N,N'-Bis(Salicylidene)Ethylenediamine supplier

Name
N,N'-BIS(SALICYLIDENE)ETHYLENEDIAMINE
EINECS 202-376-3
CAS No. 94-93-9
Article Data186
CAS DataBase
Density 1.1028 (rough estimate)
Solubility chloroform: 0.1 g/mL, clear
Melting Point 127-128 °C(lit.)
Formula C₁₆H₁₆N₂O₂
Boiling Point 411.48°C (rough estimate)
Molecular Weight 268.315
Flash Point 193.6oC
Transport Information
Appearance yellow fine crystalline powder
Safety 26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
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;
PSA 65.18000
LogP 2.63580

Synthetic route

: 90-02-8
salicylaldehyde

: 107-15-3
ethylenediamine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In ethanol Reflux;	86%

: 3949-36-8
3-acetylcoumarin

: 107-15-3
ethylenediamine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
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

Conditions	Yield
In ethanol for 0.5h; Heating;	A 30% B 35%

...Expand

: 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

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

...Expand

: 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)

: 107-15-3
ethylenediamine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
In ethanol

: 80622-20-4
2-bromo-1-salicylideneaminoethane

: 7664-41-7
ammonia

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: salen

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Kinetics; UV-irradiation;

: 90-02-8
salicylaldehyde

2-chloro-benzenediazonium-(1)-chloride: 2-chloro-benzenediazonium-(1)-chloride

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 28 percent / 33percent aq. NH3 / ethanol / 1.) 1 h, r.t., 2.) heating on the water-bath, 30 min 2: 55 percent / ethanol / 24 h / Ambient temperature View Scheme

: 1846-76-0
ethyl coumarin-3-carboxylate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 35 percent / ethanol / 0.5 h / Heating View Scheme

: 54396-25-7
N-phenyl-2-oxochromene-3-carboxamide

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CHCl3 / Heating 2: 35 percent / ethanol / 0.5 h / Heating View Scheme

: 1846-99-7
N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CHCl3 / Heating 2: 35 percent / ethanol / 0.5 h / Heating View Scheme

: 4081-35-0
N,N'-disalicylidene-1,6-hexanediamine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform-d1 / 1 h / UV-irradiation 2: ethanol / 3 h / Reflux View Scheme

: 14167-22-7
Zn(salen)

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With adenosine diphosphate tetrabutylammonium salt In dimethylsulfoxide-d6
With sodium pyrophosphate In dimethyl sulfoxide pH=7.4; Reagent/catalyst;

: 90-02-8
salicylaldehyde

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
In deuteromethanol

: 18601-34-8
(μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)]

: 138-14-7
deferoxamine mesylate

A: 14836-73-8
ferrioxamine B

B: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With sodium chloride In water Concentration;

...Expand

: 17754-90-4
4-(Diethylamino)salicylaldehyde

: 109-89-7
diethylamine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
In ethanol for 24h; Reflux;

: [FeIII(salen)(H2O)]NO3

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With sodium pyrophosphate In dimethyl sulfoxide for 0.0833333h; pH=7.4; Reagent/catalyst;

: [FeIII(salen)(H2O)]NO3

A: 90-02-8
salicylaldehyde

B: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With sodium pyrophosphate; water In dimethyl sulfoxide for 1.33333h; pH=7.4; Reagent/catalyst;

: trans-[MnII(salen)(H2O)2]

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With phenylphosphonate In dimethyl sulfoxide for 0.0333333h; pH=7.4; Reagent/catalyst; Inert atmosphere;

: trans-[MnII(salen)(H2O)2]

A: 90-02-8
salicylaldehyde

B: 94-93-9
N,N'-ethylenebis(salicylideneimine)

Conditions

Conditions	Yield
With water In dimethyl sulfoxide for 0.0666667h; pH=7.4; Inert atmosphere;

: 7439-89-6
iron

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 18601-34-8
(μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)]

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 1.3h; Electrochemical reaction; Inert atmosphere;	99%

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 18653-98-0
N,N'-bis(2-hydroxybenzyl)ethylenediamine

Conditions

Conditions	Yield
With sodium tetrahydroborate In dichloromethane	98%
With sodium tetrahydroborate	98%
With sodium tetrahydroborate In ethanol at 20℃; Reflux;	91%

: 546-68-9
titanium(IV) isopropylate

: 75-09-2
dichloromethane

: 372-20-3
3-fluorophenol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(3-fluorophenolato)2]*0.25CH2Cl2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	97%

...Expand

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 35948-25-5
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

: 1166187-91-2
C40H34N2O6P2

Conditions

Conditions	Yield
In ethanol at 20℃; for 12h;	96.7%

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 2-bromo-1,3-2-dioxaphospholane

: 1,1-ethylenedioxy-3,4,11,12-dibenzo-6-aza-9-ammonium-2,13-dioxa-1-phospha[8.3.0(1,10)]tridecatri-3,5,11-ene bromide

Conditions

Conditions	Yield
In dichloromethane for 4h;	96%

: 546-68-9
titanium(IV) isopropylate

: 95-48-7
ortho-cresol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(2-methylphenolato)2]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	94%

...Expand

: 546-68-9
titanium(IV) isopropylate

: 371-41-5
4-Fluorophenol

: 75-09-2
dichloromethane

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(4-fluorophenolato)2]*0.375CH2Cl2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	93%

...Expand

: 546-68-9
titanium(IV) isopropylate

: 100-02-7
4-nitro-phenol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(4-nitrophenolato)2]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	93%

...Expand

: 7440-02-0
nickel

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 14167-20-5, 1160066-31-8
nickel(II) salen

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In water; acetonitrile at 20℃; for 1.5h; Electrochemical reaction;	91%

: manganese(II) chloride tetrahydrate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: C16H14N2O2(2-)*Mn(3+)*Cl(1-)*2H2O

Conditions

Conditions	Yield
In ethanol	90%

: 546-68-9
titanium(IV) isopropylate

: 75-09-2
dichloromethane

: 367-12-4
2-fluorophenol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(2-fluorophenolato)2]*0.25CH2Cl2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	89%

...Expand

: 546-68-9
titanium(IV) isopropylate

: 110-54-3
hexane

: 349-58-6
3,5-bis-(trifluoromethyl)phenol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(3,5-bis(trifluoromethyl)phenolate)2]*0.375C6H14

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	89%

...Expand

: 546-68-9
titanium(IV) isopropylate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 108-95-2
phenol

: 216670-23-4
Ti(OPh)2(N,N'-ethylenebis(salicylideneiminate))

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	89%

...Expand

: 32315-10-9
bis(trichloromethyl) carbonate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 5,10-dioxa-6,9-dioxo-18,20-diazadecahydro[5]helicene

Conditions

Conditions	Yield
With samarium; titanium tetrachloride In tetrahydrofuran for 2h; Reagent/catalyst; Temperature; Inert atmosphere; Reflux; diastereoselective reaction;	88%

: 7732-18-5
water

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 7440-66-6
zinc

: 14897-25-7
Zn(H2O)(C2H4(NCHC6H4O)2)

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.5h; Electrochemical reaction;	88%

...Expand

: 7439-89-6
iron

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 578710-63-1, 14167-12-5
N,N'-ethylenebis(salicylideneiminato)iron(II)

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.5h; Electrochemical reaction; Inert atmosphere;	88%

: 546-68-9
titanium(IV) isopropylate

: 106-44-5
p-cresol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(4-methylphenolato)2]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	88%

...Expand

Reaxys ID: 29769774: Reaxys ID: 29769774

: 7732-18-5
water

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 543689-39-0, 200950-95-4, 80786-75-0
Mn2O2(OC6H4CHNCH2CH2NHCC6H4O)2

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 1.5h; Electrochemical reaction;	87%

...Expand

: neodymium(III) chloride

: 64-17-5
ethanol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: C16H16N2O2*Nd(3+)*3Cl(1-)*2C2H6O

Conditions

Conditions	Yield
at 80℃; for 3h;	86.3%

...Expand

: 940-71-6
2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 1356329-92-4
C48H42N9O6P3

Conditions

Conditions	Yield
With Al2O3/KOH In toluene at 25℃; for 2h; regiospecific reaction;	86%

: 546-68-9
titanium(IV) isopropylate

: 108-39-4
3-methyl-phenol

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: [Ti(N,N’-ethylenebis(salicylideneiminate))(3-methylphenolato)2]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;	86%

...Expand

: 67-56-1
methanol

: uranyl acetate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: C17H17N2O5U

Conditions

Conditions	Yield
for 3h; Reflux;	85%

...Expand

: iron(III) chloride

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 38586-93-5, 16649-19-7
[1,6-bis(2-hydroxyphenyl)-2,5-diaza-hexa-1,5-diene]iron(III) chloride

Conditions

Conditions	Yield
In ethanol at 20℃; for 4h; Inert atmosphere;	85%
In ethanol Reflux;	76%
for 6h; pH=7; Reflux;
In methanol at 25℃; for 10h; Inert atmosphere;
With trimethylamine In methanol Inert atmosphere;

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 90-02-8
salicylaldehyde

Conditions

Conditions	Yield
With zirconium hydrogen sulfate; silica gel In hexane for 2.8h; Heating;	84%
With water In dimethyl sulfoxide for 0.5h; pH=7.4; Time;

: 6156-78-1
manganese (II) acetate tetrahydrate

: 94-93-9
N,N'-ethylenebis(salicylideneimine)

: 19478-47-8, 51436-86-3, 53318-90-4
[((bis(salicylidene)ethylenediamine)(-2H))Mn(acetate)]

Conditions

Conditions	Yield
In ethanol for 2h; Reflux;	83%

N,N'-Bis(Salicylidene)Ethylenediamine Chemical Properties

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:

N,N'-Bis(Salicylidene)Ethylenediamine 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.

N,N'-Bis(Salicylidene)Ethylenediamine Consensus Reports

Reported in EPA TSCA Inventory.

N,N'-Bis(Salicylidene)Ethylenediamine Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits toxic fumes of NO_x.
Hazard Codes:
Irritant Xi
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

N,N'-Bis(Salicylidene)Ethylenediamine 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.

Product Name

N,N'-BIS(SALICYLIDENE)ETHYLENEDIAMINE

Synthetic route

N,N'-Bis(Salicylidene)Ethylenediamine Chemical Properties

N,N'-Bis(Salicylidene)Ethylenediamine Toxicity Data With Reference

N,N'-Bis(Salicylidene)Ethylenediamine Consensus Reports

N,N'-Bis(Salicylidene)Ethylenediamine Safety Profile

N,N'-Bis(Salicylidene)Ethylenediamine Specification

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