100-22-1

Name	N,N,N',N'-Tetramethyl-1,4-phenylenediamine
CAS	100-22-1
EINECS(EC#)	202-831-6
Molecular Formula	C10H16N2
MDL Number	MFCD00008309
Molecular Weight	164.25
MOL File	100-22-1.mol

Synonyms

1,4-BIS(DIMETHYLAMINO)BENZENE N,N,N',N'-TETRAMETHYL-1,4-PHENYLENEDIAMINE N,N,N',N'-TETRAMETHYL-P-PHENYLENEDIAMINE WURSTER'S REAGENT 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 n,n,n’,n’-tetramethyl-4-benzenediamine N,N,N’,N’-Tetramethyl-benzene-1,4-diamine n,n,n’,n’-tetramethyl-p-fenylendiamin N,N,N’,N’-Tetramethyl-p-phenyl n,n,n’,n’-tetramethyl-p-phenylenediamin p-Bis(dimethylamino)benzene p-Phenylenediamine, N,N,N',N'-tetramethyl- Tetramethyl-p-phenyldiamine Tetramethyl-p-phenylenediamine TL 85 tl85

Chemical Properties

Appearance	purple to brown crystalline powder
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.	Refrigerator (+4°C)
form	powder
pka	5.92±0.12(Predicted)
color	off-white to gray
Stability:	Stable, but may be air or light sensitive. Combustible. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents.
Water Solubility	slightly in cold, more in hot water
Sensitive	Air & Light Sensitive
Merck	14,9228
BRN	1564025
CAS DataBase Reference	100-22-1(CAS DataBase Reference)
NIST Chemistry Reference	1,4-Benzenediamine, N,N,N',N'-tetramethyl-(100-22-1)
EPA Substance Registry System	N,N,N',N'-Tetramethyl-p-phenylenediamine (100-22-1)

Safety Data

Hazard Codes	Xn
Risk Statements	R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . R40:Limited evidence of a carcinogenic effect. R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) . S36:Wear suitable protective clothing . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S22:Do not breathe dust . less more
RIDADR	UN 2811 6.1/PG 3
WGK Germany	1
RTECS	ST4200000
F	10
TSCA	Yes
HazardClass	6.1(a)
PackingGroup	II
HS Code	29215190
Toxicity	LD50 oral in bird - wild: 23700ug/kg less more

Hazard Information

General Description

Leaflets or a drab green solid.

Reactivity Profile

N,N,N',N'-TETRAMETHYL-P-PHENYLENEDIAMINE(100-22-1) 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.

Air & Water Reactions

This compound may be sensitive to air and heat. . Insoluble in water.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. It is an irritant.

Fire Hazard

This chemical is probably combustible.

Chemical Properties

purple to brown crystalline powder

Uses

In the form of the hydrochloride as a reagent in analytical chemistry.

Uses

N,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

Safety Profile

Poison by ingestion. Moderatelytoxic by inhalation. Mutation data reported. When heatedto decomposition it emits toxic fumes of NOx.

Purification Methods

Crystallise 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.]

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