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35554-44-0

Basic Information
CAS No.: 35554-44-0
Name: Imazalil
Article Data: 6
Cas Database
Molecular Structure:
Molecular Structure of 35554-44-0 (Imazalil)
Formula: C14H14Cl2N2O
Molecular Weight: 297.184
Synonyms: Enilconazole;CGA 41333;1H-Imidazole,1-[2-(2,4-dichlorophenyl)-2- (2-propenyloxy)ethyl]-;Deccozil S 75;1-[2-(2,4-dichlorophenyl)-2-prop-2-enoxy-ethyl]imidazole nitrate;1-[20(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole;lmazalil;1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;(±)-l-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-l H-imidazole;
EINECS: 252-615-0
Density: 1.23 g/cm3
Melting Point: 52.7 °C
Boiling Point: 448.5 °C at 760 mmHg
Flash Point: 225.1 °C
Solubility: 0.018 g/100 mL in water
Appearance: slightly yellow to brown solidified oil
Hazard Symbols: HarmfulXn, DangerousN
Risk Codes: 20/22-41-50/53
Safety: 26-39-60-61
Transport Information: UN 2588
PSA: 27.05000
LogP: 4.13380
Synthetic route
24155-42-8

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

107-05-1

3-chloroprop-1-ene

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20℃; for 1h;
Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 30℃; for 3h; Solvent; Temperature;
95.6%
Stage #1: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol With potassium hydroxide In water; dimethyl sulfoxide at 20 - 35℃; for 1h;
Stage #2: 3-chloroprop-1-ene In water; dimethyl sulfoxide at 35 - 40℃; Reagent/catalyst;
68%
288-32-4

1H-imidazole

107-05-1

3-chloroprop-1-ene

4252-78-2

2,2',4'-trichloroacetophenone

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
Stage #1: 2,2',4'-trichloroacetophenone With tris(triphenylphosphine)ruthenium(II) chloride; acetic acid; triethylamine at 70℃; for 9h;
Stage #2: 1H-imidazole With N,N-dimethyl acetamide; sodium hydroxide at 50 - 100℃; for 5h;
Stage #3: 3-chloroprop-1-ene at 105℃; for 6h; Reagent/catalyst; Solvent;
64.4%
106-95-6

allyl bromide

24155-42-8

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide17%
24155-42-8

1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-ol

allyl halide

allyl halide

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
74-93-1

methylthiol

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

1-(2-(2,4-dichlorophenyl)-2-(3-(methylthio)propoxy)ethyl)-1H-imidazole

Conditions
ConditionsYield
With C38H28Au2F12FeN2O8P2S4 In 1,4-dioxane at 45℃; for 20h; Inert atmosphere; Glovebox; Sealed tube;99%
94-99-5

2,4-Dichlorobenzyl chloride

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

1-[β-(Allyloxy)-2,4-dichlorophenethyl]-3-(2,4-dichlorobenzyl)imidazolium chloride hydrate

2-chloroaceto-p-fluoroanilide

2-chloroaceto-p-fluoroanilide

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

57265-11-9

1-[β-(Allyloxy)-2,4-dichlorophenethyl]-3-[N-(p-fluorophenyl)-carbamoylmethyl]imidazolium chloride

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

(+)-imazalil

(-)-imazalil

Conditions
ConditionsYield
With Lux Cellulose-2 (cellulose tris-(3-chloro-4-methylphenylcarbamate) In hexane; isopropyl alcohol at 20℃; Thermodynamic data; Reagent/catalyst; Temperature; Resolution of racemate;
35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

A

166734-82-3

S-(+)-imazalil

B

166734-81-2

R-(−)-imazalil

Conditions
ConditionsYield
With CHIRALCEL OJ column (10 µm; 250*4.6 mm) In methanol; ethanol; hexane Solvent; Resolution of racemate;

2-(aminooxy)acetic acid hemihydrochloride

35554-44-0

1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole

imazalil hapten

Conditions
ConditionsYield
Stage #1: 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole With potassium permanganate; sodium periodate In 1,4-dioxane at 20℃; for 4h;
Stage #2: 2-(aminooxy)acetic acid hemihydrochloride In 1,4-dioxane at 60℃; for 24h;
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    Product Name:Imazalil Formula:C14H14Cl2N2O Molecular Weight:297.20 CAS No.:35554-44-0 EINECS:252-615-0 Density:1.23 g/cm3 Melting Point:52.7 °C Boiling Point:448.5 °C at 760 mmHg Flash Point:225.1 °C Solubility:0.018 g

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    Chemical Name imazalil Synonyms Bromazil;MAZAL;1-[2-(Allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole,Imazalil;Enilconazole;FLO-PRO;allyl (RS)-1-(2,4-dichlorophenyl)-2-imidazol-1-ylethyl ether;Fcundal;Florasan;rac-1-[(2R)-2-(2,

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Specification

The IUPAC name of Fungaflor is 1-[2-(2,4-dichlorophenyl)-2-prop-2-enoxyethyl]imidazole. With the CAS registry number 35554-44-0, it is also named as Enilconazole. The classification codes are Agricultural Chemical; Antifungal; Drug / Therapeutic Agent; Fungicide; Fungicide, bactericide, wood preservative; Fungicides, industrial; Pesticides; Reproductive Effect; Skin / Eye Irritant. It is slightly yellow to brown solidified oil which is soluble in ethanol, methanol, benzene, xylene, heptane, hexane, petroleum ether and other organic solvents. Besides, this chemccal is highly toxic and flammable. When heated to decomposition it emits toxic fumes of Cl and NOx. So the storage environment should be well- ventilated, low-temperature and dry. Keep Fungaflor separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.58; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.33; (4)ACD/LogD (pH 7.4): 3.49; (5)ACD/BCF (pH 5.5): 17.36; (6)ACD/BCF (pH 7.4): 251.91; (7)ACD/KOC (pH 5.5): 118.56; (8)ACD/KOC (pH 7.4): 1720.44; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.573; (13)Molar Refractivity: 79.38 cm3; (14)Molar Volume: 240.7 cm3; (15)Polarizability: 31.46×10-24 cm3; (16)Surface Tension: 40.8 dyne/cm; (17)Enthalpy of Vaporization: 67.99 kJ/mol; (18)Vapour Pressure: 8.16E-08 mmHg at 25°C; (19)Rotatable Bond Count: 6; (20)Exact Mass: 296.048319; (21)MonoIsotopic Mass: 296.048319; (22)Topological Polar Surface Area: 27; (23)Complexity: 291.

Preparation of Fungaflor: It can be obtained by the following method:

Uses of Fungaflor: It is a fungicide widely used in agriculture, particularly in the growing of citrus fruits. It is also used in veterinary medicine as a topical antimycotic.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation and if swallowed, but also very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. What's more, it has risk of serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear eye / face protection. This material and its container must be disposed of as hazardous waste. Avoid release to the environment. Refer to special instructions / safety data sheets. 

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1ccc(c(Cl)c1)C(OC\C=C)Cn2ccnc2
2. InChI:InChI=1/C14H14Cl2N2O/c1-2-7-19-14(9-18-6-5-17-10-18)12-4-3-11(15)8-13(12)16/h2-6,8,10,14H,1,7,9H2 
3. InChIKey:PZBPKYOVPCNPJY-UHFFFAOYAI

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 640mg/kg (640mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 309, 1981.
rabbit LD50 skin 4200mg/kg (4200mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A230, Pg. 1983,
rat LC50 inhalation 16gm/m3/4H (16000mg/m3)   Pesticide Manual. Vol. 9, Pg. 482, 1991.
rat LD50 intraperitoneal 155mg/kg (155mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 309, 1981.
rat LD50 oral 227mg/kg (227mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 309, 1981.
rat LD50 skin 4200mg/kg (4200mg/kg)   Pesticide Manual. Vol. 9, Pg. 482, 1991.