4-Chloro-7-nitrobenzofurazan

Base Information

• Chemical Name: 4-Chloro-7-nitrobenzofurazan
• CAS No.: 10199-89-0
• Deprecated CAS: 1431536-46-7
• Molecular Formula: C6H2ClN3O3
• Molecular Weight: 199.553
• Hs Code.: 29349990
• European Community (EC) Number: 233-496-4
• NSC Number: 228140
• UNII: EQF2794IRE
• DSSTox Substance ID: DTXSID2064995
• Nikkaji Number: J76.301B
• Wikidata: Q229939
• ChEMBL ID: CHEMBL1743207
• Mol file: 10199-89-0.mol

Synonyms:4 Chloro 7 nitrobenzofurazan;4-Chloro-7-nitrobenzofurazan;7 Chloro 4 nitrobenzofurazan;7-Chloro-4-nitrobenzofurazan;Chloride, NBD;Chloride, Nitrobenzoxadiazole;Chloronitrobenzoxadiazole;NBD Chloride;NBF Cl;NBF-Cl;Nitrobenzoxadiazole Chloride

Chemical Property of 4-Chloro-7-nitrobenzofurazan

Chemical Property:

• Appearance/Colour: yellow to light brown crystalline powder
• Vapor Pressure: 0.000269mmHg at 25°C
• Melting Point: 97-99 °C(lit.)
• Refractive Index: 1.679
• Boiling Point: 333.144 °C at 760 mmHg
• PKA: -5.65±0.50(Predicted)
• Flash Point: 155.28 °C
• PSA: 84.74000
• Density: 1.712 g/cm³
• LogP: 2.30760
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol, dimethylsulfoxide, dimethylformamide and ch
• Water Solubility.: soluble
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 198.9784686
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

NBC1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/38
• Safety Statements: 36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C2=NON=C2C(=C1)Cl)[N+](=O)[O-]
• Uses: 4-Chloro-7-nitrobenzofurazan is nonfluorescent until it reacts with primary or secondary amines to produce a fluorescent product. 4-Chloro-7-nitrobenzofurazan has been extensively used as a derivatizing reagent for chromatography analysis of amino acids and low molecular weight amines. A fluorescent reagent 4-Chloro-7-nitrobenzofurazan is used as a derivatizing reagent for chromatography analysis of amino acids and low molecular weight amines. It is utilized in the preparation of fluorescent phospholipid-derivative, hydroxynaphthofurazan and 4-chloro-7-nitrobenzofurazan- didecanoylphosphatidylethanolamine. It serves as a fluorescent reagent to label free sulfhydryls and N-terminals within proteins and trapping agent for cysteine sulfenic acid. It is a sensitive chromogenic and fluorogenic reagent. It reacts with trans-1-methoxy-3-(trimethylsilyloxy)-1,3-butadiene (Danishefsky's diene) to prepare regioselectively the silyl enol ether. Further, it is used to label peptides, proteins and other biomolecules. In addition it is used in the synthesis of fluorescent phospholipid-derivative, NBD-didecanoylphosphatidylethanolamine, functionalized hydroxynaphthofurazan and 7-nitrobenzofurazan (NBD)-labeled maleimide.

Technology Process of 4-Chloro-7-nitrobenzofurazan

There total 8 articles about 4-Chloro-7-nitrobenzofurazan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 54.0%

4-chloro-2,1,3-benzoxadiazole (7116-16-7) → NBD chloride (10199-89-0)

Guidance literature:

With sodium nitrate; sulfuric acid; at 0 - 85 ℃; for 0.583333h;

DOI:10.3762/bjoc.13.76

Reference yield:

2,6-dichloronitrosobenzene (1194-66-7) → NBD chloride (10199-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) NaN₃, DMSO, (ii) (heating)

2: HNO₃, H₂SO₄

With sulfuric acid; nitric acid;

DOI:10.1021/jm00308a027

Reference yield:

2,6-Dichloroaniline (608-31-1) → NBD chloride (10199-89-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 23 °C / Inert atmosphere

2: sodium azide / dimethyl sulfoxide / 2.5 h / 23 °C / Inert atmosphere

3: sodium nitrate; sulfuric acid / water / 0.07 h / 0 °C / Inert atmosphere

With sodium nitrate; sodium azide; sulfuric acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2011.02.111

upstream raw materials:

4-chloro-2,1,3-benzoxadiazole

2,6-dichloronitrosobenzene

2,6-Dichloroaniline

2,6-dichloronitrobenzene

Downstream raw materials:

4'-[(2-n-Butyl-6-(7-nitro-benzofurazan-4-yl-amino)-benzimidazol-1-yl)-methyl]biphenyl-2-carboxylic acid

C₃₉H₄₆N₄O₉S

C₅₅H₆₇N₁₁O₁₄S

C₈₇H₁₀₉N₂₅O₂₄S

Refernces

• 1、 B?rgardts, Markus,Müller, Thomas J. J.. "Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes". . p. 768 - 778. Retrieved 2017.
• 2、 Jung, Michael E.,Dong, Timothy A.,Cai, Xiaolu. "Improved synthesis of 4-amino-7-nitrobenz-2,1,3-oxadiazoles using NBD fluoride (NBD-F)". body text. p. 2533 - 2535. Retrieved 2011/06/21.