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4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)

CAS No.
7478-69-5
Chemical Name:
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)
Synonyms
4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE);1,1-Bis[4-(dimethylamino)phenyl]ethene;Bis(p-dimethylaminophenyl)-1,1 ethylene;4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE);4,4'-EthenylidenebisN,N-dimethyl-aniline;4,4’-ethenylidenebis[n,n-dimethyl-benzenamin;4,4'-Ethenylidenebis(N,N-dimethylbenzenamine);4,4'-(1,1-Ethenediyl)bis(N,N-dimethylaniline);BenzenaMine,4,4'-ethenylidenebis[N,N-diMethyl-;4,4'-(ethene-1,1-diyl)bis(N,N-dimethylaniline)
CBNumber:
CB3364938
Molecular Formula:
C18H22N2
Molecular Weight:
266.38
MDL Number:
MFCD00192575
MOL File:
7478-69-5.mol
MSDS File:
SDS
Last updated:2026-05-28 05:32:21
Product description Number Pack Size Price
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) AldrichCPR T341428 1 unit $197
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Aldrich T341428 1g $179
4-Vinylidenebis(N,N-dimethylaniline) 303399 250.00mg $43
4-Vinylidenebis(N,N-dimethylaniline) 303399 1.00g $82
4-Vinylidenebis(N,N-dimethylaniline) 303399 5.00g $315

4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Properties

Melting point 119-121 °C(lit.)
storage temp. 2-8°C
Appearance Yellow to brown Solid
FDA UNII 2R30ZAL17Y
EPA Substance Registry System Benzenamine, 4,4'-ethenylidenebis[N,N-dimethyl- (7478-69-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P280-P305+P351+P338
Hazard Codes  T
Risk Statements  45-46-20/21/22-36/37/38
Safety Statements  53-23-26-36/37/39-45
WGK Germany  3
TSCA  TSCA listed

4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) price More Price(27)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich T341428 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) AldrichCPR 7478-69-5 1 unit $197 2026-04-30 Buy
Sigma-Aldrich T341428 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Aldrich 7478-69-5 1g $179 2024-03-01 Buy
Matrix Scientific 303399 4-Vinylidenebis(N,N-dimethylaniline) 7478-69-5 250.00mg $43 2026-05-19 Buy
Matrix Scientific 303399 4-Vinylidenebis(N,N-dimethylaniline) 7478-69-5 1.00g $82 2026-05-19 Buy
Matrix Scientific 303399 4-Vinylidenebis(N,N-dimethylaniline) 7478-69-5 5.00g $315 2026-05-19 Buy
Product number Packaging Price Buy
T341428 1 unit $197 Buy
T341428 1g $179 Buy
303399 250.00mg $43 Buy
303399 1.00g $82 Buy
303399 5.00g $315 Buy

4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Chemical Properties,Uses,Production

Uses

4'-VIN-based bis(N,N-dimethylaniline), abbreviated as DPE-(NMe2)2, is a yellow needle-like crystal. 4'-VIN-based bis(N,N-dimethylaniline) can be prepared from 4,4-bis(dimethylamino)benzophenone. Literature reports its use in the preparation of hydrogenated styrene-butadiene rubber.

Synthesis

Methyltriphenylphosphonium bromide

1779-49-3

Michler's ketone

90-94-8

4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)

7478-69-5

The synthesis of BDADPE was carried out by the classical Wittig reaction under argon atmosphere using 4,4'-bis(dimethylamino)benzophenone as substrate (for details, refer to the method of Hirao [29]). The procedure was as follows: methyltriphenylphosphonium bromide (45.58 g, 127.6 mmol) was added to a round-bottomed flask equipped with a reflux condenser and a magnetic stirrer with freshly distilled tetrahydrofuran (THF, 500 mL). Subsequently, potassium tert-butoxide (138.4 mL of a 1.0 M THF solution, 138.4 mmol) was slowly added dropwise to the reaction flask through a constant pressure dropping funnel. The reaction mixture was stirred at 0 °C for 2 hours. Next, a solution of anhydrous THF (690 mL) of 4,4'-bis(dimethylamino)benzophenone (21.4 g, 79.75 mmol) was added dropwise to the reaction mixture at 0 °C via a constant pressure dropping funnel. The orange-brown reaction mixture was heated and refluxed with stirring for 7 h. The reaction was quenched with distilled water upon completion. The resulting mixture was extracted three times with ether. The combined ether layers were washed sequentially with aqueous NaHCO3 and saturated aqueous NaCl and then dried with anhydrous MgSO4. After filtration, the ether layer was poured into hexane to precipitate triphenylphosphine oxide. Purification by fast column chromatography (eluent: petroleum ether/ethyl acetate, 2:1 v/v) afforded BDADPE in 92% yield (19.52 g, 73.37 mmol) with an Rf-value of 0.76. The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 2.96 (s, 12H, 2×N(CH3)2), 5.19 (s , 2H, CH2=C), 6.68-6.70 (d, 4H, aromatic proton neighbor of N(CH3)2), 7.25-7.28 (d, 4H, aromatic proton with N(CH3)2).

References

[1] Polymer, 2013, vol. 54, # 12, p. 2958 - 2965

1779-49-3
90-94-8
7478-69-5
Synthesis of 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) from Methyltriphenylphosphonium bromide and Michler's ketone

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4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Spectrum

4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) 4,4’-ethenylidenebis[n,n-dimethyl-benzenamin 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE), TECH., 90% Bis(p-dimethylaminophenyl)-1,1 ethylene 1,1-Bis[4-(dimethylamino)phenyl]ethene 4,4'-(1,1-Ethenediyl)bis(N,N-dimethylaniline) 4,4'-Ethenylidenebis(N,N-dimethylbenzenamine) N,N,N',N'-Tetramethyl[4,4'-(1,1-ethenediyl)bisaniline] BenzenaMine,4,4'-ethenylidenebis[N,N-diMethyl- 4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) 4-[1-[4-(dimethylamino)phenyl]ethenyl]-N,N-dimethylaniline 4,4'-EthenylidenebisN,N-dimethyl-aniline 4,4'-(ethene-1,1-diyl)bis(N,N-dimethylaniline) 7478-69-5 H2CCC6H4NCH322