4,4'-Methylenebis(N,N-dimethylaniline)

Base Information

• Chemical Name: 4,4'-Methylenebis(N,N-dimethylaniline)
• CAS No.: 101-61-1
• Deprecated CAS: 30135-64-9
• Molecular Formula: C17H22N2
• Molecular Weight: 254.375
• Hs Code.: 29215990
• European Community (EC) Number: 202-959-2
• NSC Number: 36782,9029,4892
• UN Number: 3259
• UNII: L6SPP9K4WQ
• DSSTox Substance ID: DTXSID5020869
• Nikkaji Number: J5.152G
• Wikidata: Q27116024
• NCI Thesaurus Code: C44402
• Metabolomics Workbench ID: 67549
• ChEMBL ID: CHEMBL1613260
• Mol file: 101-61-1.mol

Synonyms:4,4'-methylenebis(N,N-dimethylbenzenamine);4,4'-tetramethyldiaminodiphenylmethane;BDDM;bis(dimethylamino)diphenylmethane;methane base;N,N,N',N'-tetramethyl-4,4'-methylenedianiline;reduced Michler's ketone;tetra-base

Chemical Property of 4,4'-Methylenebis(N,N-dimethylaniline)

Chemical Property:

• Appearance/Colour: yellow to tan crystals
• Melting Point: 88-89 °C(lit.)
• Refractive Index: 1.5794 (estimate)
• Boiling Point: 390 °C at 760 mmHg
• PKA: 5.57±0.12(Predicted)
• Flash Point: 173.9 °C
• PSA: 6.48000
• Density: 1.039 g/cm³
• LogP: 3.40940
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 254.178298710
• Heavy Atom Count: 19
• Complexity: 220
• Transport DOT Label: Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

Bis[4-(dimethylamino)phenyl]methane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, Xi
• Hazard Codes: T,N,Xi
• Statements: 45-50/53
• Safety Statements: 53-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: CN(C)C1=CC=C(C=C1)CC2=CC=C(C=C2)N(C)C
• Uses: Has been used in manufacture of dyes. As reagent for lead: Dtsch. Med. Wochenschr. 52, 1855 (1926). 4,4'-Methylenebis(N,N-dimethylaniline)is used as a chemical intermediate in the manufacture of dyes and for its hydrochloric salt and is also used as an analytical reagent in the determination of lead.

Technology Process of 4,4'-Methylenebis(N,N-dimethylaniline)

There total 231 articles about 4,4'-Methylenebis(N,N-dimethylaniline) 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: 81.0%

N,N-dimethyl-aniline (121-69-7,77733-26-7) → N,N,N',N'-tetramethylbenzidine (366-29-0) + 4,4'-methylene-bis(N,N-dimethylaniline) (101-61-1)

Guidance literature:

N,N-dimethyl-aniline; With antimonypentachloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

In dichloromethane; at 20 ℃; for 1h; Concentration; Inert atmosphere; Reflux; Alkaline conditions;

DOI:10.3998/ark.5550190.0014.304

Reference yield: 50.0%

4,4'-bis(dimethylamino)benzhydrol (119-58-4) → 4,4'-methylene-bis(N,N-dimethylaniline) (101-61-1) + 4-dimethylamino-benzaldehyde (100-10-7)

Guidance literature:

With iodine; hypophosphorous acid; In acetic acid; at 60 ℃; for 24h;

DOI:10.1016/S0040-4039(00)02159-6

Reference yield: 47.0%

carbon tetrabromide (558-13-4) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → tris[4-(dimethylamino)phenyl]methane (603-48-5) + crystal violet bromide (3571-43-5) + 4,4'-methylene-bis(N,N-dimethylaniline) (101-61-1)

Guidance literature:

In acetonitrile; Heating;

DOI:10.1081/SCC-120020199

upstream raw materials:

3-chlorobenzoic 2-cyclopropylacetic peroxyanhydride

N,N-dimethyl-aniline

formic acid

4,4'-bis(dimethylamino)benzhydrol

Downstream raw materials:

auramine O

bis(p-dimethylaminophenyl)methanone

1,1,2,2-tetrakis-(4-dimethylamino-phenyl)-ethane

thiomichlersketone

Refernces

• 1、 Swan. "-". . p. 2015. Retrieved 1969.
• 2、 Brown,White. "-". . p. 3755. Retrieved 1957.
• 3、 Wann, Steven R.,Thorsen, Peter T.,Kreevoy, Maurice M.. "Reduction of Carboxylic Acid Derivatives by BH4(1-) in Acidic Dimethyl Sulfoxide". . p. 2579 - 2581. Retrieved 1981.
• 4、 Pac,Sakurai. "-". . p. 1865. Retrieved 1968.
• 5、 Reverdin,de la Harpe. "-". . p. 211. Retrieved 1892.
• 6、 Choo Yin,Deeming. "-". . p. 351,354. Retrieved 1978.
• 7、 Akiyama, Takeo,Kato, Kohji,Kajitani, Masatsugu,Sakaguchi, Yoshio,Nakamura, Junko,et al.. "Photochemical Trifluoromethylation of Some Aromatic and Heteroaromatic Compounds with Trifluoromethyl Bromide". . p. 3531 - 3538. Retrieved 1988.
• 8、 Morozova, Varvara,Mayer, Peter,Berionni, Guillaume. "Scope and Mechanisms of Frustrated Lewis Pair Catalyzed Hydrogenation Reactions of Electron-Deficient C￡C Double Bonds". . p. 14508 - 14512. Retrieved 2015.
• 9、 Fischer. "-". . p. 116. Retrieved 1881.
• 10、 Sakakibara et al.. "-". . p. 3592,3596. Retrieved 1979.