Dimethenamid

Base Information

• Chemical Name: Dimethenamid
• CAS No.: 87674-68-8
• Molecular Formula: C12H18ClNO2S
• Molecular Weight: 275.799
• Hs Code.: 2934999026
• European Community (EC) Number: 618-045-5
• UNII: 8504Z6C4XZ
• DSSTox Substance ID: DTXSID4032376
• Nikkaji Number: J3.032.849C,J646.758J
• Wikipedia: Dimethenamid
• Wikidata: Q3028201
• Metabolomics Workbench ID: 143655
• ChEMBL ID: CHEMBL1565335
• Mol file: 87674-68-8.mol

Synonyms:2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(1-methoxy-2-propanyl)acetamide;dimethenamid

Chemical Property of Dimethenamid

Chemical Property:

• Appearance/Colour: Yellow-brown viscous liquid
• Vapor Pressure: 4.57E-06mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: 1.551
• Boiling Point: 382.9 °C at 760 mmHg
• PKA: 1.16±0.50(Predicted)
• Flash Point: 185.4 °C
• PSA: 57.78000
• Density: 1.195 g/cm³
• LogP: 2.97160
• Storage Temp.: 0-6°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 275.0746777
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

Dimethenamid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 22-51/53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CSC(=C1N(C(C)COC)C(=O)CCl)C
• Uses: Preemergence herbicide for use in food crops.

Technology Process of Dimethenamid

There total 4 articles about Dimethenamid 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: 90.64%

N-[(Methoxymethyl)ethyl]-2,4-dimethyl-thiophene-3-amine (87676-07-1) + chloroacetyl chloride (79-04-9) → dimethenamid (87674-68-8)

Guidance literature:

In hexane; for 15h; Reflux; Green chemistry; Industrial scale;

Reference yield:

2,4-dimethyl-3-amino-thiophene (87685-15-2) + Methoxyacetone (5878-19-3) + chloroacetyl chloride (79-04-9) → dimethenamid (87674-68-8)

Guidance literature:

2,4-dimethyl-3-amino-thiophene; Methoxyacetone; With toluene-4-sulfonic acid; In cyclohexane;

With hydrogen; In toluene; at 20 ℃;

chloroacetyl chloride; With potassium carbonate; In dichloromethane;

Reference yield:

2,5-dimethyl-3-thia-adipic acid (106014-16-8) → dimethenamid (87674-68-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium acetate; acetic anhydride / 7 h / 120 °C / Inert atmosphere

1.2: 30 °C / pH 7 - 8

2.1: hydroxylamine hydrochloride / methanol / 7 h / Reflux

3.1: toluene-4-sulfonic acid / cyclohexane

3.2: ligand-containing iridium catalyst / 20 °C

With hydroxylamine hydrochloride; sodium acetate; acetic anhydride; toluene-4-sulfonic acid; In methanol; cyclohexane;

upstream raw materials:

N-[(Methoxymethyl)ethyl]-2,4-dimethyl-thiophene-3-amine

chloroacetyl chloride

2,4-dimethyl-3-amino-thiophene

Methoxyacetone

Refernces

• 1、 -. "Method for preparing 3 - amino -2, 4 -dimethylthiophene (by machine translation)". Paragraph 0094; 0095. . Retrieved 2019/08/12.
• 2、 -. "Herbicidal mixtures having a synergistic effect". . . Retrieved 2008/06/13.