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537-45-1

Basic Information
CAS No.: 537-45-1
Name: 2,6-DIBROMOQUINONE-4-CHLOROIMIDE
Molecular Structure:
Molecular Structure of 537-45-1 (2,6-DIBROMOQUINONE-4-CHLOROIMIDE)
Formula: C6H2Br2ClNO
Molecular Weight: 299.349
Synonyms: p-Benzoquinoneimine, 2,6-dibromo-N-chloro- (6CI,7CI);2,6-Dibromo-1,4-benzoquinone-4-chlorimide;2,6-Dibromo-N-chloro-p-benzoquinoneimine;2,6-Dibromoquinone chlorimide;4-(Chloroimino)-2,6-dibromo-2,5-cyclohexadien-1-one;BQC reagent;N-Chloro-2,6-dibromoquinoneimine;NSC 528;
EINECS: 208-667-1
Density: 2.18 g/cm3
Melting Point: 76-84 °C
Boiling Point: 295.9 °C at 760 mmHg
Flash Point: 132.8 °C
Appearance: yellow to ochre-colored powder
Hazard Symbols: HarmfulXn
Risk Codes: 5-20/21
Safety: 36/37
PSA: 29.43000
LogP: 2.72150
Synthetic route
99-28-5

2,6-dibromo-4-nitrophenol

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

Conditions
ConditionsYield
With hydrogenchloride; tin anschliessendes Behandeln mit wss. NaOCl bei -5grad bis -3grad;
19643-45-9

2,6-dibromo-1,4-benzoquinone

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

Conditions
ConditionsYield
With sodium hypochlorite; ammonia
609-21-2

2,6-dibromo-4-aminophenol

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

Conditions
ConditionsYield
With hydrogenchloride; sodium hypochlorite at 0℃;
With sodium hydroxide; chlorine
19643-45-9

2,6-dibromo-1,4-benzoquinone

7664-41-7

ammonia

sodium hypochlorite

sodium hypochlorite

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

19643-45-9

2,6-dibromo-1,4-benzoquinone

56-40-6

glycine

sodium hypochlorite

sodium hypochlorite

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

tin double salt of 2.6-dibromo-4-amino-phenol

tin double salt of 2.6-dibromo-4-amino-phenol

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

Conditions
ConditionsYield
With water; calcium chloride
609-21-2

2,6-dibromo-4-aminophenol

calcium chloride

calcium chloride

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

56967-16-9

4-amino-2,6-dibromo-phenol; hydrochloride

sodium hypochlorite

sodium hypochlorite

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

Conditions
ConditionsYield
at 0℃;
537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

83891-03-6

norfluoxetine

C6H2Br2ClNO*C16H16F3NO

Conditions
ConditionsYield
at 20℃; for 1h;76%
494-19-9

9,10-dihydrodibenzazepine

537-45-1

2,6-Dibrom-1,4-benzochinon-4-chlorimin

2,6-Dibrom-4-(5H-10,11-dihydrodibenzo[b,f]azepin-2-ylimino)-cyclohexa-2,5-dien-1-on

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

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Chemistry

IUPAC Name: 2,6-Dibromo-N-chloroquinonimine
Synonyms of 2,6-Dibromo-N-chloroquinonimine (CAS NO.537-45-1): 2,5-Cyclohexadien-1-one, 2,6-dibromo-4- (chloroimino)- ; 2, 6-Dibromo-p-benzoquinone-4-chlorimine ; 2, 6-Dibromoquinone-4-chloroimide ; 2,5-Cyclohexadien-1-one, 2,6-dibromo-4-(chloroimino)- ; 2,6-Dibromo-4-(chloroimino)-2,5-cyclohexadien-1-one
CAS NO: 537-45-1
Molecular Formula: C6H2Br2ClNO
Molecular Weight: 299.35
Molecular Structure:
EINECS: 208-667-1
H bond acceptors: 11
H bond donors: 5
Freely Rotating Bonds: 7
Polar Surface Area: 158.3 Å2
Molar Refractivity: 97.126 cm3
Molar Volume: 230.677 cm3
Surface Tension: 80.44 dyne/cm
Index of Refraction: 1.671  
Density: 2.18 g/ml 
Flash Point: 132.8°C 
Boiling Point: 295.9°C
Melting Point: 81-83°C
Storage temp: 2-8°C
Appearance: yellow to ochre-colored powder or fine
SMILES: O=C(N/C2=N/C(=O)c1ncn(c1N2)[C@@H]3O[C@@H]([C@@H](O)[C@H]3O)CO)Cc4ccccc4
InChI: InChI=1/C18H19N5O6/c24-7-10-13(26)14(27)17(29-10)23-8-19-12-15(23)21-18(22-16(12)28)20-11(25)6-9-4-2-1-3-5-9/h1-5,8,10,13-14,17,24,26-27H,6-7H2,(H2,20,21,22,25,28)/t10-,13-,14-,17-/m1/s1 Copy
InChIKey: IRSCBAKCFOLZNC-IWCJZZDYBW
Std. InChI: InChI=1S/C18H19N5O6/c24-7-10-13(26)14(27)17(29-10)23-8-19-12-15(23)21-18(22-16(12)28)20-11(25)6-9-4-2-1-3-5-9/h1-5,8,10,13-14,17,24,26-27H,6-7H2,(H2,20,21,22,25,28)/t10-,13-,14-,17-/m1/s1
Std. InChIKey: IRSCBAKCFOLZNC-IWCJZZDYSA-N

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 63mg/kg (63mg/kg)   Journal of Medicinal Chemistry. Vol. 21, Pg. 11, 1978.
rat LD oral > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 21, 1953.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Safety information of 2,6-Dibromo-N-chloroquinonimine (CAS NO.537-45-1):
Hazard Codes  Xn
Risk Statements: 5-20/21
5: Heating may cause an explosion
20/21: Harmful by inhalation and in contact with skin
Safety Statements: 36/37
36/37: Irritating to eyes and respiratory system
WGK Germany: 3
RTECS  GU5435000
F  4.4Poison by intraperitoneal route. A storage hazard. May explode at room temperature. Explodes when heated above 50°C. When heated to decomposition it emits very toxic fumes of Br, Cl, and NOx.

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. 
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store in a tightly closed container. Store in a dry area. Keep refrigerated. (Store below 4°C/39°F.)