3-Quinuclidinyl benzilate

Base Information

• Chemical Name: 3-Quinuclidinyl benzilate
• CAS No.: 6581-06-2
• Molecular Formula: C21H23 N O3
• Molecular Weight: 337.419
• Hs Code.: 2933391000
• European Community (EC) Number: 636-245-0
• NSC Number: 173698,168347
• DSSTox Substance ID: DTXSID00894168
• Nikkaji Number: J366.287J,J62.255I
• Wikipedia: 3-Quinuclidinyl_benzilate
• Wikidata: Q223068
• Pharos Ligand ID: M6R6LHTLVNN6
• ChEMBL ID: CHEMBL12980
• Mol file: 6581-06-2.mol

Synonyms:Benzilate, Quinuclidinyl;Quinuclidinyl Benzilate

Chemical Property of 3-Quinuclidinyl benzilate

Chemical Property:

• Vapor Pressure: 1.75E-08mmHg at 25°C
• Melting Point: 164oC
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 439oC at 760 mmHg
• PKA: 11.28±0.29(Predicted)
• Flash Point: 219.3oC
• PSA: 49.77000
• Density: 1.25g/cm3
• LogP: 2.49780
• Storage Temp.: 2-8°C
• Solubility.: chloroform: but decomposes within 24 hrssoluble
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 337.16779360
• Heavy Atom Count: 25
• Complexity: 442
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

(±)-Quinuclidinylbenzilate powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T+
• Statements: 22-26
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Chemical Weapons
• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O
• Recent ClinicalTrials: Sequential Trial on Reduced Intensity Conditioning (RIC) Allogeneic Transplantation
• Description: The 3-quinuclidinyl benzilate (3-QNB) was first discovered by Hoffmann-La Roche in 1951 during research investigation that involved development of antispasmodic agents, resembling atropine, for treating gastrointestinal conditions. Soon after, the US Army investigated 3-QNB under the name of EA2277 agent and was standardized for use in chemical munitions in 1961 under the name agent of BZ. The United States declared complete destruction of its stockpile of BZ by 1989. Moreover, Agent 15 is speculated either to be identical to BZ or a closely related derivative, and has similar physicochemical properties as BZ. In 1998, Agent 15 was speculated to be stockpiled by Iraq but later on intelligence reports did not find any conclusive evidence for such claim1. The BZ is a glycolate anticholinergic chemical related to atropine, scopolamine, and, hyoscyamine. It is odorless, nonirritating, and is stable in most solvents. It has a half-life of 3–4 weeks in moist air and is extremely persistent in soil, water, and most surfaces. BZ has a slow onset and a long duration-of-action. The rate of BZ action climaxed after 9.5 h of exposure and the duration-of-action could last up to 96 h. Moreover, most of the causalities of BZ exposure will require physical restraint and continuous monitoring to prevent self-injury and paranoia symptoms during recovery2. Recent speculation about the usage of Agent 15 in Syrian civil war had been reported but no confirmation findings had been established3.
• Uses: 3-quinuclidinyl benzilate(BZ) is a nonlethal chemical warfare agent that following a delayed onset is incapacitating and causes severe hallucinations. US Army intended to use BZ in critical point situations such as special operation, incapacitating adversaries during raid, and overcoming fortified field positions. Medically, BZ is used as a muscarinic receptor antagonist.

Technology Process of 3-Quinuclidinyl benzilate

There total 8 articles about 3-Quinuclidinyl benzilate 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:

Benzilic acid (76-93-7) + 3-quinuclidinol (1619-34-7) → quinuclidinyl benzilate (6581-06-2)

Guidance literature:

In toluene;

DOI:10.1007/BF00766839

Reference yield:

3-methylquinuclidine (695-88-5) + Benzilic acid (76-93-7) → quinuclidinyl benzilate (6581-06-2)

Guidance literature:

Benzilic acid; With 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h;

3-methylquinuclidine; In N,N-dimethyl-formamide; at 80 ℃; for 18h;

DOI:10.3389/fphar.2018.00344

Reference yield:

3-quinuclidinol (1619-34-7) → quinuclidinyl benzilate (6581-06-2)

Guidance literature:

With sodium; toluene; Behandeln mit Chlor-diphenyl-acetylchlorid und Erwaermen des Reaktionsgemisches mit wss. Salzsaeure;

DOI:10.1021/ja01129a020

upstream raw materials:

3-quinuclidinol

methyl benzilate

Benzilic acid

3-Quinuclidinone

Refernces

• 1、 Tanaka, Ken-Ichiro,Yamakawa, Naoki,Yamashita, Yasunobu,Asano, Teita,Kanda, Yuki,Takafuji, Ayaka,Kawahara, Masahiro,Takenaga, Mitsuko,Fukunishi, Yoshifumi,Mizushima, Tohru. "Identification of mepenzolate derivatives with long-acting bronchodilatory activity". . . Retrieved 2018/04/17.
• 2、 Godovikov, N. N.,Dorofeeva, N. A.,Kardanov, N. A.,Trifonova, S. A.,Shelkovnikov, S. A.. "SYNTHESIS AND MUSCARINOLYTIC ACTIVITY OF QUINUCLIDINYL BENZYLATE IODOALKYLATES". . p. 602 - 604. Retrieved 2007/10/02.