Acetobromo-α-D-glucose - ≥98%, contains2% CaCO3 as stabilizer , CAS No.572-09-8

CAS: 572-09-8 Cat. No.: T110108 Molecular Weight: 411.20 Beilstein Registry Number: 96669 EC Number: 209-339-0

GRADE & PURITY ≥98%, contains2% CaCO3 as stabilizer

Synonyms

Acetobromo-alpha-D-glucose | 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide (stabilized with CaCO3) | 1-Bromo-α-D-glucose tetraacetate

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Intermediate in synthesis of β-glucosides.
An Intermediate in synthesis of ∫-glucosides

Application

Acetobromo-α-D-glucose is used as a possible poly (ethylene terephthalate) (PET) surface modification reagent to increase its blood compatibility.

Specifications

Synonyms

Acetobromo-alpha-D-glucose | 2, 3, 4, 6-Tetra-O-acetyl-α-D-glucopyranosyl Bromide (stabilized with CaCO3) | 1-Bromo-α-D-glucose tetraacetate

Specifications & Purity

≥98%, contains2% CaCO3 as stabilizer

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• IUPAC Name: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate
• InChIKey: CYAYKKUWALRRPA-RGDJUOJXSA-N
• INCHI: 1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Molecular Weight: 411.20
• Beilstein: 96669
• Reaxy-Rn: 1299080
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1299080&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Tetracarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Tetracarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Tetracarboxylic acids and derivatives
• Alternative Parents: Oxanes Monosaccharides Carboxylic acid esters Oxacyclic compounds Dialkyl ethers Organobromides Organic oxides Hydrocarbon derivatives Carbonyl compounds Alkyl bromides
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Tetracarboxylic acid or derivatives - Oxane - Monosaccharide - Carboxylic acid ester - Oxacycle - Organoheterocyclic compound - Ether - Dialkyl ether - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Carbonyl group - Alkyl halide - Alkyl bromide - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in chloroform, water (reacts), abs. ethanol (0.05 g/ml), acetone, dichloromethane, ether, ethyl, methanol, and THF
• Sensitivity: Moisture & Light & Heat sensitive
• Specific Rotation[α]: 198 ° (C=3, CHCl3)
• Melt Point(°C): 83-88°C
• Molecular Weight: 411.200 g/mol
• XLogP3: 1.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 410.021 Da
• Monoisotopic Mass: 410.021 Da
• Topological Polar Surface Area: 114.000 Ų
• Heavy Atom Count: 24
• Formal Charge: 0
• Complexity: 506.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Xianhu Wei, Qihui Gu, Ying Feng, Youxiong Zhang, Ying Li, Shuhong Zhang, Jumei Zhang, Shi Wu, Xiaojuan Yang, Qinghua Ye, Yu Ding, Juan Wang, Moutong Chen, Qingping Wu.  (2022)  Sensitive and Selective Detection of Enterococcus faecalis Using a New Turn-on Fluorogenic β-glucosidase Substrate Combined with a Modified Selective Broth.  PHOTOCHEMISTRY AND PHOTOBIOLOGY,  99  (1): (68-77).  [PMID:35699359] [10.1111/php.13662]