Iminodiacetic acid supplier

Name
Iminodiacetic acid
EINECS 205-555-4
CAS No. 142-73-4
Article Data59
CAS DataBase
Density 1.436 g/cm³
Solubility water: 2.43 g/100 mL (5 °C)
Melting Point 243 °C (dec.)(lit.)
Formula C₄H₇NO₄
Boiling Point 370.6 °C at 760 mmHg
Molecular Weight 133.104
Flash Point 177.9 °C
Transport Information
Appearance white or yellowish crystalline powder
Safety 26-36-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Aceticacid, iminodi- (6CI,8CI);((Carboxymethyl)amino)acetic acid;Acetic acid,2,2'-iminobis-;Aminodiacetic acid;Diglycin;Diglycine;IDA;IDA(chelating agent);IMDA;Iminobis(acetic acid);N-(Carboxymethyl)glycine;NSC 18467;a-Iminodiacetic acid;
PSA 86.63000
LogP -0.86390

Synthetic route

: 628-87-5
iminodiacetonitrile

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With sodium hydroxide at 60 - 65℃; for 1h; Time;	97.25%
With water; calcium hydroxide at 25℃; for 5h;	90%
With Alcaligenes faecalis ZJUTBX11 cells encapsulated in alginate-chitosan-alginate membrane liquid core capsules In aq. buffer at 35℃; pH=7.5; Kinetics; Reagent/catalyst; pH-value; Enzymatic reaction;

: 111-42-2
2,2'-iminobis[ethanol]

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 160℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature;	96%
With nitrogen; hydrogen; copper In sodium hydroxide; water	90.2%
With sodium hydroxide at 160℃; for 4h; Reagent/catalyst;	29%
With copper; sodium hydroxide In water at 160℃; for 6.33333h; Inert atmosphere;

: 628-87-5
iminodiacetonitrile

A: α-(cyanomethylamino)acetic acid

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With Sphingomonas wittichii nitrilase NIT158; water In aq. phosphate buffer at 37℃; for 24h; pH=7.3; pH-value; Temperature; Solvent; Enzymatic reaction; enantiospecific reaction;	A 73% B n/a

: 71449-79-1
N-formyliminodiacetic acid

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydrogenchloride at 100℃; for 5h;	64%

: 79-11-8
chloroacetic acid

: 56-40-6
glycine

A: 139-13-9
nitrilotriacetic acid

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With lithium hydroxide for 144h; Ambient temperature;	A 12.5 g B 39%
With lithium hydroxide for 6h; Ambient temperature;	A 12.5 g B 39%

...Expand

: 117659-76-4
ethylenediamine tetraacetic acid

A: 50-00-0
formaldehyd

B: 298-12-4
Glyoxilic acid

C: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With ozone In water Kinetics; Oxidation;	A 15% B 32% C 20%

...Expand

: 50-00-0
formaldehyd

: 151-50-8
potassium cyanide

A: 79-14-1
glycolic Acid

B: 139-13-9
nitrilotriacetic acid

C: 56-40-6
glycine

D: 142-73-4
iminodiacetic acid

...Expand

: 50-00-0
formaldehyd

: 151-50-8
potassium cyanide

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With water

: 6829-40-9
aminomalonic acid diethyl ester

A: 617-45-8
aspartic Acid

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With chloroacetic acid ester; sodium ethanolate und Verseifung des Reaktionsgemisches mit kalter 3prozentiger Kalilauge; DL-aspartic acid;

: 1116-43-4
methanediyldiimino-tetra-acetonitrile

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydrogenchloride
With barium dihydroxide

: 139-13-9
nitrilotriacetic acid

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydrogenchloride at 190 - 200℃;

: 21954-96-1
2,2′-iminobis(acetamide)

: furan-2,3,5(4H)-trione pyridine (1:1)

: 142-73-4
iminodiacetic acid

: 408539-90-2
bis-glycyl-amine

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 19247-05-3
N,N-dicarboxymethyl hydrazine

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With water; sodium nitrite

: 100-97-0
hexamethylenetetramine

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydrogen cyanide Verseifung des entstandenen Dinitrils;

: 3987-53-9
N-benzyliminodiacetic acid

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With palladium; acetic acid Hydrogenation;

: 6829-40-9
aminomalonic acid diethyl ester

: 141-52-6
sodium ethanolate

: 105-39-5
chloroacetic acid ethyl ester

A: 617-45-8
aspartic Acid

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
und Verseifen des Reaktionsgemisches mit kalter 3prozentiger Kalilauge;

...Expand

: 6829-40-9
aminomalonic acid diethyl ester

: 105-39-5
chloroacetic acid ethyl ester

A: 617-45-8
aspartic Acid

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With sodium ethanolate und Verseifung des Reaktionsprodukts mit kalter 3prozentiger Kalilauge;

...Expand

: 107-16-4
glycolonitrile

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With ammonia Behandeln des entstandenen Dinitrils mit Barytwasser;

: 79-11-8
chloroacetic acid

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With ammonia
With ammonia; zinc(II) chloride

: 56-40-6
glycine

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With water; mercury dichloride at 40℃;

: 139-13-9
nitrilotriacetic acid

A: 56-40-6
glycine

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With iron(III) at 135℃; for 24h;

: 132916-53-1
C24H25NO4P(1+)*Br(1-)

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydroxide In water

: 2562-31-4
potassium hydrogen salt of iminodiacetic acid

A: C4H7NO4*H(1+)

B: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With nitric acid at 25℃; Thermodynamic data; heats of reaction, and dilution, heat of reaction;

: C4H5NO4(2-)*Mg(2+)

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
In water at 23℃; Equilibrium constant; Thermodynamic data; ΔH;

: 7647-01-0
hydrogenchloride

: 254991-24-7
4-benzenesulfonyl-piperazine-2,6-dione

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
at 140 - 150℃; im Rohr;

: (4-amino-2-oxo-2,3-dihydro-imidazol-1-yl)-acetic acid amide

aq. barium hydroxide solution: aq. barium hydroxide solution

: 142-73-4
iminodiacetic acid

4-benzenesulfonyl-2.6-dioxo-piperazine: 4-benzenesulfonyl-2.6-dioxo-piperazine

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
With hydrogenchloride at 140 - 150℃;

: 7732-18-5
water

: 107-18-6
allyl alcohol

oxygen: oxygen

CaCO3: CaCO3

charcoal: charcoal

: 142-73-4
iminodiacetic acid

Conditions

Conditions	Yield
at 100 - 110℃;

...Expand

: 67-56-1
methanol

: 142-73-4
iminodiacetic acid

: 6096-81-7
dimethyl iminodiacetate

Conditions

Conditions	Yield
Stage #1: methanol; iminodiacetic acid With oxalyl dichloride at 0 - 60℃; Stage #2: With sodium carbonate In water	100%
With boron trifluoride methanol complex for 9h; Heating;	96%
With hydrogenchloride for 2h; Heating;	83%

: 100-51-6
benzyl alcohol

: 142-73-4
iminodiacetic acid

: 138397-85-0
dibenzyl 2,2'-azanediyldiacetate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 12h; Heating;	100%
With toluene-4-sulfonic acid In toluene at 80℃; for 18h;	96%

: 1120-71-4
1,3-propanesultone

: 142-73-4
iminodiacetic acid

: 2,2'-((3-sulfopropyl)azanediyl)diacetic acid

Conditions

Conditions	Yield
In water at 85℃; for 4h;	100%
In water at 85℃; for 4h;
With water at 85℃; for 4h;

: 50-00-0
formaldehyd

: 1809-20-7
diisopropyl hydrogenphosphonate

: 142-73-4
iminodiacetic acid

: 2,2'-{[(diisopropoxyphosphoryl)methyl]azanediyl}-diacetic acid

Conditions

Conditions	Yield
Stage #1: formaldehyd; iminodiacetic acid With iminodiacetic acid hydrochloride In acetonitrile at 60℃; for 1.5h; Stage #2: diisopropyl hydrogenphosphonate In acetonitrile at 80℃; for 5h;	100%

...Expand

: 67-56-1
methanol

: 142-73-4
iminodiacetic acid

: 39987-25-2, 62491-02-5
dimethyl iminodiacetate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at -10 - 20℃;	99%
With thionyl chloride at -10 - 20℃;	99%
With thionyl chloride for 12h; Heating;	98%

: 684-16-2
Hexafluoroacetone

: 142-73-4
iminodiacetic acid

: 148431-05-4
3-carboxymethyl-2,2-bis(trifluoromethyl)-oxazolidin-5-one

Conditions

Conditions	Yield
In dimethyl sulfoxide	98%
In dimethyl sulfoxide	86%

: 67-63-0
isopropyl alcohol

: 142-73-4
iminodiacetic acid

: (Isopropoxycarbonylmethyl-amino)-acetic acid isopropyl ester; hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 24h;	98%

: 598-78-7
(R,S)-2-chloropropionic acid

: 142-73-4
iminodiacetic acid

: 22149-55-9
α-alanine-N-diacetic acid

Conditions

Conditions	Yield
at 120℃; Temperature;	97%

: 108-31-6
maleic anhydride

: 142-73-4
iminodiacetic acid

: C8H7NO9(4-)*4Na(1+)

Conditions

Conditions	Yield
Stage #1: maleic anhydride With water at 25℃; for 1h; Stage #2: With potassium hydroxide at 45 - 55℃; for 0.25h; pH=6 - 6.5; Stage #3: iminodiacetic acid Reagent/catalyst; Further stages;	96.23%

: 142-73-4
iminodiacetic acid

: 4385-40-4
2,6-dicarbonylmorpholine

Conditions

Conditions	Yield
With acetic anhydride at 150℃; for 2h;	96.2%

: 110-16-7
maleic acid

: 142-73-4
iminodiacetic acid

: C8H7NO9(4-)*4Na(1+)

Conditions

Conditions	Yield
Stage #1: maleic acid With sodium hydroxide In water at 45 - 55℃; for 0.25h; pH=5 - 6.5; Stage #2: With sodium tungstate In water for 2.25h; Stage #3: iminodiacetic acid Reagent/catalyst; Further stages;	96.12%

: 292638-85-8
acrylic acid methyl ester

: 142-73-4
iminodiacetic acid

: methyl N,N-bis(carboxymethyl)-3-aminopropionate

Conditions

Conditions	Yield
With hydrogenchloride In water	96%

: 617-89-0
furan-2-ylmethanamine

: 142-73-4
iminodiacetic acid

: 1267110-21-3
1-furan-2-ylmethyl-piperazine-2,6-dione

Conditions

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	96%

: 107-06-2
1,2-dichloro-ethane

: 142-73-4
iminodiacetic acid

: 60-00-4
ethylenediaminetetraacetic acid

Conditions

Conditions	Yield
Stage #1: 1,2-dichloro-ethane; iminodiacetic acid With sodium hydrogencarbonate In toluene at 80 - 90℃; for 10.5h; Stage #2: With sodium hydroxide In water at 70 - 80℃; for 8.5h; Reflux;	95.29%
With 1,4-dioxane; alkali carbonate at 80 - 125℃;
With alkali carbonate; water at 80 - 125℃;

: 501-53-1
benzyl chloroformate

: 142-73-4
iminodiacetic acid

: 17335-88-5
2,2’-{[(benzyloxy)carbonyl]imino}diacetic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃;	95%
With sodium hydroxide for 2h; Ambient temperature;	94%
	73%

: 23911-26-4
diethylenetriaminepentaacetic dianhydride

: 142-73-4
iminodiacetic acid

: 1357357-01-7
C22H33N5O16

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h;	95%

: dysprosium(III) chloride hexahydrate

: 142-73-4
iminodiacetic acid

: Dy(3+)*HOOCCH2NHCH2COO(1-)*HN(CH2COO)2(2-)=Dy(C4H6NO4)(C4H5NO4)

Conditions

Conditions	Yield
With sodium hydroxide In water at 170℃; for 72h; Autoclave;	95%

: 50-00-0
formaldehyd

: 2785-87-7
2-methoxy-4-n-propylphenol

: 142-73-4
iminodiacetic acid

: C15H21NO6

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 90℃; for 11h; Reflux;	95%

...Expand

: 156-87-6
propan-1-ol-3-amine

: 142-73-4
iminodiacetic acid

: 2,2'-iminobis[N-(3-hydroxypropyl)acetamide]

Conditions

Conditions	Yield
at 20℃; for 12h; Reflux;	95%

: 75-15-0
carbon disulfide

: 142-73-4
iminodiacetic acid

: bis(carboxymethyl)-dithiocarbamic acid, tripotassium salt

Conditions

Conditions	Yield
With potassium hydroxide In methanol; water at 20℃;	95%

: 142-73-4
iminodiacetic acid

: 86015-23-8
Diallyl 3-azaglutarate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene	94.6%

: 1192215-18-1
2-(7-isopropyl-1-methylazulen-4-yl)ethyl N-succinimidyl carbonate

: 142-73-4
iminodiacetic acid

: 1192215-23-8
N-[2-(7-isopropyl-1-methylazulen-4-yl)ethoxycarbonyl]iminodiacetic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; Schotten-Baumann reaction;	94%

: 3731-51-9
(2-aminomethylpyridine)

: 142-73-4
iminodiacetic acid

: 1267532-02-4
1-(pyridin-2-ylmethyl)piperazine-2,6-dione

Conditions

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	94%

: 7663-77-6
1-(3-aminopropyl)-2-pyrrolidone

: 142-73-4
iminodiacetic acid

: 1421691-43-1
1-[3-(2-oxo-pyrrolidin-1-yl)-propyl]-piperazine-2,6-dione

Conditions

Conditions	Yield
at 85℃; for 0.05h; Microwave irradiation;	94%

: 50-00-0
formaldehyd

: 29665-59-6
2-methyl-4-(n-dodecyl)phenol

: 142-73-4
iminodiacetic acid

: 2,2'-((5-dodecyl-2-hydroxy-3-methylbenzyl)azanediyl)diacetic acid

Conditions

Conditions	Yield
Stage #1: formaldehyd; iminodiacetic acid With sodium hydroxide In ethanol; water Stage #2: 2-methyl-4-(n-dodecyl)phenol In ethanol; water at 95℃; for 6h;	94%

...Expand

: 50-00-0
formaldehyd

: 142-73-4
iminodiacetic acid

: 5994-61-6
phosphonomethylimino-di-acetic acid

Conditions

Conditions	Yield
With hydrogenchloride; phosphorous acid In water at 100 - 120℃; under 7500.75 - 9000.9 Torr;	93.1%
With phosphonic Acid for 3h; Reflux; Green chemistry;	90.3%
Stage #1: iminodiacetic acid With phosphonic Acid In water Reflux; Stage #2: formaldehyd In water at 130 - 136℃; for 1.75h; Product distribution / selectivity;	67.3%

: 50-00-0
formaldehyd

: 142-73-4
iminodiacetic acid

: 4408-64-4
N-methyliminodiacetic acid

Conditions

Conditions	Yield
Stage #1: iminodiacetic acid With formic acid at 90℃; for 0.5h; Stage #2: formaldehyd In water for 1h; Reflux;	93%
With formic acid In water at 90℃; for 1.5h;	88%
With formic acid In water Reflux;	87%

: 818-08-6
di(n-butyl)tin oxide

: 142-73-4
iminodiacetic acid

: 123376-12-5
HN(CH2CO2)2Sn(C4H9)2

Conditions

Conditions	Yield
In ethanol; toluene 6 h at 77 ° C; distn. under atmospheric pressure, filtration, solid washed with toluene and acetone, recrystn. from methanol/benzene;	93%

Iminodiacetic acid Consensus Reports

Reported in EPA TSCA Inventory.

Iminodiacetic acid Specification

The Iminodiacetic acid is an organic compound with the formula C₄H₇NO₄. The IUPAC name of this chemical is 2-(carboxymethylamino)acetic acid. With the CAS registry number 142-73-4, it is also named as 2,2'-Iminodiacetic acid. The product's categories are Glycine Derivatives; Others; Peptide Synthesis; Unnatural Amino Acid Derivatives. Besides, it is a white or yellowish crystalline powder, which should be stored in a closed and dry place. It is the glyphosate herbicide intermediate which is used as raw material of amino acid-type chelating resin, it is also the important raw materials and intermediates of rubber and electroplating industry.

Physical properties about Iminodiacetic acid are: (1)ACD/LogP: -1.40; (2)ACD/LogD (pH 5.5): -4.89; (3)ACD/LogD (pH 7.4): -4.92; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 55.84 Å²; (12)Index of Refraction: 1.501; (13)Molar Refractivity: 27.3 cm³; (14)Molar Volume: 92.6 cm³; (15)Polarizability: 10.82×10^-24cm³; (16)Surface Tension: 64.8 dyne/cm; (17)Density: 1.436 g/cm³; (18)Flash Point: 177.9 °C; (19)Enthalpy of Vaporization: 67.81 kJ/mol; (20)Boiling Point: 370.6 °C at 760 mmHg; (21)Vapour Pressure: 1.65E-06 mmHg at 25°C.

Preparation: this chemical can be prepared by (carboxymethyl-formyl-amino)-acetic acid. This reaction will need reagent 1 M HCl. The reaction time is 5 hours with reaction temperature of 100 °C. The yield is about 64%.

Uses of Iminodiacetic acid: it can be used to produce iminodi-acetic acid diethyl ester. It will need reagent SOCl₂.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CNCC(=O)O
(2)InChI: InChI=1/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
(3)InChIKey: NBZBKCUXIYYUSX-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
(5)Std. InChIKey: NBZBKCUXIYYUSX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)		National Technical Information Service. Vol. AD277-689,

Product Name

Iminodiacetic acid

Synthetic route

Iminodiacetic acid Consensus Reports

Iminodiacetic acid Specification

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