cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

• ChemBase ID: 105134
• Molecular Formular: C22H19Cl2NO3
• Molecular Mass: 416.29716
• Monoisotopic Mass: 415.07419883
• SMILES: CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1
• Canonical SMILES: N#CC(c1cccc(c1)Oc1ccccc1)OC(=O)C1C(C1(C)C)C=C(Cl)Cl
• InChI: InChI=1S/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3
• InChIKey: KAATUXNTWXVJKI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• IUPAC Traditional name: ustaad; ammo
• Synonyms: α-Cyano-(3-phenoxy-phenyl)-methyl 3-(2,2-dichloro-vinyl)-2,2-dimethyl-cyclo-pro-pane-carboxylate; Cypermethrin; Cypermethrin solution; 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic Acid Cyano(3-phenoxyphenyl)methyl Ester; NRDC-149; FMC-30980; PP-383; Arrivo; Basathrin; Cymbush; Demon; Flectron; Ripcord; Ammo; Avicade; Barricade; (alpha)-alpha-Cyano-3-Phenoxybenzyl-2,2-Dimethyl-3-(2,2-Dichlorovinyl) Cyclopropane Carboxylate; CYPERMETHRIN; α-Cypermethrin; Alphamethrine; 氯氰菊酯; 氯氰菊酯 溶液; 顺式氯氰菊酯; 腈二氯苯醚菊酯

Database IDs

• CAS Number: 67375-30-8; 52315-07-8
• EC Number: 257-842-9
• MDL Number: MFCD00055328
• Beilstein Number: 8444118
• PubChem SID: 162092545
• PubChem CID: 2912
• CHEBI ID: 4042
• ATC CODE: QP53AC08; P03BA02
• CHEMBL: 373204
• Chemspider ID: 2809
• KEGG ID: D07763
• MeSH Name: Cypermethrin
• Unique Ingredient Identifier: 1TR49121NP
• Wikipedia Title: Cypermethrin

CALCULATED PROPERTIES

• Acid pKa: 10.619197
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.4439845
• LogD (pH = 7.4): 5.443726
• Log P: 5.443988
• Molar Refractivity: 119.0916 cm^3
• Polarizability: 42.396534 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Metanol
• Apperance: Viscous Yellow Oil
• Melting Point: 60-80 °C (140-176 °F) (technical material) (depending on purity and cis/tans ratio)
• Boiling Point: Very high (decomposes slowly at or above 220 °C (428 °F))
• Flash Point: 100 °C; 2 °C; 212 °F; 35.6 °F
• Density: 1.25 at 20 °C; 1.12 at 22 °C (water = 1)
• Refractive Index: n20/D 1.57
• Vapor Pressure: Practically zero (1.4 x 10-9 mm Hg (190 nPa) at 20 °C), 0.51 nPa at 70 °C

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS: GZ1250000; GZ1251400
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T); Harmful (Xn)
• UN Number: 1648; 2761; 2810; 2811
• German water hazard class: 2; 3
• Hazard Class: 3; 6.1
• Packing Group: 2; 3; III
• Australian Hazchem: 2X
• Risk Statements: 11-20/21/22-36-52/53; 20/22-37-50/53; 25-37-48/22-50/53; R:25
• Safety Statements: 16-26-36/37-61; 24-36/37/39-60-61; 36/37/39-45-60-61; S:28-29-36/37/39-45
• EU Classification: T7
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 151
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08; GHS09
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H302-H312-H319-H332-H412; H301-H335-H373-H410; H302-H332-H335-H410
• GHS Precautionary statements: P210-P273-P280-P305 + P351 + P338; P261-P273-P301 + P310-P501; P261-P273-P501
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1648 3/PG 2; UN 2810 6.1/PG 3; UN 2811 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Concentration: 100 ng/μL in acetonitrile
• Grade: analytical standard; certified reference material; PESTANAL®, analytical standard; TraceCERT®
• Packaging: ampule of 100 mg; ampule of 250 mg
• Suitability: passes test for identity (NMR)
• Description: mixture of isomers
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H19Cl2NO3

DETAILS

MP Biomedicals - 02158896

Mixture of 8 isomers
Cypermethrin is a Type II pyrethrin and a potent inhibitor of calcineurin (protein phosphatase 2B).

Sigma Aldrich - C2237

Biochem/physiol Actions
Type II pyrethrin. A potent inhibitor of calcineurin (protein phosphatase 2B).

Sigma Aldrich - 51991

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 45806

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 45835

Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Sigma Aldrich - 36128

Application
Commission Regulation (EU) No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin
Legal Information
PESTANAL is a registered trademark of Sigma-Aldrich Laborchemikalien GmbH

Toronto Research Chemicals - C989000

Synthetic pyrethroid insecticide, usually exists as a mixture of cis and trans isomers. Ectoparasiticide.

REFERENCES

• Elliot, M., et al.: Pestic. Sci., 6, 537 (1975)
• Cantalamessa, F., et al.: Arch. Toxicol., 67, 510 (1993)