Pyrrolidine-1-carbodithioate

Base Information

• Chemical Name: Pyrrolidine-1-carbodithioate
• CAS No.: 5108-96-3
• Molecular Formula: C5H9NS2^.NH3
• Molecular Weight: 164.296
• Hs Code.: 29339990
• European Community (EC) Number: 225-834-4
• Nikkaji Number: J439.222A
• Mol file: 5108-96-3.mol

Synonyms:ammonium pyrrolidine dithiocarbamate;ammonium tetramethylene dithiocarbamate;pyrrolidine dithiocarbamate;pyrrolidine dithiocarbamic acid;pyrrolidine dithiocarbamic acid, ammonium salt;pyrrolidine dithiocarbamic acid, sodium salt;Pyrrolidinedithiocarbamate

Chemical Property of Pyrrolidine-1-carbodithioate

Chemical Property:

• Appearance/Colour: pale yellow crystalline solid
• Vapor Pressure: 0.000178mmHg at 25°C
• Melting Point: 150-155 °C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 199.7 °C at 760 mmHg
• Flash Point: 74.6 °C
• PSA: 77.37000
• Density: 1.117 (estimate)
• LogP: 1.55870
• Storage Temp.: 2-8°C
• Sensitive.: Hygroscopic
• Solubility.: 190g/l
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 146.00981661
• Heavy Atom Count: 8
• Complexity: 91.1

Purity/Quality:

98% ^*data from raw suppliers

Pyrrolidinedithiocarbamate ammonium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1CCN(C1)C(=S)[S-]
• Description: Pyrrolidinedithiocarbamic acid (PDTC) is a metal chelating compound that potently and reversibly inhibits NF-κB activation in vitro (100 μM). At 300 μM, it prevents TNF-α gene expression and protein production in human monocytes after LPS application. In vascular smooth muscle cells, PDTC (10 μM) arrests the cell cycle at the G1 phase with upregulation of p21Cip1 through the p38 MAPK pathway. PDTC (100 μM) also has antioxidant properties.
• Uses: Ammonium pyrrolidinedithiocarbamate has been used:to inhibit nuclear factor κB (NF-κB) mobilization and TNF (tumor necrosis factor) production in human monocytesto reduce neutrophil activity in ratsto prevent Ca2+ influx in adriamycin (ADR)-treated podocytesto abrogate the microRNA-146a promoter luciferase reporter activity in human brain cells 1-Pyrrolidinecarbodithioic Acid induces apoptosis in rat smooth muscle cells and inhibits apoptosis in leukemia HL-60 cells. It also prevents induction of nitric oxide synthetase by inhibiting translation of NOS mRNA

Technology Process of Pyrrolidine-1-carbodithioate

There total 1 articles about Pyrrolidine-1-carbodithioate 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: 85.0%

pyrrolidine (123-75-1) + carbon disulfide (75-15-0,12122-00-8) → ammonium tetramethylenedithiocarbamate (5108-96-3)

Guidance literature:

With ammonium hydroxide; In diethyl ether; for 1h;

DOI:10.1016/j.ejmech.2005.07.008

Reference yield: 95.7%

ammonium tetramethylenedithiocarbamate (5108-96-3) + (benzoylaminomethyl)triethylammonium chloride (78134-74-4) → benzamidomethyl pyrroldinedithiocarbamate

Guidance literature:

With triethylamine; In water; at 20 ℃; for 1h;

DOI:10.3390/50700927

Reference yield: 90.1%

ammonium tetramethylenedithiocarbamate (5108-96-3) + methyl 4-(2-bromoacetyl)benzoate (56893-25-5) → methyl 4-(2-((pyrrolidine-1-carbonothioyl)thio)acetyl)benzoate (1593781-46-4)

Guidance literature:

In acetone; at 20 ℃; for 8h;

DOI:10.1021/acs.inorgchem.7b02243

upstream raw materials:

pyrrolidine

carbon disulfide

Downstream raw materials:

p-nitrobenzyl 3-<<3-<(1-pyrrolidinylcarbothioyl)thio>propyl>thio>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(PPh3)Pt(Cl)(κ(2)S,S-S2CNC4H8)

(PPh3)Pt(κS,S2CNC4H8)-(κ(2)S,S-S2CNC4H8)

(PPh3)Pd(Cl)(κ(2)S,S-S2CNC4H8)

Refernces

• 1、 Kumar,Shukla,Ramrakhyani,et al.. "Synthesis of new dithiocarbamates as potential anthelmintic antimicrobial and insecticidal agents". . p. 681 - 682. Retrieved 2007/10/02.