Grundinformationen
- Standard-SMILES
O=C(O)CNCC(=O)O- InChIKey
NBZBKCUXIYYUSX-UHFFFAOYSA-N- Summenformel
- C4H7NO4
- Durchschnittliche Molmasse
- 133,1 g/mol
- Monoisotopische Masse
- 133,0375077
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Iminodiacetic acid
- IUPAC
- 2-(carboxymethylamino)acetic acid
- Lokaler Name
- Iminodi(essigsure)
- Englischer Name
- Iminodiacetic acid
- Summenformel
- C4H7NO4
- Molmasse
- 133.1
Namen und Synonyme
IMINODIACETIC ACID142-73-4Iminodiethanoic acid2,2'-Iminodiacetic acidAminodiacetic acidDiglycinDiglykokollN-(Carboxymethyl)glycineGlycine, N-(carboxymethyl)-DiglycocollHampshireIminobis(acetic acid)
Weitere Namen anzeigen
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
Datenbank-Bezeichner
- CAS
142-73-4- PubChem CID
- 8897
- DTXSID
DTXSID2027098- ChEMBL
CHEMBL461164- ChEBI
CHEBI:24786- UNII
- XQM2L81M8Z
- EC Number
- 205-555-4
- Nikkaji
- J386G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -3,3
- Polarare Oberfläche (TPSA)
- 86,6 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 108
Experimentelle und physikochemische Eigenschaften
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 243 °C · 243 °C (dec.) (lit.)
- Siedepunkt
- 245.59 °C · 245.59°C (rough estimate)
- Dichte
- 1.5325 · 1.5325 (rough estimate)
- Brechungsindex
- 1.454 · 1.4540 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 42 g/l · 42g/l
- Aggregatzustand
- Crystalline Powder
- pka
- 2.98 · 2.98, 9.89(at 25℃)
- Farbe
- White or yellow
- PH
- 2.2 · 2.2-2.3 (H2O, 20℃)(saturated solution)
- Wasserlöslichkeit
- 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 Datenbank
- 142 · 142-73-4(CAS DataBase Reference)
- NIST chemische Informationen
- Glycine, N-(carboxymethyl)-(142-73-4)
- EPA chemische Informationen
- Glycine, N-(carboxymethyl)- (142-73-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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%)
Sicherheit und Schutzausrüstung
Protective Action Criteria (PAC)
0.82 [mg/m3]
9.0 [mg/m3]
54 [mg/m3]
Toxikologische Informationen
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.
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29224995
- RTECS-Nr.
- AI2975000
- risk_code
- 36/37/38
- Toxizität
- LD50 orally in Rabbit: > 2000 mg/kg
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Speicherklasse
- 11 - Combustible Solids
- Giftige Stoffe Daten
- 142-73-4(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2
Chemie und Industrie
Pharmakologische Informationen
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.
Verwendung und Herstellung
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
Anwendungen
VerwendenIminodiacetic 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.
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Ergänzende Hinweise
DefinitionChEBI: An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.
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