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Bromessigsäure
2-BROMOACETIC ACID · bromoacetic · MONOBROMOACETIC ACID · Bromoethanoic acid · 2-Bromoethanoic acid · alpha-Bromoacetic acid · Bromoacetic acid in ethyleneglycol, ca. 10% BrCH2CO2H, 35% glycol balance ester · tontu
Identifikatoren & physikalische Daten
| CAS No. | 79-08-3 |
|---|---|
| Summenformel | C2H3BrO2 |
| Durchschnittliche Molmasse | 138,95 g/mol |
| Monoisotopische Masse | 137,93164 g/mol |
| SMILES | O=C(O)CBr |
| InChIKey | KDPAWGWELVVRCH-UHFFFAOYSA-N |
| PubChem CID | 6227 |
| ChEMBL | CHEMBL60851 |
| EC No. | 201-175-8 |
| DTXSID | DTXSID7021495 |
| Lokaler Name | Bromessigsäure |
Chemische & physikalische Eigenschaften
| XLogP | 0,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 37,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 42 |
| LogP (Verteilungskoeffizient) | 0.41log Kow = 0.41 |
| Dichte | Density: 1.9335 at 50 °C |
| Color/Form | Hexagonal or rhomboidal hygroscopic crystalsColorless, deliquescent crystals |
| Löslichkeit | 1750000In water, 6.36X10+5 mg/L at 25 °CMiscible with waterMiscible with ethanol, ethersoluble in acetone, benzeneslightly soluble in chloroformSoluble in methanolchloroform: soluble10%, clear, colorless |
| Corrosivity | Strong irritant to skin and tissues |
| Flammpunkt | 113 °C (235 °F) - closed cup>110°C |
| Siedepunkt | 208208 °C208 °C @760 [mm Hg]208 °C(lit.) |
| Decomposition | When heated to decomposition it emits toxic fumes of /bromide/. |
| Schmelzpunkt | 5050 °C46-49 °C |
| Dampfdruck | 0.11 [mmHg]0.119 mm Hg at 25 °C1 mm Hg @ 550C |
| Brechungsindex | Index of refraction: 1.4804 at 50 °C/D1.4804 (estimate) |
| Henry-Konstante | Henry's Law constant = 6.52X10-9 atm-cu m/mole at 25 °C1.5×103 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| Lagerbedingungen | Store below +30°C. |
| pKa (Säurekonstante) | 2.69(at 25℃) |
| Aggregatzustand | Crystalline Mass or Crystalline Powder, Flakes, Crystals and/or Chunks |
| Farbe | White to yellow |
| Spezifische Wärmekapazität | Cp(gas): 0.58 J/(g·K), at 25℃ |
| Merck | 14,1400 |
| BRN | 506167 |
| InChI | 1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5) |
| InChIKey | KDPAWGWELVVRCH-UHFFFAOYSA-N |
| SMILES | NC(=O)C=C || OC(=O)CBr |
| LogP (Verteilungskoeffizient) | -2.3 at 22℃ |
| CAS Datenbank | 79-08-3(CAS DataBase Reference) |
| NIST chemische Informationen | Acetic acid, bromo-(79-08-3) |
| EPA chemische Informationen | Bromoacetic acid (79-08-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]H311: Toxic in contact with skin [Danger Acute toxicity, dermal]H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H317: May cause an allergic skin reaction [Warning Sensitization, Skin]H331: Toxic if inhaled [Danger Acute toxicity, inhalation]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P260, P261, P262, P264, P270, P271, P272, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P333+P317, P361+P364, P362+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Acetic acid, bromo-Status: Active Update: 22-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/13566Bromoacetic acid: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT-Kennzeichnung | Corrosive |
| Brandgefahren | Excerpt from ERG Guide 156 [Substances - Toxic and/or Corrosive (Combustible / Water-Sensitive)]:Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). Vapors may travel to source of ignition and flash back. Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water. (ERG, 2024)· Combustible material: may burn but does not ignite readily.· Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff.· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.). |
Anwendungen & Verwendung
Verwenden
Bromoacetic acid is used in organic synthesis and as an alkylating agent. It is also used as a biochemical for proteomics research. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, dyes and agrochemicals.
Herstellung & Synthese
synthetische
Bromoacetic acid is commonly prepared via α-bromination of acetic acid with bromine under dehydrating conditions provided by acetic anhydride. Pyridine may be employed as a solvent and acid scavenger. The overall stoichiometric equation is: CH₃COOH + Br₂ → BrCH₂COOH + HBr