537-45-1

Basic information

• Product Name: 2,6-DIBROMOQUINONE-4-CHLOROIMIDE
• Synonyms: 2,6-dibromo-n-chloro-p-benzoquinoneimide;2,6-DIBROMO-QUININE-4-CHLOROIMIDE;2,6-Dibromoquinone chlorimide, typically 98%;2,6-Dibromo-4-chloro-p-quinoneimide;2,6-Dibromo-p-benzoquinone-4-chloroimide;BQC;2,6-Dibromo-N-chloro-p-benzoquinoneimine,97%;2,6-Dibromoquinone-4-chlorimide, reagent grade
• CAS NO: 537-45-1
• Molecular Formula: C₆H₂Br₂ClNO
• Molecular Weight: 299.35
• EINECS: 208-667-1
• Mol File: 537-45-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 76-84 °C
• Boiling Point: 295.9 °C at 760 mmHg
• Flash Point: 132.8 °C
• Appearance: Yellow to ochre/Powder or Fine Crystalline Needles
• Density: 2.1919 (rough estimate)
• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.6110 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -4.72±0.20(Predicted)
• Stability: Light Sensitive
• Merck: 14,3026
• BRN: 2094249
• CAS DataBase Reference: 2,6-DIBROMOQUINONE-4-CHLOROIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIBROMOQUINONE-4-CHLOROIMIDE(537-45-1)
• EPA Substance Registry System: 2,6-DIBROMOQUINONE-4-CHLOROIMIDE(537-45-1)

Safety Data

• Hazard Codes: Xn
• Statements: 5-20/21-36/37/38-22
• Safety Statements: 36/37-37/39-26
• WGK Germany: 3
• RTECS: GU5435000
• F: 4.4
• TSCA: Yes
• Hazardous Substances Data: 537-45-1(Hazardous Substances Data)

Usage

Chemical Properties

yellow to ochre-colored powder or fine

Uses

2,6-Dibromoquinone-4-chloroimide is a reagent for the determination of phenols after TLC, organophosphorus compounds, and cyanides.

Definition

A reagent used for spot visualizations in chromotographic systems.

Hazard

Highly sensitive to heat; explodes at 120C, decomposes with rapid heat evolution at 60C.

InChI:InChI=1/C6H2Br2ClNO/c7-4-1-3(10-9)2-5(8)6(4)11/h1-2H

Synthetic route

2,6-dibromo-4-nitrophenol (99-28-5) → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

Conditions	Yield
With hydrogenchloride; tin anschliessendes Behandeln mit wss. NaOCl bei -5grad bis -3grad;

2,6-dibromo-1,4-benzoquinone (19643-45-9) → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

Conditions	Yield
With sodium hypochlorite; ammonia

2,6-dibromo-4-aminophenol (609-21-2) → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

Conditions	Yield
With hydrogenchloride; sodium hypochlorite at 0℃;
With sodium hydroxide; chlorine

2,6-dibromo-1,4-benzoquinone (19643-45-9) + ammonia (7664-41-7) + sodium hypochlorite → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

2,6-dibromo-1,4-benzoquinone (19643-45-9) + glycine (56-40-6) + sodium hypochlorite → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

tin double salt of 2.6-dibromo-4-amino-phenol → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

Conditions	Yield
With water; calcium chloride

2,6-dibromo-4-aminophenol (609-21-2) + calcium chloride → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

water (7732-18-5) + 4-amino-2,6-dibromo-phenol; hydrochloride (56967-16-9) + sodium hypochlorite → 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1)

Conditions	Yield
at 0℃;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + norfluoxetine (83891-03-6) → C6H2Br2ClNO*C16H16F3NO

Conditions	Yield
at 20℃; for 1h;	76%

9,10-dihydrodibenzazepine (494-19-9) + 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) → 2,6-Dibrom-4-(5H-10,11-dihydrodibenzo[b,f]azepin-2-ylimino)-cyclohexa-2,5-dien-1-on

Conditions	Yield
With sodium hydrogencarbonate In acetic acid at 20℃; for 1h;	15.9%

8-quinolinol (148-24-3) + 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) → 4-(8-acetoxy-[5]quinolylimino)-2,6-dibromo-cyclohexa-2,5-dienone (109817-84-7)

Conditions	Yield
With 1,4-dioxane; sodium carbonate Behandeln des Reaktionsprodukts mit Acetanhydrid und Pyridin;

2-methyl-8-quinolinol (826-81-3) + 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + acetic anhydride (108-24-7) → 4-(8-acetoxy-2-methyl-[5]quinolylimino)-2,6-dibromo-cyclohexa-2,5-dienone (109590-42-3)

Conditions	Yield
With 1,4-dioxane; water; sodium carbonate Reagens 4: Pyridin;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + potassium ethyl xanthogenate (140-89-6) → 2,6-dibromo-[1,4]benzoquinon-4-(S-ethoxythiocarbonyl-thio oxime ) (112625-78-2)

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + sodium salicylate (54-21-7) → 5-(3,5-dibromo-4-hydroxy-anilino)-2-hydroxy-benzoic acid

Conditions	Yield
With sodium hydroxide; diethyl ether; water man reduziert die entstandene Verbindung durch Eintragen von Traubenzucker in die alkalische Loesung; Einleiten von Schwefeldioxid;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + N,N-dimethyl-aniline (121-69-7) → 2,6-dibromo-[1,4]benzoquinone-4-(4-dimethylamino-phenylimine) (197961-56-1)

Conditions	Yield
With ethanol at 30℃;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + 2-Phenylphenol (90-43-7) → 2,6-dibromo-[1,4]benzoquinon-4-(6-acetoxy-biphenyl-3-ylimine) (112552-37-1)

Conditions	Yield
With 1,4-dioxane; sodium carbonate anschliessend mit Acetanhydrid;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + phenol (108-95-2) → 2,6-dibromophenolindophenol (2582-33-4)

Conditions	Yield
in mit Borax gepufferter Loesung;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + phenol (108-95-2) → 2,6-dibromophenolindophenol sodium salt (5415-23-6)

Conditions	Yield
With ethanol in alkal. Loesung;

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + phenol (108-95-2) + alkali → dibromoindophenol

2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) + trazodone (19794-93-5) → [trazodone][2,6-dibromoquinone-4-chloroimide]

Conditions	Yield
In methanol; chloroform at 20℃; for 1h;

diethylbarbituric acid (57-44-3) + 2,6-Dibrom-1,4-benzochinon-4-chlorimin (537-45-1) → C8H12N2O3*C6H2Br2ClNO

Conditions	Yield
In methanol at 60℃; for 0.75h;

Upstream product

• 7732-18-5 water 
• 56967-16-9 4-amino-2,6-dibromo-phenol; hydrochloride 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 56-40-6 glycine 
• 7664-41-7 ammonia 
• 99-28-5 2,6-dibromo-4-nitrophenol 
• 609-21-2 2,6-dibromo-4-aminophenol 

Downstream Products

• 197961-56-1 2,6-dibromo-[1,4]benzoquinone-4-(4-dimethylamino-phenylimine) 
• 112552-37-1 2,6-dibromo-[1,4]benzoquinon-4-(6-acetoxy-biphenyl-3-ylimine) 
• 2582-33-4 2,6-dibromophenolindophenol 
• 5415-23-6 2,6-dibromophenolindophenol sodium salt 
• 112625-78-2 2,6-dibromo-[1,4]benzoquinon-4-(S-ethoxythiocarbonyl-thio oxime ) 
• 109817-84-7 4-(8-acetoxy-[5]quinolylimino)-2,6-dibromo-cyclohexa-2,5-dienone