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T-Butylphosphine, with the chemical formula (CH3)3C–P, is a colorless, flammable gas that serves as a versatile ligand in organometallic chemistry and catalysis. Known for its strong reducing properties, T-butylphosphine is generally stable at room temperature and pressure, but can decompose violently under certain conditions such as heating or exposure to oxidizing agents. T-BUTYLPHOSPHINE plays a significant role in various industrial applications, including the synthesis of pharmaceuticals, production of polymers, fine chemicals, and in the semiconductor industry for electronic and optoelectronic devices.

2501-94-2

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2501-94-2 Usage

Uses

Used in Pharmaceutical Synthesis:
T-Butylphosphine is used as a reagent in the synthesis of pharmaceuticals for its strong reducing capabilities, which facilitate the production of various medicinal compounds.
Used in Polymer Production:
In the polymer industry, T-Butylphosphine is used as a catalyst to enhance the efficiency of polymerization processes, contributing to the creation of high-quality polymers.
Used in Fine Chemicals Production:
T-Butylphosphine is utilized as a ligand in the production of fine chemicals, where its organometallic chemistry properties are leveraged to improve the synthesis of specialty chemicals.
Used in Semiconductor Industry:
T-Butylphosphine is employed in the semiconductor industry as a component in the production of electronic and optoelectronic devices, where its properties are essential for achieving desired material characteristics and performance.

Check Digit Verification of cas no

The CAS Registry Mumber 2501-94-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,0 and 1 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2501-94:
(6*2)+(5*5)+(4*0)+(3*1)+(2*9)+(1*4)=62
62 % 10 = 2
So 2501-94-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H11P/c1-4(2,3)5/h5H2,1-3H3

2501-94-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butylphosphane

1.2 Other means of identification

Product number -
Other names dimethyl phosphino ethane

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:2501-94-2 SDS

2501-94-2Synthetic route

(dimethylamino)dibromoborane
7360-64-7

(dimethylamino)dibromoborane

lithium tert-butylphosphide
67877-34-3, 112215-24-4

lithium tert-butylphosphide

A

1,3-di-tert-butyl-2,4-bis(dimethylamino)-1,2,3,4-diphosphadiboretane
122501-55-7, 112438-33-2

1,3-di-tert-butyl-2,4-bis(dimethylamino)-1,2,3,4-diphosphadiboretane

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
In pentane under N2 or Ar or in vac., cooled to -45°C, addn. of LiPHtBu in pentane, warmed to ambient temp.; filtration of insolubles, from filtrate evapn. of volatiles; elem. anal.;A 95%
B n/a
dichlorodimethylaminoborane
1113-31-1

dichlorodimethylaminoborane

lithium tert-butylphosphide
67877-34-3, 112215-24-4

lithium tert-butylphosphide

A

1,3-di-tert-butyl-2,4-bis(dimethylamino)-1,2,3,4-diphosphadiboretane
122501-55-7, 112438-33-2

1,3-di-tert-butyl-2,4-bis(dimethylamino)-1,2,3,4-diphosphadiboretane

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
In pentane byproducts: LiCl; under N2 or Ar or in vac., cooled to -45°C, addn. of LiPHtBu in pentane, warmed to ambient temp.; filtration of insolubles, from filtrate evapn. of volatiles; elem. anal.;A 95%
B n/a
C4H11AlCl3P

C4H11AlCl3P

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With triethylamine In toluene88%
tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In butyl diglyme at 20 - 100℃;82%
With lithium aluminium tetrahydride at 20℃; for 3h; Schlenk technique; Inert atmosphere;82%
With lithium aluminium tetrahydride In diethylene glycol dimethyl ether at -78℃;80%
With lithium aluminium tetrahydride In dibutyl ether
With lithium aluminium tetrahydride
tert-butyldifluorophosphine
29149-32-4

tert-butyldifluorophosphine

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With ethyl trimethylsilyl ether at 20℃; for 1h;65%
S-ethyl tert-butylthiophosphinite
105414-84-4

S-ethyl tert-butylthiophosphinite

acetyl chloride
75-36-5

acetyl chloride

sodium thioethylate
811-51-8

sodium thioethylate

A

ethyl thioacetate
625-60-5

ethyl thioacetate

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

C

S,S-diethyl tert-butyldithiophosphonite
78187-17-4

S,S-diethyl tert-butyldithiophosphonite

D

tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

Conditions
ConditionsYield
for 20h; Ambient temperature; sealed;A 51%
B 24%
C n/a
D n/a
isobutene
115-11-7

isobutene

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With phosphan; toluene-4-sulfonic acid at 110℃; for 14h;37%
1,4-dipotassium-1,2,3,4-tetra-t-butyl-tetraphosphane
7621-12-7

1,4-dipotassium-1,2,3,4-tetra-t-butyl-tetraphosphane

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With water In 1,4-dioxane
t-Butylfluorphosphan

t-Butylfluorphosphan

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

tert-butyldifluorophosphine
29149-32-4

tert-butyldifluorophosphine

C

C8H19FP2

C8H19FP2

Conditions
ConditionsYield
Ambient temperature;
t-Butyl-t-butylaminophosphan

t-Butyl-t-butylaminophosphan

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

(CH3)3CP[HNC(CH3)3]2
228703-72-8

(CH3)3CP[HNC(CH3)3]2

C

C12H29NP2

C12H29NP2

Conditions
ConditionsYield
Ambient temperature;
tert-butylbis(trimethylsilyl)phosphine
42491-33-8

tert-butylbis(trimethylsilyl)phosphine

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

tert-butyl(trimethylsilyl)phosphine
67033-70-9

tert-butyl(trimethylsilyl)phosphine

Conditions
ConditionsYield
With trans-Crotonaldehyde other reagent: mesityl oxide;
methanesulfonic acid
75-75-2

methanesulfonic acid

n-heptane
142-82-5

n-heptane

isobutene
115-11-7

isobutene

phosphine

phosphine

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

di-tert-butylphosphine

di-tert-butylphosphine

Conditions
ConditionsYield
at 60℃; under 24271.8 - 25742.8 Torr;
at 60℃; under 24271.8 - 25742.8 Torr;
1,2-Di-tert-butyldiphosphane
90600-97-8

1,2-Di-tert-butyldiphosphane

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

tert-Butyldiphosphan
82240-49-1

tert-Butyldiphosphan

C

1,2-Di-tert-butyltriphosphan

1,2-Di-tert-butyltriphosphan

D

PH3, P3H5

PH3, P3H5

Conditions
ConditionsYield
With diphosphane In 1,2-dimethoxyethane at 60℃; for 1h; THF; Title compound not separated from byproducts;
With diphosphane In 1,2-dimethoxyethane at 60℃; for 1h; THF; Yield given. Title compound not separated from byproducts;
tris(tert-butylphosphino)phosphane

tris(tert-butylphosphino)phosphane

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

1,2-Di-tert-butyldiphosphane
90600-97-8

1,2-Di-tert-butyldiphosphane

C

higher tert-butylphosphanes

higher tert-butylphosphanes

Conditions
ConditionsYield
at -30℃; Mechanism; disproportination and decomposition studies;
(Et2P(CH2)2PEt2)Ni(η-Me3SiPPCMe3)
115713-55-8

(Et2P(CH2)2PEt2)Ni(η-Me3SiPPCMe3)

A

bis{1,2-bis(diethylphosphino)ethane}nickel(0)
54910-60-0

bis{1,2-bis(diethylphosphino)ethane}nickel(0)

B

(((C2H5)2PCH2CH2P(C2H5)2)Ni)2P2
96555-93-0

(((C2H5)2PCH2CH2P(C2H5)2)Ni)2P2

C

Methoxytrimethylsilane
1825-61-2

Methoxytrimethylsilane

D

tert-butylphosphine
2501-94-2

tert-butylphosphine

E

1,2-Di-tert-butyldiphosphane
90600-97-8

1,2-Di-tert-butyldiphosphane

Conditions
ConditionsYield
With methanol In toluene excess CH3OH, reaction proceeds slowly at 0°C and rapidly at 20°C; observed by NMR-spectroscopy;
((C6H11)2PCH2CH2P(C6H11)2)Ni(HPPC(CH3)3)
115713-56-9

((C6H11)2PCH2CH2P(C6H11)2)Ni(HPPC(CH3)3)

A

((C6H11)2PCH2CH2P(C6H11)2Ni)2P2
96555-95-2

((C6H11)2PCH2CH2P(C6H11)2Ni)2P2

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
In toluene 5 d at 80°C;
tert-butylphosphine trimethylaluminum complex

tert-butylphosphine trimethylaluminum complex

A

tert-butylphosphine
2501-94-2

tert-butylphosphine

B

trimethylaluminum
75-24-1

trimethylaluminum

Conditions
ConditionsYield
In gas above 298 K;
tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

A

1,2,3,4-Tetra-tert-butyl-tetraphosphetane
79082-91-0, 5995-07-3

1,2,3,4-Tetra-tert-butyl-tetraphosphetane

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

C

1,2-Di-tert-butyldiphosphane
90600-97-8

1,2-Di-tert-butyldiphosphane

Conditions
ConditionsYield
With triethylsilane; gallium(III) trichloride In chlorobenzene at 100℃; for 168h;
tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

A

1,2,3,4-Tetra-tert-butyl-tetraphosphetane
79082-91-0, 5995-07-3

1,2,3,4-Tetra-tert-butyl-tetraphosphetane

B

tert-butylphosphine
2501-94-2

tert-butylphosphine

Conditions
ConditionsYield
With triethylsilane; gallium(III) trichloride In chlorobenzene at 100℃; for 168h;
tert-butylphosphine
2501-94-2

tert-butylphosphine

t-butylphosphine-borane

t-butylphosphine-borane

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran; hexane at 0℃; for 1h;99%
tert-butylphosphine
2501-94-2

tert-butylphosphine

borane tetrahydrofuran

borane tetrahydrofuran

tert-butylphosphine-borane
162053-46-5

tert-butylphosphine-borane

Conditions
ConditionsYield
In tetrahydrofuran; hexane (Ar); transferring of soln. of t-BuPH2 in hexane to flask via syringe, slowly addn. of BH3-THF complex in THF at 0°C , stirring for 1 h at this temp.; removal of solvents under vac., distn. in vac.;99%
tris(3,4,5-trifluorophenyl)borane
148892-97-1

tris(3,4,5-trifluorophenyl)borane

tert-butylphosphine
2501-94-2

tert-butylphosphine

tris(3,4,5-trifluorophenyl)boron-tert-butylphosphine adduct
184044-79-9

tris(3,4,5-trifluorophenyl)boron-tert-butylphosphine adduct

Conditions
ConditionsYield
In light petroleum (inert atmosphere); stirring (48 h); decantation, drying (vac.), further material from the supernatant; no reliable elemental analysis;99%
tert-butylphosphine
2501-94-2

tert-butylphosphine

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

tris(pentafluorophenyl)boron-tert-butylphosphine adduct
184044-76-6

tris(pentafluorophenyl)boron-tert-butylphosphine adduct

Conditions
ConditionsYield
In light petroleum (inert atmosphere); stirring (48 h); decantation, drying (vac.), further material from the supernatant; no reliable elemental analysis;99%
tert-butylphosphine
2501-94-2

tert-butylphosphine

tris(2,6-difluorophenyl)borane triethylphosphine oxide
146355-09-1

tris(2,6-difluorophenyl)borane triethylphosphine oxide

tris(2,6-difluorophenyl)boron-tert-butylphosphine adduct
184044-78-8

tris(2,6-difluorophenyl)boron-tert-butylphosphine adduct

Conditions
ConditionsYield
In light petroleum (inert atmosphere); stirring (48 h); decantation, drying (vac.), further material from the supernatant; no reliable elemental analysis;99%
tert-butylphosphine
2501-94-2

tert-butylphosphine

diborane
19287-45-7

diborane

tert-butylphosphine-borane
162053-46-5

tert-butylphosphine-borane

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃;99%
tricarbonylcyclopentadienylmolybdenum(II) chloride
12128-23-3

tricarbonylcyclopentadienylmolybdenum(II) chloride

tert-butylphosphine
2501-94-2

tert-butylphosphine

cis-dicarbonyl(chloro)(η5-cyclopentadienyl)(tert-butylphosphine)molybdenum(II)

cis-dicarbonyl(chloro)(η5-cyclopentadienyl)(tert-butylphosphine)molybdenum(II)

Conditions
ConditionsYield
In methyl cyclohexane under N2; equimolar mixt. of Mo complex and ligand in methylcyclohexaneheated at 70°C for 1 h; cooled to room temp.; concd. in vac.; crystd. at 0°C; filtered; washed with pentane; dried in vac.; elem. anal.;98%
pentamethylcyclopentadienyl tantalum(V) tetrachloride

pentamethylcyclopentadienyl tantalum(V) tetrachloride

tert-butylphosphine
2501-94-2

tert-butylphosphine

C5(CH3)5TaCl4(PH2C(CH3)3)
406943-02-0

C5(CH3)5TaCl4(PH2C(CH3)3)

Conditions
ConditionsYield
In toluene in dry Ar atmosphere C5(CH3)5TaCl4 suspended in toluene, equimolar amt. of PH2C(CH3)3 added, stirred at room temp. until clear soln. obtained; solvent removed to dryness, residue extd. with-pentane, cooled to 5 °C, crystn.; elem. anal.;96%
tert-butylphosphine
2501-94-2

tert-butylphosphine

pivalaldehyde
630-19-3

pivalaldehyde

C9H21OP
1246895-41-9

C9H21OP

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃;96%
tert-butylphosphine
2501-94-2

tert-butylphosphine

benzaldehyde
100-52-7

benzaldehyde

t-butylbenzylphosphine oxide

t-butylbenzylphosphine oxide

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃;95%
tert-butylphosphine
2501-94-2

tert-butylphosphine

1,5-dihydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide
187879-67-0

1,5-dihydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide

2-tert-butyl-1,3-dihydro-isophosphindole 2-oxide
104229-83-6

2-tert-butyl-1,3-dihydro-isophosphindole 2-oxide

Conditions
ConditionsYield
Multistep reaction;94%
With n-butyllithium; dihydrogen peroxide; sodium sulfate In tetrahydrofuran94%
pentamethylcyclopentadienyl niobium(V) tetrachloride
80432-35-5

pentamethylcyclopentadienyl niobium(V) tetrachloride

tert-butylphosphine
2501-94-2

tert-butylphosphine

C5(CH3)5NbCl4(PH2C(CH3)3)
499219-54-4

C5(CH3)5NbCl4(PH2C(CH3)3)

Conditions
ConditionsYield
In toluene; pentane in dry Ar atmosphere C5(CH3)5NbCl4 suspended in toluene, equimolar amt. of PH2C(CH3)3 added, stirred at room temp. until clear soln. obtained; solvent removed to dryness, residue extd. with-pentane, cooled to 5 °C, crystn.; elem. anal.;94%
tert-butylphosphine
2501-94-2

tert-butylphosphine

di-tert-butyldichloromethylenediphosphine
78463-57-7, 74399-62-5, 74399-57-8

di-tert-butyldichloromethylenediphosphine

tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

1,2,3,4-Tetra-tert-butyl-[1,2,3,4]tetraphospholane

1,2,3,4-Tetra-tert-butyl-[1,2,3,4]tetraphospholane

Conditions
ConditionsYield
In toluene at 60℃; for 12h;93%
mesytaldehyde
487-68-3

mesytaldehyde

tert-butylphosphine
2501-94-2

tert-butylphosphine

C14H23OP
1246895-43-1

C14H23OP

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃;93%
[(η(5)-cyclopentadienyl)Fe(CO)3] tetrafluoroborate

[(η(5)-cyclopentadienyl)Fe(CO)3] tetrafluoroborate

tert-butylphosphine
2501-94-2

tert-butylphosphine

[(tert-butyl)phosphane]dicarbonyl(η(5)-cyclopentadienyl)iron(II) tetrafluoroborate
215736-16-6

[(tert-butyl)phosphane]dicarbonyl(η(5)-cyclopentadienyl)iron(II) tetrafluoroborate

Conditions
ConditionsYield
In acetonitrile byproducts: CO; N2-atmosphere; stirring Fe-complex with slight excess of phosphine (70°C, 20 h); concn. (vac.), pptn. on ether addn., filtration, drying (vac.); elem. anal.;91%
In acetonitrile byproducts: CO; N2 atmosphere, mixing of cooled soln. of Fe complex (0°C) with phosphane, stirring (60°C, 10 h); reduction of volume (vacuum), pptn. (ether), filtration, washing (ether), drying (vacuum); elem. anal.;85%
methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside
3150-16-1

methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside

tert-butylphosphine
2501-94-2

tert-butylphosphine

(methyl 3-deoxy-4,6-oxo-benzylidene-α-D-pyranopyranoside)-3-tert-butylphosphine

(methyl 3-deoxy-4,6-oxo-benzylidene-α-D-pyranopyranoside)-3-tert-butylphosphine

Conditions
ConditionsYield
Stage #1: tert-butylphosphine In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Schlenk technique; Inert atmosphere;
Stage #2: methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside In tetrahydrofuran for 6h; Schlenk technique;
90%
bis(diethylamino)chlorophosphine
685-83-6

bis(diethylamino)chlorophosphine

tert-butylphosphine
2501-94-2

tert-butylphosphine

1,1,3,3-Tetrakis(diethylamino)-2-tert-butyl-triphosphan

1,1,3,3-Tetrakis(diethylamino)-2-tert-butyl-triphosphan

Conditions
ConditionsYield
With n-butyllithium 1.) Et2O, n-hexane, reflux, 0.5 h, 2.) n-pentane, -78 deg C, 1 h;89%
(η5-cyclopentadienyl)Re(NO)(P(C6H5)3)(CF3SO3)
92695-35-7

(η5-cyclopentadienyl)Re(NO)(P(C6H5)3)(CF3SO3)

tert-butylphosphine
2501-94-2

tert-butylphosphine

Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)(1+)*OSO2CF3(1-)={Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)}OSO2CF3

Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)(1+)*OSO2CF3(1-)={Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)}OSO2CF3

Conditions
ConditionsYield
In benzene addn. of P(t-Bu)H2 to complex in a Schlenk tube with stirring, react. time 3 h; addn. of hexane, ppt. filtered, washed with hexane, dissolved in THF, slowly addn. of ether, ppt. filtered, dried under oil pump vac.; elem. anal.;89%
Re(C5H5)(P(C6H5)3)(OSO2CF3)(NO)

Re(C5H5)(P(C6H5)3)(OSO2CF3)(NO)

tert-butylphosphine
2501-94-2

tert-butylphosphine

Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)(1+)*OSO2CF3(1-)={Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)}OSO2CF3

Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)(1+)*OSO2CF3(1-)={Re(C5H5)(P(C6H5)3)(PH2C(CH3)3)(NO)}OSO2CF3

Conditions
ConditionsYield
In benzene addn. of P(t-Bu)H2 to complex in a Schlenk tube with stirring, react. time 3 h; addn. of hexane, ppt. filtered, washed with hexane, dissolved in THF, slow addn. of ether by vapor diffusion, ppt. filtered, dried under oil pump vac., pure by 1H- and 31P-NMR;88%
tert-butylphosphine
2501-94-2

tert-butylphosphine

bis(diphenylphosphino)methane
28240-64-4

bis(diphenylphosphino)methane

tert-butyldichlorophosphine
25979-07-1

tert-butyldichlorophosphine

2,3-Di-tert-butyl-1,4-diphenyl-[1,2,3,4]tetraphospholane

2,3-Di-tert-butyl-1,4-diphenyl-[1,2,3,4]tetraphospholane

Conditions
ConditionsYield
In toluene at 60 - 80℃; for 12h;86%
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

tert-butylphosphine
2501-94-2

tert-butylphosphine

tert-butylbis(trimethylsilyl)phosphine
42491-33-8

tert-butylbis(trimethylsilyl)phosphine

Conditions
ConditionsYield
Stage #1: tert-butylphosphine With n-butyllithium In diethyl ether at -78 - 20℃; for 2.25h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: chloro-trimethyl-silane In diethyl ether at -78 - 20℃;
86%
2-chloroacetylenephosphonic acid dimethyl ester
19519-59-6

2-chloroacetylenephosphonic acid dimethyl ester

tert-butylphosphine
2501-94-2

tert-butylphosphine

dimethyl <(tert-butylphosphino)ethynyl>phosphonate

dimethyl <(tert-butylphosphino)ethynyl>phosphonate

Conditions
ConditionsYield
85%
diiron nonacarbonyl
15321-51-4

diiron nonacarbonyl

tert-butylphosphine
2501-94-2

tert-butylphosphine

Fe(CO)4{PH2(C(CH3)3)}
85737-35-5

Fe(CO)4{PH2(C(CH3)3)}

Conditions
ConditionsYield
In diethyl ether byproducts: Fe(CO)5; strirring at room temp. for 24 h in dark; filtration, removing Fe(CO)5, distn.; elem. anal.;84%
tert-butylphosphine
2501-94-2

tert-butylphosphine

(5aS,9aS)-octahydrobenzo[e][1,3,2]dioxathiepine 3,3-dioxide
1252080-10-6

(5aS,9aS)-octahydrobenzo[e][1,3,2]dioxathiepine 3,3-dioxide

(3aS,7aS)-2-(tert-butyl)octahydro-1H-isophosphindole 2-sulfide
1252080-12-8

(3aS,7aS)-2-(tert-butyl)octahydro-1H-isophosphindole 2-sulfide

Conditions
ConditionsYield
Stage #1: tert-butylphosphine With n-butyllithium In tetrahydrofuran; octane; hexane at -78 - 20℃; for 1h; Inert atmosphere;
Stage #2: (5aS,9aS)-octahydrobenzo[e][1,3,2]dioxathiepine 3,3-dioxide In tetrahydrofuran; octane; hexane at -78 - 20℃; for 4h; Inert atmosphere; Further stages;
81%
Stage #1: tert-butylphosphine With n-butyllithium In tetrahydrofuran; octane; hexane at -78 - 20℃;
Stage #2: (5aS,9aS)-octahydrobenzo[e][1,3,2]dioxathiepine 3,3-dioxide With n-butyllithium In tetrahydrofuran; octane; hexane at -78 - 20℃;
Stage #3: With sulfur In tetrahydrofuran; octane; hexane; water at 20℃; for 2h; optical yield given as %ee;
81%
tert-butylphosphine
2501-94-2

tert-butylphosphine

di-tert-butylantimony chloride
4718-00-7

di-tert-butylantimony chloride

C12H28PSb

C12H28PSb

Conditions
ConditionsYield
Stage #1: tert-butylphosphine With n-butyllithium In hexane; pentane at 0℃; Schlenk technique; Inert atmosphere;
Stage #2: di-tert-butylantimony chloride In hexane; pentane at -20 - 20℃; Schlenk technique; Inert atmosphere;
81%
tert-butylphosphine
2501-94-2

tert-butylphosphine

dimesitylfluoroborane
436-59-9

dimesitylfluoroborane

(Mes)2BP(H)(C(CH3)3)
118496-13-2

(Mes)2BP(H)(C(CH3)3)

Conditions
ConditionsYield
In diethyl ether 0°C, stirring for 1 h at room temp.;80%

2501-94-2Relevant academic research and scientific papers

Synthesis and characterization of bridged dimeric and trimeric Group 13/15 complexes containing primary phosphidotBu)PH>- and arsenido tBu)AsH>- units

Atwood, David A.,Cowley, Alan H.,Harris, Paul R.,Jones, Richard A.,Koschmieder, Stefan U.,Nunn, Christine M.

, p. 61 - 67 (1993)

Addition of the primary phosphine tBuPH2 or the primary arsine tBuAsH2 to tBu3M (M = Ga, Al) followed by heating or photolysis affords the complexes tBu2M(μ-E(tBu)H)>n (1; M = Ga, E = P; n = 2; 2, M = Al, E = P, n = 2; 3, M = Ga, E = As, n = 3; 4, M = Al, E = As, n = 3).For each compound, the degree of association was assessed on the basis of 1H, 31P, 13C NMR and mass spectroscopy.The anti-isomer of 1 (1a) was also characterized by X-ray crystallography.Crystal data for 1a; C24H56Ga2P2, monoclinic, space group C2/m, a 17.124(7), b 11.755(7), c 8.700(3) Angstroem, V 1561.94(15) Angstroem3, Z = 4, Dcalc 1.157 g cm-3, μ(MoKα) 18.3 cm-1.A total of 1501 unique reflections was measured over the range 3.0 2θ 50.0 deg (θ-2θ scan mode) and 1263 of these with I above 3?(I) were used in the refinement to afford final R and Rw values of 0.059 and 0.070, respectively.

LITHIUM ALKYL ALUMINATES AS ALKYL TRANSFER REAGENTS

-

Paragraph 0187-0190, (2022/02/27)

The invention relates to lithium alkyl aluminates according to the general formula Li[AlR4] and to a method for preparing same, starting from LiAlH4 and RLi in an aprotic solvent. The invention also relates to compounds according to the general formula Li[AlR4] which can be obtained using the claimed method, and to the use thereof. The invention also relates to the use of a lithium alkyl aluminate Li[AlR4] as a transfer reagent for transferring at least one radical R to an element halide or metal halide and to a method for transferring at least one radical R to a compound E(X)q for preparing a compound according to the general formula E(X)q-pRp, where E=aluminium, gallium, indium, thallium, germanium, tin, lead, antimony, bismuth, zinc, cadmium, mercury, or phosphorus, X=halogen, q=2, 3 or 4, and p=1, 2, 3 or 4. The invention also relates to compounds which can be obtained using such a method, to the use thereof, and to a substrate which has an aluminium layer or a layer containing aluminium on one surface.

A Simple Strategy for the Preparation of P-Chirogenic Trost Ligands with Different Absolute Configurations

Du, Peng,Lu, Xiao-Bing

supporting information, (2020/08/05)

P-chirogenic compounds are useful ligands and organocatalysts in asymmetric synthesis. However, the lack of preparative methods and their configurational instability have significantly hampered their development. Herein, we report a simple strategy for the preparation of enantiomerically pure P,C-chirogenic diphosphines. Amidation of the borane adducts of rac-phosphinobenzoic acids with enantiomerically pure trans-1,2-diaminocyclohexane afforded a 1:2:1 mixture of the diastereomers (C*,C*,Rp,Rp), (C*,C*,Rp,Sp), and (C*,C*,Sp,Sp), which were separated by column chromatography on silica gel. The prepared (C*,C*,Rp,Rp) and (C*,C*,Sp,Sp) stereoisomers were identical to those obtained from the enantiopure phosphines, which were synthesized by a multi-step route using chiral auxiliaries. Hence, this simple, short and convenient route towards P,C-chirogenic diphosphines obviates the use of chiral auxiliaries and enables the access to diphosphines with differently configured P-stereocenters.

NOVEL VINYL PHOSPHINES AND PHOTO-INITIATORS OBTAINABLE THEREFROM

-

Page/Page column 47, (2019/10/04)

The present invention relates to a highly efficient process to prepare alkyl and vinyl phosphines which are useful as starting materials for novel bisacylphosphine oxides, bisacylphosphinic acids, salts, and derivatives thereof each bearing a vinyl functionality bound to the phosphorous atom as well as a versatile process for the preparation of the latter.

Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes

Pearce, Kyle G.,Borys, Andryj M.,Clark, Ewan R.,Shepherd, Helena J.

supporting information, p. 11530 - 11536 (2018/09/21)

Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P-P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)-Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into the competing mechanisms involved.

Rhodium(I)-Catalyzed Intermolecular Hydroacylation of α-Keto Amides and Isatins with Non-Chelating Aldehydes

Kou, Kevin G. M.,Longobardi, Lauren E.,Dong, Vy M.

supporting information, p. 2233 - 2237 (2015/07/27)

The application of the bidentate, electron-rich bisphosphine ligand, 1,3-bis(dicyclohexyl)phosphine-propane (dcpp), in rhodium(I)-catalyzed intermolecular ketone hydroacylation is herein described. Isatins and α-keto amides are shown to undergo hydroacylation with a variety of non-chelating linear and branched aliphatic aldehydes. Also reported is the synthesis of new bidentate chiral phosphine ligands, and their application in hydroacylation is discussed.

Alkyl group VA metal compounds

-

Page 6, (2008/06/13)

A method of preparing Group VA organometal compounds in high yield and high purity by the reaction of a Grignard reagent with a Group VA metal halide in certain ethereal solvents is provided. A method of preparing Group VA organometal hydrides is also provided.

Practical P-chiral phosphane ligand for Rh-catalyzed asymmetric hydrogenation

Liu, Duan,Zhang, Xumu

, p. 646 - 649 (2007/10/03)

A highly electron-donating and conformationally rigid P-chiral bis(trialkylphospholane) ligand 2 (DuanPhos) has been prepared in both enantiomeric forms through a concise synthesis. Rh-2 complex has exhibited remarkably high enantio-selectivities (up to >99% ee) and reactivities (up to 10,000 TON) for the hydrogenation of a wide variety of functionalized prochiral alkenes (5 different types), which provides a very practical catalytic system for the preparation of various synthetically useful chiral compounds. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Highly pure monoalkylphosphine and method for producing same

-

, (2008/06/13)

A highly pure monoalkylphosphine which is useful as a starting material for producing a compound semiconductor, and a method for producing same in high yield are provided. A highly pure monoalkylphosphine represented by the general formula RPH2 (wherein R is an alkyl group having 1 to 8 carbon atoms) has a purity of not less than five nines, and is substantially free of sulfur and silica. In the method of producing said highly pure monoalkylphosphine, anhydrous hydrofluoric acid is used as a catalyst for a reaction between phosphine and an alkene, and the reaction is carried out in the presence of an organic solvent having a boiling point higher than that of the resulting monoalkylphosphine; the resulting reaction mixture is contacted with an alkali solution so that the remaining catalyst is removed into an aqueous phase in the form of a fluoride salt; next, the obtained reaction mixture is contacted with an alkali hydride and the impurities are removed, then distillation is carried out.

Thermal Stability of the tert-Butylphosphine-Trimethylaluminum Complex

Mitrofanov,Yablokov

, p. 1864 - 1866 (2007/10/03)

The tert-butylphosphine-trimethylaluminum complex was prepared. It is a viscous liquid with a low vapor pressure. The equilibrium thermal dissociation of the complex in the 350-385 K range was studied. The enthalpy of dissociation is 63.7±1.5 kJ mol-1. Irrveresible thermal decomposition of the complex starts at 470 K. The decomposition curves have a complex shape. A possible decomposition mechanism is proposed.

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