N,N,N',N'-Tetramethyl-1,4-phenylenediamine

N,N,N',N'-Tetramethyl-1,4-phenylenediamine Basic information
Product Name:N,N,N',N'-Tetramethyl-1,4-phenylenediamine
Synonyms:N,N,N',N'-TETRAMETHYL-1,4-PHENYLENEDIAMINE;N,N,N',N'-TETRAMETHYL-P-PHENYLENEDIAMINE;1,4-BIS(DIMETHYLAMINO)BENZENE;1,4-bis(dimethylamino)-benzen;4-Benzenediamine,N,N,N’,N’-tetramethyl-1;Benzene, 1,4-bis(dimethylamino)-;N,N,N',N'-Tetramethyl-1,4-Benzenediamine;N,N,N',N'-Tetramethyl-p-fenylendiamin
CAS:100-22-1
MF:C10H16N2
MW:164.25
EINECS:202-831-6
Product Categories:
Mol File:100-22-1.mol
N,N,N',N'-Tetramethyl-1,4-phenylenediamine Structure
N,N,N',N'-Tetramethyl-1,4-phenylenediamine Chemical Properties
Melting point 49-51 °C(lit.)
Boiling point 260 °C(lit.)
density 0.9743 (rough estimate)
refractive index 1.5700 (estimate)
Fp >230 °F
storage temp. Store below +30°C.
pka5.92±0.12(Predicted)
form powder
color off-white to gray
Water Solubility slightly in cold, more in hot water
Sensitive Air & Light Sensitive
Merck 14,9228
BRN 1564025
Stability:Stable, but may be air or light sensitive. Combustible. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
CAS DataBase Reference100-22-1(CAS DataBase Reference)
NIST Chemistry Reference1,4-Benzenediamine, N,N,N',N'-tetramethyl-(100-22-1)
EPA Substance Registry SystemN,N,N',N'-Tetramethyl-p-phenylenediamine (100-22-1)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-40-36/37/38
Safety Statements 28-28A-36-26-22
RIDADR UN 2811 6.1/PG 3
WGK Germany 1
RTECS ST4200000
10
TSCA Yes
HazardClass 6.1(a)
PackingGroup II
HS Code 29215190
ToxicityLD50 oral in bird - wild: 23700ug/kg
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
N,N,N',N'-Tetramethyl-1,4-phenylenediamine Usage And Synthesis
Chemical Propertiespurple to brown crystalline powder
UsesIn the form of the hydrochloride as a reagent in analytical chemistry.
UsesN,N,N',N'-Tetramethyl-p-phenylenediamine is a reducing co-substrate for heme peroxidases. It is used for detection of peroxidases on polyacrylamide gels.
Synthesis Reference(s)The Journal of Organic Chemistry, 29, p. 488, 1964 DOI: 10.1021/jo01025a506
General DescriptionLeaflets or a drab green solid.
Air & Water ReactionsN,N,N',N'-Tetramethyl-1,4-phenylenediamine may be sensitive to air and heat. . Insoluble in water.
Reactivity ProfileN,N,N',N'-Tetramethyl-1,4-phenylenediamine can burn in air to give toxic NOx gases . 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.
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition N,N,N',N'-Tetramethyl-1,4-phenylenediamine emits toxic fumes. It is an irritant.
Fire HazardN,N,N',N'-Tetramethyl-1,4-phenylenediamine is probably combustible.
Safety ProfilePoison by ingestion. Moderatelytoxic by inhalation. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx.
Purification MethodsCrystallise the amine from pet ether or water. It can be sublimed or dried carefully in a vacuum line, and stored in the dark under nitrogen. It has been recrystallised from its melt. [Beilstein 13 H 74, 13 I 22, 13 II 40, 13 III 111, IV 107.]
N,N,N',N'-Tetramethyl-1,4-phenylenediamine Preparation Products And Raw materials
Raw materials5-Hydroxytryptophan-->N,N,N',N'-Tetramethyl-1,4-phenylenediamine
HEXAMINE 1,4-Dimorpholinobenzene N,N-Diethyl-1,4-phenylenediamine 1,4-Diamino-2-nitrobenzene Tetramethyl-1,4-phenylenediamine,2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE,2,3,5,5-TETRAMETHYL-1,4-PHENYLENEDIAMINE,2,3,5,6-TETRAMETHYL-1,4-PHENYLENEDIAMINE 98+% N,N'-1,4-PHENYLENEDIMALEIMIDE N,N,N',N'-Tetramethyl-1,4-phenylenediamine N-Methyl-2-pyrrolidone N,N,N',N'-Tetramethylethylenediamine N-Methylolacrylamide N-(1-ACETYL-2,3-DIHYDRO-(1H)-INDOL-5-YL)-N'-ETHYL-N-(1-METHYLPIPERIDIN-4-YL)UREA (-)-2-[METHYLAMINO]-1-PHENYLPROPANE p-Phenylenediamine dihydrochloride Hexamethylenetetramine N,N-Dimethyl-1,4-phenylenediamine 4-Aminodiphenylamine p-Phenylenediamine o-Phenylenediamine

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