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Cyclanilide

Cyclanilide structure

CAS No:
113136-77-9
Formula:
C11H9Cl2NO3
Chemical Name:
Cyclanilide
Synonyms:
Cyclopropanecarboxylic acid,1-[[(2,4-dichlorophenyl)amino]carbonyl]-;1-[[(2,4-Dichlorophenyl)amino]carbonyl]cyclopropanecarboxylic acid;Cyclanilide;RPA 90946;1-[(2,4-Dichlorophenyl)carbamoyl]cyclopropane-1-carboxylic acid;1-((2,4-Dichlorophenyl)carbamoyl)cyclopropanecarboxylicacid
Categories:
Agrochemicals > Plant Growth Regulators

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Description

A white or pale yellow, crystalline or powdery solid. No characteristic odor.

Cyclanilide Basic Attributes

Molecular Weight：

274.1

Exact Mass：

274.10

EC Number：

419-150-7

HScode：

2924299020

Characteristics

PSA：

66.40000

XLogP3：

2.54

Density：

1.4691-1.4820 g/cm³ @ Temp: 20 °C

Melting Point：

195.5 °C

Boiling Point：

513.2±50.0 °C(Predicted)

Flash Point：

259.0±32.9 °C

Refractive Index：

1.654

Water Solubility：

Solubility (g/100 ml): acetone 5.29; acetonitrile 0.50; dichloromethane 0.17; ethylacetate 3.18; hexane <0.0001; methanol 5.91; 1-octanol 6.72; 2-propanol 6.82.

Storage Conditions：

0-6°C

Vapor Pressure：

0mmHg at 25°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

wgk germany：

hazard class code：

22-51/53

safety instructions：

Marks：

Xn,N

Stability/Shelf Life：

Stable for 14 days at 54 deg C; stable for 30 days at 50 deg C; stable for 90 days at 35 deg C; stable for 1 yr at room temp; stable for 14 days of continual exposure to artificial sunlight (23 deg C); stable to metals over the range of 30-150 deg C; degraded between 40-90 deg C in the presence of metal ions.

Precautionary statement(s)：

P273

Hazard Statements：

H302-H411

Cyclanilide Use and Manufacturing

Methods of Manufacturing

First synthesize cyclopropyl-1, 1-dicarboxylic acid ethyl ester. Place 1000 mL of dichloroethane, 160 g of K2CO3, and 2.4 g of tetrabutylammonium bromide in a reaction flask, heat to reflux, and add 120 g of diethyl malonate dropwise within 0.5 h. After the completion of the dropping, the reaction was refluxed for 6h, cooled, 300mL of water was added, stirred, and liquid-separated. The organic layer was dried with anhydrous Na2SO4, and the dichloroethane was recovered at atmospheric pressure. The 94-98°C/1333.22Pa fraction was collected under reduced pressure, for a total of 116g. The rate is 83%, the product is a colorless oily liquid with a special fragrance. Synthesis of cyclopropionamide acid. 4.6g sodium metal, 100mL methanol, heat and concentrate to dryness, add 150mL anhydrous toluene and 32.4 2, 4-dichloroaniline, stir, dropwise add 31.6g cyclopropyl-1, 1-dicarboxylic acid ethyl ester at room temperature, After the completion of the dropping, the temperature was fractionated to 110°C, 250 mL of water was added, hydrolyzed under reflux for 2 h, cooled and liquid-separated. The water was acidified to pH<3 with dilute hydrochloric acid, and a large amount of white solid was precipitated. It was filtered, washed with water, and dried to obtain 42.7 g of product, mp191～ 193℃[literature value 192～193.5℃]. The yield was 76.8% and the purity was 98.6%.

Uses

Cyclanilide is a plant growth regulator that functions by interactting with auxin-regulated processes. Cyclanilide is commonly used on cotton plants to either suppress vegetative growth or accelerate senescence. Cyclanilide is also used as a bioregulator of deciduous fruit trees.

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