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1100-88-5

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1100-88-5 Usage

Chemical Properties

Benzyltriphenylphosphonium Chloride is a white to off white powder, It is highly soluble in water and polarizable solvents. It is a quaternary phosphonium salt mainly used in organic synthesis as a wittig reagent and as a phase transfer catalyst in the production of fluoroelastomers and printing inks.

Uses

Benzyltriphenylphosphonium Chloride was used as a reagent in the organic synthesis of several compounds including that of stabilised phosphonium ylides containing saturated oxygen heterocycles. Also used in the synthesis of novel substituted cis-stilbene derivatives which display antimicrobial activity.

Application

Benzyltriphenylphosphonium chloride can be used as a reactant for the synthesis of:Platinum chloro-tetrazole complexes via azidation.Trans-stilbenes and cinnamates via Wittig olefination.Achiral N-hydroxyformamide inhibitors of ADAM-TS4 and ADAM-TS5 for osteoarthritis treatment.Pentiptycenes for use as light-driven molecular brakes.Archipelago structures for formation of petroleum asphaltenes.It is also used as a crosslinking agent for tube-like natural halloysite / fluorelastomer nanocomposites.Crosslinking agent for tube-like natural halloysite / fluorelastomer nanocompositesReactant for synthesis of:Platinum chloro tetrazole complexes via azidationTrans-stilbenes and cinnamates via Wittig olefinationAchiral N-hydroxyformamide inhibitors of ADAM-TS4 and ADAM-TS5 for osteoarthritis treatmentPentiptycenes for use as light-driven molecular brakesReactant for formation of archipelago structures for formation of petroleum asphaltenes

Flammability and Explosibility

Notclassified

Purification Methods

Wash it with Et2O and crystallise it from EtOH (six-sided plates). It is hygroscopic and forms crystals with one molecule of H2O. [Michaelis & Soden Justus Liebigs Ann Chem 229 320 1885, Kr.hnke Chem Ber 83 291 1950, Beilstein 16 IV 994.]

Check Digit Verification of cas no

The CAS Registry Mumber 1100-88-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,0 and 0 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1100-88:
(6*1)+(5*1)+(4*0)+(3*0)+(2*8)+(1*8)=35
35 % 10 = 5
So 1100-88-5 is a valid CAS Registry Number.
InChI:InChI=1/C25H22P.ClH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1

1100-88-5 Well-known Company Product Price

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  • TCI America

  • (B0824)  Benzyltriphenylphosphonium Chloride  >98.0%(HPLC)(T)

  • 1100-88-5

  • 25g

  • 250.00CNY

  • Detail
  • TCI America

  • (B0824)  Benzyltriphenylphosphonium Chloride  >98.0%(HPLC)(T)

  • 1100-88-5

  • 500g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (A14034)  Benzyltriphenylphosphonium chloride, 99%   

  • 1100-88-5

  • 25g

  • 264.0CNY

  • Detail
  • Alfa Aesar

  • (A14034)  Benzyltriphenylphosphonium chloride, 99%   

  • 1100-88-5

  • 100g

  • 799.0CNY

  • Detail
  • Alfa Aesar

  • (A14034)  Benzyltriphenylphosphonium chloride, 99%   

  • 1100-88-5

  • 500g

  • 3595.0CNY

  • Detail
  • Alfa Aesar

  • (36639)  Benzyltriphenylphosphonium chloride, 97%   

  • 1100-88-5

  • 250g

  • 688.0CNY

  • Detail
  • Aldrich

  • (B32807)  Benzyltriphenylphosphoniumchloride  99%

  • 1100-88-5

  • B32807-25G

  • 266.76CNY

  • Detail
  • Aldrich

  • (B32807)  Benzyltriphenylphosphoniumchloride  99%

  • 1100-88-5

  • B32807-100G

  • 801.45CNY

  • Detail

1100-88-5SDS

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 Benzyltriphenylphosphonium chloride

1.2 Other means of identification

Product number -
Other names benzyltriphenilphosphonium chloride

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:1100-88-5 SDS

1100-88-5Synthetic route

benzyl chloride
100-44-7

benzyl chloride

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;100%
In toluene Inert atmosphere; Reflux;98%
In toluene for 18h; Inert atmosphere; Reflux;98%
benzyltrimethylammonium chloride
56-93-9

benzyltrimethylammonium chloride

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
at 250℃; for 0.166667h; Irradiation;95%
chloromethyltriphenylphosphonium chloride
5293-84-5

chloromethyltriphenylphosphonium chloride

Benzyltriphenylphosphonium dimethyldithiocarbamate
110637-73-5

Benzyltriphenylphosphonium dimethyldithiocarbamate

A

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

B

Dimethylthiocarbamoylsulfanylmethyl-triphenyl-phosphonium; chloride
110637-64-4

Dimethylthiocarbamoylsulfanylmethyl-triphenyl-phosphonium; chloride

Conditions
ConditionsYield
In 1,2-dimethoxyethane for 2.5h; Ambient temperature;A 80%
B 50%
benzyl chloroformate
501-53-1

benzyl chloroformate

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

methyl chloroformate
79-22-1

methyl chloroformate

triphenyl(phenylmethylene)phosphorane
16721-45-2

triphenyl(phenylmethylene)phosphorane

A

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

B

<α-(methoxycarbonyl)benzylidene>triphenylphosphorane
1106-06-5

<α-(methoxycarbonyl)benzylidene>triphenylphosphorane

Conditions
ConditionsYield
In benzene Ambient temperature;
triphenylphosphine
603-35-0

triphenylphosphine

benzyl alcohol
100-51-6

benzyl alcohol

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
With hydrogenchloride for 12h; Heating; Yield given;
phenyldiazomethane
908094-04-2

phenyldiazomethane

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
With copper(l) chloride
[α-(phenylphosphanyl)benzylidene]triphenylphosphorane
205433-91-6

[α-(phenylphosphanyl)benzylidene]triphenylphosphorane

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; diethyl ether at 0℃; for 0.5h;
[α-(phenylphosphanyl)benzylidene]triphenylphosphorane
205433-91-6

[α-(phenylphosphanyl)benzylidene]triphenylphosphorane

A

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

B

phenylphosphane
638-21-1

phenylphosphane

C

tetraphenyl-cyclotetraphosphane
1104-52-5, 75494-90-5

tetraphenyl-cyclotetraphosphane

D

Triphenyl-(phenyl-phenylphosphanyl-methyl)-phosphonium; chloride

Triphenyl-(phenyl-phenylphosphanyl-methyl)-phosphonium; chloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; dichloromethane at 0℃; for 0.0833333h; Further byproducts given;
C31H25ClP2

C31H25ClP2

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 89 percent / LiAlH4 / tetrahydrofuran / -40 °C
2: 1 M HCl / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C
View Scheme
benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: n-butyl-lithium / hexane; benzene
2: benzene / Ambient temperature
View Scheme
benzyl bromide
100-39-0

benzyl bromide

alcoholic potash

alcoholic potash

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene / Ambient temperature
2: n-butyl-lithium / hexane; benzene
3: benzene / Ambient temperature
View Scheme
triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: benzene / Ambient temperature
2: n-butyl-lithium / hexane; benzene
3: benzene / Ambient temperature
View Scheme
{C18H15PC6H5CH2}{NiBr2Cl(Triphenylphosphin)}

{C18H15PC6H5CH2}{NiBr2Cl(Triphenylphosphin)}

A

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

B

triphenylphosphine
603-35-0

triphenylphosphine

C

nickel dibromide

nickel dibromide

Conditions
ConditionsYield
thermal decompn.;
dichlorotriphenyl-λ4-phosphane
19171-57-4

dichlorotriphenyl-λ4-phosphane

benzylmagnesium chloride
6921-34-2

benzylmagnesium chloride

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Stage #1: chloro(triphenyl)phosphonium chloride; benzylmagnesium chloride In tetrahydrofuran; dichloromethane at -41℃; for 0.75h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; water for 0.166667h; Solvent; Temperature;
Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: oxalyl dichloride / 1 h / 20 °C / Inert atmosphere
2.1: dichloromethane; tetrahydrofuran / 0.75 h / -41 °C / Inert atmosphere
2.2: 0.17 h
View Scheme
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

phenylmethanethiol
100-53-8

phenylmethanethiol

3-benzylthio-2-methylpropanoic acid
106664-91-9

3-benzylthio-2-methylpropanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium bicarbonate100%
K-t-amylate

K-t-amylate

[3AR-(3aα,6α,7aβ)]-Hexahydro-3a,6-epoxyisobenzofuran-1-ol

[3AR-(3aα,6α,7aβ)]-Hexahydro-3a,6-epoxyisobenzofuran-1-ol

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

[1R-[1α,2α(E),4α]]-2-(2-Phenylethenyl)-7-oxabicyclo[2.2.1]heptane-1-methanol

[1R-[1α,2α(E),4α]]-2-(2-Phenylethenyl)-7-oxabicyclo[2.2.1]heptane-1-methanol

Conditions
ConditionsYield
In tetrahydrofuran; hexane98.7%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

iron(III) chloride
7705-08-0

iron(III) chloride

((C6H5)3PCH2C6H5)(1+)*FeCl4(1-)=((C6H5)3PCH2C6H5)FeCl4
36021-10-0

((C6H5)3PCH2C6H5)(1+)*FeCl4(1-)=((C6H5)3PCH2C6H5)FeCl4

Conditions
ConditionsYield
In water to aq. soln. of phosphonium salt was added aq. soln. of FeCl3 with stirring at room temp., crystalline solid formed; filtn., drying, recrystn. from n-butanol; elem. anal.;98.3%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

benzyltriphenylphosphonium periodate

benzyltriphenylphosphonium periodate

Conditions
ConditionsYield
With sodium periodate at 20℃; for 0.333333h;98%
C48H42O6
863647-14-7

C48H42O6

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

C90H78

C90H78

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium chloride With n-butyllithium In hexane; water at -78 - 0℃;
Stage #2: C48H42O6 In tetrahydrofuran; hexane at 25℃; for 3h;
98%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; Reagent/catalyst;98%
Multi-step reaction with 2 steps
1: 1.) BuLi / 1) THF, hexane, room temperature, 30 min; 2) THF, hexane, room temperature, 3 h
2: 1 h / 850 °C / 0 - 0.01 Torr
View Scheme
Multi-step reaction with 2 steps
1: 1.) BuLi / 1) THF, hexane, room temperature, 30 min; 2) THF, hexane, room temperature, 3 h
2: 1 h / 850 °C / 0 - 0.01 Torr
View Scheme
Multi-step reaction with 3 steps
1: NaH, Dimethylsulfoxide
2: 60 percent / dimethylsulfoxide / 0.5 h / Ambient temperature
3: 0.03 h / 180 °C
View Scheme
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

benzyltriphenylphosphonium nitrate

benzyltriphenylphosphonium nitrate

Conditions
ConditionsYield
With sodium nitrate In water at 20℃;98%
sodium 4-styrenesulfonate
2695-37-6

sodium 4-styrenesulfonate

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

C8H7O3S(1-)*C25H22P(1+)

C8H7O3S(1-)*C25H22P(1+)

Conditions
ConditionsYield
In dichloromethane; water98%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

triphenyl(phenylmethylene)phosphorane
16721-45-2

triphenyl(phenylmethylene)phosphorane

Conditions
ConditionsYield
With n-butyllithium In hexane97%
With sodium ethanolate
With n-butyllithium In diethyl ether for 0.5h;
tungsten(VI) oxychloride

tungsten(VI) oxychloride

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

tert-butylamine
75-64-9

tert-butylamine

2{P(CH2C6H5)(C6H5)3}(1+)*{W4O4Cl10(NC(CH3)3)4}(2-)={P(CH2C6H5)(C6H5)3}2{W4O4Cl10(NC(CH3)3)4}

2{P(CH2C6H5)(C6H5)3}(1+)*{W4O4Cl10(NC(CH3)3)4}(2-)={P(CH2C6H5)(C6H5)3}2{W4O4Cl10(NC(CH3)3)4}

Conditions
ConditionsYield
In toluene addn. of butylamine to WOCl4 and phosphonium salt soln. under N2; refluxing, 6h; evapn.; extn. (CH2Cl2); filtration; diffusion of hexane into soln.; crystn.; elem. anal.;97%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

benzyltriphenylphosphonium peroxodisulfate

benzyltriphenylphosphonium peroxodisulfate

Conditions
ConditionsYield
With sodium persulfate In water at 20℃; for 0.333333h;96%
cis-bis(dimethylsulfoxide)dichloroplatinum(II)
15274-33-6

cis-bis(dimethylsulfoxide)dichloroplatinum(II)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

triphenylbenzylphosphonium-Pt(dimethyl sulfoxide)Cl3
120272-57-3

triphenylbenzylphosphonium-Pt(dimethyl sulfoxide)Cl3

Conditions
ConditionsYield
In acetonitrile addn. of org. ligand to suspn. of Pt-complex (20°C); solvent removal (vac., room temp.); oily residue crystn. under a layer of ethanol, ppt. filtered out, washed with ethanol and ether and air-dried (75°C); elem. anal.;96%
trichlorotris(tetrahydrofuran)chromium(III)
10170-68-0, 16997-54-9

trichlorotris(tetrahydrofuran)chromium(III)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

1,2-bis-(2-propylphosphino)benzene
96284-01-4

1,2-bis-(2-propylphosphino)benzene

benzyltriphenylphosphonium tetrachloro{o-phenylenebis(isopropylphosphine)}chromate(III)
142903-49-9

benzyltriphenylphosphonium tetrachloro{o-phenylenebis(isopropylphosphine)}chromate(III)

Conditions
ConditionsYield
In toluene addn. of C6H4(Pi-PrH)2 to a soln. of CrCl3(thf)3 and (PPh3(CH2Ph))Cl in toluene (1:1:1 molar ratio) under stirring (under O2-free N2 or Ar), refluxing (12 h), pptn.; washing (toluene, 2 times); elem. anal.;96%
Li(1+)*C6F5(1-)=Li(C6F5)
1076-44-4

Li(1+)*C6F5(1-)=Li(C6F5)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

thallium (III) chloride
13453-32-2

thallium (III) chloride

(C6H5)3PCH2C6H5(1+)*[Tl(C6F5)4](1-)=((C6H5)3PCH2C6H5)[Tl(C6F5)4]
75579-15-6

(C6H5)3PCH2C6H5(1+)*[Tl(C6F5)4](1-)=((C6H5)3PCH2C6H5)[Tl(C6F5)4]

Conditions
ConditionsYield
In diethyl ether TlCl3 added to LiC6F5 soln. at -78°C, stirred for 15 min, allowed to warm to room temp., stirred for 3 h under N2, a few drops of H2O added, Ph3BzPCl added; exposed to air for 10 min, filtered, evapd., recrystd. (CH2Cl2/hexane);elem. anal.;96%
TiCl(N(CH3)2)2(N(CH3)2H)2(1+)*TiNB(C6F5)3Cl2(N(CH3)2H)2(1-)*0.5CH2Cl2=TiCl(NC2H6)2(NC2H7)4TiNB(C6F5)3Cl2*0.5CH2Cl2

TiCl(N(CH3)2)2(N(CH3)2H)2(1+)*TiNB(C6F5)3Cl2(N(CH3)2H)2(1-)*0.5CH2Cl2=TiCl(NC2H6)2(NC2H7)4TiNB(C6F5)3Cl2*0.5CH2Cl2

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

C6H5CH2P(C6H5)3(1+)*TiNB(C6F5)3Cl2(N(CH3)2H)2(1-)=P(C6H5)3(CH2C6H5)(NC2H7)2TiNB(C6F5)3Cl2

C6H5CH2P(C6H5)3(1+)*TiNB(C6F5)3Cl2(N(CH3)2H)2(1-)=P(C6H5)3(CH2C6H5)(NC2H7)2TiNB(C6F5)3Cl2

Conditions
ConditionsYield
In dichloromethane (N2, Schlenk) to a soln. of complex in CH2Cl2 was added solid C6H5CH2P(C6H5)3Cl, stirred at room temp.; volatiles were removed under reduced pressure, the foam was washed with toluene; elem. anal.;96%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(+/-)-1,1-dimethylethyl 4-oxo-2-(phenylmethyl)-1-piperidinecarboxylate
193480-28-3

(+/-)-1,1-dimethylethyl 4-oxo-2-(phenylmethyl)-1-piperidinecarboxylate

2-Benzyl-4-[1-phenyl-meth-(E)-ylidene]-piperidine-1-carboxylic acid tert-butyl ester
313950-43-5

2-Benzyl-4-[1-phenyl-meth-(E)-ylidene]-piperidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium chloride With potassium tert-butylate In tetrahydrofuran deprotonation;
Stage #2: (+/-)-1,1-dimethylethyl 4-oxo-2-(phenylmethyl)-1-piperidinecarboxylate In tetrahydrofuran at 23℃; Wittig reaction; Further stages.;
95%
5-formyl-10-methoxybenzo[c]phenanthrene
858943-02-9

5-formyl-10-methoxybenzo[c]phenanthrene

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

5-(β-phenylethenyl)-10-methoxybenzo[c]phenanthrene
858943-08-5

5-(β-phenylethenyl)-10-methoxybenzo[c]phenanthrene

Conditions
ConditionsYield
With sodium hydroxide In water for 0.25h; Wittig reaction;95%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(2R,3S,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol

(2R,3S,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol

Conditions
ConditionsYield
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran at 45℃; Wittig olefination;95%
Au(I)(C6Cl5)(tetrahydrothiophene)

Au(I)(C6Cl5)(tetrahydrothiophene)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(C6H5CH2P(C6H5)3)(1+)*(AuC6Cl5Cl)(1-)=(C6H5CH2P(C6H5)3)(Au(C6Cl5)Cl)

(C6H5CH2P(C6H5)3)(1+)*(AuC6Cl5Cl)(1-)=(C6H5CH2P(C6H5)3)(Au(C6Cl5)Cl)

Conditions
ConditionsYield
In dichloromethane byproducts: tetrahydrothiophene; N2 atmosphere, stirring (15 min, room temp.); concn. (evapn.), pptn. on n-hexane addn.; elem. anal.;95%
(Et4N){Pt(3,5-dimethylpyrazole)Cl5}*H2O

(Et4N){Pt(3,5-dimethylpyrazole)Cl5}*H2O

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(benzyltriphenylphosphonium){Pt(3,5-dimethylpyrazole)Cl3}
135143-71-4

(benzyltriphenylphosphonium){Pt(3,5-dimethylpyrazole)Cl3}

Conditions
ConditionsYield
With (N2H5)2SO4 In water water added to mixt. of hydrazine sulfate and Pt-complex, heated at 60-70°C for 5min, cooled, filtered, BzlPPh3Cl soln. added to filtrate, stirred for 10min; product filtered off, washed with hot water (3 times, alcohol, ether (3 times), dried in air at 90°C; elem. anal.;95%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

benzyltriphenylphosphonium chlorochromate

benzyltriphenylphosphonium chlorochromate

Conditions
ConditionsYield
With chromium(VI) oxide; hydrogenchloride In water at 20℃; for 15h;94%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(4R,5R)-4-[tert-Butoxycarbonyl-((S)-2-methyl-3-oxo-propyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester
392725-03-0

(4R,5R)-4-[tert-Butoxycarbonyl-((S)-2-methyl-3-oxo-propyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

A

(4R,5R)-4-[tert-Butoxycarbonyl-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

(4R,5R)-4-[tert-Butoxycarbonyl-((E)-(R)-2-methyl-4-phenyl-but-3-enyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

B

(4R,5R)-4-[tert-Butoxycarbonyl-((E)-(S)-2-methyl-4-phenyl-but-3-enyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

(4R,5R)-4-[tert-Butoxycarbonyl-((E)-(S)-2-methyl-4-phenyl-but-3-enyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium chloride With n-butyllithium In hexane; benzene at 20℃; for 1h; Wittig reaction;
Stage #2: (4R,5R)-4-[tert-Butoxycarbonyl-((S)-2-methyl-3-oxo-propyl)-amino]-5-isobutoxy-azepane-1-carboxylic acid 2-trimethylsilanyl-ethyl ester In hexane; benzene at 20℃; for 5h;
A 94%
B n/a
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

2,3,4-tri-O-benzyl-D-lyxopyranose

2,3,4-tri-O-benzyl-D-lyxopyranose

(2R,3R,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol

(2R,3R,4R)-2,3,4-tri-benzyloxy-6-phenylhex-5-en-1-ol

Conditions
ConditionsYield
With sodium hydride; dimethyl sulfoxide In tetrahydrofuran at 45℃; Wittig olefination;94%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

benzyltriphenylphosphonium trichloro(dimethylsulfoxide)platinate(II)
120272-57-3

benzyltriphenylphosphonium trichloro(dimethylsulfoxide)platinate(II)

Conditions
ConditionsYield
In dimethyl sulfoxide byproducts: KCl; mixing Pt complex, P compd., DMSO, stirring at room temp. for 5 min; slow evapn., isolation of crystals, elem. anal.;94%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

9,10-phenanthrenequinone
84-11-7

9,10-phenanthrenequinone

2,3-dihydro-2,3-diphenylphenanthro[9,10-b]furan

2,3-dihydro-2,3-diphenylphenanthro[9,10-b]furan

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium chloride With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.0333333h;
Stage #2: 9,10-phenanthrenequinone In dimethyl sulfoxide at 20℃; for 0.5h;
94%
benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

zinc(II) chloride
7646-85-7

zinc(II) chloride

2((C2H5)3PCH2C6H5)(1+)*Zn2Cl6(2-)=((C2H5)3PCH2C6H5)2Zn2Cl6

2((C2H5)3PCH2C6H5)(1+)*Zn2Cl6(2-)=((C2H5)3PCH2C6H5)2Zn2Cl6

Conditions
ConditionsYield
In further solvent(s) to 150°C hot soln. of phosphonium salt in n-octanol added soln. of anhydrous ZnCl2 in n-octanol, temp. increased to 185-187°C, ppt. formed after 30 min; ppt. filtered at 150°C; recrystn. from n-octanol or acetonitrile; elem. anal.;93.7%
1,1,1-trifluoroacetophenone
434-45-7

1,1,1-trifluoroacetophenone

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

1,2-diphenyl-3,3,3-trifluoroprop-1-ene
77542-08-6

1,2-diphenyl-3,3,3-trifluoroprop-1-ene

Conditions
ConditionsYield
With sodium ethanolate In ethanol93.5%
(η4-5-phenyl-2,4-pentadienal)(η5-cyclopentadienyl)rhodium(I)

(η4-5-phenyl-2,4-pentadienal)(η5-cyclopentadienyl)rhodium(I)

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

(C6H5CHCHCHCHCHCHC6H5)Rh(C5H5)

(C6H5CHCHCHCHCHCHC6H5)Rh(C5H5)

Conditions
ConditionsYield
With n-butyllithium In diethyl ether; hexane Ph3P(CH2Ph)Br suspended in dry Et2O was treated under N2 with n-BuLi inhexane and stirred for 2 h, Rh-complex was added, the mixt. stirred at room temp. overnight and then heated under reflux for 5 h; the ether was removed in vacuo, residue washed with 3:2 MeOH-water and with a little cold MeOH, recrystd. from acetone; elem. anal.;93%

1100-88-5Relevant articles and documents

Stereospecific on-Surface Cyclodehydrogenation of Bishelicenes: Preservation of Handedness from Helical to Planar Chirality

Irziqat, Bahaaeddin,Cebrat, Aleksandra,Baljozovi?, Milo?,Martin, Kévin,Parschau, Manfred,Avarvari, Narcis,Ernst, Karl-Heinz

, p. 13523 - 13526 (2021)

-

-

Grayson,M.,Keough,P.T.

, p. 3919 - 3924 (1960)

-

Arylmethyloxyphenyl derivatives: Small molecules displaying P-glycoprotein inhibition

Colabufo, Nicola Antonio,Berardi, Francesco,Perrone, Roberto,Rapposelli, Simona,Digiacomo, Maria,Balsamo, Aldo

, p. 6607 - 6613 (2006)

Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D 2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [3H]vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.

-

Wittig,G.,Schlosser,M.

, p. 1023 - 1028 (1962)

-

Structure-Activity-Relationship-Aided Design and Synthesis of xCT Antiporter Inhibitors

Cirillo, Davide,Sarowar, Shahin,?yvind Enger, Per,Bj?rsvik, Hans-René

, p. 2650 - 2668 (2021/06/01)

The xCT antiporter is a cell membrane protein involved in active counter-transportation of glutamate (outflux) with cystine (influx) over the human cell membrane. This feature makes the xCT antiporter a crucial element of the biosynthesis of the vital free radical scavenger glutathione. The prodrug sulfasalazine, a medication for the treatment of ulcerative colitis, was previously proven to inhibit the xCT antiporter. Starting from sulfasalazine, a molecular scaffold jumping followed by SAR-assisted design and synthesis provided a series of styryl hydroxy-benzoic acid analogues that were biologically tested in vitro for their ability to decrease intracellular glutathione levels using four different cancer cell lines: A172 (glioma), A375 (melanoma), U87 (glioma) and MCF7 (breast carcinoma). Depletion of glutathione levels varied among the compounds as well as among the cell lines. Flow cytometry using propidium iodide and the annexin V marker demonstrated minimal toxicity in normal human astrocytes for a promising candidate molecule (E)-5-(2-([1,1′-biphenyl]-4-yl)vinyl)-2-hydroxybenzoic acid.

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