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L04151 Acetobromo-alpha-D-glucose, 97%, stab. with 2% calcium carbonate

CAS Number
572-09-8
Synonyms
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

Stock No. Size Price ($) Quantity Availability
L04151-09 10g 83.30
L04151-18 50g 279.00
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Acetobromo-alpha-D-glucose, 97%, stab. with 2% calcium carbonate

MDL
MFCD00063254
EINECS
209-339-0

Chemical Properties

Formula
C14H19BrO9
Formula Weight
411.22
Melting point
84-89°
Storage & Sensitivity
Store at -20°C. Moisture Sensitive.
Solubility
Soluble in ether, chloroform, ethanol, acetone, dichloromethane, ether, ethyl, methanol, and tetrahydrofuran. Insoluble in water.

Applications

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.

Notes

Store in a cool place. Incompatible with strong oxidizing agents, acids, magnesium and aluminum.

Literature References

Glycosyl isothiocyanates have been prepared in good yield by heating fully O-acetylated glycosyl bromides with KSCN in the absence of solvent. With acetobromo-ɑ-D-glucose, displacement was accompanied by stereochemical inversion: Synthesis, 1228 (1995).

Reaction with Bis(cyclopentadienyl)­titanium dichloride, A11456 results in 1,2-elimination providing a convenient route to the glycal: J. Org. Chem., 60, 7055 (1995).

Forget, S. M.; Jee, A.; Smithen, D. A.; Jagdhane, R.; Anjum, S.; Beaton, S. A.; Palmer, D. R. J.; Syvitski, R. T.; Jakeman, D. L. Kinetic evaluation of glucose 1-phosphate analogues with a thymidylyltransferase using a continuous coupled enzyme assay. Org. Biomol. Chem. 2015, 13 (3), 866-875.

Xu, Y.; Wang, W.; Cai, Y.; Yang, X.; Wang, P. G.; Zhao, W. A convenient and efficient synthesis of glycals by zinc nanoparticles. RSC Adv. 2014, 4 (87), 46662-46665.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,60
Beilstein
96669
Harmonized Tariff Code
2940.00
TSCA
No

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