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Cas Database |
| Name |
4-Dimethylaminostyrene |
EINECS | N/A |
| CAS No. | 2039-80-7 | Density | 0.959 g/cm3 |
| PSA | 3.24000 | LogP | 2.39560 |
| Solubility | N/A | Melting Point |
16.8 °C |
| Formula | C10H13N | Boiling Point | 241.6 °C at 760 mmHg |
| Molecular Weight | 147.22 | Flash Point | 97.5 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | Risk Codes | N/A | |
| Molecular Structure |
|
Hazard Symbols | N/A |
| Synonyms |
Aniline,N,N-dimethyl-p-vinyl- (6CI,7CI,8CI);4-(Dimethylamino)styrene;4-(N,N-Dimethylamino)styrene;4-Ethenyl-N,N-dimethylaniline;4-Vinyl-N,N-dimethylaniline;N,N-Dimethyl-4-vinylaniline;N,N-Dimethyl-p-aminostyrene;N,N-Dimethyl-p-vinylaniline;NSC 3471;p-(Dimethylamino)styrene;p-(N,N-Dimethylamino)styrene;p-Vinyldimethylaniline; |
Article Data | 63 |
4-Dimethylaminostyrene Synthetic route
- 586-77-6
4-bromo-N,N-dimethylaniline
- 7486-35-3
tri-n-butyl(vinyl)tin
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| With tris(dibenzylideneacetone)dipalladium (0); 2,8,9-tribenzyl-2,3,8,9-tetraaza-1-phosphabicyclo[3,3,3]undecane; cesium fluoride In tetrahydrofuran at 20℃; for 14h; Stille cross-coupling; | 97% |
| With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; cesium fluoride In 1,4-dioxane at 20℃; for 24h; Inert atmosphere; | 73% |
- 1779-49-3
Methyltriphenylphosphonium bromide
- 100-10-7
4-dimethylamino-benzaldehyde
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran for 0.25h; Stage #2: 4-dimethylamino-benzaldehyde In tetrahydrofuran Wittig olefination; Further stages.; | 94% |
| Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: 4-dimethylamino-benzaldehyde In tetrahydrofuran; hexane at 0 - 20℃; for 16h; Wittig Olefination; Inert atmosphere; | 94% |
| Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.666667h; Stage #2: 4-dimethylamino-benzaldehyde In tetrahydrofuran; hexane at 25℃; for 12h; | 90% |
| Conditions | Yield |
|---|---|
| With dioxathion; caesium carbonate; palladium dichloride In tetrahydrofuran; water at 85℃; for 22h; Suzuki-Miyaura reaction; | 93% |
| Conditions | Yield |
|---|---|
| With cis,cis,cis-tetrakis[(diphenylphosphanyl)methyl]cyclopentane; potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki reaction; | 89% |
- 78-08-0
Triethoxyvinylsilane
- 586-77-6
4-bromo-N,N-dimethylaniline
A
- 7478-69-5
1,1-Bisethylene
B
- 2039-80-7
N,N-dimethy-4-vinylaniline
C
- 22210-79-3
(E)-1,2-bis-[4-(dimethylamino)phenyl]ethene
| Conditions | Yield |
|---|---|
| With sodium hydroxide; poly(ethylene glycol) 2000; palladium diacetate In water at 150℃; for 2h; Hiyama reaction; | A n/a B 86% C n/a |
| Conditions | Yield |
|---|---|
| Stage #1: Triethoxyvinylsilane With sodium hydroxide In water at 20℃; for 0.0833333h; Sealed tube; Stage #2: 4-bromo-N,N-dimethylaniline With palladium diacetate In water at 140℃; for 3h; Reagent/catalyst; Sealed tube; | 86% |
- 71089-15-1
1-(4-N,N-dimethylaminophenyl)propane
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| With [CuCl(ClIPr)]; sodium t-butanolate; tert-butyl alcohol In tetrahydrofuran; hexane at 40℃; for 20h; Inert atmosphere; chemoselective reaction; | 82% |
- 698-70-4
4-Iodo-N,N-dimethylaniline
- 1826-67-1
vinyl magnesium bromide
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| Stage #1: vinyl magnesium bromide With gallium(III) trichloride In tetrahydrofuran; hexane; dimethyl sulfoxide at 25℃; Stage #2: 4-Iodo-N,N-dimethylaniline With tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran; hexane; dimethyl sulfoxide Heating; | 81% |
- 100-10-7
4-dimethylamino-benzaldehyde
- 18107-18-1
diazomethyl-trimethyl-silane
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| With (IMes)CuCl; triphenylphosphine; isopropyl alcohol In 1,4-dioxane; diethyl ether at 60℃; for 16h; | 81% |
- 27200-84-6
methyl triphenylphosphonium bromide
- 100-10-7
4-dimethylamino-benzaldehyde
- 2039-80-7
N,N-dimethy-4-vinylaniline
| Conditions | Yield |
|---|---|
| With potassium tert-butylate In tetrahydrofuran at 22℃; for 18h; Inert atmosphere; | 78% |
| With n-butyllithium 1) hexane, ether, 4 h, r.t. 2) 25 deg C, ether or benzene; Yield given. Multistep reaction; | |
| With n-butyllithium 1.) diethyl ether, hexane, 4 h, room temp., 2.) 12 h, reflux; Yield given. Multistep reaction; |
4-Dimethylaminostyrene Specification
The 4-Dimethylaminostyrene, with the CAS registry number 2039-80-7, is also known as p-(Dimethylamino)styrene. It belongs to the product category of Naphthyridine,Quinoline. This chemical's molecular formula is C10H13N and molecular weight is 147.22. Its IUPAC name is called 4-ethenyl-N,N-dimethylaniline.
Physical properties of 4-Dimethylaminostyrene: (1)ACD/LogP: 3.21; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.01; (4)ACD/LogD (pH 7.4): 3.2; (5)ACD/BCF (pH 5.5): 102.15; (6)ACD/BCF (pH 7.4): 159.73; (7)ACD/KOC (pH 5.5): 839.01; (8)ACD/KOC (pH 7.4): 1311.91; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 51.49 cm3; (14)Molar Volume: 153.3 cm3; (15)Surface Tension: 35.4 dyne/cm; (16)Density: 0.959 g/cm3; (17)Flash Point: 97.5 °C; (18)Enthalpy of Vaporization: 47.86 kJ/mol; (19)Boiling Point: 241.6 °C at 760 mmHg; (20)Vapour Pressure: 0.0356 mmHg at 25°C.
Preparation: this chemical can be prepared by 2-methanesulfonyl-benzothiazole and 4-dimethylamino-benzaldehyde. This reaction will need reagent LDA and solvent tetrahydrofuran, hexane. The reaction time is 3 hours with reaction temperature of -78 ℃. The yield is about 44%.
Uses of 4-Dimethylaminostyrene: it can be used to produce trans-1,2-bis[p-(dimethylamino)phenyl]cyclobutane at ambient temperature. This reaction will need reagent Fe(NO3)3 and solvent methanol with reaction time of 1.5 hours. The yield is about 81%.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CN(C)C1=CC=C(C=C1)C=C
(2)InChI: InChI=1S/C10H13N/c1-4-9-5-7-10(8-6-9)11(2)3/h4-8H,1H2,2-3H3
(3)InChIKey: GQWAOUOHRMHSHL-UHFFFAOYSA-N
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