Tabun

Base Information

• Chemical Name: Tabun
• CAS No.: 77-81-6
• Deprecated CAS: 102490-55-1
• Molecular Formula: C₅H₁₁N₂O₂P
• Molecular Weight: 162.128
• UN Number: 2810
• UNII: S45M750QSH
• DSSTox Substance ID: DTXSID80861631
• Nikkaji Number: J4.213G
• Wikipedia: Tabun_(nerve_agent)
• Wikidata: Q143289
• ChEMBL ID: CHEMBL446997
• Mol file: 77-81-6.mol

Synonyms:N,N-dimethylamido-O-ethyl cyanophosphate;tabun

Chemical Property of Tabun

Chemical Property:

• Vapor Pressure: 0.0389mmHg at 25°C
• Melting Point: -50°
• Refractive Index: nD20 1.4250
• Boiling Point: 240°C at 760 mmHg
• PKA: -4.71±0.70(Predicted)
• Flash Point: 98.9°C
• PSA: 63.14000
• Density: 1.14g/cm³
• LogP: 1.25868
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 162.05581460
• Heavy Atom Count: 10
• Complexity: 193

Purity/Quality:

Safty Information:

• Pictogram(s): Very toxic by inhalation, cholinesterase inhibitor, a military nerve gas, fatal dose (man) 0.01 mg/kg.
• Hazard Codes: Very toxic by inhalation, cholinesterase inhibitor, a military nerve gas, fatal dose (man) 0.01 mg/kg.

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chemical Weapons
• Canonical SMILES: CCOP(=O)(C#N)N(C)C
• Description: Tabun is a nonpersistent organophosphorus nerve agent that was first synthesized in 1936 by the German scientist Dr Gerhard Schrader, who would later be known as ‘the father of the nerve agents.’ Dr Schrader was developing new insecticides when he accidentally discovered tabun, the first of the nerve agents. During initial experiments testing tabun on insects, Dr. Schrader and his laboratory assistant were exposed to the vapors and quickly became ill. After learning of its properties and improving its manufacturing, the German government began synthesizing stockpiles of tabun in 1942 and had close to 13 000 tons by the end of World War II. The Allies did not become aware of tabun or other German-made nerve agents until the end of the war. Much of the German stockpiles of tabun were destroyed by dumping into the sea where it decomposes over time. Due to their greater lethality, soman and sarin were eventually favored over tabun by the Allied nations. However, the ease of manufacturing tabun makes it a feasible option for countries that are beginning to establish a chemical weapons capability. Due in part to the simplicity and widespread knowledge about its synthesis, Iraq stockpiled and used tabun against Iranian troops in 1984 in the first confirmed instance of nerve agent use in theater.
• Uses: Tabun is a nerve agent used in chemical warfare. It was the first of the G series of nerve agents to be described and hence was given the designation GA.

Technology Process of Tabun

There total 2 articles about Tabun 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:

ethanol (64-17-5) + sodium cyanide (143-33-9,25596-52-5) + N,N-dimethylphosphoroamidic dichloride (677-43-0) → tabun (77-81-6,93957-08-5,93957-09-6)

Guidance literature:

With chlorobenzene;

Reference yield:

→ tabun (77-81-6,93957-08-5,93957-09-6)

Guidance literature:

/BRN= 1769182/;

Reference yield:

tabun (77-81-6,93957-08-5,93957-09-6) + water (7732-18-5) → hydrogen cyanide (74-90-8) + dimethyl amine (124-40-3)

Guidance literature:

at 25 ℃; Geschwindigkeit der Reaktion in Loesungen vom pH 3, vom pH 4.0, und vom pH 5;

upstream raw materials:

ethanol

sodium cyanide

N,N-dimethylphosphoroamidic dichloride

Downstream raw materials:

hydrogen cyanide

dimethyl amine

ethyl phosphate

dimethyl phosphoramidic acid monoethyl ester