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Basic Information
CAS No.: 728-40-5
Name: DI-TERTBUTYLNITROPHENOL
Article Data: 42
Molecular Structure:
Molecular Structure of 728-40-5 (DI-TERTBUTYLNITROPHENOL)
Formula: C14H21 N O3
Molecular Weight: 251.326
Synonyms: Phenol,2,6-di-tert-butyl-4-nitro- (6CI,7CI,8CI);2,6-Bis(1,1-dimethylethyl)-4-nitrophenol; 2,6-Di-tert-butyl-4-nitrophenol;4-Nitro-2,6-bis-(1,1-dimethylethyl)phenol; 4-Nitro-2,6-di-tert-butylphenol; BAY28589; Bayer 28589; NSC 81682
Density: 1.078
Melting Point: 154-156℃
Boiling Point: 307℃
Flash Point: 118℃
Safety: Explodes when heated to 100°C. May explode spontaneously. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and PHENOLS.
PSA: 66.05000
LogP: 4.41860
Synthetic route
1516-95-6

2,6-di-tert-butyl-anisole

728-40-5

4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With sodium nitrite In acetic acid94%

(2,6-Di-tert-butyl-phenyl)-methanol

728-40-5

4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With sodium nitrite In acetic acid94%

(2,6-Di-tert-butyl-phenyl)-dimethyl-amine

728-40-5

4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With sodium nitrite In acetic acid94%
128-39-2

2,6-di-tert-butylphenol

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4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With aluminum(III) nitrate nonahydrate; oxalic acid at 20℃; for 0.5h; Grinding; neat (no solvent);92%
With tert.-butylnitrite In tetrahydrofuran at 20℃; for 12h;72%
With nitric acid In cyclohexane; acetic acid at 10 - 20℃; for 0.25h;65%
128-39-2

2,6-di-tert-butylphenol

10102-44-0

Nitrogen dioxide

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4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
In hexane at 28℃; for 1h; Nitration;75%
128-39-2

2,6-di-tert-butylphenol

A

2455-14-3

3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone

B

728-40-5

4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With sodium nitrite In acetic acidA 30%
B 58%
With Nitrogen dioxide In methanol at 20℃; for 1h;
88-26-6

3,5-di-tert-butyl-4-hydroxybenzyl alcohol

A

719-22-2

2,6-Di-tert-butyl-1,4-benzoquinone

B

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4-nitro-2,6-di-tert-butylphenol

Conditions
ConditionsYield
With nitric acid; sodium nitrite In tetrachloromethane Ambient temperature;A 37%
B 31%
105654-11-3

2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide

A

728-40-5

4-nitro-2,6-di-tert-butylphenol

B

105654-17-9

2,4,5,5-tetramethyl-2-<2-(1-hydroxy-3,5-di-tert-butylcyclohexadien-2,5-onyl)-1-ethyl>-3-imidazoline 3-oxide

C

1-nitroso-2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide

D

1-nitroso-2,4,5,5-tetramethyl-2-<2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-ethyl>-3-imidazoline 3-oxide

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature; Yields of byproduct given;A 7%
B 18%
C n/a
D n/a
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature;A 7%
B 18%
C n/a
D n/a
With hydrogenchloride; sodium nitrite In ethanol for 3h; Ambient temperature; Yield given;A 7%
B 18%
C n/a
D n/a
381-73-7

Difluoroacetic acid

56577-75-4

2,6-Di-tert-butyl-4-nitro-phenol anion

A

728-40-5

4-nitro-2,6-di-tert-butylphenol

B

83193-04-8

2,2-difluoroacetate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Rate constant; Equilibrium constant;
79-43-6

dichloro-acetic acid

56577-75-4

2,6-Di-tert-butyl-4-nitro-phenol anion

A

728-40-5

4-nitro-2,6-di-tert-butylphenol

B

83193-04-8

2,2-difluoroacetate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Equilibrium constant; Rate constant;
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  • 2,6-di-tert-butyl-4-nitrophenol

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    728-40-5

    2,6-di-tert-butyl-4-nitrophenol

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Chemistry

Molecular Structure of 2,6-Di-tert-butyl-4-nitrophenol (728-40-5):

IUPAC Name: 2,6-Ditert-butyl-4-nitrophenol 
Molecular Formula: C14H21NO3
Molecular Weight: 251.321440 g/mol
Canonical SMILES: CC(C)(C)C1=CC(=CC(=C1O)C(C)(C)C)[N+](=O)[O-]
InChI: InChI=1S/C14H21NO3/c1-13(2,3)10-7-9(15(17)18)8-11(12(10)16)14(4,5)6/h7-8,16H,1-6H3
InChIKey: FCGKUUOTWLWJHE-UHFFFAOYSA-N
Index of Refraction: 1.525
Molar Refractivity: 71.45 cm3
Molar Volume: 233 cm3
Surface Tension: 36.7 dyne/cm
Density: 1.078 g/cm3
Flash Point: 118 °C
Enthalpy of Vaporization: 56.89 kJ/mol
Boiling Point: 306.6 °C at 760 mmHg
Vapour Pressure: 0.000423 mmHg at 25 °C
Water Solubility: 6.046 mg/L at 25 °C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 580mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toxicology and Applied Pharmacology. Vol. 3, Pg. 713, 1961.
guinea pig LD50 oral 800mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toxicology and Applied Pharmacology. Vol. 3, Pg. 713, 1961.
mouse LD50 intraperitoneal 700mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toxicology and Applied Pharmacology. Vol. 3, Pg. 713, 1961.
rat LD50 intraperitoneal 260mg/kg BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Toxicology and Applied Pharmacology. Vol. 3, Pg. 713, 1961.
rat LD50 oral 250mg/kg   "Pesticide Index," Frear, E.H., ed., State College, PA, College Science Pub., 1969Vol. 4, Pg. 141, 1969.

 

Safety Profile

Safety Information of 2,6-Di-tert-butyl-4-nitrophenol (728-40-5):
RIDADR: 2811
HazardClass: 6.1(b)
PackingGroup: III
Explodes when heated to 100°C. May explode spontaneously. See also NITRO COMPOUNDS of AROMATIC HYDROCARBONS and PHENOLS.

Specification

  2,6-Di-tert-butyl-4-nitrophenol (728-40-5) is also called for 2,6-Bis(1,1-dimethylethyl)-4-nitrophenol ; 4-06-00-03493 (Beilstein Handbook Reference) ; AI3-25569 ; BAY 28589 ; Bayer 28589 ; Bayer 4889 ; ENT 25,569 ; NSC 81682 ; Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitro- ; Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitro- (9CI) ; Phenol, 2,6-di-tert-butyl-4-nitro- .