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CAS RN: 84-58-2 | Product Number: D1070

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone


Purity: >97.0%(T)
Synonyms:
  • DDQ
Documents:
25G
$104.00
7   3   ≥100 
250G
$632.00
1   1   ≥60 

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Product Number D1070
Purity / Analysis Method >97.0%(T)
Molecular Formula / Molecular Weight C__8Cl__2N__2O__2 = 227.00 
Physical State (20 deg.C) Solid
Storage Temperature Refrigerated (0-10°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Moisture Sensitive,Heat Sensitive
CAS RN 84-58-2
Reaxys Registry Number 747939
PubChem Substance ID 87567635
SDBS (AIST Spectral DB) 5029
Merck Index (14) 3063
MDL Number

MFCD00001593

Specifications
Appearance Yellow to Amber to Dark purple powder to crystal
Purity(Iodometric Titration) min. 97.0 %
Properties (reference)
Melting Point 214 °C
Solubility (soluble in) Benzene, Dioxane, Methanol
Solubility (slightly sol. in) dichloromethane, Chloroform
GHS
Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H301 + H311 + H331 : Toxic if swallowed, in contact with skin or if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P261 : Avoid breathing dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P301 + P310 + P330 : IF SWALLOWED: Immediately call a POISON CENTER/doctor. Rinse mouth.
P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water.Call a POISON CENTER/doctor if you feel unwell.
P304 + P340 + P311 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor.
P403 + P233 : Store in a well-ventilated place. Keep container tightly closed.
P405 : Store locked up.
Related Laws:
RTECS# GU4825000
Transport Information:
UN Number (DOT-AIR) UN3439
Class (DOT-AIR) 6.1
Packing Group (TCI-A) III
HS Number 2926.90.4801
Application
TCI Practical Example: The Construction of Rubicene through the Scholl Reaction.

Used Chemicals

Procedure

To a solution of 9,10-diphenylanthracene (200 mg, 0.61 mmol) and DDQ (412 mg, 1.8 mmol, 3.0 equiv) in dichloromethane (19 mL) was added TfOH (1 mL) at 0 °C and the mixture was stirred for 1 hour. The reaction mixture was quenched with sat. NaHCO3 aq. (20 mL), filtered through celite pad and the insoluble was washed with dichloromethane (100 mL). The organic layer was washed with sat. NaHCO3 aq. and dried over Na2SO4.The solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:dichloromethane = 0:1 - 1:3 on silica gel) to give rubicene (131 mg, 67%) as a red solid.

実施者コメント

The reaction mixture was monitored by TLC (hexane:dichloromethane = 3:2, Rf = 0.37).
The color of reaction mixtures changed like below;
Before adding TfOH: yellow
After adding TfOH: blue
After quenching with sat. NaHCO3 aq.: red.

Analytical Data(Rubicene)

1H NMR (400 MHz, CDCl3); δ 8.62 (d, J = 8.6 Hz, 2H), 8.34 (d, J = 7.6 Hz, 2H), 8.04 (d, J = 6.8 Hz, 2H), 7.98 (d, J = 7.0 Hz, 2H), 7.79 (dd, J = 8.6, 6.6 Hz, 2H), 7.45 (td, J = 7.6, 0.8 Hz, 2H), 7.39 (td, J = 7.6, 0.8 Hz, 2H).

Lead Reference


Application
Deprotection of Bn Groups using DDQ(2,3-Dichloro-5,6-dicyano-1,4-benzoquinone)

D1070

References

  • Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
    • P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.


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