N , N ′ -di- sec -butyl- p -phenylenediamine

Structural formula
	Mixture of three stereoisomers - structural formula without stereochemistry
General
Surname	N , N ′ -di- sec -butyl- p -phenylenediamine
Molecular formula	C 14 H 24 N 2
Brief description	red liquid with an amine-like odor
External identifiers / databases
EC number	202-992-2
ECHA InfoCard	100.002.721
PubChem	7589
ChemSpider	7308
Wikidata	Q6951318
properties
Molar mass	220.36 g mol −1
Physical state	liquid
density	0.94 g cm −3
Melting point	18 ° C
boiling point	313 ° C
Vapor pressure	1.6 mbar (20 ° C)
solubility	very sparingly soluble in water (0.315 g l −1 at 25 ° C); soluble in organic solvents;
Refractive index	1.539 (20 ° C)
safety instructions
H and P phrases	H: 301 + 311 + 331-314-317-373-410
	P: 273-280-301 + 310 + 330-305 + 351 + 338 + 310-333 + 313
Toxicological data	2810 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 148 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N , N ′ -di- sec -butyl- p -phenylenediamine belongs to the group of aminobenzenes .

Stereochemistry

From the structural formula it can be seen that the compound contains two equally substituted stereocenters, consequently there are three stereoisomers:

( R , R ) - N , N ′ -di- sec -butyl- p -phenylenediamine
( S , S ) - N , N ′ -di- sec -butyl- p -phenylenediamine
meso - N , N ′ -di- sec -butyl- p -phenylenediamine

When the term “ N , N ′ -di- sec -butyl- p- phenylenediamine” is used without a stereochemical prefix , the mixture of the three stereoisomers is always meant here and in the scientific literature.

Extraction and presentation

N , N '-di- sec -butyl- p -phenylenediamine can be obtained by reductive alkylation of p -phenylenediamine or by reductive amination of sec -butylamine and hydroquinone .

properties

N , N ′ -di- sec -butyl- p -phenylenediamine is a very difficult to ignite, air-sensitive, little volatile, red liquid with an amine-like odor, which is very sparingly soluble in water. Your aqueous solution has an alkaline reaction.

use

N , N '-di- sec -butyl- p -phenylenediamine is used as an antioxidant and stabilizer .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on N, N'-di-sec-butyl-p-phenylenediamine Template: link text check / apostrophe in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
^ GWA Milne: Gardner's Commercially Important Chemicals Synonyms, Trade Names, and Properties . John Wiley & Sons, 2005, ISBN 0-471-73661-9 , pp. 193 ( limited preview in Google Book search).
↑ ^a ^b Data sheet N, N′-di-sec-butyl-p-phenylenediamine, 95% from Sigma-Aldrich , accessed on January 29, 2019 ( PDF ).
^ Entry on N, N′-di-sec-butyl-p-phenylenediamine in the Hazardous Substances Data Bank , accessed on July 7, 2015.
↑ Eastman: SAFETY DATA SHEET

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k Entry on N, N'-di-sec-butyl-p-phenylenediamine Template: link text check / apostrophe in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[G._W._A._Milne-2] GWA Milne: Gardner's Commercially Important Chemicals Synonyms, Trade Names, and Properties . John Wiley & Sons, 2005, ISBN 0-471-73661-9 , pp. 193 ( limited preview in Google Book search).

[Sigma-3] Data sheet N, N′-di-sec-butyl-p-phenylenediamine, 95% from Sigma-Aldrich , accessed on January 29, 2019 ( PDF ).

[HSDB-4] Entry on N, N′-di-sec-butyl-p-phenylenediamine in the Hazardous Substances Data Bank , accessed on July 7, 2015.

[eastman-5] Eastman: SAFETY DATA SHEET