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Basic Information
CAS No.: 94-93-9
Name: N,N'-BIS(SALICYLIDENE)ETHYLENEDIAMINE
Article Data: 186
Molecular Structure:
Molecular Structure of 94-93-9 (N,N'-BIS(SALICYLIDENE)ETHYLENEDIAMINE)
Formula: C16H16N2O2
Molecular Weight: 268.315
Synonyms: o-Cresol, a,a'-(ethylenedinitrilo)di- (8CI);1,2-Bis[[(2-hydroxyphenyl)methylene]amino]ethane;1,2-Ethanedi(salicylaldimine);1,2-Ethanediamine,N,N'-bis[(2-hydroxyphenyl)methylene]-;1,6-Bis(2-hydroxyphenyl)-2,5-diazahexa-1,5-diene;NSC2079;a,a'-(Ethylenedinitrilo)di-o-cresol;
EINECS: 202-376-3
Density: 1.1028 (rough estimate)
Melting Point: 127-128 °C(lit.)
Boiling Point: 411.48°C (rough estimate)
Flash Point: 193.6oC
Solubility: chloroform: 0.1 g/mL, clear
Appearance: yellow fine crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26
PSA: 65.18000
LogP: 2.63580
Synthetic route
90-02-8

salicylaldehyde

107-15-3

ethylenediamine

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;100%
In ethanol at 20℃; for 4h; Reflux;100%
In methanol at 20℃;99%
107-15-3

ethylenediamine

69-72-7

salicylic acid

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol for 1h; Reflux; Inert atmosphere;99.6%
89-95-2

2-methyl-benzyl alcohol

107-15-3

ethylenediamine

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
for 0.0111111h; microwave irradiation;98%
In benzene Heating;92%
In benzene for 3h; Heating;85%
90-01-7

salicylic alcohol

107-15-3

ethylenediamine

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
Stage #1: ethylenediamine In ethanol at 20℃; Green chemistry;
Stage #2: salicylic alcohol With oxygen In ethanol at 20℃; under 760.051 Torr; for 1.46667h; Catalytic behavior; Green chemistry;
95%
With oxygen In toluene at 90℃; Sealed tube;79%
118-93-4

o-hydroxyacetophenone

107-15-3

ethylenediamine

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol Reflux;86%
3949-36-8

3-acetylcoumarin

107-15-3

ethylenediamine

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol for 24h; Ambient temperature;55%
74555-99-0

N-(4-bromophenyl)-2-oxo-2H-chromene-3-carboxamide

107-15-3

ethylenediamine

A

74556-05-1

N-(2-Amino-ethyl)-N'-(4-bromo-phenyl)-malonamide

B

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol for 0.5h; Heating;A 30%
B 35%
74556-01-7

coumarin-3-carboxy-(4-bromo-3-methyl)-anilide

107-15-3

ethylenediamine

A

N-(2-Amino-ethyl)-N'-(4-bromo-3-methyl-phenyl)-malonamide

B

94-93-9

N,N'-ethylenebis(salicylideneimine)

Conditions
ConditionsYield
In ethanol for 0.5h; Heating;A 32%
B 35%

N,N'-bis(salicylidene)-1,2-ethylenediamine zinc

64-19-7

acetic acid

94-93-9

N,N'-ethylenebis(salicylideneimine)

N,N'-disalicyliden-ethylenediamine; magnesium salt

64-19-7

acetic acid

94-93-9

N,N'-ethylenebis(salicylideneimine)

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Chemistry

Chemistry informtion about N,N'-Bis(Salicylidene)Ethylenediamine (CAS NO.94-93-9) is:
IUPAC Name: (6e)-6-[[2-[[(E)-(6-Oxocyclohexa-2,4-Dien-1-Ylidene)Methyl]Amino]Ethylamino]Methylidene]Cyclohexa-2,4-Dien-1-One
Synonyms: Alpha,Alpha'-Diethylenedinitrilodi-O-Cresol ; A,A'-(Ethylenedinitrilo)Di-O-Cresol ; 2,2'-Ethylenebis(Nitrilomethylidene)Diphenol ; 2-[((2-[(2-Hydroxybenzylidene)Amino]Ethyl)Imino)Methyl]Phenol ; Labotest-Bb Lt00772290 ; Bis-(Salicylidene)-Ethylenediamine ; Bis(Salicylaldehyde)Ethylene Diamine ; Ethylene-Bis(Salicylimine)
MF: C16H16N2O2
MW: 268.31
EINECS: 202-376-3 
Density: 1.13 g/cm3
Melting Point: 127-128 °C(lit.)
Flash Point: 294.1 °C
Boiling Point: 448.8 °C at 760 mmHg
Vapour Pressure: 1.14E-08 mmHg at 25°C
Enthalpy of Vaporization: 73.46 kJ/mol
Solubility chloroform: 0.1 g/mL, clear
Merck: 14,8322
BRN: 535296
Following is the molecular structure of N,N'-Bis(Salicylidene)Ethylenediamine (CAS NO.94-93-9) is:

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
rat LDLo oral 500mg/kg (500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:
IrritantXi
Risk Statements:
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
WGK Germany: 3
RTECS: SL3780000

Specification

 N,N'-Bis(Salicylidene)Ethylenediamine (CAS NO.94-93-9) is a yellow fine crystalline powder.
First Aid Measures:
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion: Get medical aid. Wash mouth out with water.
Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician: Treat symptomatically and supportively. 
Handling and Storage
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.