Tribufos

Base Information

• Chemical Name: Tribufos
• CAS No.: 78-48-8
• Molecular Formula: C12H27 O P S3
• Molecular Weight: 314.518
• European Community (EC) Number: 201-120-8
• UN Number: 2811,2902
• UNII: 53075G8GRF
• DSSTox Substance ID: DTXSID1024174
• Nikkaji Number: J2.827D
• Wikidata: Q2537076
• Metabolomics Workbench ID: 55992
• ChEMBL ID: CHEMBL1901047
• Mol file: 78-48-8.mol

Synonyms:butifos;butyl phosphorotrithioate;butyphos;DEF;S,S,S-tributyl phosphorotrithioate;S,S,S-tributyl trithiophosphate;tribufos;tributyl S,S,S-phosphorotrithioate;tributylphosphine oxide;trisbutylphosphine oxide

Chemical Property of Tribufos

Chemical Property:

• Vapor Pressure: 1.73E-06mmHg at 25°C
• Melting Point: Below -25oC
• Refractive Index: nD20 1.534
• Boiling Point: 407.8 °C at 760 mmHg
• Flash Point: 200.4 °C
• PSA: 102.78000
• Density: 1.074 g/cm³
• LogP: 6.69440
• Storage Temp.: 0-6°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 314.09616600
• Heavy Atom Count: 17
• Complexity: 179
• Transport DOT Label: Poison

Purity/Quality:

97%, ^*data from raw suppliers

1,2,4-TributylPhosphorotrithioate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 24/25-50/53
• Safety Statements: 36/37-45-61-60

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCCCSP(=O)(SCCCC)SCCCC
• Description: DEF is a cholinesterase-inhibiting organophosphorus pesticide compound used as a cotton defoliant that was registered in 1960.DEF is a colorless to pale-yellow transparent liquid with a skunk-like odor.It is completely miscible with n-hexane, dichloromethane, toluene, and 2-propanol and has an octanol–water partition coefficient of 3.31×105 at 25°C. DEF toxicity is primarily attributed to inhibition of various esterases, including acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), neuropathic target esterase (NTE), and carboxylesterase, resulting in increased accumulation of endogenous acetylcholine (ACh) in cholinergic nerve terminals and related effector organs.
• Uses: DEF is an organophosphate chemical used as a cotton defoliant to facilitate mechanical harvesting. Recommended application rate is ～1–2.5 pints per acre per year applied as a diluted spray. Two products containing DEF as their active ingredient include DEF 6, manufactured by Bayer Corporation, and Folex 6 DC, manufactured by Amvac Chemical Co. Used for pest control in industrial agriculture (tends to be more toxic agents), organophosphates of low to intermediate toxicity are used to control ectoparasites on farm and companion animals and humans (head lice), and for home and garden pest control. Defoliant. 1,2,4-Tributylphosphorotrithioate is a defoliant for cotton.

Technology Process of Tribufos

There total 3 articles about Tribufos 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: 83.0%

n-butanethiol (109-79-5) → S,S,S-tributylphosphorotrithioate (78-48-8)

Guidance literature:

n-butanethiol; With phosphorus; potassium hydroxide; In dimethyl sulfoxide; toluene; at 20 ℃; for 7h; Schlenk technique;

With dihydrogen peroxide; In dimethyl sulfoxide; toluene; at 20 ℃; for 0.5h; Schlenk technique;

DOI:10.1039/c9gc04452c

Reference yield:

merphos (150-50-5) → S,S,S-tributylphosphorotrithioate (78-48-8)

Guidance literature:

With dihydrogen peroxide; In dimethyl sulfoxide; toluene; at 20 ℃; for 0.5h; Schlenk technique;

DOI:10.1021/acs.orglett.1c01695

Reference yield:

→ S,S,S-tributylphosphorotrithioate (78-48-8)

Guidance literature:

BuSH, POCl3;

upstream raw materials:

n-butanethiol

merphos

Downstream raw materials:

4-Methylbenzolthiosulfonsaeure-S-butylester

n-butanethiol

Refernces

• 1、 Zhang, Yue,Cai, Ziman,Chi, Yangyang,Zeng, Xiangzhe,Chen, Shuanghui,Liu, Yan,Tang, Guo,Zhao, Yufen. "Diphenyl Diselenide-Catalyzed Synthesis of Triaryl Phosphites and Triaryl Phosphates from White Phosphorus". supporting information. p. 5158 - 5163. Retrieved 2021/07/20.
• 2、 -. "Process for the production of S,S,S-tributylphosphorotrithioate". . . Retrieved 2008/06/13.