Bis(tetrabutylammonium) dichromate

Bis(tetrabutylammonium) dichromate Property

Melting point:

139-143 °C (lit.)

solubility 

sol dichloromethane, chloroform.

form 

powder to crystaline

color 

Light yellow to Brown

Water Solubility 

Soluble in water.

Exposure limits

OSHA: Ceiling 0.1 mg/m3
NIOSH: IDLH 15 mg/m3; TWA 0.0002 mg/m3

Safety

Hazard Codes 

O,T,N

Risk Statements 

49-8-43-50/53

Safety Statements 

53-45-60-61

RIDADR 

UN 1479 5.1/PG 2

WGK Germany 

2

F 

8

HazardClass 

5.1

PackingGroup 

III

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H272May intensify fire; oxidizer

H317May cause an allergic skin reaction

H350May cause cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P308+P313IF exposed or concerned: Get medical advice/attention.

Bis(tetrabutylammonium) dichromate Chemical Properties,Usage,Production

Uses

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

Application

Bis(tetrabutylammonium) Dichromate (TBADC) is a mild selective oxidizing agent for benzylic and allylic alcohols^[1]. It can oxidize carbon-halogen bonds^[2].

Preparation

Preparative Method of Bis(tetrabutylammonium) Dichromate (TBADC): a concentrated aqueous solution (300 mL) of Potassium Dichromate (29.4 g, 0.1 mol) is added to a saturated aqueous solution (300 mL) of Tetra-n-butylammonium Bromide (64.4 g, 0.2 mol). TBADC precipitates and can be removed by filtration (62.8 g, 90% yield).

reaction suitability

reagent type: oxidant

storage

Bis(tetrabutylammonium) dichromate was reported to be a toxic agent. The reagent should be handled in a fume hood.

Purification Methods

Wash it with water and dry it in a vacuum. Recrystallise it from hexane (m 79-80o). [Santaniello & Ferraboschi Synth Commun 10 75 1980, Beilstein 4 IV 556.] (Possible CARCINOGEN.)

References

1. (a) Santaniello, E.; Ferraboschi, P. SC 1980, 10, 75. (b) Luzzio, F. A.; Guziec, F. S. OPP 1988, 20, 533.
2. Landini, D.; Rolla, F. CI(L) 1979, 213.