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2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
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Name

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

 EINECS 209-339-0
CAS No. 572-09-8 Density 1.49 g/cm3
PSA 114.43000 LogP 0.46440
Solubility decomposes in water Melting Point 86-89 °C
Formula C14H19BrO9 Boiling Point 412 °C at 760 mmHg
Molecular Weight 411.203 Flash Point 203 °C
Transport Information N/A Appearance white fluffy solid
Safety 24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 572-09-8 (2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide) Hazard Symbols IrritantXi
Synonyms

a-D-Glucopyranosyl bromide,2,3,4,6-tetraacetate;Glucopyranosylbromide, tetraacetate, a-D- (8CI);1-Bromo-2,3,4,6-tetra(O-acetyl)-a-D-pyranoglucose;2,3,4,6-Tetra-O-acetyl-1-a-bromo-D-glucopyranose;2,3,4,6-Tetraacetyl-a-D-glucopyranosyl bromide;Acetobromo-D-glucose;Acetobromoglucose;D-Acetobromoglucose;Tetra-O-acetyl-a-D-glucopyranosylbromide;Tetra-O-acetyl-a-D-glucosyl bromide;a-Acetobromoglucose;a-D-Acetobromoglucose;

Article Data 343

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Synthetic route

604-69-3

β-D-glucose pentaacetate

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide In dichloromethane Ambient temperature;100%
With hydrogen bromide; acetic acid at 20℃; for 4h;100%
With hydrogen bromide at 20℃; for 1.16667h;100%
83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5

D-glucose pentaacetate

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid at 20℃; Product distribution / selectivity;100%
With hydrogen bromide; acetic acid at 20℃; for 2h;100%
With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 3h;100%
604-68-2

α-D-glucopyranose peracetylate

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid100%
Stage #1: α-D-glucopyranose peracetylate With hydrogen bromide; acetic acid
Stage #2: at 0 - 20℃; for 2h;		98%
With acetic anhydride; phosphorus tribromide In water at 0℃; for 1h;95%
492-62-6

alpha-D-glucopyranose

506-96-7

Acetyl bromide

108-24-7

acetic anhydride

64-19-7

acetic acid

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With perchloric acid In methanol at 20℃; for 2h;99%
2872-65-3, 14581-81-8, 17042-40-9, 84380-06-3, 105260-62-6

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; for 24h;97%
3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3

2,3,4,5-tetra-O-acetyl-D-glucopyranose

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In dichloromethane at 0℃; for 8h;96%
With pyridine; (PhO)3P*Br2 In dichloromethane for 0.0833333h;89%
With hydrogen bromide; acetic anhydride In dichloromethane at 20℃; for 4h;85%
2280-44-6

D-Glucose

108-24-7

acetic anhydride

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
Stage #1: D-Glucose With Acetyl bromide In methanol
Stage #2: acetic anhydride With acetic acid		95%
Stage #1: D-Glucose; acetic anhydride With perchloric acid; acetic acid at 20℃; for 0.5h;
Stage #2: With Acetyl bromide In methanol for 2h;		90%
Stage #1: D-Glucose; acetic anhydride With sodium acetate at 100℃; for 5h;
Stage #2: With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 6h;		90%
492-62-6

alpha-D-glucopyranose

108-24-7

acetic anhydride

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
Stage #1: alpha-D-glucopyranose; acetic anhydride With perchloric acid at 30 - 40℃; for 1h;
Stage #2: With phosphorus; bromine at 20℃; Cooling with ice;
Stage #3: With water at 20℃; for 3.16667h;		90%
With hydrogen bromide; acetic acid at 20℃; for 11h;89%
With hydrogen bromide; acetic acid at 20℃; for 11h;85.88%
3891-59-6

Penta-O-acetyl-aldehydo-D-glucose

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide In dichloromethane; acetic acid at 20℃; for 6h;86%
With hydrogen bromide In acetic acid
160227-12-3

4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

A

4753-07-5

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

B

572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

C

3068-32-4

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Conditions
ConditionsYield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; Yields of byproduct given;A 82%
B n/a
C n/a

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Chemical Properties

 Product Name: Acetobromglucose (CAS NO.572-09-8)


Molecular Formula: C14H19BrO9
Molecular Weight: 411.20g/mol
Mol File: 572-09-8.mol
EINECS: 209-339-0
Appearance: White powder
Melting Point: 83-88 ºC
Boiling point: 412 °C at 760 mmHg
Flash Point: 203 °C
Density: 1.49 g/cm3
Water Solubility: Decomposes
Surface Tension: 47.9 dyne/cm
Enthalpy of Vaporization: 66.46 kJ/mol
Vapour Pressure: 5.35E-07 mmHg at 25°C
XLogP3-AA: 1.5
H-Bond Donor: 0
H-Bond Acceptor: 9
Structure Descriptors of Acetobromglucose (CAS NO.572-09-8):
  IUPAC Name: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]acetate
  Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
  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
  InChI: 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 
  InChIKey: CYAYKKUWALRRPA-RGDJUOJXSA-N

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Safety Profile

Safety Information of Acetobromglucose (CAS NO.572-09-8):
Safety Statements: S24/25
24:  Avoid contact with skin 
25:  Avoid contact with eyes 

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Specification

  Acetobromglucose , its CAS NO. is 572-09-8, the synonyms are EINECS 209-339-0 ; 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide ; alpha-D-Glucopyranosyl bromide, tetraacetate .

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