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223964

Sigma-Aldrich

Bis(tetrabutylammonium) dichromate

99%

Synonym(s):

TBADC, Tetrabutylammonium dichromate

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About This Item

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

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

Storage Class Code

5.1B - Oxidizing hazardous materials

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)

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