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4-(Dimethylamino)phenyldiphenylphosphine

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Name

4-(Dimethylamino)phenyldiphenylphosphine

EINECS 228-193-9
CAS No. 739-58-2 Density N/A
PSA 16.83000 LogP 3.51080
Solubility N/A Melting Point 151-154 °C(lit.)
Formula C20H20NP Boiling Point 417.5 °C at 760 mmHg
Molecular Weight 305.359 Flash Point 206.3 °C
Transport Information N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 739-58-2 (4-(DIMETHYLAMINO)PHENYLDIPHENYLPHOSPHINE) Hazard Symbols IrritantXi
Synonyms

Aniline,p-(diphenylphosphino)-N,N-dimethyl- (6CI,7CI,8CI);4-(Diphenylphosphino)-N,N-dimethylaniline;[4-(Dimethylamino)phenyl]diphenylphosphine;[p-(Dimethylamino)phenyl]diphenylphosphine;

Article Data 16

4-(Dimethylamino)phenyldiphenylphosphine Synthetic route

586-77-6

4-bromo-N,N-dimethylaniline

1079-66-9

chloro-diphenylphosphine

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
Stage #1: 4-bromo-N,N-dimethylaniline With magnesium In tetrahydrofuran for 10h; Inert atmosphere; Reflux;
Stage #2: chloro-diphenylphosphine With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 11h; Reflux; Inert atmosphere;
96%
With tetrabutylammonium tetrafluoroborate; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide electrochemical coupling;70%
With tetrabutylammonium tetrafluoroborate; (2,2'-bipyridine)nickel(II) dibromide In N,N-dimethyl-formamide Electrolysis;70%
797-72-8

(4-(dimethylamino)phenyl)diphenylphosphine oxide

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
With 1,3-diphenyl-disiloxane In toluene at 110℃; Sealed tube; chemoselective reaction;89%
829-85-6

diphenylphosphane

1197-19-9

4-cyano-N,N-dimethylaniline

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); 8-quinolinol; potassium tert-butylate In 1,4-dioxane at 90℃; for 16h; Catalytic behavior; Schlenk technique; Inert atmosphere;70%
29972-74-5

(4-dimethylamino-phenyl)-phosphonous acid dichloride

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
With sodium; chlorobenzene; benzene ueber mehrere Stufen;
29972-74-5

(4-dimethylamino-phenyl)-phosphonous acid dichloride

phenylmagnesium bromide

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
In diethyl ether
121-69-7

N,N-dimethyl-aniline

1079-66-9

chloro-diphenylphosphine

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
With pyridine; aluminium trichloride In benzene
586-77-6

4-bromo-N,N-dimethylaniline

1499-21-4

Diphenylphosphinic chloride

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium; iodine / tetrahydrofuran / 1.5 h / 60 °C
1.2: 18 h / 0 - 23 °C
2.1: 1,3-diphenyl-disiloxane / toluene / 110 °C / Sealed tube
View Scheme
29892-37-3

chloro(dimethylsulfide) gold(I)

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

137008-26-5

[(4-dimethylaminophenyl)diphenylphosphine]gold(I) chloride

Conditions
ConditionsYield
In tetrahydrofuran byproducts: (CH3)2S; under N2; dropwise addn. of soln. of phosphane to suspension of Au-compd. at 0°C, stirred for 15 min, warmed to room temp.; concd., pptn. by addn. of pentane, dried (high vac.); elem. anal.;97%
byproducts: (CH3)2S; according to: D. B. Dyson, R. V. Parish, C. A. McAuliffe, R. Fields, Hyperfine interact. 40 (1988) 327.;97.5%
1701-93-5

silver thiocyanate

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

C82H80Ag2N6P4S2

Conditions
ConditionsYield
In acetonitrile Reflux;92%

[Fe2(CO)6{μ-SCH2CH(CH2CH3)S}]

739-58-2

4-(N,N-Dimethylamino)triphenylphosphine

[Fe2(CO)5{Ph2P(4-C6H4NMe2)}{μ-SCH2CH(CH2CH3)S}]

Conditions
ConditionsYield
With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;91%

4-(Dimethylamino)phenyldiphenylphosphine Specification

The Benzenamine,4-(diphenylphosphino)-N,N-dimethyl-, with the CAS registry number 739-58-2, is also known as [p-(Dimethylamino)phenyl]diphenylphosphine. It belongs to the product categories of Mitsunobu Reaction; Phosphine Ligands; Phosphines (Mitsunobu Reaction); Synthetic Organic Chemistry. This chemical's molecular formula is C20H20NP and molecular weight is 305.35. What's more, its systematic name is 4-(diphenylphosphanyl)-N,N-dimethylaniline.

Physical properties of Benzenamine,4-(diphenylphosphino)-N,N-dimethyl- are: (1)ACD/LogP: 5.80; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.78; (4)ACD/LogD (pH 7.4): 5.8; (5)ACD/BCF (pH 5.5): 14329.84; (6)ACD/BCF (pH 7.4): 15033.75; (7)ACD/KOC (pH 5.5): 32406.28; (8)ACD/KOC (pH 7.4): 33998.13; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 16.83 Å2; (13)Flash Point: 206.3 °C; (14)Enthalpy of Vaporization: 67.09 kJ/mol; (15)Boiling Point: 417.5 °C at 760 mmHg; (16)Vapour Pressure: 3.52E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by diphenylphosphinous acid chloride and 4-bromo-N,N-dimethyl-aniline by electrolysis. This reaction will need reagent Bu4NBF4 and solvent dimethylformamide. This reaction will also need catalyst (2,2'-bipy)NiBr2. The yield is about 70%.

Benzenamine,4-(diphenylphosphino)-N,N-dimethyl- can be prepared by diphenylphosphinous acid chloride and 4-bromo-N,N-dimethyl-aniline by electrolysis

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: c3c(P(c1ccccc1)c2ccc(cc2)N(C)C)cccc3
(2)InChI: InChI=1S/C20H20NP/c1-21(2)17-13-15-20(16-14-17)22(18-9-5-3-6-10-18)19-11-7-4-8-12-19/h3-16H,1-2H3
(3)InChIKey: GOEGBJDTWXTPHP-UHFFFAOYSA-N

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