N,N,N',N'-Tetramethyl-P-phenylenediamine

Base Information

• Chemical Name: N,N,N',N'-Tetramethyl-P-phenylenediamine
• CAS No.: 100-22-1
• Molecular Formula: C10H16N2
• Molecular Weight: 164.25
• Hs Code.: 29215190
• European Community (EC) Number: 202-831-6
• UNII: P4P3AC32ZB
• DSSTox Substance ID: DTXSID5026124
• Nikkaji Number: J4.980H
• Wikipedia: Wurster%27s_blue,Wurster's_blue
• Wikidata: Q408762
• ChEMBL ID: CHEMBL1393325
• Mol file: 100-22-1.mol

Synonyms:tetramethyl-p-phenylenediamine

Chemical Property of N,N,N',N'-Tetramethyl-P-phenylenediamine

Chemical Property:

• Appearance/Colour: purple to brown crystalline powder
• Melting Point: 49-51 °C(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 260.572 °C at 760 mmHg
• PKA: 5.92±0.12(Predicted)
• Flash Point: 104.895 °C
• PSA: 6.48000
• Density: 0.993 g/cm³
• LogP: 1.81860
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air & Light Sensitive
• Water Solubility.: slightly in cold, more in hot water
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 164.131348519
• Heavy Atom Count: 12
• Complexity: 108

Purity/Quality:

98%,99%, ^*data from raw suppliers

N,N,N',N'-Tetramethyl-1,4-phenylenediamine for synthesis. CAS 100-22-1, EC Number 202-831-6, chemical formula C H -1,4-N(CH ) ., for synthesis ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40-36/37/38
• Safety Statements: 28-28A-36-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CN(C)C1=CC=C(C=C1)N(C)C
• Uses: In the form of the hydrochloride as a reagent in analytical chemistry. 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.

Technology Process of N,N,N',N'-Tetramethyl-P-phenylenediamine

There total 67 articles about N,N,N',N'-Tetramethyl-P-phenylenediamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1,4-phenylenediamine (106-50-3) → N,N,N',N'-tetramethyl-para-phenylenediamine (100-22-1)

Guidance literature:

With sodium tetrahydroborate; In 2,2,2-trifluoroethanol; for 16h; Reflux;

DOI:10.1055/s-0030-1258384

Reference yield:

methanol (67-56-1) + p-phenylenediamine hydrochloride (540-24-9,55972-71-9) → N,N,N',N'-tetramethyl-para-phenylenediamine (100-22-1)

Guidance literature:

at 170 - 200 ℃;

Reference yield:

methanol (67-56-1) + benzene-1,4-diamine hydrochloride (624-18-0,55972-71-9) → N,N,N',N'-tetramethyl-para-phenylenediamine (100-22-1)

Guidance literature:

at 150 ℃;

DOI:10.1021/ja01877a013

upstream raw materials:

methanol

p-phenylenediamine hydrochloride

benzene-1,4-diamine hydrochloride

4-dimethylaminophenylamine dihydrochloride

Downstream raw materials:

N-(4-(dimethylamino)phenyl)-N-methylnitrous amide

N,N,N'-trimethyl-p-phenylenediamine

tetra-N-methyl-p-phenylenediamine,radical ion[1+]; bromide

N,N,N',N'-Tetramethyl-p-phenylenediamine Iodide Cation Radical

Refernces

• 1、 Maruthamuthu, Pichai,Venkatasubramanian, Lakshmanan,Dharmalingam, Periasamy. "A Fast Kinetic Study of the Formation and Decay of N,N,N',N'-Tetramethyl-p-phenylenediamine Radical Cation in Aqueous Solution". . p. 359 - 364. Retrieved 1986.
• 2、 Liu, You-Cheng,Liu, Zhong-Li,Wu, Lung-Min,Chen, Ping. "A FACILE GENERATION OF RADICAL CATIONS VIA THE ACTION OF NITROXIDES". . p. 4201 - 4202. Retrieved 1985.
• 3、 Chen, Yuhui,Freunberger, Stefan A.,Peng, Zhangquan,Fontaine, Olivier,Bruce, Peter G.. "Charging a Li-O2 battery using a redox mediator". . p. 489 - 494. Retrieved 2013.
• 4、 Nelsen, Stephen F.,Chen, Ling-Jen,Ramm, Michael T.,Voy, Gilbert T.,Powell, Douglas R.,Accola, Molly A.,Seehafer, Troy R.,Sabelko, Jobiah J.,Pladziewicz, Jack R.. "Intermolecular electron-transfer reactions involving hydrazines". . p. 1405 - 1412. Retrieved 1996.
• 5、 Compton, Richard G.,Coles, Barry A.,Gooding, Justin J.,Fisher, Adrian C.,Cox, Timothy I.. "Chronoamperometry at Channel Electrodes. Experimental Applications of Double Electrodes". . p. 2446 - 2451. Retrieved 1994.
• 6、 Hirata, Yoshinori,Mataga, Noboru. "Monophotonic Ionization through a Long-Lived Ion Pair: N,N,N',N'-Tetramethyl-p-phenylenediamine in Acetonitrile Solution". . p. 1680 - 1682. Retrieved 1983.
• 7、 Steenken, Steen,Vieira, Abel J. S. C.. "Water-assisted intramolecular electron transfer from the ring to the side chain in N,N,N′,N′-tetraalkyl-para-phenylenediamine radicals - The reverse of side chain deprotonation of radical cations". . p. 571 - 573. Retrieved 2001.
• 8、 Zhang, Xu,Jiang, Yilin,Fei, Honghan. "UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source". . p. 11928 - 11931. Retrieved 2019.
• 9、 Nickel, Ulrich,Chen, Yao-Hong,Schneider, Siegfried,Silva, Maria I.,Burrows, Hugh D.,Formosinho, Sebastiao J.. "Mechanism and Kinetics of the Photocatalyzed Oxidation of p-Phenylenediamines by Peroxydisulfate in the Presence of Tri-2,2'-bipyridylylruthenium(II)". . p. 2883 - 2888. Retrieved 1994.
• 10、 Hazra,Steenken. "PATTERN OF OH RADICAL ADDITION TO CYTOSINE AND 1-, 3-, 5-, AND 6-SUBSTITUTED CYTOSINES. ELECTRON TRANSFER AND DEHYDRATION REACTIONS OF THE OH ADDUCTS.". . p. 4380 - 4386. Retrieved 1983.