Hexamethylphosphoramide supplier

Name
Hexamethylphosphoramide
EINECS 211-653-8
CAS No. 680-31-9
Article Data81
CAS DataBase
Density 1.03 g/cm³
Solubility miscible with water
Melting Point 7 °C(lit.)
Formula C₆H₁₈N₃OP
Boiling Point 233 °C at 760 mmHg
Molecular Weight 179.202
Flash Point 94.7 °C
Transport Information
Appearance clear colorless to light amber liquid
Safety 53-45-9
Risk Codes 45-46
Molecular Structure
Hazard Symbols T
Synonyms Phosphorictriamide, hexamethyl- (6CI,8CI,9CI);ENT 50,882;Eastman Inhibitor HPT;HMPA;HMPT;HMPTA;HPT;Hempa;Hexametapol;Hexamethylorthophosphoric triamide;
PSA 36.60000
LogP 0.77930

Synthetic route

: 124-40-3
dimethyl amine

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: C11H30N6P(1+)

C: 137334-99-7
1,1,1,3,3,3-hexakis(dimethylamino)-1λ5,3λ5-diphosphazenium fluoride

Conditions

Conditions	Yield
Multistep reaction;	A n/a B n/a C 93%
Yield given. Multistep reaction;

...Expand

: 603-35-0
triphenylphosphine

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions

Conditions	Yield
With Oxone In tetrahydrofuran; methanol Ambient temperature;	93%

: 1608-26-0
Hexamethylphosphorous triamide

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions

Conditions	Yield
With benzenesulfonyl chloride In diethyl ether	92%
With substituted 3-hydroperoxy-1,2-benzisothiazole 1,1-dioxide In dichloromethane at 0℃; for 0.75h;	98 % Spectr.
With oxygen; fullerene-C60 In 1,2-dichloro-benzene at 20℃;

: 124-38-9
carbon dioxide

: 49778-01-0
iminotris(dimethylamino)phosphorane

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: N,N,N',N',N'',N''-hexamethylphosphorimidic triamide cyanate

Conditions

Conditions	Yield
In benzene for 48h;	A 91% B 89%

...Expand

: 49778-01-0
iminotris(dimethylamino)phosphorane

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: N,N,N',N',N'',N''-hexamethylphosphorimidic triamide cyanate

Conditions

Conditions	Yield
With carbon dioxide In benzene for 48h;	A 91% B 89%

: CaCl2*3(N(CH3)2)3PO

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: CaCl2*2(N(CH3)2)3PO

Conditions

Conditions	Yield
In neat (no solvent) heated (vac., 200°C); residue dissolved in C6H6; hexane added; vac. (100°C); elem.anal.;	A n/a B 89.1%

: 1608-26-0
Hexamethylphosphorous triamide

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 61904-00-5
tris(dimethylamino)methylphosphonium tetraphenylborate

Conditions

Conditions	Yield
With dimethylselenuranylidene derivative of 1,3-indandione In dichloromethane for 12h; Product distribution; Ambient temperature; other reagent, other time;	A n/a B 89%

: 1,1'-azodicarbonyl-dipiperidine

: 1608-26-0
Hexamethylphosphorous triamide

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 1355083-83-8
2,5-di(piperidin-1-yl)-1,3,4-oxadiazole

Conditions

Conditions	Yield
at 20℃; for 0.25h;	A n/a B 85%

...Expand

: 694-59-7
pyridine N-oxide

: bromo-tris-dimethylamino-phosphonium hexafluorophosphate

: 108-91-8
cyclohexylamine

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 15513-16-3
N-cyclohexylpyridin-2-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃;	A n/a B 83%

...Expand

: 1605-65-8
N,N,N',N'-Tetramethylphosphorodiamidic chloride

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 115-26-4
dimefox

C: 354-43-8
N,N-dimethylphosphoramidic difluoride

Conditions

Conditions	Yield
With sodium hexaflorophosphate In various solvent(s) at 200℃; for 0.25h;	A 2% B 77% C 15%

...Expand

: 124-40-3
dimethyl amine

: 10025-87-3, 12599-09-6, 63736-95-8
trichlorophosphate

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane at 0℃; Inert atmosphere; Schlenk technique;	70%

: 555-16-8
4-nitrobenzaldehdye

: 76486-69-6
tris(dimethylamino)<(ethoxycarbonyl)methylene>phosphorane

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 953-26-4
ethyl 4-nitrocinnamate

Conditions

Conditions	Yield
In ethanol at 80℃; for 4h;	A n/a B 63.7%

...Expand

: C14H22N5OP

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 4846-25-7
2-[(furan-2-yl)methyl]propanedinitrile

Conditions

Conditions	Yield
With water In benzene	A n/a B 62.3%

: C14H22N5OP

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 4846-25-7
2-[(furan-2-yl)methyl]propanedinitrile

Conditions

Conditions	Yield
With water In benzene	A n/a B 62.3%

: 100-52-7
benzaldehyde

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: amarine

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 140℃; for 1h;	A 55% B 12%

: 98-86-2
acetophenone

: 13754-82-0
N,N,N',N',N'',N''-hexamethylphosphorohydrazonic triamide

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: hexamethyl-N'''-(α-methylbenzylidene)phosphorohydrazonic triamide

Conditions

Conditions	Yield
With barium(II) oxide In benzene for 1h;	A 32% B 52%

...Expand

: 140476-47-7
2-thiocyanatoethyl phosphorodichloridite

: 124-40-3
dimethyl amine

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 140476-50-2
S-(2-chloroethyl) tetramethylphosphorodiamidothioate

Conditions

Conditions	Yield
In diethyl ether for 2h; Ambient temperature;	A 14% B 49%

...Expand

: tetra(dimethylamido)phosphonium bromide

A: 67-56-1
methanol

B: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

C: 124-40-3
dimethyl amine

D: hydrochloride of heptamethylphosphorimidic triamide

Conditions

Conditions	Yield
With sodium hydroxide at 230℃; under 9 Torr; Product distribution; Mechanism;	A n/a B 40% C n/a D 45%

...Expand

: 1608-26-0
Hexamethylphosphorous triamide

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 3732-82-9
tris(dimethylamino)phosphorus sulfide

Conditions

Conditions	Yield
With sulfur dioxide at 0℃; for 1h;	A 5% B 20%
With sulfur dioxide at -78℃; Mechanism; var. in presence of o-dibromobenzene;
With sulfur dioxide at -78℃; Yield given;

: 124-40-3
dimethyl amine

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

Conditions

Conditions	Yield
With trichlorophosphate
With toluene; trichlorophosphate
With tetrachloromethane; trichlorophosphate

: 623-03-0
4-Cyanochlorobenzene

: C4H12O4P(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonate(4-chloro-phenylmethylidyne)-methyl-ammonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 139-66-2
diphenyl sulfide

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 105229-70-7
methyldiphenylsulfonium trifluoromethanesulfonate

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 945-51-7
1,1'-sulfinylbisbenzene

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Diphenylmethylsulfoxonium triflate

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 4107-65-7
2,4-dimethoxybenzonitrile

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonate(2,4-dimethoxy-phenylmethylidyne)-methyl-ammonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 1194-02-1
4-fluorobenzonitrile

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonate(4-fluoro-phenylmethylidyne)-methyl-ammonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 623-00-7
4-bromobenzenecarbonitrile

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonate(4-bromo-phenylmethylidyne)-methyl-ammonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 1223-31-0
bis(4-nitrophenyl)sulfide

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonatemethyl-bis-(4-nitro-phenyl)-sulfonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 104-85-8
para-methylbenzonitrile

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: 136139-18-9
(N-methyl)(4-methyl-phenyl)carbonitrilium trifluoromethylsulfonate

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: 874-90-8
4-methoxybenzonitrile

: C7H21N3OP(1+)*CF3O3S(1-)

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Trifluoro-methanesulfonate(4-methoxy-phenylmethylidyne)-methyl-ammonium;

Conditions

Conditions	Yield
In sulfolane at 30℃; Equilibrium constant;

...Expand

: C7H21N3OP(1+)*CF3O3S(1-)

: 333-27-7
methyl trifluoromethanesulfonate

A: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

B: Dimethylsulfat

Conditions

Conditions	Yield
With /BRN= 506008/ In sulfolane at 30℃; Equilibrium constant; further compounds;

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 603-33-8
triphenylbismuthane

: diphenylbismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 10050-08-5
tri-o-tolylbismuth

: bis(2-methylphenyl)bismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 5142-75-6
tri(p-tolyl)bismuth

: bis(4-methylphenyl)bismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 88756-72-3
(4-chlorophenyl)bis(2-methylphenyl)bismuthane

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: (4-chlorophenyl)(2-methylphenyl)bismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 176704-27-1
(4-chlorophenyl)bis(2-methoxyphenyl)bismuthane

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: (4-chlorophenyl)(2-methoxyphenyl)bismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 83724-41-8
tris(2-methoxyphenyl)bismuthine

: bis(2-methoxyphenyl)bismuth triflate - (hexamethylphosphoric triamide)2 complex

Conditions

Conditions	Yield
In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane Ar-atmosphere; mixing BiAr3, 2 equivs. of HMPA and 1 equiv. of Me3SiOTf at 0°C, stirring for 0.5-2 h at room temp.; evapn.; elem. anal.;	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 7439-91-0
lanthanum

: 1,3,5,7-cycloocatetraene

: 209743-19-1
(C8H8)La(OP(N(CH3)2)3)4(1+)*La(C8H8)2(1-)=[(C8H8)La(OP(N(CH3)2)3)4][La(C8H8)2]

Conditions

Conditions	Yield
iodine In tetrahydrofuran Ar-atmosphere; stirring (50°C, 10 d); crystn. on concg. (-20°C);	100%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 1493-13-6
trifluorormethanesulfonic acid

: tris(dimethylamino)(hydroxy)phosphonium trifluoromethanesulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 3h;	100%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 82113-65-3
bis(trifluoromethanesulfonyl)amide

: tris(dimethylamino)(hydroxy)phosphonium bis(trifluoromethanesulfonyl)azanide

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 3h;	100%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 386704-06-9
2-chloro-6-(trifluoromethyl)nicotinonitrile

: 935518-01-7
2-dimethylamino-6-(trifluoromethyl)pyridine-3-carbonitrile

Conditions

Conditions	Yield
at 150℃; for 48h;	100%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 16029-98-4
trimethylsilyl iodide

: C9H27N3OPSi(1+)*I(1-)

Conditions

Conditions	Yield
In toluene for 0.166667h; Inert atmosphere; Schlenk technique; Glovebox;	100%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 1158-51-6
triphenyltin(IV) azide

: azido(hexamethylphosphoramide)triphenyltin(IV)

Conditions

Conditions	Yield
In toluene components dissoln. (heating or stirring), crystn. on soln. leaving overnight at room temp.;	99%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 1050381-21-9
(C8H8)U(N(C2H5)3)(SP(C6H5)2CC(C6H5)CHC(C6H5)C(P(C6H5)2S)PCH3)(1+)*B(C6H5)4(1-)=((C8H8)U(N(C2H5)3)(C42H34S2P3))B(C6H5)4

: 1050381-32-2
(C8H8)U(OP(N(CH3)2)3)(SP(C6H5)2CC(C6H5)CHC(C6H5)C(P(C6H5)2S)PCH3)(1+)*B(C6H5)4(1-)=C80H80BN3OP4S2U

Conditions

Conditions	Yield
In tetrahydrofuran under Ar; OP(NMe2)3 added to U complex in THF; evapd. to dryness; elem. anal.;	99%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 38117-54-3
cyclopentadienyl iron(II) dicarbonyl dimer

Reaxys ID: 28905417: Reaxys ID: 28905417

: YbFp2(HMPA)4

Conditions

Conditions	Yield
Stage #1: N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: cyclopentadienyl iron(II) dicarbonyl dimer In tetrahydrofuran at 20℃; for 16h;	99%

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 152385-10-9
methy(oxo)bis(η(2)-peroxo)rhenium(VII)

: 182506-55-4
(hexamethylphosphoramide)methyl(oxo)-bis(η(2)-peroxo)rhenium(VII)

Conditions

Conditions	Yield
In diethyl ether N2-atmosphere; dropwise addn. of 1 equiv. HMPA to Re-complex at 0°C (pptn.); collection (filtration), washing (Et2O, pentane), drying (vac.); elem. anal.;	98%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 606-27-9
methyl 2-nitrobenzoate

: C13H22N6O2P(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: N,N,N,N,N,N-hexamethylphosphoric triamide With trichloroisocyanuric acid In tetrahydrofuran at 0℃; for 2h; Stage #2: methyl 2-nitrobenzoate With guanidine hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran Reflux; Stage #3: With potassium hexafluorophosphate In tetrahydrofuran Reagent/catalyst; Solvent; Heating;	97.3%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 73954-61-7
pentapropylphosphorodiamidimidic bromide

: <propylamino>tris(dimethylamino)phosphonium bromide

Conditions

Conditions	Yield
at 20℃; for 24h;	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: bis(hexamethylphosphorotriamide)hydrogen tribromide

Conditions

Conditions	Yield
With hydrogen bromide; bromine	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 75-77-4
chloro-trimethyl-silane

: 156-62-7
calcium cyanamide

A: CaCl2*2(N(CH3)2)3PO

B: 1000-70-0
bis(trimethylsilyl)carbodi-imide

Conditions

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide HMPTA added to suspn. of CaCN2 in Me3SiCl (stirring); heated to 60°C; heated gradually (120°C, 3 h); cooled; hexane added; ppt. filtered off; dried (vac., 90°C); liquid phase fractionated; elem.anal.;	A 97% B n/a

...Expand

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 2700-22-3
Benzylidenemalononitrile

: N-(3,3-dicyano-2-phenylpropyl)-N,N,N,N,N-pentamethylphosphoric triamide

Conditions

Conditions	Yield
With eosin y In dichloromethane at 20℃; for 16h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; Irradiation;	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 60595-33-7
2-(3-cyanobenzylidene)malononitrile

: N-(3,3-dicyano-2-(3-cyanophenyl)propyl)-N,N,N,N,N-pentamethylphosphoric triamide

Conditions

Conditions	Yield
With eosin y In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation;	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 18896-73-6
(2-Phenyl-1-cyanethen)-phosphonsaeurediethylester

: diethyl (1-cyano-3-(methyl(tetramethylphosphono)amino)-2-phenylpropyl)phosphonate

Conditions

Conditions	Yield
With eosin y In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation;	97%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: chloro-N,N,N',N',N'',N''-hexamethyltriamidophosphonium dichlorophosphate

Conditions

Conditions	Yield
With trichlorophosphate for 24h;	96%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: CrCl3*2N(CH3)3

: 32715-16-5, 76124-04-4, 76124-05-5
CrCl3(((CH3)2N)3PO)3

Conditions

Conditions	Yield
In benzene (N2), CrCl3*2NMe3 and organic compound in benzene reacted; elem. anal.;	96%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 22123-53-1
2-neopentylidenemalononitrile

: N-(2-(dicyanomethyl)-3,3-dimethylbutyl)-N,N,N,N,N-pentamethylphosphoric triamide

Conditions

Conditions	Yield
With eosin y In dichloromethane at 20℃; for 16h; Inert atmosphere; Irradiation;	96%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 55666-41-6
tert-butyl 2-nitrobenzoate

: C13H22N6O2P(1+)*F6P(1-)

Conditions

Conditions	Yield
Stage #1: N,N,N,N,N,N-hexamethylphosphoric triamide With trichloroisocyanuric acid In toluene at 0℃; for 2h; Stage #2: tert-butyl 2-nitrobenzoate With guanidine hydrochloride; N-ethyl-N,N-diisopropylamine In toluene Reflux; Stage #3: With potassium hexafluorophosphate In toluene Heating;	95.3%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 13091-23-1
4-chloro-3-nitropyridine

: 5028-26-2
3-nitro-4-(N,N-dimethylamino)pyridine

Conditions

Conditions	Yield
With sodium sulfide at 155℃; for 4h;	95%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: diphenylmethyl 3-(2-oxoazetidin-4-yl)-oxy-4-(4-toluenesulfonyl)oxy-butyrate

: diphenylmethyl 3-(2-oxoazetidin-4-yl)-oxy-4-bromo-butyrate

Conditions

Conditions	Yield
With lithium bromide	95%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 7705-08-0
iron(III) chloride

: Fe(NO3)2(Cl)(hexamethylphosphoric triamide)2

Conditions

Conditions	Yield
With AgNO3 In acetonitrile byproducts: AgCl; dropwise addn. of AgNO3 in CH3CN to a soln. of anhydrous FeCl3 and HMPA in CH3CN, pptn. of AgCl, stirring of suspension for 1 h and let standing overnight; filtration, evapn. to dryness, washing with pentane and diethyl ether, drying under vac.;	95%

: 680-31-9
N,N,N,N,N,N-hexamethylphosphoric triamide

: 6,6-dimethyl-1,2,6-oxathiastanninan-2,2-dioxide monohydrate

: (CH3)2Sn(OP((CH3)2N)3)OSO2(CH2)3

Conditions

Conditions	Yield
In chloroform to a soln. of heterocyclus is added soln. of HMPT; warming the mixt. for 1 h at 50°C; removing all volatile parts in vac., crystn. by addn. of hexane to oil residue, recrystn. from CH2Cl2/hexane; elem. anal.;	95%

Hexamethylphosphoramide Chemical Properties

Molecule structure of Hexamethylphosphoramide (CAS NO.680-31-9):

IUPAC Name: N-[Bis(dimethylamino)phosphoryl]-N-methylmethanamine
Molecular Weight: 179.200381 g/mol
Molecular Formula: C₆H₁₈N₃OP
Density: 1.032 g/cm³
Melting Point: 7 °C(lit.)
Boiling Point: 233 °C at 760 mmHg
Flash Point: 94.7 °C
Index of Refraction: 1.464
Molar Refractivity: 47.88 cm³
Molar Volume: 173.4 cm³
Surface Tension: 34.3 dyne/cm
Enthalpy of Vaporization: 46.97 kJ/mol
Vapour Pressure: 0.0572 mmHg at 25 °C
Water Solubility: miscible
Freezing Point: 7 °C
XLogP3: 0.3
H-Bond Acceptor: 4
Rotatable Bond Count: 3
Exact Mass: 179.118749
MonoIsotopic Mass: 179.118749
Topological Polar Surface Area: 26.8
Heavy Atom Count: 11
Canonical SMILES: CN(C)P(=O)(N(C)C)N(C)C
InChI: InChI=1S/C6H18N3OP/c1-7(2)11(10,8(3)4)9(5)6/h1-6H3
InChIKey: GNOIPBMMFNIUFM-UHFFFAOYSA-N
EINECS: 211-653-8
Classification Code: Agricultural Chemical ; Chemosterilants; Insect attractant, repellent and chemosterilant; Insecticide;
Mutation data; Pesticides; Reproductive Effect; Skin / Eye Irritant; TSCA Flag S [Substance is identified in a proposed or final SNUR (Significant New Use Rule) under TSCA]; Tumor data

Hexamethylphosphoramide Uses

Hexamethylphosphoramide (CAS NO.680-31-9) is a useful polar aprotic solvent and additive in organic synthesis.
Hexamethylphosphoramide is used as a solvent for polymers, gases, and organometallic compounds. It usefully improves the selectivity of lithiation reactions, because it breaks up the oligomers of lithium bases such as butyllithium. Hexamethylphosphoramide also used gas chromatography stationary phase, violet inhibitors, rocket fuel additives to reduce the freezing point, chemical sterilization agent.

Hexamethylphosphoramide Production

Hexamethylphosphoramide is producted by reacting of alkali chlorine and phosphorus.

Hexamethylphosphoramide Toxicity Data With Reference

1.	dns-hmn:hla 125 mg/L	PMRSDJ Progress in Mutation Research. 5 (1985),375.
2.	cyt-hmn:lym 500 mg/L	MUREAV Mutation Research. 156 (1985),19.
3.	sce-rat:lvr 2 g/L	PMRSDJ Progress in Mutation Research. 5 (1985),287.
4.	ihl-rat TCLo:50 ppb/52W-C:CAR	AJPAA4 American Journal of Pathology. 106 (1982),8.
5.	orl-rat LD50:2650 mg/kg	NATUAS Nature. 211 (1966),146.
6.	skn-rat LDLo:3500 mg/kg	NATUAS Nature. 211 (1966),146.
7.	orl-mus LD50:2400 mg/kg	NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. 70 (1974),114P.
8.	ipr-mus LD50:1600 mg/kg	PMRSDJ Progress in Mutation Research. 1 (1981),682.
9.	ivn-mus LD50:800 mg/kg	CHINAG Chemistry and Industry.(36),(1966),1529.
10.	orl-rbt LDLo:1500 mg/kg	JEENAI Journal of Economic Entomology. 48 (1955),139.
11.	skn-rbt LD50:2600 mg/kg

Hexamethylphosphoramide Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 15 , 1977,p. 211.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Hexamethylphosphoramide Safety Profile

Hazard Codes: Toxic T
Risk Statements: 45-46
R45:May cause cancer.
R46:May cause heritable genetic damage.
Safety Statements: 53-45-9
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S9:Keep container in a well-ventilated place.
RIDADR: 2810
WGK Germany: 3
RTECS: TD0875000
F: 8
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 680-31-9(Hazardous Substances Data)
Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion, skin contact, intraperitoneal, and intravenous routes. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits very toxic fumes of phosphine, PO_x, and NO_x.

Hexamethylphosphoramide Standards and Recommendations

ACGIH TLV: Animal Carcinogen, Suspected Human Carcinogen
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen

Hexamethylphosphoramide Specification

Hexamethylphosphoramide (CAS NO.680-31-9) is also named as AI3-50882 ; CCRIS 332 ; ENT 50882 ; Eastman ; Inhibitor HPT ; HSDB 2031 ; Hempa ; Hexametapol ; Hexamethyl phosphoramide ; Hexamethylfosforamid ; Hexamethylfosforamid [Czech] ; Hexamethylorthophosphoric triamide ; Hexamethylphosphoric acid triamide ; Hexamethylphosphoric triamide ; N,N,N,N,N,N-Hexamethylphosphoric triamide ; NSC 113131 ; NSC 7967 ; Phosphoric acid hexamethyltriamide ; Phosphoric hexamethyltriamide ; Phosphoric triamide, hexamethyl- ; Phosphoric tris(dimethylamide) ; Phosphoryl hexamethyltriamide ; Tris(dimethylamino)phosphine oxide ; Tris(dimethylamino)phosphorus oxide ; Tris-(dimethylamid) kyseliny fosforecne ; Tris-(dimethylamid) kyseliny fosforecne [Czech] . Hexamethylphosphoramide (CAS NO.680-31-9) is clear colorless to light amber liquid with a spicy odor. It is soluble in water. Hexamethylphosphoramide may react with strong oxidizing agents and strong acids. It is susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. Hexamethylphosphoramide is combustible.

Product Name

Hexamethylphosphoramide

Synthetic route

Hexamethylphosphoramide Chemical Properties

Hexamethylphosphoramide Uses

Hexamethylphosphoramide Production

Hexamethylphosphoramide Toxicity Data With Reference

Hexamethylphosphoramide Consensus Reports

Hexamethylphosphoramide Safety Profile

Hexamethylphosphoramide Standards and Recommendations

Hexamethylphosphoramide Specification

Related Products

Hot Products