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Iminodiacetic acid

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Name

Iminodiacetic acid

EINECS 205-555-4
CAS No. 142-73-4 Density 1.436 g/cm3
PSA 86.63000 LogP -0.86390
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 N/A Appearance white or yellowish crystalline powder
Safety 26-36-37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 142-73-4 (Iminodiacetic acid) Hazard Symbols IrritantXi
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;

Article Data 59

Iminodiacetic acid Synthetic route

628-87-5

iminodiacetonitrile

142-73-4

iminodiacetic acid

Conditions
ConditionsYield
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
ConditionsYield
With sodium hydroxide In water at 160℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature;96%
With nitrogen; hydrogen; copper In sodium hydroxide; water90.2%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
117659-76-4

ethylenediamine tetraacetic acid

A

50-00-0

formaldehyd

B

298-12-4

Glyoxilic acid

C

142-73-4

iminodiacetic acid

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

50-00-0

formaldehyd

151-50-8

potassium cyanide

142-73-4

iminodiacetic acid

Conditions
ConditionsYield
With water
6829-40-9

aminomalonic acid diethyl ester

A

617-45-8

aspartic Acid

B

142-73-4

iminodiacetic acid

Conditions
ConditionsYield
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
ConditionsYield
With hydrogenchloride
With barium dihydroxide

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,

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