ChemicalBook > CAS DataBase List > 2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE

2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE

Product Name
2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE
CAS No.
186689-07-6
Chemical Name
2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE
Synonyms
2-NBDG;NBD-GLUCOSE;2-NBD-Glucose;2-NBDG min. 95%;2-NBDG, 10 mM in DMSO;Alitretinoin Impurity 14;2-NBD-Glucose, Fluorescent glucose uptake probe;2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose;2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE;D-Glucose, 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-
CBNumber
CB7380499
Molecular Formula
C12H14N4O8
Formula Weight
342.26
MOL File
Mol file
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2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE Property

Melting point:
137 - 140°C
Boiling point:
740.0±70.0 °C(Predicted)
Density 
1.750±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in DMSO (up to 10 mg/ml).
form 
solid
pka
12.96±0.20(Predicted)
color 
Dark yellow to orange/red
biological source
synthetic
BRN 
7603370
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChI
InChI=1S/C12H14N4O8/c17-3-6(11(20)12(21)8(19)4-18)13-5-1-2-7(16(22)23)10-9(5)14-24-15-10/h1-3,6,8,11-13,18-21H,4H2/t6-,8+,11+,12+/m0/s1
InChIKey
QUTFFEUUGHUPQC-ILWYWAAHSA-N
SMILES
O=C[C@H](NC1C2C(C([N+]([O-])=O)=CC=1)=NON=2)[C@H]([C@@H]([C@@H](CO)O)O)O
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Safety

WGK Germany 
3
HS Code 
2934999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML4177
Product name
2-NBDG
Purity
≥97% (HPLC)
Packaging
1 unit
Price
$141.55
Updated
2025/07/31
Sigma-Aldrich
Product number
72987
Product name
2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose
Purity
≥97% (HPLC)
Packaging
1mg
Price
$334
Updated
2025/07/31
TCI Chemical
Product number
N1178
Product name
2-NBDG
Packaging
5MG
Price
$300
Updated
2025/07/31
Cayman Chemical
Product number
11046
Product name
2-NBDG
Purity
≥98% (mixture of α and β)
Packaging
1mg
Price
$39
Updated
2024/03/01
Cayman Chemical
Product number
11046
Product name
2-NBDG
Purity
≥98% (mixture of α and β)
Packaging
5mg
Price
$117
Updated
2024/03/01
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2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE Chemical Properties,Usage,Production

Description

2-NBDG is a fluorescent derivative of glucose whose uptake is competitively inhibited by D-glucose , but not L-glucose or sucrose, in E. coli. It has been used to monitor glucose uptake by bacteria and live mammalian cells and in tumor biopsies. 2-NBDG displays excitation/emission maxima of 475/550 nm, respectively.

Uses

2-NBDG is a fluorescent glucose uptake indicator, used in real-time confocal, high-resolution, or wide-field fluorescence microscopy as well as in flow cytometry.

storage

Store at -20°C

References

[1] KAZUAKI YOSHIOKA. A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake activity of Escherichia coli[J]. Biochimica et biophysica acta. General subjects, 1996, 1289 1: Pages 5-9. DOI:10.1016/0304-4165(95)00153-0
[2] K YAMADA. Measurement of glucose uptake and intracellular calcium concentration in single, living pancreatic beta-cells.[J]. The Journal of Biological Chemistry, 2000, 275 29: 22278-22283. DOI:10.1074/jbc.m908048199
[3] A. LOAIZA L B O Porras. Glutamate Triggers Rapid Glucose Transport Stimulation in Astrocytes as Evidenced by Real-Time Confocal Microscopy[J]. The Journal of Neuroscience, 2003, 5 1: 7337-7342. DOI:10.1523/jneurosci.23-19-07337.2003

2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE Preparation Products And Raw materials

Raw materials

Preparation Products

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2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE Suppliers

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View Lastest Price from 2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
2-NBDG 186689-07-6
Price
US $0.00/G
Min. Order
10G
Purity
98%min
Supply Ability
30kg/month
Release date
2023-02-15

186689-07-6, 2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSERelated Search:

CASTANOSPERMINE benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride C6-NBD-CERAMIDE BZ-VAL-GLY-ARG-AMC TRIFLUOROACETATE SALT (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride Thianaphthene Benzothiazole Dibenzothiophene N,N-Dimethylformamide

  • 2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE
  • 2-NBDG
  • 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose
  • 2-NBDG min. 95%
  • 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose, 90%, mixed Isomers
  • 2-NBD-Glucose
  • 2-NBDG [2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)Amino)-2-Deoxyglucose] *CAS#: 186689-07-6*
  • 2-NBDG,2-(N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose
  • NBD-GLUCOSE
  • D-Glucose, 2-deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-
  • 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-D-glucose >=97% (HPLC)
  • 2-(N-(7-NITROBENZ-2-OXA-1,3-DIAZOL-4-YL)AMINO)-2-DEOXYGLUCOSE (NBDG)
  • Alitretinoin Impurity 14
  • 2-NBD-Glucose, Fluorescent glucose uptake probe
  • 2-NBDG, 10 mM in DMSO
  • (2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]hexanal
  • 2-Deoxy-2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]-<sc>D</sc>-glucose
  • 186689-07-6