4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)
Uses- Product Name
- 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
- Formula Weight
- 266.38
- MOL File
- 7478-69-5.mol
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Property
- Melting point:
- 119-121 °C(lit.)
- storage temp.
- 2-8°C
- Appearance
- Yellow to brown Solid
- EPA Substance Registry System
- Benzenamine, 4,4'-ethenylidenebis[N,N-dimethyl- (7478-69-5)
Safety
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- T341428
- Product name
- 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)
- Purity
- Aldrich<sup>CPR</sup>
- Packaging
- 1 unit
- Price
- $185
- Updated
- 2025/07/31
- Product number
- T341428
- Product name
- 4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE)
- Purity
- Aldrich
- Packaging
- 1g
- Price
- $179
- Updated
- 2024/03/01
- Product number
- V757010
- Product name
- 4-Vinylidenebis(N,N-dimethylaniline)
- Packaging
- 100mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- V757010
- Product name
- 4-Vinylidenebis(N,N-dimethylaniline)
- Packaging
- 500mg
- Price
- $200
- Updated
- 2021/12/16
- Product number
- 2581AL
- Product name
- 4,4'-Vinylidenebis(n,n-dimethylaniline)
- Packaging
- 5g
- Price
- $482
- Updated
- 2021/12/16
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Chemical Properties,Usage,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
1779-49-3
90-94-8
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
4,4'-VINYLIDENEBIS(N,N-DIMETHYLANILINE) Preparation Products And Raw materials
Raw materials
Preparation Products
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