N,N-Dimethyl-1,4-phenylenediamine

Base Information

• Chemical Name: N,N-Dimethyl-1,4-phenylenediamine
• CAS No.: 99-98-9
• Molecular Formula: C8H12N2
• Molecular Weight: 136.197
• Hs Code.: 29215900
• European Community (EC) Number: 202-807-5
• NSC Number: 1493
• UN Number: 2811
• UNII: 7GZH2FMK7X
• DSSTox Substance ID: DTXSID6025149
• Nikkaji Number: J3.998E
• Wikipedia: Dimethyl-4-phenylenediamine
• Wikidata: Q409957
• Metabolomics Workbench ID: 50260
• ChEMBL ID: CHEMBL36296
• Mol file: 99-98-9.mol

Synonyms:1,4-Benzenediamine,N,N-dimethyl- (9CI);p-Phenylenediamine, N,N-dimethyl- (8CI);1-Amino-4-(dimethylamino)benzene;4-(Dimethylamine)aniline;4-(Dimethylamino)aniline;4-(Dimethylamino)benzenamine;4-(N,N-Dimethylamino)aniline;4-(N,N-Dimethylamino)phenylamine;4-Amino-N,N-dimethylaniline;C.I. 76075;DMPD;Dimethyl-p-phenylenediamine;N,N-Dimethyl-1,4-benzenediamine;N,N-Dimethyl-1,4-diaminobenzene;N,N-Dimethyl-1,4-phenylenediamine;N,N-Dimethyl-p-benzenediamine;N,N-Dimethyl-p-phenylenediamine;N-(4-Aminophenyl)-N,N-dimethylamine;NSC 1493;[4-(Dimethylamino)phenyl]amine;p-(Dimethylamino)aniline;p-(Dimethylamino)phenylamine;p-Amino-N,N-dimethylaniline;p-Aminodimethylaniline;

Chemical Property of N,N-Dimethyl-1,4-phenylenediamine

Chemical Property:

• Appearance/Colour: grey to black solid
• Vapor Pressure: 0.0107mmHg at 25°C
• Melting Point: 34-36 °C(lit.)
• Refractive Index: 1.626
• Boiling Point: 262 °C at 760 mmHg
• PKA: 6?+-.0.12(Predicted)
• Flash Point: 88.6 °C
• PSA: 29.26000
• Density: 1.049 g/cm
• LogP: 1.91600
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: 11 g/L (20 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 93.4
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N,N-Dimethyl-p-phenylenediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 28-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CN(C)C1=CC=C(C=C1)N
• Uses: Base for production of methylene blue, photodeveloper, reagent for detection of hydrogen sulfide, reagent for cellulose, organic synthesis, reagent for certain bacteria. N,N-Dimethyl-p-phenylenediamine is a redox indicator. Readily forms stable, red radical cation, involved in a variety of redox reactions. 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.

Technology Process of N,N-Dimethyl-1,4-phenylenediamine

There total 179 articles about N,N-Dimethyl-1,4-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: 95.0%

methyl yellow (60-11-7) → 4-amino-N,N-dimethylaniline (99-98-9) + aniline (62-53-3)

Guidance literature:

With formic acid; zinc; In methanol; at 20 ℃; for 0.133333h;

DOI:10.1016/S0040-4039(01)02370-X

Reference yield: 30.0%

N,N-Dimethyl-4-nitroaniline (100-23-2) → 4-amino-N,N-dimethylaniline (99-98-9) + methyl orange (6257-64-3)

Guidance literature:

With Ru/C; sodium hydroxide; In tetrahydrofuran; ethanol; at 120 ℃; for 24h; Microwave irradiation;

DOI:10.1002/adsc.201200356

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-dimethylamino-4'-(N,N-dimethylamino)benzylideneaniline (10050-89-2) + acetic acid (64-19-7,77671-22-8) → 4-amino-N,N-dimethylaniline (99-98-9) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

upstream raw materials:

N,N'-dibenzoyl-N-(4-dimethylamino-phenyl)-hydrazine

2,3-dimethyl-4-nitroso-aniline

4-nitroso-N,N-dimethylaniline hydrochloride

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

Downstream raw materials:

nicotinic acid-(4-dimethylamino-anilide)

isonicotinic acid-(4-dimethylamino-anilide)

3-oxo-3-phenyl-propionic acid-(4-dimethylamino-anilide)

2,5-bis<<(4-dimethylamino)phenyl>amino>-3,6-dichloro-1,4-benzoquinone

Refernces

• 1、 Freed,Faulkner. "". . p. 2097,2098-2102. Retrieved 1971.
• 2、 Rollett,Gantz. "-". . p. 63. Retrieved 1939.
• 3、 Sarkar, Deblina,Chowdhury, Monalisa,Das, Prasanta Kumar. "Naphthalimide-Based Azo-Functionalized Supramolecular Vesicle in Hypoxia-Responsive Drug Delivery". . p. 3480 - 3492. Retrieved 2022/03/27.
• 4、 Wang, Dongsheng,Fan, Mingyue,He, Tingyu,Zeng, Fanming,Hu, Xiaoli,Li, Chun,Su, Zhongmin. "Cu/CuxS-Embedded N,S-Doped Porous Carbon Derived in Situ from a MOF Designed for Efficient Catalysis". supporting information. p. 11468 - 11476. Retrieved 2021/06/14.