68127-59-3

Basic information

• Product Name: (Z)-(1RS,3RS)-3-(2-Chloro-3,3,3-trifluoroprope- nyl)-2,2-dimethylcyclopropanecarboxylic acid
• Synonyms: (Z)-(1RS,3RS)-3-(2-Chloro-3,3,3-trifluoroprope- nyl)-2,2-dimethylcyclopropanecarboxylic acid;(1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylic acid
• CAS NO: 68127-59-3
• Molecular Formula: C₉H₁₀ClF₃O₂
• Molecular Weight: 242.6227096
• Mol File: 68127-59-3.mol

Chemical Properties

• Boiling Point: 271.6°Cat760mmHg
• Flash Point: 118.1°C
• Appearance: /
• Density: 1.449g/cm³
• Vapor Pressure: 0.009-1.218Pa at 20-59.9℃
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.01±0.42(Predicted)
• CAS DataBase Reference: (Z)-(1RS,3RS)-3-(2-Chloro-3,3,3-trifluoroprope- nyl)-2,2-dimethylcyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(1RS,3RS)-3-(2-Chloro-3,3,3-trifluoroprope- nyl)-2,2-dimethylcyclopropanecarboxylic acid(68127-59-3)
• EPA Substance Registry System: (Z)-(1RS,3RS)-3-(2-Chloro-3,3,3-trifluoroprope- nyl)-2,2-dimethylcyclopropanecarboxylic acid(68127-59-3)

Safety Data

• Hazardous Substances Data: 68127-59-3(Hazardous Substances Data)

Usage

Uses

(±)-Cyhalothric Acid is a useful reagent for the preparation of Tefluthrin (T013800(P)), which is a pyrethroid based insecticide. Tefluthrin is used in the control of a broad range of soil pests, including members of the Coleoptera, Lepidoptera, and Diptera.

Upstream product

• 107686-54-4 4-(1,1-Dichloro-2,2,2-trifluoro-ethyl)-6,6-dimethyl-3-oxa-bicyclo[3.1.0]hexan-2-one 
• 71461-40-0 ethyl (+/-)-cis,trans-3-<(E,Z)-2-chloro-3,3,3-trifluoroprop-1-enyl>-2,2-dimethylcyclopropanecarboxylate 
• 187592-70-7 4-(1,1-dichloro-2,2,2-trifluoroethyl)-6,6-dimethyl-3-oxabicyclo<3.1.0>hexan-2-one 
• 103654-93-9 2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol 
• 107686-52-2 4-(2,4-dioxobutoxy)-5,5-dichloro-6,6,6-trifluoro-2-methyl-2-hexene 
• 107686-53-3 4-diazoacetoxy-5,5-dichloro-6,6,6-trifluoro-2-methyl-2-hexene 

Downstream Products

• 68127-98-0 (+/-)-cis-Z-cyhalothric acid chloride 

Relevant articles and documents

PRACTICAL AND STEREOCONTROLLED SYNTHESES OF BOTH (1R*,3S*)- AND (1R*,3R*)-3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATES

The title compounds of (1R*,3S*) configuration were prepared from 3-formyl-2,2-dimethylcyclopropanecarboxylate by addition of CF3CCl2ZnCl, acetylation, and reductive β-elimination with zinc, whereas the (1R*,3R*) isomer was derived from Me2C=CHCH(OH)CCl2CF3 by diazoacetylation, Cu(II) catalyzed intramolecular cyclization, and the zinc reduction.

Synthesis and X-Ray Crystal Structure of a New Potent Pyrethroid Acid, (+/-)-cis-3--2,2-dimethylcyclopropanecarboxylic Acid

Single-crystal X-ray analysis of the title compound has established its structure and molecular geometry.Crystals are monoclinic, space group P21/c, with a = 9.487(4), b = 8.009(4), c = 16.214(6) Angstroem, β = 119.91(1) deg, Z = 4.The structure was solved by direct methods and refined by full-matrix least-squares calculations to R 0.056 over 1242 reflections measured by diffractometer.The crystals contain centrosymmetric hydrogen-bonded dimers (O...O 2.65 Angstroem) in which the carboxy and vinyl substituents are in a 'bisecting' orientation, and the C=O group and one of hydrogen atoms on each methyl group point over the cyclopropane ring.The bond lengths in the ring reflect the substitution pattern.