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Iodessigsäure
IA · iodoacetate · monoiodoacetate · iodoacetic · lodoacetic acid · MONOIODOACETIC ACID · SKL245 · CH2ICOOH
Identifikatoren & physikalische Daten
| CAS No. | 64-69-7 |
|---|---|
| Summenformel | C2H3IO2 |
| Durchschnittliche Molmasse | 185,95 g/mol |
| Monoisotopische Masse | 185,91777734 g/mol |
| SMILES | O=C(O)CI |
| InChIKey | JDNTWHVOXJZDSN-UHFFFAOYSA-N |
| PubChem CID | 5240 |
| ChEMBL | CHEMBL376280 |
| ChEBI | CHEBI:74571 |
| EC No. | 200-590-1 |
| DTXSID | DTXSID5025445 |
| Lokaler Name | Iodessigsäure |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 42,9 |
| Stoffklassen | Other Classes -> Organic Acids |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Halogenated fatty acids [FA0109] |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| Color/Form | Colorless or white crystalsWhite to yellow powder or flakes |
| Löslichkeit | greater than or equal to 100 mg/mL at 70.7 °F (NTP, 1992)Soluble in waterSoluble in alcoholvery slightly soluble in etherSoluble in ethanol, petroleum etherslightly soluble in ether, chloroformH2O: soluble, clear to hazy600 g/L (20 ºC) |
| Corrosivity | Corrosive |
| Siedepunkt | Decomposes (NTP, 1992)208°C |
| Decomposition | When heated to decomposition it emits toxic fumes of /iodine/. |
| Schmelzpunkt | 181 °F (NTP, 1992)82-83 °CColorless or white crystals. MP: 210 °C. Soluble in water, alcoholvery slightly soluble in ether. Hygroscopic in moist air /Iodoacetic acid, sodium salt/79 °C |
| Physical Description | Iodoacetic acid appears as colorless or white crystals. (NTP, 1992)Colorless or white solid[Merck Index] Pale yellow crystalline flakesSoluble in water[MSDSonline] |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Dissociation Constants | pKa = 3.18 at 25 °C |
| Dichte | 2.2003 (estimate) |
| Flammpunkt | 208°C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 3.12(at 25℃) |
| Farbe | faintly yellow |
| Biologische Quelle | synthetic |
| Merck | 14,5025 |
| BRN | 1739079 |
| Henry-Konstante | 2.4×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, bases, strong reducing agents. Store at -20 C. |
| InChI | 1S/C2H3IO2/c3-1-2(4)5/h1H2,(H,4,5) |
| InChIKey | JDNTWHVOXJZDSN-UHFFFAOYSA-N |
| SMILES | OC(=O)CI |
| CAS Datenbank | 64-69-7(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, iodo-(64-69-7) |
| EPA chemische Informationen | Iodoacetic acid (64-69-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P264, P270, P280, P301+P316, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, iodo-Iodoacetic acid: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Flash point data for this chemical are not available, but it is probably non-flammable. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Exposure to this compound may cause irritation of the skin, eyes and mucous membranes and may lead to contact dermatitis or severe burns. |
| Gefahrenübersicht | A strong skin, eye, and mucous membrane irritant[HSDB] May cause severe burns[CAMEO] Corrosive to skin[eChemPortal: ERMA] Causes severe burns[eChemPortal: ESIS] A corrosive substance that can cause severe injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitis[MSDSonline] |
| Reaktive Gruppe | Acids, Carboxylic |
| Reactivity Profile | IODOACETIC ACID reacts vigorously with bases and is corrosive. (NTP, 1992) |
| Air and Water Reactions | May be sensitive to heat, light, and air. Water soluble |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides, hydrogen iodide. |
| Hazard Classes and Categories | Acute Tox. 3 (100%)Acute toxicity - category 3Acute toxicity (Oral) - Category 3Acute Tox. 3 * |
Anwendungen & Verwendung
Verwenden
Iodoacetic acid is used as a reagent for the modification of sulfhydryl groups in organic synthesis. It reacts with cysteine moiety in proteins to prevent the re-formation of disulfide bonds during protein sequencing. It is also used as a general reagent in acylation reactions as well as in glycopeptide synthesis.