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122-34-9

Basic Information
CAS No.: 122-34-9
Name: Simazine
Article Data: 23
Molecular Structure:
Molecular Structure of 122-34-9 (Simazine)
Formula: C7H12ClN5
Molecular Weight: 201.659
Synonyms: 1,3,5-Triazine-2,4-diamine,6-chloro-N,N'-diethyl- (9CI);2,4-Bis(ethylamino)-6-chloro-s-triazine;2,4-Di(ethylamino)-6-chloro-1,3,5-triazine;2-Chloro-4,6-bis(ethylamino)-s-triazine;2-Chloro-4,6-di(ethylamino)triazine;Aktinit S;Aquazine;Azotop;BatazinaFLO;Bitemol S 50;CAT;CAT (pesticide);CET;Geigy 27692;Gesatop D;H 1803;Herbatoxol S;Herbazin;Herbazin 50;Herbex;Hungazin DT;Radocon;Simanex;Simatox;Simatsin-neste;Simazin;Tafazine;Tafazine 50W;Triazine A 384;W 6658;Yrodazin;
EINECS: 204-535-2
Density: 1.302 g/cm3
Melting Point: 225 °C
Boiling Point: 365.8 °C at 760 mmHg
Flash Point: 175 °C
Solubility: 0.0005 g/100 mL in water
Appearance: White powder
Hazard Symbols: HarmfulXn,DangerousN
Risk Codes: 40-50/53-39/23/24/25-23/24/25-11
Safety: 36/37-46-60-61-45
Transport Information: UN 2811
PSA: 62.73000
LogP: 1.53460
Synthetic route
108-77-0

1,3,5-trichloro-2,4,6-triazine

75-04-7

ethylamine

122-34-9

Simazine

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 0 - 50℃; for 1.5h;92%
With sodium carbonate In water; acetone at 0 - 20℃;81%
With sodium hydrogencarbonate In acetone at 20℃; for 4h; pH=7;70%
3440-19-5

2-ethylamino-4,6-dichloro-[1,3,5]triazine

75-04-7

ethylamine

122-34-9

Simazine

Conditions
ConditionsYield
With sodium hydroxide In water at 25 - 40℃;
122-34-9

Simazine

124-40-3

dimethyl amine

16268-59-0

2,4-Bisethylamino-6-dimethylamino-1,3,5-triazin

Conditions
ConditionsYield
With water; sodium carbonate for 1.5h; Heating;95%
122-34-9

Simazine

616-38-6

carbonic acid dimethyl ester

1014-70-6

2,4-Bis(ethylamino)-6-methylthio-1,3,5-triazine

Conditions
ConditionsYield
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere;93%
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere;84%
122-34-9

Simazine

20611-81-8

disodium cyanamide

53736-39-3

2,4-Bisethylamino-6-cyanamino-1,3,5-triazin

Conditions
ConditionsYield
In water; dimethyl sulfoxide at 140℃; for 0.5h;85.5%
In water; N,N-dimethyl-formamide at 130 - 135℃; for 0.5h;40%
122-34-9

Simazine

110-80-5

2-ethoxy-ethanol

30360-73-7

2,4-Bisethylamino-6-(2-ethoxy-ethoxy)-1,3,5-triazin

Conditions
ConditionsYield
With disodium cyanamide In water for 1.5h; Heating;82.5%
122-34-9

Simazine

99-92-3

4-Aminoacetophenone

840528-65-6

2,4-bis(ethylamino)-6-(4'-acetylphenylamino)-1,3,5-triazine

Conditions
ConditionsYield
With sodium carbonate In water; N,N-dimethyl-formamide for 12h; Reflux;78%
122-34-9

Simazine

105-58-8

Diethyl carbonate

30360-82-8

N2,N4-diethyl-6-(ethylthio)-1,3,5-triazine-2,4-diamine

Conditions
ConditionsYield
With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere;76%
122-34-9

Simazine

94-09-7

p-aminoethylbenzoate

119712-29-7

ethyl(2,4-bis-ethylamino-s-triazin-6-yl)aminobenzoate

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Heating;73%
122-34-9

Simazine

141-43-5

ethanolamine

125101-20-4

2-(4,6-Bis-ethylamino-[1,3,5]triazin-2-ylamino)-ethanol

Conditions
ConditionsYield
With sodium methylate70%
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    simazine

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Chemistry

Molecule structure of Simazine (CAS NO.122-34-9):

IUPAC Name: 6-chloro-2-N,4-N-diethyl-1,3,5-triazine-2,4-diamine 
Molecular Weight: 201.65668 g/mol
Molecular Formula: C7H12ClN5 
Density: 1.318 g/cm3 
Boiling Point: 365.8 °C at 760 mmHg 
Flash Point: 175 °C
Index of Refraction: 1.622
Molar Refractivity: 53.9 cm3
Molar Volume: 152.9 cm3
Polarizability: 21.37×10-24 cm3
Surface Tension: 58.4 dyne/cm 
Enthalpy of Vaporization: 61.21 kJ/mol
Vapour Pressure: 1.53E-05 mmHg at 25 °C
XLogP3: 2.2
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Tautomer Count: 5
Exact Mass: 201.078123
MonoIsotopic Mass: 201.078123
Topological Polar Surface Area: 62.7
Heavy Atom Count: 13
Complexity: 131
Canonical SMILES: CCNC1=NC(=NC(=N1)Cl)NCC
InChI: InChI=1S/C7H12ClN5/c1-3-9-6-11-5(8)12-7(13-6)10-4-2/h3-4H2,1-2H3,(H2,9,10,11,12,13)
InChIKey: ODCWYMIRDDJXKW-UHFFFAOYSA-N

Uses

 Simazine (CAS NO.122-34-9) can be widely used as a residual non-selective herbicide. In European Union states (EU directive 91/414/EEC), it is banned . It acts by inhibiting photosynthesis like atrazine. After application, It remains active in the soil for 2-7 months.

Production

 Simazine can be prepared in the laboratory from cyanuric chloride crystals and a strong solution of ethyl amine which is at least 50 percent by number in water. The reaction is highly exothermic and is therefore best carried out in an ice bath below 10 °C. It is also essential to carry out the synthesis in a fume hood since cyanuric chloride decomposes at high temperatures into hydrogen chloride and hydrogen cyanide both of which are highly toxic by inhalation.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral > 5gm/kg (5000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984,
mammal (species unspecified) LD50 oral 2014mg/kg (2014mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
National Technical Information Service. Vol. PB288-416,
mammal (species unspecified) LD50 unreported 1400mg/kg (1400mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(6), Pg. 81, 1979.
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04003,
mouse LDLo oral 5gm/kg (5000mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 27(8), Pg. 22, 1962.
pigeon LD50 oral > 5gm/kg (5000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984,
rabbit LD50 oral > 5gm/kg (5000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A369, Pg. 1984,
rabbit LD50 skin > 10200mg/kg (10200mg/kg)   Yakkyoku. Pharmacy. Vol. 37, Pg. 427, 1986.
rat LC50 inhalation 9800mg/m3/4H (9800mg/m3)   Farm Chemicals Handbook. Vol. -, Pg. C275, 1991.
rat LD50 oral 971mg/kg (971mg/kg)   Fundamental and Applied Toxicology. Vol. 7, Pg. 299, 1986.
rat LD50 skin > 5gm/kg (5000mg/kg)   Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 315, 1990.
rat LD50 unreported 1390mg/kg (1390mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 7(5), Pg. 54, 1963.

Specification

 Simazine (CAS NO.122-34-9) is an off-white crystalline compound which is sparingly soluble in water. Simazine (CAS NO.122-34-9) is also called 1-Chloro-3,5-bis(ethylamino)-2,4,6-triazine ; 2,4-Bis(aethylamino)-6-chlor-1,3,5-triazin ;
2,4-Bis(aethylamino)-6-chlor-1,3,5-triazin [German] ; 2,4-Bis(ethylamino)-6-chloro-s-triazine ; 2-Chloro-4,6-bis(ethylamino)-1,3,5-triazine ; 2-Chloro-4,6-bis(ethylamino)-s-triazine ; 4-26-00-01208 (Beilstein Handbook Reference) ; 6-Chloro-N,N'-diethyl-1,3,5-triazine-2,4-diamine ; 6-Chloro-N2,N4-diethyl-1,3,5-triazine-2,4-diamine ; A 2079 ; AI3-51142 ; Aktinit S ; Amizine ; Aquazine ; Azotop ; BRN 0010895 ; Batazina ; Batazine FLO ; Bitemol ; Bitemol S 50 ; CAT ; CAT (herbicide) ; CCRIS 1469 ; CDT ; CET ; Caswell No. 740 ; Cekusan ; Cekusima ; Cekuzina-S ; EPA Pesticide ; Chemical Code 080807 ; G 27692 ; G-27692 ; Geigy 27,692 ; Gesapun ; Gesaran ; Gesatop ; Gesatop 50 ; H 1803 ; HSDB 1765 ; Herbatoxol S ; Herbazin ; Primatel S ; Primatol S ; Princep ; Simanex ; Simatsin-neste ; Simazine 80W ; Symazine ; Tafazine ; Tafazine (VAN) ; Tafazine 50-W ; Taphazine ; Triazine A 384 ; W 6658 ; Yrodazin ; Zeapur .