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193992

Sigma-Aldrich

N,N-Dimethyl-p-phenylenediamine

97%

Synonym(s):

4-(Dimethylamino)aniline, 4-Amino-N,N-dimethylaniline, N,N-Dimethyl-1,4-phenylenediamine, DMPPDA

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About This Item

Linear Formula:
(CH3)2NC6H4NH2
CAS Number:
99-98-9
Molecular Weight:
136.19
Beilstein:
508105
EC Number:
202-807-5
MDL number:
MFCD00007860
UNSPSC Code:
12352100
PubChem Substance ID:
24851626
NACRES:
NA.21
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Quality Level

200

Assay

97%

form

solid

bp

262 °C (lit.)

mp

34-36 °C (lit.)

functional group

amine

SMILES string

CN(C)c1ccc(N)cc1

InChI

1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3

InChI key

BZORFPDSXLZWJF-UHFFFAOYSA-N

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General description

N,N-Dimethyl-p-phenylenediamine (DPD, DMPD) is an aromatic amine mainly used as an intermediate to produce dyes.[1] Its oxidation reaction with H2O2 in the presence of iron(III) catalyst has been used for the spectrophotometric detection of trace quantities of iron (III).[2] Cyclovoltammetric studies have been conducted to evaluate the electrochemical oxidation of DMPD at various pH. DMPD on oxidation under basic conditions has been reported to undergo hydrolytic decomposition.[3]

Application

N,N-Dimethyl-p-phenylenediamine may be used for the preparation of molecular compounds with tetracyano-p-quinodimethane (TCNQ). Polarized absorption spectra of these molecular compounds were investigated.[4]

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310,H331

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Oral - Acute Tox. 3 Inhalation

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

195.8 °F - closed cup

Flash Point(C)

91 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8559
BCCM3661
BCCJ7194
BCCL0949
BCCB5667

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Spectrophotometric catalytic determination of an ultratrace amount of iron (III) in water based on the oxidation of N, N-dimethyl-p-phenylenediamine by hydrogen peroxide.
Hirayama K and Unohara N.
Analytical Chemistry, 60(23), 2573-2577 (1988)
An historical review of the use of dye precursors in the formulation of commercial oxidation hair dyes.
Corbett JF.
Dyes and Pigments, 41(1), 127-136 (1999)
Polarized Absorption Spectra of Single Crystals of Ion Radical Salts. I. Molecular Compounds of 7, 7, 8, 8-Tetracyano-p-quinodimethane with N, N, N', N'-Tetramethyl-p-phenylenediamine and N, N-Dimethyl-p-phenylenediamine.
Kuroda H, et al.
Bulletin of the Chemical Society of Japan, 41(12), 2855-2858 (1968)
Mechanism diversity in anodic oxidation of N, N-dimethyl-p-phenylenediamine by varying pH.
Maleki A and Nematollahi D.
Journal of Electroanalytical Chemistry, 704, 75-79 (2013)
S Marroquí et al.
Journal of bacteriology, 183(3), 854-864 (2001-02-24)
We isolated a Tn5-induced Rhizobium tropici mutant that has enhanced capacity to oxidize N,N-dimethyl-p-phenylendiamine (DMPD) and therefore has enhanced respiration via cytochrome oxidase. The mutant had increased levels of the cytochromes c(1) and CycM and a small increase in the
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. in what volume the 5 gm N,N-dimethyl-p-phenylenediamine is prepared? I need to calculate as i am using this compound in my research

    1 answer

    1. This material is a solid with a published melting point of 34-36 °C. The solubility is tested in chloroform at 5% or 50 mg/mL. The density is reported by the Chemical Abstract Service (CAS) as being 1.036 g/cm³.

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