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223964

Sigma-Aldrich

Bis(tetrabutylammonium) dichromate

99%

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Synonym(s):
TBADC, Tetrabutylammonium dichromate
Linear Formula:
[(CH3CH2CH2CH2)4N]2Cr2O7
CAS Number:
56660-19-6
Molecular Weight:
700.92
EC Number:
260-315-6
MDL number:
MFCD00013104
UNSPSC Code:
12352116
PubChem Substance ID:
24853415
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

reaction suitability

reagent type: oxidant

mp

139-143 °C (lit.)

SMILES string

[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC

InChI

1S/2C16H36N.2Cr.7O/c2*1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;;;;;;;;;/h2*5-16H2,1-4H3;;;;;;;;;/q2*+1;;;;;;;;2*-1

InChI key

MMKQSIQNDMIVIN-UHFFFAOYSA-N

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Application

Bis(tetrabutylammonium) dichromate (TBADC) is a mild oxidizing agent which can be used as a reagent for:
  • Preparation of nitrophenol derivatives and quinones under aprotic reaction conditions.
  • Conversion of oximes to carbonyl compounds under microwave irradiation.
  • Catalyst precursor for gas phase dehydration of acetic acid to ketene.

Reagent for:
  • Preparation of nitrophenol derivatives and quinones under aprotic reaction conditions
  • Conversion of oximes to carbonyl compounds under microwave irradiation

  • Catalyst precursor for catalytic gas phase dehydration of acetic acid to ketene
  • Crosslinking agent

Signal Word

Danger

Hazard Statements

H272,H317,H350,H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 1B - Ox. Sol. 2 - Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Regeneration of carbonyl compounds from oximes using BTBAD under microwave irradiation.
Murugan R and Reddy BSR
Chemistry Letters (Jpn), 33(8), 1038-1039 (2004)
Catalytic gas phase dehydration of acetic acid to ketene.
Waters T, et al.
International Journal of Mass Spectrometry, 228(2-3), 599-611 (2003)
Bis-tetrabutylammonium Dichromate as a Neutral and Selective Oxidant of Hydroxy Compounds.
Santaniello E and Ferraboschi P
Synthetic Communications, 10(1), 75-81 (1980)
Nitration of phenolic compounds and oxidation of hydroquinones using tetrabutylammonium chromate and dichromate under aprotic conditions.
Pourali AR and Goli A
Journal of Chemical Sciences (Bangalore), 123(1), 63-67 (2011)
Bis (tetrabutylammonium) Dichromate.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)

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