2-Thiocytosine

Base Information

• Chemical Name: 2-Thiocytosine
• CAS No.: 333-49-3
• Deprecated CAS: 139424-16-1,5807-22-7,5807-22-7
• Molecular Formula: C4H5 N3 S
• Molecular Weight: 127.17
• Hs Code.: 29335995
• European Community (EC) Number: 206-374-3
• NSC Number: 211571,45755
• DSSTox Substance ID: DTXSID0059823
• Nikkaji Number: J86.992I
• Wikidata: Q20892009
• Mol file: 333-49-3.mol

Synonyms:2-thiocytosine

Chemical Property of 2-Thiocytosine

Chemical Property:

• Appearance/Colour: Beige toYellow Powder
• Vapor Pressure: 0.0602mmHg at 25°C
• Melting Point: 285-290 °C (dec.)(lit.)
• Refractive Index: 1.749
• Boiling Point: 232.1°Cat760mmHg
• PKA: 7.91±0.10(Predicted)
• Flash Point: 94.1°C
• PSA: 90.60000
• Density: 1.53g/cm³
• LogP: 0.92870
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Water (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 127.02041835
• Heavy Atom Count: 8
• Complexity: 170

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Amino-2-mercaptopyrimidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(NC(=S)N=C1)N
• Uses: This compound has been shown to inhibit iodothyronine 5’-deiodinase, the enzyme responsible for the 5’-deiodination of thyroxine in human liver cells. 2-Thiocytosine has been used to investigate the reactions involved in hole transfer (HT) in X-irradiated doped cytosine monohydrate.

Technology Process of 2-Thiocytosine

There total 11 articles about 2-Thiocytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 48.0%

3,3-bis(ethyloxy)propanenitrile (2032-34-0) + thiourea (17356-08-0) → 2-thiocytosine (333-49-3)

Guidance literature:

With sodium; In butan-1-ol; at 40 - 50 ℃; for 5h; Inert atmosphere;

Reference yield: 38.0%

2-thiocytidine (13233-20-0,13239-97-9) → 2-thiouracil (141-90-2,156-82-1) + 2-thiocytosine (333-49-3) + 2-thiouridine (20235-78-3)

Guidance literature:

With formic acid; water; at 60 ℃; for 1296h; pH=3;

DOI:10.1038/nchem.2664

Reference yield: 29.0%

(3aS)-2t-hydroxymethyl-6-imino-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]thiazolo[3,2-a]pyrimidin-3c-ol → 2-thiocytosine (333-49-3)

Guidance literature:

With sodium hydrogensulfide; In water; at 20 - 35 ℃; for 3h; pH=7; UV-irradiation;

DOI:10.1038/s41557-019-0225-x

upstream raw materials:

2,4-dithiouracil

3,3-bis(ethyloxy)propanenitrile

thiourea

4-amino-2-thioxo-1,2-dihydro-pyrimidine-5-carboxylic acid

Downstream raw materials:

2-p-chlorobenzylthiocytosine

Refernces

• 1、 Xu, Jianfeng,Green, Nicholas J.,Gibard, Clémentine,Krishnamurthy, Ramanarayanan,Sutherland, John D.. "Prebiotic phosphorylation of 2-thiouridine provides either nucleotides or DNA building blocks via photoreduction". . p. 457 - 462. Retrieved 2019/04/08.
• 2、 Xu, Jianfeng,Tsanakopoulou, Maria,Magnani, Christopher J.,Szabla, Rafa?,?poner, Judit E.,?poner, Ji?í,Góra, Robert W.,Sutherland, John D.. "A prebiotically plausible synthesis of pyrimidine β-ribonucleosides and their phosphate derivatives involving photoanomerization". . p. 303 - 309. Retrieved 2017/04/03.