101-72-4

Basic information

• Product Name: N-Isopropyl-N'-phenyl-1,4-phenylenediamine
• Synonyms: 1,4-Benzenediamine, N-(1-methylethyl)-N'-phenyl-;1,4-Benzenediamine,N-(1-methylethyl)-N’-phenyl-;4010 NA;4010na;4-Anilino-N-isopropylaniline;4-Benzenediamine,N-(1-methylethyl)-N’-phenyl-1;Akrochem antioxidant pd1;Antigen 3c
• CAS NO: 101-72-4
• Molecular Formula: C₁₅H₁₈N₂
• Molecular Weight: 226.32
• EINECS: 202-969-7
• Product Categories: ANTIDEGRADANTS
• Mol File: 101-72-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: 72-76°C
• Boiling Point: 161°C
• Flash Point: 161°C/1mm
• Appearance: dark grey to black solid
• Density: 1,17 g/cm3
• Vapor Pressure: 0.007Pa at 20℃
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated)
• PKA: 6.76±0.32(Predicted)
• Water Solubility: <0.1 g/100 mL at 18 oC
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: N-Isopropyl-N'-phenyl-1,4-phenylenediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Isopropyl-N'-phenyl-1,4-phenylenediamine(101-72-4)
• EPA Substance Registry System: N-Isopropyl-N'-phenyl-1,4-phenylenediamine(101-72-4)

Safety Data

• Hazard Codes: Xi,N,Xn
• Statements: 36/37/38-50/53-43-22
• Safety Statements: 26-36-61-60-37-24
• RIDADR: 3077
• RTECS: ST2650000
• TSCA: Yes
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 101-72-4(Hazardous Substances Data)

Usage

Description

N-Isopropyl-N'-phenyl-1,4-phenylenediamine is a dark gray to black solid with an aromatic odor. It is a N-substituted diamine that is 1,4-phenylenediamine substituted at one N with an isopropyl group and at the other with a phenyl group.

Uses

Used in Rubber Industry:
N-Isopropyl-N'-phenyl-1,4-phenylenediamine is used as an antioxidant and antidegradant in various types of rubber, including natural rubber, styrene-butadiene, nitrile-butadiene, butadiene, and chloroprene rubber. It protects rubber against oxidation, ozone, flex-cracking, and poisoning by copper and manganese, thereby enhancing the durability and performance of rubber products.
Used in Tyre Industry:
N-Isopropyl-N'-phenyl-1,4-phenylenediamine is used in the production of tyres, where it serves as an essential component in the rubber formulation. Its antioxidant and antidegradant properties help to improve the resistance of tyres to various environmental factors, such as heat, ozone, and mechanical stress, ensuring their longevity and reliability.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1265, 1964 DOI: 10.1021/jo01028a511

Air & Water Reactions

May be sensitive to heat, air, light and moisture during long term storage. Insoluble in water.

Reactivity Profile

N-Isopropyl-N'-phenyl-1,4-phenylenediamine reacts with oxidizing agents . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

N-Isopropyl-N'-phenyl-1,4-phenylenediamine is combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

This rubber chemical is used as an antioxidant and antiozonant. The main occupational sources are tires.

Upstream product

• 156-10-5 p-nitrosodiphenylamine 
• 67-64-1 acetone 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 67-63-0 isopropyl alcohol 
• 101-75-7 4-(Phenylazo)diphenylamine 

Downstream Products

• 335668-42-3 4,13-dithia-7,10-dioxa-1,16-bis[N-isopropyl-4-(phenylamino)-anilino]-2,15-dihydroxyhexadecane 
• 944727-83-7 C₂₅H₃₈N₂ 
• 944728-32-9 GBFE 
• 944727-89-3 C₃₅H₅₈N₂ 
• 371965-85-4 ethyl 2-{[5-anilino-2-(isopropylamino)phenyl]sulfanyl}acetate 
• 371965-84-3 ethyl 2-{[5-anilino-2-(isopropylamino)phenyl]sulfanyl}propanoate 
• 52870-43-6 N-isopropyl-N'-phenyl-1,4-benzoquinonediimine 

Relevant articles and documents

Functionalization of amines by 'one pot-free solvent' reductive alkylation with a recyclable catalyst

The ability to attach a preformed rhodium and iridium homogeneous catalyst to a support would have a distinct advantage over the 'one pot-free solvent' reductive alkylation of primary amines to form IPPD and DMPPD. (C) 2000 Elsevier Science Ltd.

Easily transportable and meterable mixtures of aromatic oils and phenylenediamines having high stability in storage

This invention relates to easily conveyable and easily meterable mixtures having high stability in storage, containing aromatic mineral oils and phenylenediamines, the content of phenylenediamines in the mixture being 1 to 99 wt. %. The mixtures of mineral oils and phenylenediamines according to the invention are used in the production of rubbers and rubber articles.

2-Propanol derivatives as corrosion inhibitors

New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.