Organic thiocyanates

Phenyl thiocyanate and phenyl isothiocyanate are isomers.

Organic thiocyanates are organic compounds containing the functional group RSCN. the organic group is attached to sulfur: R−S−C≡N has a S–C single bond and a C≡N triple bond.[1]

Organic thiocyanates are valued building blocks. They allow to access efficiently various sulfur containing functional groups and scaffolds.[2]

## Contents

* 1 Synthesis
* 2 Reactions
* 3 See also
* 4 References

## Synthesis

Several synthesis routes exist, the most common being the reaction between alkyl halides and alkali thiocyanate in aqueous media.[3] Illustrative is the preparation of isopropyl thiocyanate by treatment of isopropyl bromide with sodium thiocyanate in boiling ethanol.[4] The main complication with this route is the competing formation of alkyisothiocyanates. "SN1-type" substrates (e.g., benzyl halides) tend to give the isothiocyanate derivatives.

Some organic thiocyanates are generated by cyanation of organosulfur compounds. Sulfenyl chlorides (RSCl) and thiosulfates (RSSO3−) react with alkali metal cyanides to give thiocyanates with displacement of chloride and sulfite, respectively.

Arylthiocyanates can often be obtained by thiocyanogenation, i.e. the reaction of thiocyanogen. This reaction is favored for electron-rich aromatic substrates.[1]

## Reactions

Organic thiocyanates are hydrolyzed to thiocarbamates in the Riemschneider thiocarbamate synthesis.

## See also

* Isothiocyanate, isomers of organic thiocyanates with the formula R−N=C=S
* Methyl thiocyanate, the simplest organic thiocyanate

## References

1. ↑ 1.0 1.1 R. G. Guy (1977). "Syntheses and Preparative Applications of Thiocyanates". in Saul Patai. Cyanates and Their Thio Derivatives: Part 2, Volume 2. PATAI'S Chemistry of Functional Groups. pp. 619–818. doi:10.1002/9780470771532.ch2. ISBN 9780470771532.
2. ↑ Castanheiro, Thomas; Suffert, Jean; Donnard, Morgan; Gulea, Mihaela (2016-02-01). "Recent Advances in the Chemistry of Organic Thiocyanates". Chem. Soc. Rev. 45 (3): 494–505. doi:10.1039/c5cs00532a. ISSN 1460-4744. PMID 26658383.
3. ↑ "Synthesis of thiocyanates". https://www.organic-chemistry.org/synthesis/C1S/thiocyanates.shtm.
4. ↑ R. L. Shriner (1931). "Isopropyl Thiocyanate". Organic Syntheses 11: 92. doi:10.15227/orgsyn.011.0092.

* v
* t
* e

Functional groups

| Only carbon,
hydrogen,
and oxygen|

| Hydrocarbons|

* Allene
* Alkene (Allyl group

|

Other|

* Acetoxy
* Acetyl
* Acryloyl
* Acyl
* Aldehyde
* Alkoxy (Methoxy)
* Benzoyl
* Carbonyl
* Carboxyl
* Carboxylic anhydride
* Dioxirane
* Epoxide
* Ester
* Ether
* Ethylenedioxy
* Hydroxy
* Ketone
* Methylenedioxy
* Peroxide (Organic)
* Ynone

Only one
element
apart from
C, H, O|

| Nitrogen|

* Amine
* Azo compound
* Cyanate
* Hydrazone
* Imide
* Imine
* Isocyanate
* Isonitrile
* Nitrene
* Nitrile
* Nitro compound
* Nitroso compound
* Organic amide
* Oxime

|

Phosphorus|

* Phosphonate
* Phosphonous

Sulfur|

* Disulfide
* Sulfone
* Sulfonic acid
* Sulfoxide
* Thial
* Thioester
* Thioether
* Thioketone
* Thiol

Selenium|

* Selenol
* Selenonic acid
* Seleninic acid
* Selenenic acid
* Selone

Tellurium|

* Tellurol
* Telluroketone

Other|

* Isothiocyanate
* Phosphoramide
* Sulfenyl chloride
* Sulfonamide
* Thiocyanate

See also chemical classification, chemical nomenclature ([[Chemistry:IUPAC nomenclature of inorganic, IUPAC nomenclature of organic chemistry|organic]])

* v
* t
* e

Thyroid hormone receptor modulators

Receptor
(ligands)|

| THR|

* Agonists: Dextrothyroxine
* DIMIT
* DITPA
* Eprotirome (KB-2115)
* KB-141
* KB-2611
* KB-130015
* Levothyroxine
* Liothyronine
* Liotrix
* MB-07344
* MB-07811
* MGL-3196 (VIA-3196)
* Sobetirome (GC-1, GRX-431)
* Thyroxine
* Tiratricol (TRIAC)
* Triiodothyronine
* Thyroid extract
* VK-0214
* VK-2809
* ZYT1

* Antagonists: 1-850
* NH3
* Tetraiodothyroacetic acid (Tetrac)

|

Transporter
(blockers)|

| NIS

* Inhibitors: Cyanogenic glycosides
* Perchlorates (e.g., potassium perchlorate)
* Pertechnetates (e.g., sodium pertechnetate]])
* Thiocyanates

|

Enzyme
(inhibitors)|

| TPO|

* Inhibitors: Benzylthiouracil
* Carbimazole
* Genistein
* Methimazole
* Methylthiouracil
* Propylthiouracil
* 2-Thiouracil
* Thiourea

|

DIO|

* Inhibitors: Dexpropranolol
* Iopanoic acid
* Ipodate sodium (sodium iopodate)
* Propranolol
* Propylthiouracil

Others|

* Iodine
* Iodine-131
* Selenium
* Thyroglobulin
* Tyrosine

* See also: Receptor/signaling modulators
* Nuclear receptor modulators

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*[THR]: Thyroid hormone receptor
*[NIS]: Sodium-iodide symporter
*[TPO]: Thyroid peroxidase
*[DIO]: Iodothyronine deiodinase