,6-Hexanedithiol

It may be prepared through various chemical reactions. Many of them come with a huge loss of energy and severe environmental problems.

Its one-pot synthesis method is safe and effective with any environmental repercussions. In this case, Cyclohexane is the main regent.

Cyclohexane is treated with a bioenergetic catalyst and Cyclohexane is converted to 1,6-Hexanedithiol.

Occurrence

Hexane 1,6-dithiol has somehow a meaty and fatty odor. Its smell resembles fungus and sulfur smell. It is reported to occur in boiled beef.

Non-Compatible Reactions

 It tastes burnt, fatty also meaty on dilution. This is not prone to oxidation and not compatible with bases, reducing agents, and alkali metals.

Chemical Importance, Uses, And Reaction Of 1,6-Hexanedithiol

1,6 hexanedithiol
1,6 hexanedithiol

Use in the Flavoring Industry

1, 6-Hexadithiol is used as a flavoring agent in the food industry mainly. It is used along with many spices.

It is also used as a flavoring agent including Tobacco Flavor and edible blended flavors. Since it is having a meaty odor so it’s used in beef and poultry soups also.

Use In Polymer Synthesis

It has a self-assembling property that is characteristic of polymers. They form self-chains to give self-assembled properly arranged monolayers (SAMs). This is the reason it is used in the synthesis of synthetic rubber.

Use In Structural Determination

1, 6-Hexanedithiol is often polymerized over the surface of Gold. It is used in many Techniques such as X-ray diffraction, Scanning Tunneling Microscopy (STM), and TLC for structural determination of various compounds in the presence of Uric Acid in the Ascorbic Acid.

It may be used for the adsorption of one chemical over the surface of another one.1

Synthesis Of Organic Compound

It can be used as a synthesis of various organic compounds. It is also used in the oxidation of Ascorbic acid.

Use As Protecting Group in Chemistry

Somehow we want to protect any certain atom or molecule from undergoing into reaction. For this purpose, other compounds are used as protecting groups that become attached to such molecules and prevent them from undergoing a certain reaction.

 These 1,6-Hexanedithiols involving the mercapto group are often used as protecting groups2 in certain organic chemical reactions.

Use As A Chemical Sensor

It is used for the identification of various groups and chemicals in chemistry. This is the reason it is referred to as a chemical sensor. It may be used in specific recognition of the alkyl mercury group. In this case,1,6-Hexanedithiol is used as a receptor. It is used in monolayer form.3

Use as Toxin

1,6-Hexanedithiol is combustible liquid. It may catch fire easily. It is also toxic to be swallowed and is harmful if inhaled. It also causes harmful effects on the skin if get touched by it. It is a strong irritant to the eyes, respiratory tract, and skin.

Use As An Oxidizing Agent

Mainly 1,6-Hexanedithiol is used as an oxidizing agent for the oxidation of various organic compounds.  Electrolytic oxidation of Ascorbic Acid is done by using 1,6-Haxanedithiol by using a gold electrode modified with1,6-Hexanedithiol.4

Health Impacts Of 1,6-Hexanedithiol

It may cause some behavioral disorders like Somnolence causing general depression. It may also cause muscle weakness.

Precautionary Measures

  1. It should be avoided from direct heat and sunlight.
  2. It must be stored in a dry place at room temperature.
  3. Must be handled with care.
  4. It should be stored in glass pots.
  5. Must be kept out of the reach of children.
  6. Eyes must be rinsed immediately if came into contact with it and helped with medical advice.
  7. Gloves must be used along with face, eyes, and body protection.
  8. Care should be taken in using them as additives. Chemical Advisory Committee advocates that thiol compounds quantity used in food must be less than 1.00 ppm. Its normal value to be used is 0.005-0.2ppm.

Conclusion

1,6-Hexanedithiol is an intrinsic organic compound. It has many novel properties and comes with a variety of uses.

Polymer synthesis, adsorption, and chemical sensitivity are their main attributes. Anyhow, it comes with toxic behavior as a strong irritant. Therefore, care is needed to handle it.

References
2- Kocieński. (1970, January 1). 5.1 introduction. Thieme E-Books & E-Journals. RetrievedNovember 29, 2021. 
3- Ji, H. F., Zhang, Y., Purushotham, V. V., Kondu, S., Ramachandran, B., Thundat, T., & Haynie, D. T. (2005). 1, 6-Hexanedithiol monolayer as a receptor for specific recognition of alkylmercury. Analyst, 130(12), 1577-1579.
4- Sivanesan, A., Kannan, P., & John, S. A. (2007). Electrocatalytic oxidation of ascorbic acid using a single layer of gold nanoparticles immobilized on 1, 6-hexanedithiol modified gold electrode. Electrochimica Acta, 52(28), 8118-8124.
Maria Zhang

Maria Zhang

Maria Zhang, an experienced chemical industrial expert with more than 10 years of experience. She has worked with a range of industries, from large-scale manufacturing and research to smaller-scale projects. With her expertise, you can learn differently chemical knowledge!

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