Basic information
- Standard SMILES
O=C(O)CNCC(=O)O- InChIKey
NBZBKCUXIYYUSX-UHFFFAOYSA-N- Molecular formula
- C4H7NO4
- Average molar mass
- 133.1 g/mol
- Monoisotopic mass
- 133.0375077
Overview
Iminodiacetic acid is an amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group. It has a role as a chelator. It is a glycine derivative, an amino dicarboxylic acid and a non-proteinogenic alpha-amino acid. It is a conjugate acid of an iminodiacetate.
Names & identifiers
- Preferred name
- Iminodiacetic acid
- IUPAC
- 2-(carboxymethylamino)acetic acid
- English name
- Iminodiacetic acid
- Molecular formula
- C4H7NO4
- Molecular weight
- 133.1
Names & synonyms
IMINODIACETIC ACID142-73-4Iminodiethanoic acid2,2'-Iminodiacetic acidAminodiacetic acidDiglycinDiglykokollN-(Carboxymethyl)glycineGlycine, N-(carboxymethyl)-DiglycocollHampshireIminobis(acetic acid)
Show more names
IDA2,2'-azanediyldiacetic acid2,2’-iminobis-aceticaciIMinodiacetic2,2’-iminodiaceticacidn-(carboxymethyl)-glycineDIGLYCOLAMIDIC ACID
Acetic acid, iminodi-IMDA2-[(carboxymethyl)amino]acetic acidUSAF DO-55IDA (chelating agent)Iminodi(acetic acid)Acetic acid, 2,2'-iminobis-DTXSID2027098
Database identifiers
- CAS
142-73-4- PubChem CID
- 8897
- DTXSID
DTXSID2027098- ChEMBL
CHEMBL461164- ChEBI
CHEBI:24786- UNII
- XQM2L81M8Z
- EC Number
- 205-555-4
- Nikkaji
- J386G
Properties
Computed structural properties
- XLogP
- -3.3
- Topological polar surface area
- 86.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 108
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Chelating Agents
Color/FormORTHORHOMBIC CRYSTALS
SolubilityPRACTICALLY INSOL IN ACETONE, METHANOL, ETHER, BENZENE, CARBON TETRACHLORIDE, HEPTANE; SOL IN WATER @ 5 °C: 2.43 G/100 ML
Melting Point247.50 °C. @ 760.00 mm Hg
Physical Description
Dry Powder
Solid; [Merck Index] Light brown crystalline solid; [MSDSonline]
Solid
Dissociation ConstantsPKA1: 2.98; PKA2: 9.89
Other Experimental Properties
FORMS SALTS WITH ACIDS & BASES
220-250 °C (COMMERCIAL)
DECOMP @ 247.5 °C
Physicochemical properties
- Melting point
- 243 °C · 243 °C (dec.) (lit.)
- Boiling point
- 245.59 °C · 245.59°C (rough estimate)
- Density
- 1.5325 · 1.5325 (rough estimate)
- refractive index
- 1.454 · 1.4540 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 42 g/l · 42g/l
- form
- Crystalline Powder
- pka
- 2.98 · 2.98, 9.89(at 25℃)
- color
- White or yellow
- PH
- 2.2 · 2.2-2.3 (H2O, 20℃)(saturated solution)
- Water Solubility
- 2.43 g/100 · 2.43 g/100 mL (5 ºC)
- Merck
- 14 · 14,4917
- BRN
- 878499 · 878499
- Major Application
- peptide synthesis
- InChI
- 1S/C4H7NO4/c6-3(7)1-5-2-4(8)9/h5H,1-2H2,(H,6,7)(H,8,9)
- InChIKey
- NBZBKCUXIYYUSX-UHFFFAOYSA-N
- SMILES
- OC(=O)CNCC(O)=O
- LogP
- 1.84 · 1.840 (est)
- CAS DataBase Reference
- 142 · 142-73-4(CAS DataBase Reference)
- FDA UNII
- 2 L81M8Z · XQM2L81M8Z
- NIST Chemistry Reference
- Glycine, N-(carboxymethyl)-(142-73-4)
- EPA Substance Registry System
- Glycine, N-(carboxymethyl)- (142-73-4)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- WGK Germany
- 1 · 1
- RTECS
- 2975000 · AI2975000
- TSCA
- TSCA listed
- HS Code
- 29224995 · 29224995
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- Hazardous Substances Data
- 142 · 142-73-4(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: > 2000 mg/kg
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 20.1% (55 of 274) of reports.
Warning
H315 (56.9%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 274 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Glycine, N-(carboxymethyl)-
Glycine, N-(carboxymethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Glycine, N-(carboxymethyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Iminodiacetic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryEmergency medical treatment: symptomatic drug ingestion; Not tumorigenic when 0.5% solution added to drinking water of rats for most of their lifespans; [HSDB] Intraperitoneal LD50 (mouse) = 250 mg/kg; [RTECS] An irritant; [MSDSonline]
Hazard Classes and CategoriesSkin Irrit. 2 (56.9%)
Safety & protection
Protective Action Criteria (PAC)
0.82 [mg/m3]
9.0 [mg/m3]
54 [mg/m3]
Toxicology
Non-Human Toxicity ExcerptsNO TUMORIGENICITY IN RATS GIVEN 0.5% IMINODIACETIC ACID IN DRINKING WATER, WITH OR WITHOUT NANO2 OR NANO3, FOR MOST OF THEIR LIFESPANS. DOSE WAS 20 ML SOLN/ANIMAL 5 DAYS A WK.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- AI2975000
- hs_code
- 29224995
- Toxicity
- LD50 orally in Rabbit: > 2000 mg/kg
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
- Hazardous Substances Data
- 142-73-4(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of Action
LEAD NITRATE ALONE OR CHELATED WITH DIFFERENT CHELATING AGENTS INCL IMINODIACETIC ACID (IDA) WAS ADMIN TO PREGNANT RATS ON DAYS 9, 11 OR 16 OF GESTATION. THE LEAD-CHELATE COMPLEX EITHER REDUCED OR EQUALED BUT DID NOT ENHANCE THE OVERALL EMBRYO OR FETAL TOXICITY. THERE WERE NO QUALITATIVELY DIFFERENT EFFECTS PRODUCED WITH CHELATED LEAD VERSUS LEAD ALONE. THE CHELATING AGENTS WERE MORE EFFECTIVE AFTER DAY 9 THAN DAYS 11 OR 16. EDTA PRODUCED THE GREATEST REDUCTION IN OVERALL EFFECT, WHILE IDA PROVIDED THE LEAST PROTECTION.
MeSH Pharmacological ClassificationChemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS.
Absorption, Distribution and ExcretionPLACENTAL PERMEABILITY & TRANSFER OF LEAD NITRATE ALONE & CHELATED WITH IMINODIACETIC ACID (PBIDA) IN RATS WERE STUDIED. LITTLE OR NO DIFFERENCES IN MATERNAL BLOOD OR FETAL LEAD CONTENT WERE OBSERVED WITH PBIDA COMPLEX.
Uses & manufacturing
Uses
Used as a buffer/sequestrant in electroplating applications and to make surfactants, chelating resins, and polymeric amides; Used as IDA, a chelating agent; [HSDB]
Electroplating [Category: Plate]
HAS BEEN SUGGESTED AS INTERMEDIATE IN MFR OF COMPLEX SALTS, CHELATING AGENTS
CHEM INT FOR SURFACTANTS, CHELATING RESINS, POLYMERIC AMIDES; BUFFER/SEQUESTRANT IN ELECTROPLATING APPLICATIONS
U.S. Exports
(1972) No Data
(1975) No Data
U.S. Imports
(1972) No Data
(1975) No Data
U.S. Production
2020: 39,683 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Industry UsesChelating agent
Methods of Manufacturing
HYDROGENATION OF NITRILOTRIACETIC ACID IN PRESENCE OF PALLADIUM/CARBON CATALYST; AMMONOLYSIS OF CHLOROACETIC ACID
OBTAINED FROM NITRILOTRIACETIC ACID...BY HCL-HYDROLYSIS IN BOMB TUBE: SCHWARZENBACH ET AL, HELV CHIM ACTA 28, 1133 (1945); BY OXYGENATION IN PRESENCE OF PALLADIUM/CARBON CATALYST: TETENBAUM, STONE, CHEM COMMUN 1970, 1699. IMINODIACETIC ACID & NITRILOTRIACETIC ACID ARE FORMED UPON BOILING CHLOROACETIC ACID WITH CONCN AQ AMMONIA: HEINTZ, ANN 149, 88 (1869)
General Manufacturing Information
Not Known or Reasonably Ascertainable
Glycine, N-(carboxymethyl)-: ACTIVE
Applications
UsesIminodiacetic acid can be used:In the preparation of iminodiacetic acid (IDA)-type adsorbent for protein purification.As a catalyst along with iron (FeCl3) complexes for methyl methacrylate (MMA) polymerization. In the preparation of chelating resins with glycidyl methacrylate for the selective removal and recovery of metal ions from industrial waste water.As a reagent for the preparation of pinene-derived iminodiacetic acid (PIDA), which is in turn used as a ligand for the synthesis of diastereoselective oxiranyl C(sp3) boronates from the corresponding olefins.In the surface functionalization of multi-walled carbon nanotubes (MWCNTs) which is further utilized as a sorbent for the separation of heavy metal ions.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.
Related reactions
87 records
Linked notes
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