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2283-11-6

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2283-11-6 Usage

Chemical Properties

clear colorless to yellow-orange liquid

Uses

Different sources of media describe the Uses of 2283-11-6 differently. You can refer to the following data:
1. suzuki reaction
2. Tris(diethylamino)phosphine [(Et2N)3P] can be used as a reagent to synthesize: 1,1′-Dialkylisoindigo derivatives by reacting with various 1-alkylisatins via deoxygenation reaction.1-Aminomethylisatins by treating with isatin and primary and secondary amines.It can also be used in the deoxygenation of some cyclic α-diketones using fullerene C60.

Check Digit Verification of cas no

The CAS Registry Mumber 2283-11-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,8 and 3 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 2283-11:
(6*2)+(5*2)+(4*8)+(3*3)+(2*1)+(1*1)=66
66 % 10 = 6
So 2283-11-6 is a valid CAS Registry Number.
InChI:InChI=1/C12H30N3P/c1-7-13(8-2)16(14(9-3)10-4)15(11-5)12-6/h7-12H2,1-6H3

2283-11-6 Well-known Company Product Price

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  • Alfa Aesar

  • (A12490)  Hexaethyl phosphorous triamide, 97%   

  • 2283-11-6

  • 5g

  • 599.0CNY

  • Detail
  • Alfa Aesar

  • (A12490)  Hexaethyl phosphorous triamide, 97%   

  • 2283-11-6

  • 25g

  • 1729.0CNY

  • Detail
  • Alfa Aesar

  • (A12490)  Hexaethyl phosphorous triamide, 97%   

  • 2283-11-6

  • 100g

  • 6670.0CNY

  • Detail
  • Aldrich

  • (253189)  Tris(diethylamino)phosphine  97%

  • 2283-11-6

  • 253189-5G

  • 661.05CNY

  • Detail
  • Aldrich

  • (253189)  Tris(diethylamino)phosphine  97%

  • 2283-11-6

  • 253189-25G

  • 1,987.83CNY

  • Detail

2283-11-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name N-[bis(diethylamino)phosphanyl]-N-ethylethanamine

1.2 Other means of identification

Product number -
Other names tris-diethylamino phosphine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2283-11-6 SDS

2283-11-6Synthetic route

diethylamine
109-89-7

diethylamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With phosphorus trichloride In diethyl ether at 20℃; for 24h; Inert atmosphere;94%
With phosphorus trichloride at 0 - 25℃; for 60h;80%
With phosphorus trichloride In pentane78%
tetrakis(diethylamino)phosphonium iodide
81175-48-6

tetrakis(diethylamino)phosphonium iodide

A

ethylimino-tris(diethylamino)phosphorane
78050-98-3

ethylimino-tris(diethylamino)phosphorane

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With ammonia; sodium at -30℃; for 3h;A 3%
B 89%
N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With phosphorus trichloride In acetonitrile82%
piperazine
110-85-0

piperazine

N,N'-dimethyl-N,N'-diphenylphosphorodiamidous chloride
40535-50-0

N,N'-dimethyl-N,N'-diphenylphosphorodiamidous chloride

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

P,P'-(1,4-piperazinediyl)bis

P,P'-(1,4-piperazinediyl)bis

Conditions
ConditionsYield
With triethylamine In benzene at 20℃; for 6h;A 80%
B n/a
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In benzene for 1h; Heating;80%
C12H30N3O3PS

C12H30N3O3PS

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
at 160℃; for 0.5h;73%
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

2-vinylphenylmagnesium halogenide

2-vinylphenylmagnesium halogenide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

(2-vinylphenyl)bis(diethylamino)phosphine
107531-53-3

(2-vinylphenyl)bis(diethylamino)phosphine

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h;A n/a
B 66%
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

allylmagnesium halogenide

allylmagnesium halogenide

A

allylbis(diethylamino)phosphine
31480-07-6

allylbis(diethylamino)phosphine

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h;A 62%
B n/a
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

2-allylphenylmagnesium halogenide

2-allylphenylmagnesium halogenide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

(2-allylphenyl)bis(diethylamino)phosphine
107531-54-4

(2-allylphenyl)bis(diethylamino)phosphine

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h;A n/a
B 62%
tetrakis(diethylamino)phosphonium bromide
81175-49-7

tetrakis(diethylamino)phosphonium bromide

A

ethylimino-tris(diethylamino)phosphorane
78050-98-3

ethylimino-tris(diethylamino)phosphorane

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With sodium amide at 180℃; under 0.02 Torr; Product distribution; Mechanism;A 52%
B n/a
diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

vinylmagnesium halogenide

vinylmagnesium halogenide

A

Diethylamino(divinyl)phosphine
63034-50-4

Diethylamino(divinyl)phosphine

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h;A 50%
B n/a
diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

allylmagnesium halogenide

allylmagnesium halogenide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

diallyldiethylaminophosphine

diallyldiethylaminophosphine

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h;A n/a
B 50%
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

A

tetraethyldiaminophosphine
41291-42-3

tetraethyldiaminophosphine

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl etherA 30%
B n/a
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

ethanolamine
141-43-5

ethanolamine

A

3--2-(diethylamino)-1,3,2-oxazaphospholidine
81374-83-6

3--2-(diethylamino)-1,3,2-oxazaphospholidine

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With triethylamine In benzene at 0 - 5℃; for 24h;A 27%
B 18%
N,N,N',N'-tetraethyl-N'',N''-succinylphosphorous triamide

N,N,N',N'-tetraethyl-N'',N''-succinylphosphorous triamide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

N,N-diethyl-N',N',N'',N''-disuccinylphosphorous triamide

N,N-diethyl-N',N',N'',N''-disuccinylphosphorous triamide

Conditions
ConditionsYield
Disproportionation; Heating;A n/a
B 23%
diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

diethylamine
109-89-7

diethylamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

sodium N,N-diethyldithiocarbamate
148-18-5

sodium N,N-diethyldithiocarbamate

A

tris(diethylthiocarbamato-S,S')phosphorus(III)
69267-80-7

tris(diethylthiocarbamato-S,S')phosphorus(III)

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In benzeneA 2.3 g
B 2.5 g
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

methylthiomethylphosphonous bis(diethylamide)
124008-75-9

methylthiomethylphosphonous bis(diethylamide)

A

C6H15ClNPS

C6H15ClNPS

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
Ambient temperature; Title compound not separated from byproducts;
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

diethylamine
109-89-7

diethylamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With triethylamine
tetraethyldiamidophosphorous acid imidazolide
128592-05-2

tetraethyldiamidophosphorous acid imidazolide

diethylamine
109-89-7

diethylamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 72h;
Tetraethylphosphorodiamidous Acid 3,5-Dimethylpyrazolide
135474-17-8

Tetraethylphosphorodiamidous Acid 3,5-Dimethylpyrazolide

diethylamine
109-89-7

diethylamine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In 1,4-dioxane at 60℃; for 2h;
tris(diethylamino)(dimethylamino)phosphonium iodide

tris(diethylamino)(dimethylamino)phosphonium iodide

A

phosphorous acid bis-diethylamide dimethylamide
53201-80-2

phosphorous acid bis-diethylamide dimethylamide

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
With ammonia; sodium at -60℃; for 8h; Yield given. Yields of byproduct given;
With ammonia; sodium at -30℃; for 8h; Yield given. Yields of byproduct given;
tris(diethylamino)(dipropylamino)phosphonium iodide

tris(diethylamino)(dipropylamino)phosphonium iodide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

C14H34N3P

C14H34N3P

C

C16H39N4P

C16H39N4P

Conditions
ConditionsYield
With ammonia; sodium at -30℃; for 8h; Yield given. Yields of byproduct given;
C23H47N5P2S

C23H47N5P2S

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

2-(diethylamino)-2,3-dihydro-3-methyl-1,3,2-benzothiazaphosphole
62128-55-6

2-(diethylamino)-2,3-dihydro-3-methyl-1,3,2-benzothiazaphosphole

Conditions
ConditionsYield
In diethyl ether at 20℃; for 0.0833333h; Product distribution;
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

(Dimethyl-phosphinoylmethyl)-methyl-trimethylsilanyl-amine
174966-20-2

(Dimethyl-phosphinoylmethyl)-methyl-trimethylsilanyl-amine

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

C12H31N3OP2

C12H31N3OP2

C

C12H32N3O2P3

C12H32N3O2P3

D

C12H33N3O3P4

C12H33N3O3P4

Conditions
ConditionsYield
In dichloromethane for 1h; Ambient temperature; Title compound not separated from byproducts;
diethylamine
109-89-7

diethylamine

2,2'-spirobi(3,3,3',3'-tetramethyl-5,5'-di-tert-butyl-1,1'-dioxa-3,3'-diazonia-2-phospha-4-cyclopentene) chloride

2,2'-spirobi(3,3,3',3'-tetramethyl-5,5'-di-tert-butyl-1,1'-dioxa-3,3'-diazonia-2-phospha-4-cyclopentene) chloride

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In dichloromethane for 720h; Ambient temperature;
diethylamine
109-89-7

diethylamine

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

A

diethyl amine hydrochloride
660-68-4

diethyl amine hydrochloride

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
Thermodynamic data;
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

vinylmagnesium halogenide

vinylmagnesium halogenide

A

bis((N,N-diethyl)amino)vinylphosphine
89438-02-8

bis((N,N-diethyl)amino)vinylphosphine

B

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h; Title compound not separated from byproducts;
diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

2-vinylphenylmagnesium halogenide

2-vinylphenylmagnesium halogenide

A

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

B

C20H24NP

C20H24NP

Conditions
ConditionsYield
In tetrahydrofuran at -25℃; for 1h; Title compound not separated from byproducts;
cycloheptatrienylium tetrafluoroborate
27081-10-3

cycloheptatrienylium tetrafluoroborate

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

cycloheptatrienyltris(diethylamino)phosphonium tetrafluoroborate

cycloheptatrienyltris(diethylamino)phosphonium tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane100%
diethyl [hydroxy(phenyl)methyl]phosphonate
1663-55-4

diethyl [hydroxy(phenyl)methyl]phosphonate

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

C19H36N2O4P2
212071-37-9

C19H36N2O4P2

Conditions
ConditionsYield
With iodine In benzene at 70℃; for 1h; Addition; Title compound not separated from byproducts;100%
With iodine In benzene at 75℃; for 1.5h; Yield given;
diethyl hydroxy(p-tolyl)methylphosphonate
79158-40-0

diethyl hydroxy(p-tolyl)methylphosphonate

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

C20H38N2O4P2
212071-36-8

C20H38N2O4P2

Conditions
ConditionsYield
With iodine In benzene at 70℃; for 1h; Addition; Title compound not separated from byproducts;100%
With iodine In benzene at 75℃; for 1.5h; Yield given;
With iodine 1.) C6H6, 70 deg C, 20 min, 2.) C6H6, 75 deg C, 1.5 h; Multistep reaction;
diethyl (hydroxy)(2-chlorophenyl)methylphosphonate
7506-98-1

diethyl (hydroxy)(2-chlorophenyl)methylphosphonate

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

C19H35ClN2O4P2
212071-38-0

C19H35ClN2O4P2

Conditions
ConditionsYield
With iodine In benzene at 70℃; for 1h; Addition; Title compound not separated from byproducts;100%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate
6329-56-2, 1012320-95-4, 1019779-87-3

diethyl (benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)phosphonate

C20H36N2O6P2

C20H36N2O6P2

Conditions
ConditionsYield
With iodine In benzene at 70℃; for 1h; Addition; Title compound not separated from byproducts;100%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Tocopherol
59-02-9

Tocopherol

bis(N,N-diethylamido)-O-tocopherylphosphite
562828-32-4

bis(N,N-diethylamido)-O-tocopherylphosphite

Conditions
ConditionsYield
at 90 - 100℃; for 5h;100%
4-aza-1-hydroxymethyl-10-oxa-3,5-dioxo-4-N-(p-nitrophenyl)tricyclo[5.2.11.7.02.6]dec-8-ene

4-aza-1-hydroxymethyl-10-oxa-3,5-dioxo-4-N-(p-nitrophenyl)tricyclo[5.2.11.7.02.6]dec-8-ene

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

bis(N,N-diethylamido){4-aza-10-oxa-3,5-dioxo-4-N-(p-nitrophenyl)tricyclo[5.2.11.7.02.6]dec-8-en-1-yl}methylphosphite

bis(N,N-diethylamido){4-aza-10-oxa-3,5-dioxo-4-N-(p-nitrophenyl)tricyclo[5.2.11.7.02.6]dec-8-en-1-yl}methylphosphite

Conditions
ConditionsYield
In 1,4-dioxane at 40℃; for 1h; Inert atmosphere;99%
5'-O-(4-4'-dimethoxytrityl)thymidine
40615-39-2

5'-O-(4-4'-dimethoxytrityl)thymidine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

A

5'-O-dimethoxytrityl thymidine 3'-O-phosphorbisdiethylamidite
104655-76-7

5'-O-dimethoxytrityl thymidine 3'-O-phosphorbisdiethylamidite

B

Diethyl-phosphoramidous acid bis-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Diethyl-phosphoramidous acid bis-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester

Conditions
ConditionsYield
1H-tetrazole; diisopropylamine In dichloromethane; water; acetonitrile for 0.25h; Ambient temperature; var. amine catalysts.; Title compound not separated from byproducts;A 98.5%
B 0.5%
1H-tetrazole In dichloromethane; water; acetonitrile for 0.25h; Ambient temperature; var. amine catalysts.; Title compound not separated from byproducts;A 71.5%
B 25.9%
morpholine
110-91-8

morpholine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

tris(morpholino)phosphine
5815-61-2

tris(morpholino)phosphine

Conditions
ConditionsYield
at 70℃; for 10h; var. time and temp.;98%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

tris(4-methylpiperazin-1-yl)phosphane
52893-99-9

tris(4-methylpiperazin-1-yl)phosphane

Conditions
ConditionsYield
at 70℃; for 10h;98%
tetrachloromethane
56-23-5

tetrachloromethane

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

C12H30ClN3P(1+)*CCl3(1-)
145292-97-3

C12H30ClN3P(1+)*CCl3(1-)

Conditions
ConditionsYield
at 0℃;98%
iodoform
75-47-8

iodoform

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Tris(diethylamino)methylphosphonium-iodid
40985-29-3

Tris(diethylamino)methylphosphonium-iodid

Conditions
ConditionsYield
98%
bis(2-hydroxy-3-naphthyl)methane
70654-00-1

bis(2-hydroxy-3-naphthyl)methane

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

2-diethylaminodinaphtho[1,2-d][1',2'-g]-1,3,2-dioxaphosphocane

2-diethylaminodinaphtho[1,2-d][1',2'-g]-1,3,2-dioxaphosphocane

Conditions
ConditionsYield
In 1,4-dioxane for 1h; Ambient temperature;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

polymer, MP: 248-258 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

polymer, MP: 248-258 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
In diethylene glycol dimethyl ether at 100 - 110℃; for 25h;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

polymer, MP: 274-280 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

polymer, MP: 274-280 deg C; monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
at 80 - 90℃; for 3h;98%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

poly(phosphoramidite)? MP: 274-280 deg C; Monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

poly(phosphoramidite)? MP: 274-280 deg C; Monomer(s): 1,6-hexanediol; hexaethylphosphorous triamide

Conditions
ConditionsYield
at 80 - 90℃; for 3h;98%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

methyl iodide
74-88-4

methyl iodide

Tris(diethylamino)methylphosphonium-iodid
40985-29-3

Tris(diethylamino)methylphosphonium-iodid

Conditions
ConditionsYield
In diethyl ether for 2h; warming from - 50 deg C;97%
2-diazo-indan-1,3-dione
1807-49-4

2-diazo-indan-1,3-dione

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

1-Oxo-2-{[tris(diethylamino)phosphonio]diazenyl}-1H-indene-3-olate

1-Oxo-2-{[tris(diethylamino)phosphonio]diazenyl}-1H-indene-3-olate

Conditions
ConditionsYield
In dichloromethane at -60 - 20℃; Inert atmosphere;97%
o-hydroxyacetophenone
118-93-4

o-hydroxyacetophenone

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

o-acetylphenyl tetraethyldiamidophosphite
103345-85-3

o-acetylphenyl tetraethyldiamidophosphite

Conditions
ConditionsYield
under 50 - 60 Torr; r.t., 4 h, then 50 deg C, 0.5 h;96.5%
hexafluorocyclobut-1-ene
697-11-0

hexafluorocyclobut-1-ene

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

tris(diethylamine)phosphonium-2,2,3,3,4,4-hexafluorocyclobutane ylide
175788-41-7

tris(diethylamine)phosphonium-2,2,3,3,4,4-hexafluorocyclobutane ylide

Conditions
ConditionsYield
In diethyl ether at -30 - 0℃; for 3h;96%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

Conditions
ConditionsYield
With phosphorus trichloride In acetonitrile at 20℃;95%
With phosphorus trichloride
With 2-Chloro-N,N-diethylacetamide In diethyl ether
piperidine
110-89-4

piperidine

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

tripiperidino-phosphine
13954-38-6

tripiperidino-phosphine

Conditions
ConditionsYield
at 70℃; for 10h;95%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Bromotrifluoromethane
75-63-8

Bromotrifluoromethane

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

A

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

B

(N(C2H5)2)3PClBr
89217-83-4

(N(C2H5)2)3PClBr

Conditions
ConditionsYield
In dichloromethaneA 95%
B n/a
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

Tris(diethylamino)bromphosphoniumbromid

Tris(diethylamino)bromphosphoniumbromid

Conditions
ConditionsYield
With bromine In dichloromethane at -40 - 25℃;95%
methyl 2-phenylhydrazinecarbodithioate
50878-38-1

methyl 2-phenylhydrazinecarbodithioate

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

diethyl-(5-methylsulfanyl-3-phenyl-3H-[1,3,4,2]thiadiazaphosphol-2-yl)-amine
72107-62-1

diethyl-(5-methylsulfanyl-3-phenyl-3H-[1,3,4,2]thiadiazaphosphol-2-yl)-amine

Conditions
ConditionsYield
In benzene Heating;95%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

C12H30N3O3PS

C12H30N3O3PS

Conditions
ConditionsYield
With sulfur trioxide pyridine complex In dichloromethane at -20 - 20℃;95%
triethylamine hydrofluoride

triethylamine hydrofluoride

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

triethylammonium hydridopentafluorophosphate
94586-22-8

triethylammonium hydridopentafluorophosphate

Conditions
ConditionsYield
In acetonitrile byproducts: diethylamine; room temp.; shaking; allow to stand for 1 h;; distd.;;95%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

(S)-6-bromo-2,2'-dihydroxy-1,1'-binaphthyl

(S)-6-bromo-2,2'-dihydroxy-1,1'-binaphthyl

(S)-6'-bromo-2-(diethylamino)-dinaphtho[2' ,1'-d:1'',2''-f][1,3,2]dioxaphosphepine

(S)-6'-bromo-2-(diethylamino)-dinaphtho[2' ,1'-d:1'',2''-f][1,3,2]dioxaphosphepine

Conditions
ConditionsYield
at 45 - 110℃; under 10 Torr; Inert atmosphere; neat (no solvent); diastereoselective reaction;95%
4-aza-1-hydroxymethyl-10-oxa-3,5-dioxo-4-N-(p-phenylazophenyl)tricyclo[5.2.11.7.02.6]dec-8-ene

4-aza-1-hydroxymethyl-10-oxa-3,5-dioxo-4-N-(p-phenylazophenyl)tricyclo[5.2.11.7.02.6]dec-8-ene

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

bis(N,N-diethylamido){4-aza-10-oxa-3,5-dioxo-4-N-(p-phenylazophenyl)tricyclo[5.2.11.7.02.6]dec-8-en-1-yl}methylphosphite

bis(N,N-diethylamido){4-aza-10-oxa-3,5-dioxo-4-N-(p-phenylazophenyl)tricyclo[5.2.11.7.02.6]dec-8-en-1-yl}methylphosphite

Conditions
ConditionsYield
In 1,4-dioxane at 40℃; for 1h; Inert atmosphere;95%
diazodimedone
1807-68-7

diazodimedone

hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

5,5-dimethyl-3-oxo-2-{[tris(diathylamino)phosphonio]diazenyl}cyclohex-1-ene-1-olate

5,5-dimethyl-3-oxo-2-{[tris(diathylamino)phosphonio]diazenyl}cyclohex-1-ene-1-olate

Conditions
ConditionsYield
In dichloromethane at -60 - 20℃; Inert atmosphere;95%

2283-11-6Relevant articles and documents

-

Fowell,Mortimer

, p. 2913 (1959)

-

Insignificance of P-H...P hydrogen bonding: Structural chemistry of neutral and protonated 1,8-di(phosphinyl)naphthalene

Reiter, Stephan A.,Nogai, Stefan D.,Karaghiosoff, Konstantin,Schmidbaur, Hubert

, p. 15833 - 15843 (2004)

While there is extensive information on 1,8-di(amino)naphthalene (i.e., the parent compound of the proton sponge series), the corresponding phosphorus compound has not been described. A high-yield synthesis of 1,8-di(phosphinyl)naphthalene (9) and the 1-naphthylphosphine reference compound (4) is now reported. Thermal decomposition of 9 leads to intramolecular dehydrogenative P-P coupling to afford 1,2-dihydro-1,2-diphosphaacenaphthene (10). Protonation of 9 and 4 with CF3SO3H gives quantitative yields of the monophosphonium salts 11 and 5, respectively. With excess acid and traces of moisture, the hydronium salt [C10H 6(PH2)(PH3)]+[H3O] +2[CF3SO3]- (13) is obtained. The structures of 9, 11, and 13 have been determined. Molecules of 9 have a planar naphthalene skeleton, C10H6P2, with the two -PH2 groups in a transoid conformation. The molecules form loose dimers in the crystal, the individual chiral enantiomers of which are related by a center of inversion. In contrast to the situation for the amino analogue, and despite the proximity of the two -PH2 functions, there is no intra- or intermolecular hydrogen bonding. Solutions of 9 (in CD2Cl 2) show equivalent P-bound hydrogen atoms due to conformational fluctionality. By analysis of the ABCD2XX′D′ 2C′B′A′ spin system, it was shown that, in 9, there are strong through-space pericouplings [nJ(PXP X′) = 221.6 Hz, nJ(PXH D′) = 31.7 Hz, nJ(HDHD′) = 3.9 Hz]. In the cations of 11, the C10H6P2 skeleton is also planar (by Cs symmetry), with the -PH2 and -PH3+ groups in a conformation which rules out any P-H...P hydrogen bonding. The hydronium cation and the two triflate anions in 13 are associated into an anionic network through extensive hydrogen bonding surrounding stacks of the phosphonium cations. In solution, the cations of 11 and 13 show separate 31P resonances for the two phosphorus atoms with fully resolved 1J(PH) couplings, which indicate that there is no intra- or intercationic proton exchange. By contrast, the NMR spectra of solutions of [C10H6(NH2)(NH3)] +X- salts show proton scrambling equilibrating all five N-bound hydrogen atoms, and in the crystal, the conformations of the cations feature intramolecular N-H...N hydrogen bonding.

Macrocyclic systems on the basis of phosphorus acids and 2,7-dihydroxynaphthalene

Rasadkina,Slitikov,Evdokimenkova,Nifant'ev

, p. 1208 - 1212 (2003)

Syntheses of macrocyclic systems containing three 2,7-dihydroxynaphthalene residues and three residues of thiophosphoric and phosphorous amides in various ratios are developed. Chemical properties of the obtained compounds are studied.

EPR and ENDOR spectroscopic study of the reactions of aromatic azides with gallium trichloride

Bencivenni, Giorgio,Cesari, Riccardo,Nanni, Daniele,El Mkami, Hassane,Walton, John C.

supporting information; experimental part, p. 5097 - 5104 (2010/12/24)

The reactions of gallium trichloride with phenyl and deuterio-phenyl azides, as well as with 4-methoxyphenyl azide and deuterium isotopomers, were examined by product analysis, CW EPR spectroscopy and pulsed ENDOR spectroscopy. The products included the corresponding anilines together with 4-aminodiphenylamine type dimers, and polyanilines. Complex CW EPR spectra of the radical cations of the dimers [ArNHC6H4NH 2]+ and trimers [ArNHC6H4NHC 6H4NH2]+ were obtained. These EPR spectra were analysed with the help of data from the deuterium-substituted analogues as well as the pulse Davies ENDOR spectra. DFT computations of the radical cations provided corroborating evidence and suggested the unpaired electrons were accommodated in extensive π-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.

Synthesis of N6,N6-dialkyladenine nucleosides using hexaalkylphosphorus triamides produced in situ

Lakshman, Mahesh K.,Choudhury, Asad,Bae, Suyeal,Rochttis, Eliezer,Pradhan, Padmanava,Kumar, Amit

experimental part, p. 152 - 159 (2009/07/05)

Reactions between secondary amines and phosphorus trichloride (PCl 3) leads to the formation of the corresponding tris(dialkylamino) phosphanes or hexaalkylphosphorus triamides [HAPTs: (R2N) 3P]. Treatment of silyl-protected 2′-deoxyinosine and acetyl-protected inosine with the HAPTs produced in situ, together with iodine (I2), leads to the formation of N6,N6- dialkyladenosine and -2′-deoxyadenosine. In some cases the stoichiometry of the amine is important, as is the use of a tertiary amine base. The effect of amine stoichiometry on the reaction between HAPT and I2 has been studied by 31P{1H} NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

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