Iminodiacetic acid (HCID 8897)

概要

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.

名称と識別子

優先名称: Iminodiacetic acid
IUPAC: 2-(carboxymethylamino)acetic acid
現地名: イミノ二酢酸
英語名: Iminodiacetic acid
分子式: C4H7NO4
分子量: 133.1

名称と別名

IMINODIACETIC ACID142-73-4Iminodiethanoic acid2,2'-Iminodiacetic acidAminodiacetic acidDiglycinDiglykokollN-(Carboxymethyl)glycineGlycine, N-(carboxymethyl)-DiglycocollHampshireIminobis(acetic acid)

名称をさらに表示

イミノ二酢酸ジグリシンハンプシルジグリコールアミド酸ジグリココール2,2'-イミノビス酢酸N-(カルボキシメチル)グリシンイミノジ酢酸ハンプシャー2,2'-イミノ二酢酸イミノビス酢酸イミノジエタノイックアシッドイミノジ酢酸ジメチルアミンジカルボン酸イミノ二酢酸, 98+%IDAIDA2,2'-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

データベース識別子

CAS: 142-73-4
PubChem CID: 8897
DTXSID: DTXSID2027098
ChEMBL: CHEMBL461164
ChEBI: CHEBI:24786
UNII: XQM2L81M8Z
EC Number: 205-555-4
Nikkaji: J386G

物性

構造計算による物性

XLogP: -3.3
極性表面積: 86.6 Å²
水素結合供与体数: 3
水素結合受容体数: 5
回転可能結合数: 4
重原子数: 9
形式電荷: 0
複雑度: 108

実験および物理化学的性質

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 · 3 件

Dry Powder

Solid; [Merck Index] Light brown crystalline solid; [MSDSonline]

Solid

Dissociation ConstantsPKA1: 2.98; PKA2: 9.89

物理化学的性質

融点: 243 °C · 243 °C (dec.) (lit.)
沸点: 245.59 °C · 245.59°C (rough estimate)
比重(密度): 1.5325 · 1.5325 (rough estimate)
屈折率: 1.454 · 1.4540 (estimate)
貯蔵温度: 30 °C · Store below +30°C.
溶解性: 42 g/リットル · 42g/リットル
外見: 結晶性粉末
酸解離定数(Pka): 2.98 · 2.98, 9.89(at 25℃)
色: 白または黄色
PH: 2.2 · 2.2-2.3 (H2O, 20℃)(saturated solution)
水溶解度: 2.43 g/100mL · 2.43g/100mL(5℃)
Merck: 14 · 14,4917
BRN: 878499 · 878499
主な用途: ペプチド合成
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 データベース: 142 · 142-73-4(CAS DataBase Reference)
NISTの化学物質情報: Glycine, N-(carboxymethyl)-(142-73-4)
EPAの化学物質情報: Glycine, N-(carboxymethyl)- (142-73-4)

化学的性質

化学的特性white or yellowish crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 3 件

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%)

安全と保護具

Protective Action Criteria (PAC) · 3 件

0.82 [mg/m3]

9.0 [mg/m3]

54 [mg/m3]

毒性情報

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.

安全データ

wgk: 1
tsca: TSCA listed
rtecs: AI2975000
毒性: LD50 orally in Rabbit: > 2000 mg/kg
hs_code: 29224995
risk_code: 36/37/38
化審法: (2)-1211
hazard_code: Xi
safety_code: 26-36-37/39
Hazard Classifications: Eye Irrit. 2
ストレージクラス: 11 - Combustible Solids
有毒物質データの: 142-73-4(Hazardous Substances Data)

化学と産業

薬理情報

Mechanism of Action · 1 件

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.

用途と製造

Uses · 4 件

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 · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

U.S. Production · 3 件

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 · 2 件

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)

応用分野 · 3 件

解説イミノ二酢酸，イミノニサクサン，N-(carboxymethyl)glycine．C4H7NO4(133.10)．NH(CH2COOH)2．ジグリコールアミド酸ともいう．ニトリロ三酢酸の塩酸による加水分解，または沸騰したクロロ酢酸と濃アンモニア水からつくる．斜方結晶．分解点247.5 ℃．pKa1 2.98，pKa2 9.89．メタノール，アセトン，ベンゼンに難溶．酸，塩基と塩をつくる．また，多くの金属とキレートをつくる．

用途イミノ二酢酸アニオンは三座配位子として、五員環のキレート環を持つ金属錯体を形成する。窒素原子上のプロトンは、イオン交換樹脂製造ため炭素原子に置き換えることができる。IDAは、二座配位子のグリシンより強く、四座配位子のニトリロ三酢酸より弱い錯体を形成する。

使用Iminodiacetic 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.

調製方法 · 1 件

純化方法Crystallise the acid several times from water. The N-Methyl derivative m 215o is purified by dissolving it in an equal weight of warm H2O and adding 3 volumes of MeOH [Kiematsu et al. Org Synth Coll Vol II 397 1943]. [Laberek & Martell J Am Chem Soc 74 5052 1952, Beilstein 4 III 2428, 4 IV 1176.]

上流・下流製品情報

上流原料

グリコロニトリルホルマリンジエタノールアミン固定化イミノ二酢酸青酸水酸化ナトリウム Acetamide イミノジアセトニトリルヘキサメチレンテトラミン水酸化カルシウムクロロ酢酸ナトリウム Methylenebisiminodiacetonitrile

下流製品

4-ホスホノ-3-アザブタン酸 N-(2-ヒドロキシエチル)イミノ二酢酸アリザリンコンプレクソングリシンイミノ二酢酸ジエチルメチルホスホン酸

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補足説明

定義ChEBI: An amino dicarboxylic acid that is glycine in which one of the hydrogens attached to the nitrogen is substituted by a carboxymethyl group.

Iminodiacetic acid

基本情報

概要