2,4,6-Tri-tert-butylphenol Property

Melting point:

125-130 °C (lit.)

Boiling point:

277 °C (lit.)

Density 

0.8640

vapor pressure 

0.073Pa at 25℃

refractive index 

1.5029 (estimate)

Flash point:

130 °C

storage temp. 

-70°C

solubility 

Chloroform (Slightly), DMSO (Slightly, Sonicated)

pka

12.61±0.40(Predicted)

form 

buffered aqueous glycerol solution

color 

Off-White to Pale Yellow

biological source

rabbit

Water Solubility 

insoluble

BRN 

1913256

Specific Activity

583-789nmol/min·mg

InChIKey

PFEFOYRSMXVNEL-UHFFFAOYSA-N

LogP

7.1 at 35℃

CAS DataBase Reference

732-26-3(CAS DataBase Reference)

NIST Chemistry Reference

Phenol, 2,4,6-tris(1,1-dimethylethyl)-(732-26-3)

EPA Substance Registry System

2,4,6-Tris(tert-butyl)phenol (732-26-3)

Safety

Hazard Codes 

F,C,N,Xi,Xn

Risk Statements 

11-22-34-50-53-36/37/38-51/53

Safety Statements 

26-36/37/39-45-60-61-24/25

RIDADR 

UN 2430 8/PG 3

WGK Germany 

3

RTECS 

SN3570000

F 

8-23

HazardClass 

9

PackingGroup 

III

HS Code 

29071990

Hazardous Substances Data

732-26-3(Hazardous Substances Data)

Toxicity

LD50 oral in rat: 1670mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H317May cause an allergic skin reaction

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

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

P273Avoid release to the environment.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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

2,4,6-Tri-tert-butylphenol Chemical Properties,Usage,Production

Chemical Properties

Solid. Insoluble in water; soluble in most organic solvents. Combustible.

Uses

2,4,6-Tri-tert-butylphenol is an antioxidant; used in preparation method of high-temperature resistant electromagnetic shielding electromagnetic bushing.

Flammability and Explosibility

Non flammable

Biological Activity

CDK5 is a member of the Cyclin-Dependent Kinase family th at is most abundant in the mammalian brain. Active form of CDK5, which has also been called neuronal cdc2-like kinase, is a heterodimer of CDK5 and a 25 kDa protein which is derived proteolytically from a 35 kDa brain and neuron-specific protein and is essential for the kinase activity of CDK5. CDK5 has emerged as a crucial regulator of neuronal migration in the developing central nervous system. CDK5 phosphorylates a diverse list of substrates, implicating it in the regulation of a range of cellular processes - from adhesion and motility, to synaptic plasticity and drug addiction.

Purification Methods

Distil the phenol under reduced pressure and/or recrystallise it from n-hexane or several times from 95% EtOH until the EtOH solution is colourless [Balasubramanian & Bruice J Am Chem Soc 108 5495 1986]. It has also been purified by sublimation [Yuan & Bruice J Am Chem Soc 108 1643 1986, Wong et al. J Am Chem Soc 109 3428 1987]. Purification has also been achieved by passage through a silica gel column followed by recrystallisation from n-hexane [Kajii et al. J Phys Chem 91 2791 1987]. [Beilstein 6 III 2094, 6 IV 3539.]

Toxicity evaluation

In order to study the chronic toxicity of 2,4,6-tri-tert-butylphenol (TTBP), groups of 40 Slc: Wistar rats of either sex were fed a diet containing 0, 30, 100, 300, or 1000 ppm of TTBP for up to 24 months. Hematological, biochemical, and histopathological examinations performed periodically revealed slight microcytic anemia, changes in some biochemical parameters relating to liver function, and focal necrosis of liver cells following TTBP administration, and these changes observed in females were more severe than those in males. No neoplastic responses following TTBP administration were noted. Hence, it was concluded that TTBP causes liver injury characterized by focal necrosis with microcytic anemia and elevations of serum phospholipids and cholesterol levels, presumably occurring as secondary effects following the liver injury[1].

References

[1] Matsumoto, Kiyoshi , et al. "Chronic toxicity of 2,4,6-tri-tert-butylphenol in rats." Journal of Toxicological Sciences 16.4(1991):167.