2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
Synonym(s):1-Bromo-α-D -glucose tetraacetate;2,3,4,6-Tetra-O-acetyl-α-D -glucopyranosyl bromide
- CAS NO.：572-09-8
- Empirical Formula: C14H19BrO9
- Molecular Weight: 411.2
- MDL number: MFCD00063254
- EINECS: 209-339-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-26 14:09:12
What is 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide?
Chemical properties
White Fluffy Solid
The Uses of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
An Intermediate in synthesis of ∫-glucosides
The Uses of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.
Purification Methods
If nicely crystalline, recrystallise it from Et2O/pentane or pet ether (b 40-60o). Alternatively dissolve it in diisopropyl ether (dried over CaCl2 for 24hours, then over P2O5 for 24hours) by shaking and warming (for as short a period as possible), and filter warm. Cool to ca 45o, then slowly to room temperature and finally at 5o for more than 2hours. Collect the solid, wash it with cold dry diisopropyl ether and dry it in a vacuum over Ca(OH)2 and NaOH. Store it dry in a desiccator in the dark. Solutions can be stabilised with 2% CaCO3. [Redemann & Niemann Org Synth 65 236 1987, Coll Vol III 11 1955, Beilstein 17/6 V 368.]
Properties of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
| Melting point: | 86-89 °C |
| Boiling point: | 0.125-30 °C(Press: 0.0005 Torr) |
| alpha | 194.5 º (c=2,chloroform) |
| Density | 1.49±0.1 g/cm3(Predicted) |
| storage temp. | −20°C |
| solubility | Acetontrile (Very Slightly), Chloroform (Slightly), Methanol (Slightly) |
| form | Powder |
| color | White to beige |
| Water Solubility | decomposes |
| Sensitive | Moisture Sensitive |
| Merck | 14,60 |
| BRN | 96669 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. |
| CAS DataBase Reference | 572-09-8(CAS DataBase Reference) |
Safety information for 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
| InChIKey | CYAYKKUWALRRPA-RGDJUOJXSA-N |
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