Merphos

Base Information

• Chemical Name: Merphos
• CAS No.: 150-50-5
• Molecular Formula: C12H27 P S3
• Molecular Weight: 298.518
• Hs Code.: 2931900090
• European Community (EC) Number: 205-761-4
• NSC Number: 27720
• UN Number: 3278,2903
• UNII: RN743HTX76
• DSSTox Substance ID: DTXSID6024173
• Nikkaji Number: J5.853J
• Wikidata: Q17326638
• Mol file: 150-50-5.mol

Synonyms:Folex;merphos;S,S,S-tributyl phosphorotrithioite

Chemical Property of Merphos

Chemical Property:

• Vapor Pressure: 1.2E-05mmHg at 25°C
• Melting Point: 100°C
• Boiling Point: 380.3 ºC at 760 mmHg
• Flash Point: 183.8 ºC
• PSA: 89.49000
• Density: g/cm³
• LogP: 6.81320
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 298.10125138
• Heavy Atom Count: 16
• Complexity: 110
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Merphos ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Cholinesterase inhibitor.
• Hazard Codes: Cholinesterase inhibitor.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Organophosphate Insecticides
• Canonical SMILES: CCCCSP(SCCCC)SCCCC
• Uses: Merphos is an organothiophosphorus compound used as a defoliant but the active ingredient is no longer contained in any registered pesticide product in the US and in EU. Therefore, Environmental Protection Agency (EPA) is characterizing it as canceled. The status of merphos in the EU pesticide database is ‘Not Approved’ under the Regulation EC 1107/2009 and not authorized at national level in EU countries. However a maximum level of residues (MRL) is regulated in foods as the default MRL of 0.01 mg kg-1 according to Art 18(1)(b) Reg 396/2005. Merphos was used to defoliate cotton at application rates of 1.1–2.2 kg active ingredient per acre and can induce leaf abscission in some other plants, such as roses and hydrangeas. It was particularly suited for total defoliation of cotton preparatory to machine harvesting because the natural action of the substance causes the leaves to drop in a relatively green state with fresh weight adequate to cause them to fall to the ground. The technical product used to have 95% purity. Formulation used to contain 720 g active ingredient per liter or being an emulsifiable concentrate containing 6 lb per gallon. Organophosphate pesticide used in the agriculture industry

Technology Process of Merphos

There total 10 articles about Merphos 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: 77.0%

n-butanethiol (109-79-5) + dibutyl diethylphosphoramidodithioite (52416-06-5) → merphos (150-50-5) + diethylamine (109-89-7)

Guidance literature:

for 0.5h; Ambient temperature;

Reference yield: 69.0%

dibutyl diethylphosphoramidodithioite (52416-06-5) + thiophenol (108-98-5) → merphos (150-50-5) + dibutyl phenyl phosphorotrithioite (3819-63-4) + diethylammonium benzenethiolate (92490-93-2) + butyl diphenyl phosphorotrithioite

Guidance literature:

In diethyl ether;

Reference yield: 13.0%

n-butanethiol (109-79-5) → merphos (150-50-5) + tetrathiophosphoric acid tributyl ester (1642-47-3) + dibutyl disulfide (629-45-8) + O-potassium S,S-dibutylphosphorotrithioate (1217597-47-1)

Guidance literature:

n-butanethiol; With potassium hydroxide semihydrate; In dimethyl sulfoxide; at 60 ℃;

With phosphorus; In dimethyl sulfoxide; at 125 - 128 ℃;

With hydrogenchloride; water; In dimethyl sulfoxide; pH=4;

DOI:10.1134/S0012500809070052

upstream raw materials:

n-butanethiol

dibutyl disulfide

n-butylthiotrimethylsilane

dibutyl diethylphosphoramidodithioite

Downstream raw materials:

dibutyl disulfide

dibutyl phosphorochloridodithioite

S,S,S-tributylphosphorotrithioate

4-Methylbenzolthiosulfonsaeure-S-butylester

Refernces

• 1、 Maier,van Wazer. "". . p. 3054,3056. Retrieved 1962.
• 2、 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.
• 3、 -. "Process for producing stable, low odor S,S,S-tributylphosphorothrithiote". . . Retrieved 2008/06/13.