Cinmethylin

Base Information

• Chemical Name: Cinmethylin
• CAS No.: 87818-31-3
• Molecular Formula: C₁₈H₂₆O₂
• Molecular Weight: 274.403
• Hs Code.: 29321900
• European Community (EC) Number: 402-410-9,618-074-3
• UNII: ZV3871E43Y
• DSSTox Substance ID: DTXSID3034456
• Nikkaji Number: J409.103E
• Wikidata: Q14625376
• Metabolomics Workbench ID: 67992
• ChEMBL ID: CHEMBL1903971
• Mol file: 87818-31-3.mol

Synonyms:Cinmethylin;Cinch;Argold;Cinmethylin [ISO];87818-31-3;Caswell No. 731G;EPA Pesticide Chemical Code 128837;SD95481;SD 95481;UNII-ZV3871E43Y;DTXSID3034456;ZV3871E43Y;Cinmethylin 10 microg/mL in Cyclohexane;EC 402-410-9;(+-)-exo-1-Methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo(2.2.1)heptane;7-Oxabicyclo(2.2.1)heptene exo-(+-)-1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-;7-Oxabicyclo(2.2.1)heptane, 1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-, exo-(+-)-;Cinch (Cinmethylin);(1S,2R,4R)-1-methyl-2-[(2-methylbenzyl)oxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane;(1S,2R,4R)-1-methyl-2-[(2-methylphenyl)methoxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane;(1S,2R,4R)-1-methyl-2-[(2-methylphenyl)methoxy]-4-propan-2-yl-7-oxabicyclo[2.2.1]heptane;exo-(+/-)-1-Methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo(2.2.1)heptane;exo-(+/-)-1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane;exo-(+)-cinmethylin;CINMETHYLIN [MI];cinmethylin exo-(+)-isomer;CHEBI:3708;CHEMBL1903971;SCHEMBL19302036;DTXCID60196478;(+-)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane;CHEBI:145563;(1R,2S,4S)-rel-1-Methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-7-oxabicyclo[2.2.1]heptane;Tox21_301127;AKOS025311529;(1S,2R,4R)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2.2.1]heptane;NCGC00164469-01;NCGC00248300-01;NCGC00255026-01;LS-98760;SD-95481;CAS-87818-31-3;Cinmethylin, PESTANAL(R), analytical standard;EN300-25914604;Q14625376;(1RS,2SR,4SR)-1,4-EPOXY-P-MENTH-2-YL 2-METHYLBENZYL ETHER;(+)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane;2alpha-(2-Methylbenzyloxy)-4beta-isopropyl-1beta-methyl-7-oxabicyclo[2.2.1]heptane;87818-61-9

Chemical Property of Cinmethylin

Chemical Property:

• Vapor Pressure: 0.000939mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 313 ºC
• Flash Point: 123 °C
• PSA: 18.46000
• Density: 1.04 g/cm³
• LogP: 4.24780
• Storage Temp.: 0-6°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 274.193280068
• Heavy Atom Count: 20
• Complexity: 353

Purity/Quality:

99.9% ^*data from raw suppliers

Cinmethylin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 20-51/53
• Safety Statements: 23-61-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1COC2CC3(CCC2(O3)C)C(C)C
• Isomeric SMILES: CC1=CC=CC=C1CO[C@@H]2C[C@]3(CC[C@@]2(O3)C)C(C)C
• Description: Cinmethylinwas developed by Shell Chemical Company in the early 1980s as a weed control agent for monocotyledonous species. This herbicide controls important grasses such as green foxtail (Setaria viridis) and barnyardgrass (Echinochloa crus-galli) and suppresses the growth of several broadleaf weeds such as prickly sida (Sida spinosa) and velvetleaf (Abutilon theophrasti).
• Uses: Cinmethylin is used as pre-emergence grass herbicide. Cinmethylin is member of the cineole eucalyptol family. Herbicide.

Technology Process of Cinmethylin

There total 8 articles about Cinmethylin 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: 99.5%

1-chloromethyl-2-methylbenzene (552-45-4) + (±)-2-exo-hydroxy-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1 ]heptane → (±)-2-exo-(2-methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane (87818-31-3)

Guidance literature:

With caesium carbonate; sodium hydroxide; In toluene; at 130 ℃; for 31h; Reagent/catalyst; Temperature; Catalytic behavior; Dean-Stark;

Reference yield: 53.0%

2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane (22555-57-3) + 2-methylbenzyl bromide (89-92-9) → 2-exo-[(2-methylphenyl)methoxy]-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane (87818-31-3)

Guidance literature:

2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane; With cesium chloride; sodium hydroxide; In toluene; for 6h; Dean-Stark; Heating;

2-methylbenzyl bromide; In toluene; for 60h; Heating;

Reference yield: 46.0%

→ (1S,2R,4R)-4-isopropyl-1-methyl-2-(o-tolylmethoxy)-7-oxabicyclo[2 .2.1]heptane (87818-31-3)

Guidance literature:

With Burkholderia plantarii lipase; In tert-butyl methyl ether; at 20 ℃; for 72h; Enzymatic reaction;

upstream raw materials:

TERPINEN-4-OL

1-chloromethyl-2-methylbenzene

1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile

2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane

Refernces

• 1、 -. "PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE". Page/Page column 32; 33; 34; 35; 36. . Retrieved 2018/10/25.
• 2、 -. "PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE". Page/Page column 27-28. . Retrieved 2018/04/13.