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Ethylenebis(oxyethylenenitrilo)tetraacetic acid
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Name

Ethylenebis(oxyethylenenitrilo)tetraacetic acid

 EINECS 200-651-2
CAS No. 67-42-5 Density 1.433 g/cm3
PSA 174.14000 LogP -2.03800
Solubility slightly soluble in water Melting Point 241 °C (dec.)(lit.)
Formula C14H24N2O10 Boiling Point 678.016 °C at 760 mmHg
Molecular Weight 380.352 Flash Point 363.851 °C
Transport Information N/A Appearance white to slightly off-white powder
Safety 24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 67-42-5 (Ethylenebis(oxyethylenenitrilo)tetraacetic acid) Hazard Symbols IrritantXi
Synonyms

Ethylene glycol-bis-(2-aminoethyl)tetraacetic acid;Aceticacid, [ethylenebis(oxyethylenenitrilo)]tetra- (6CI,8CI);1,2-Bis(2-aminoethoxyethane)-N,N,N',N'-tetraacetic acid;3,6-Dioxaoctane-1,8-diamine-N,N,N',N'-tetraacetic acid;Egtazic acid;Ethylene glycol bis(2-aminoethylether)-N,N,N',N'-tetraacetic acid;O,O'-Bis(2-aminoethyl)ethylene glycol-N,N,N',N'-tetraacetic acid;Ethylenebis(oxyethylenenitrilo)tetraacetic acid;

Article Data 4

Ethylenebis(oxyethylenenitrilo)tetraacetic acid Synthetic route

929-59-9

3,6-dioxa-1,8-diaminooctane

79-11-8

chloroacetic acid

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

Conditions
ConditionsYield
With sodium hydroxide
67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

23910-62-5

dianhydride of ethylene bis(oxyethylenenitrilo)tetraacetic acid

Conditions
ConditionsYield
With acetic anhydride In pyridine at 65℃; for 20h; Dehydration;98%
Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid With pyridine for 0.25h; Inert atmosphere;
Stage #2: With acetic anhydride at 65℃; for 24h; Inert atmosphere; Sealed tube;		91%
67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

5856-62-2

(S)-2-aminobutan-1-ol

850410-82-1

(-)-N,N,N',N'-tetrakis{[4-(S)-ethyloxazolin-2-yl]methyl}ethylene glycol bis(2-aminoethyl) ether

Conditions
ConditionsYield
Stage #1: ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid; (S)-2-aminobutan-1-ol In toluene for 20h; Reflux;
Stage #2: at 135℃; for 8h;		93%

europium(III) oxide

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

K(1+)*Eu(C6H12O2N2(CH2COO)4)(1-) = K[Eu(C6H12O2N2(CH2COO)4)]

Conditions
ConditionsYield
With potassium hydroxide In water suspn. stirring, heating (80°C); filtration, evapn. (vac.);90%

gadolinium(III) oxide

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

K(1+)*Gd(C6H12O2N2(CH2COO)4)(1-) = K[Gd(C6H12O2N2(CH2COO)4)]

Conditions
ConditionsYield
With potassium hydroxide In water suspn. stirring, heating (80°C); filtration, evapn. (vac.);90%

holmium(III) oxide

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

K(1+)*Ho(C6H12O2N2(CH2COO)4)(1-) = K[Ho(C6H12O2N2(CH2COO)4)]

Conditions
ConditionsYield
With potassium hydroxide In water suspn. stirring, heating (80°C); filtration, evapn. (vac.);90%

ytterbium(III) oxide

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

K(1+)*Yb(C6H12O2N2(CH2COO)4)(1-) = K[Yb(C6H12O2N2(CH2COO)4)]

Conditions
ConditionsYield
With potassium hydroxide In water suspn. stirring, heating (80°C); filtration, evapn. (vac.);90%
288-32-4

1H-imidazole

malachite

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

(3,12-bis(carboxylatomethyl)-6,9-dioxa-3,12-diazatetradecanedioate)bis(imidazole)dicopper(II)

Conditions
ConditionsYield
In water soln. of Cu salt and ligand in H2O heated under stirring (vac.), imidazole added; filtered, filtrate evapd. at room temp., recrystd. from H2O; elem. anal.;90%
67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

95-54-5

1,2-diamino-benzene

89735-41-1

ethylene glycol-bis-(β-aminoethylether) N,N,N',N'-tetrakis<2-benzimidazolyl>

Conditions
ConditionsYield
at 180℃; for 5h;87%
at 180℃; for 3h;87%
at 180 - 190℃; for 1h; Acetylation;70%

yttrium(III) oxide

67-42-5

ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid

7732-18-5

water

107-15-3

ethylenediamine

(ethylenediamine*H2)[YIII(ethyleneglycol-bis(2-aminoethylether)-N,N,N',N'-tetraacarboxylate)H2O]2*6H2O

Conditions
ConditionsYield
Stage #1: yttrium(III) oxide; ethylene glycol-bis(2-aminoethyl)-N,N,N'N,'-tetraacetic acid; water for 18h; Heating; Reflux;
Stage #2: ethylenediamine pH=6;		86.25%

Ethylenebis(oxyethylenenitrilo)tetraacetic acid Consensus Reports

Glycol ether compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Ethylenebis(oxyethylenenitrilo)tetraacetic acid Specification

1.Introduction of Ethylenebis(oxyethylenenitrilo)tetraacetic acid

The Ethylenebis(oxyethylenenitrilo)tetraacetic acid, with the CAS registry number 67-42-5, is also known as Egtazic acid. It belongs to the product categories of Analytical Chemistry; Chelating Reagents; Complexones; EDTA Analogs. Its EINECS registry number is 200-651-2. This chemical's molecular formula is C14H24N2O10 and molecular weight is 380.35. What's more, its IUPAC name is called 2-[2-[2-[2-[Bis(carboxymethyl)amino]ethoxy]ethoxy]ethyl-(carboxymethyl)amino]acetic acid. It should be stored in a sealed place. This chemical can be used in organic synthesis.

2.Physical properties of Ethylenebis(oxyethylenenitrilo)tetraacetic acid

(1)ACD/LogP: -0.388; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -5.38; (4)ACD/LogD (pH 7.4): -5.43; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 12; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 17; (12)Polar Surface Area: 174.14 Å2; (13)Index of Refraction: 1.547; (14)Molar Refractivity: 84.1 cm3; (15)Molar Volume: 265.364 cm3; (16)Polarizability: 33.34×10-24cm3; (17)Surface Tension: 69.802 dyne/cm; (18)Density: 1.433 g/cm3; (19)Flash Point: 363.851 °C; (20)Enthalpy of Vaporization: 108.482 kJ/mol; (21)Boiling Point: 678.016 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

3.Structure descriptors of Ethylenebis(oxyethylenenitrilo)tetraacetic acid

(1) SMILES: O=C(O)CN(CC(=O)O)CCOCCOCCN(CC(=O)O)CC(=O)O
(2) InChI: InChI=1S/C14H24N2O10/c17-11(18)7-15(8-12(19)20)1-3-25-5-6-26-4-2-16(9-13(21)22)10-14(23)24/h1-10H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24)
(3) InChIKey: DEFVIWRASFVYLL-UHFFFAOYSA-N
 

4.Uses of Ethylenebis(oxyethylenenitrilo)tetraacetic acid

Ethylenebis(oxyethylenenitrilo)tetraacetic acid is used to produce other chemicals. For example, it can react with benzene-1,2-diamine to get 1,8-bis[bis(benzimidazol-2'-ylmethyl)amino]-3,6-dioxaoctane. This reaction needs the temperature of 180 °C. The reaction time is 3 hours. The yield is 87 %.

Ethylenebis(oxyethylenenitrilo)tetraacetic acid can react with benzene-1,2-diamine to get 1,8-bis[bis(benzimidazol-2'-ylmethyl)amino]-3,6-dioxaoctane.

5.Safety information of Ethylenebis(oxyethylenenitrilo)tetraacetic acid

This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing and avoid contacting with skin, eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

6.The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
rat LD50 oral 3587mg/kg (3587mg/kg)   Toxicology and Applied Pharmacology. Vol. 16, Pg. 807, 1970.

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