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Triphenylphosphine (TPP)
Cas No: 603-35-0
No Data 1 Metric Ton 100 Metric Ton/Month Beijing Chemdow Co., Ltd Contact Supplier
High purity Triphenylphosphine 98% TOP1 supplier in China
Cas No: 603-35-0
No Data 100 Gram 1-1000 Metric Ton/Day Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Triphenylphosphine manufacture
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No Data 1 Kilogram 50 Metric Ton/Month Hangzhou ZeErRui Chemical Co., Ltd. Contact Supplier
High purity Triphenylphosphine with high quality and best price cas:603-35-0
Cas No: 603-35-0
USD $ 6.5-10.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
High quality Triphenyl Phosphine supplier in China
Cas No: 603-35-0
No Data No Data 30 Metric Ton/Month Simagchem Corporation Contact Supplier
Triphenylphosphine (TPP)
Cas No: 603-35-0
USD $ 1.0-3.0 / Metric Ton 1 Metric Ton 10 Metric Ton/Day Hebei yanxi chemical co.,LTD. Contact Supplier
Triphenylphosphine CAS No.603-35-0
Cas No: 603-35-0
No Data 1 Gram 1000 Kilogram/Month Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd Contact Supplier
Triphenyl phosphine
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No Data 1 Kilogram 5000 Metric Ton/Year Hefei TNJ chemical industry co.,ltd Contact Supplier
Triphenylphosphine -- CHemwill
Cas No: 603-35-0
USD $ 1.0-1.0 / Metric Ton 1 Metric Ton 5 Metric Ton/Day Chemwill Asia Co., Ltd. Contact Supplier
Triphenylphosphine;Phosphorustriphenyl
Cas No: 603-35-0
No Data 1 Kilogram 20 Metric Ton/Month Henan Allgreen Chemical Co.,Ltd Contact Supplier

603-35-0 Usage

Reactivity Profile

Triphenylphosphine reacts vigorously with oxidizing materials. .

Chemical properties

This product is colorless to pale yellow monoclinic crystal below the room temperature, colorless to pale yellow transparent oily liquid above the room temperature with skin irritation and a pungent odour. Its mp about 22 ℃and bp 360 ℃(0.1 MPa) , n25D of 1.589 and relative density of 1.184 (20 ℃). And it is miscible with alcohol, ether, benzene and acetone and other organic solvents, while insoluble in water.

Production methods

In this preparation method, phenol and phosphorus trichloride was used as raw materials. After esterification and vacuum distillation, the product namely triphenyl phosphite can be obtained.
3C6H5OH + PCl3 [15~20 ℃] → (C3H5O) 3P + 3HCl
Specific process can be classified into batch and continuous processes.
 (1) Batch process
The phenol was added into the reactor, after warming to melt phosphorus trichloride was added to react with phenol at 70~90 ℃. After the phosphorus trichloride addition was completed, the temperature of reaction mixture was raised to about 150 ℃. After the removal of hydrogen chloride and unreacted phenol dissolved under reduced pressure at a high temperature, the product can be achieved.
(2) The use of a tower reactor
Phenol was feeding under the condenser located in the upper portion of the tower, while phosphorus trichloride enters above the receptacle located in the lower portion of the tower. Both reacted in the tower, and the product was collected in the receiver, meanwhile by-product hydrogen chloride was introduced into the absorber tower via the upper end of the condenser. After some process of the crude ester such as distillation, the product can be obtained.

Uses

Combining organic compound; microcosmic salt;phosphorous compound

Uses

In organic synthesis; polymerization initiator.

Uses

1. In pesticide industry, Triphenylphosphine is used in the synthesis of an organophosphorus intermediate, trimethyl phosphite in ester exchange method. And then a series of organophosphorus pesticides such as dichlorvos, monocrotophos and phosphamidon can be further obtained. In addition, it can be used as stabilizers in the synthesis of rubber and resins, antioxidants in polyvinyl chloride, and raw material in the synthesis of alkyd resins and polyester resins.
2. Used in organic synthesis, polymerization initiator, raw materials of antibiotic drugs clindamycin, standard samples in organic trace analysis determination of phosphorus.
3. Widely used in pharmaceutical, petrochemical, paint, rubber and other industries, as catalyst, accelerator, flame retardant, heat and light stabilizer, lubricant, antioxidant etc.
4. In organic synthesis, such as synthesis of phosphorus salts and other phosphorus compounds.

description

Triphenylphosphine (TPP) is used in the synthesis of organic compounds due to its nucleophilicity and its reducing character. TPP is a highly efficient product that serves successfully in many applications, for example:
  1. The important ligands of homogeneous catalysts used in petrochemicals and fine chemicals production, as a co-catalyst in isobutanol and n-butanol production.
  2. The basic raw material of rhodium phosphine complex catalyst, It is used to prepare Wilkinson's catalyst, RhCl(PPh3)3 useful to catalyze the hydrogenation of alkenes and tetrakis(triphenylphosphine)palladium(0) that is widely used to catalyze C-C coupling reactions in organic synthesis.
  3. in vitamin synthesis and production of pharmaceutical active ingredients, crop protection products and coatings, TPP is used in synthesis of vitamin D2, vitamin A, clindamycin and other drugs. Besides it plays an important role in reactions of plant pigments.
  4. as an oxidation and UV stabilizer in plastics. In the dye industry, Triphenylphosphine is used as sensitizer, heat stabilizers, light stabilizers, antioxidants, flame retardants, antistatic agents, rubber antiozonants and analytical reagent.
  5. as an initiator of several polymerization reactions, The anionic phosphine is usually isolated as the trisodium salt which reacts with rhodium to form a complex that finds use in industrial hydroformylation reactions.
  6. It is involved in the synthesis of biaryl compounds, phosphonium salts and other phosphorus compounds.
  7. As a reducing agent, it is used to prepare aromatic amines from the corresponding aromatic N-oxides.

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx.

Chemical Properties

White, crystalline solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

Uses

PTC catalyst

Uses

It is used in the synthesis of organic and organometallic compounds.

Purification Methods

It crystallises from hexane, MeOH, diethyl ether, CH2Cl2/hexane or 95% EtOH. Dry it at 65o/<1mm over CaSO4 or P2O5. Chromatograph it through alumina using (4:1) *benzene/CHCl3 as eluent. [Blau & Espenson et al. J Am Chem Soc 108 1962 1986, Buchanan et al. J Am Chem Soc 108 1537 1986, Randolph & Wrighton J Am Chem Soc 108 3366 1986, Asali et al. J Am Chem Soc 109 5386 1987.] It has also been crystallised twice from pet ether and 5 times from Et2O/EtOH to give m 80.5o. Alternatively, dissolve it in conc HCl, and upon dilution with H2O it separates because it is weakly basic, it is then crystallised from EtOH/Et2O. It recrystallises unchanged from AcOH. [Forward et al. J Chem Soc Suppl. p121 1949, Muller et al. J Am Chem Soc 78 3557 1956.] 3Ph3P.4HCl crystallises out when HCl gas is bubbled through an Et2O solution, it has m 70-73o, but recrystallises very slowly and is deliquescent. The hydriodide, made by adding Ph3P to hydriodic acid, is not hygroscopic and decomposes at ~100o. The chlorate (1:1) salt has m 165-167o, but decomposes slowly at 100o. All salts hydrolyse in H2O to give Ph3P [IR, UV: Sheldon & Tyree J Am Chem Soc 80 2117 1958, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, Kosolapoff, Organophosphorus Compounds, Wiley 1950]. [Beilstein 16 IV 951.] § Available commercially on a polystyrene or polyethyleneglycol support.

Friedel-krogh`s method

The optimum reaction conditions: catalyst dosage 48g, reaction time 8h, the reaction temperature 400 ℃, the yield 63.5%. After sulfur, phosphorus trichloride and benzene reflux reacted directly, the generated triphenyl phosphine sulfide compound were deoxidized into triphenylphosphine by iron powder.

Hazards & Safety Information

Category: toxic substances
Toxicity degree: grading poisoning
Acute toxicity: oral-rat LD50: 700 mg/kg; Oral-Mouse LD50: 1000 mg/kg
Skin irritation Data: rabbit 500 mg/24 hours severe; Eyes-rabbit 500 mg/24 hr mild
Flammability hazard characteristics: thermal decomposition into toxic phosphide
Storage characteristics: ventilated, low-temperature and dry storehouse; stored and transported separately with food raw materials
Extinguishing agent: carbon dioxide, sand, water, foam

Name Reactions

  1. Mitsunobu reactions
    The triphenylphosphine combines with DEAD to generate a phosphonium intermediate that binds to the alcohol oxygen, activating it as a leaving group. Substitution by the carboxylate, mercaptyl, or other nucleophile completes the process.
  2. Ozonolysis reactions
    Ozonolysis allows the cleavage of alkene double bonds by reaction with ozone. Depending on the work up, different products may be isolated: reductive work-up gives either alcohols or carbonyl compounds, while oxidative work-up leads to carboxylic acids or ketones.
  3. Staudinger reactions
    Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide.
  4. Appel reactions
    The reaction of triphenylphosphine and tetrahalomethanes (CCl4, CBr4) with alcohols is a ready method to convert an alcohol to the corresponding alkyl halide under mild conditions. The yields are normally high.
    This reaction is somewhat similar to the Mitsunobu Reaction, where the combination of a phosphine, a diazo compound as a coupling reagent, and a nucleophile are used to invert the stereochemistry of an alcohol or displace it.
Name Reactions (Mitsunobu Ozonolysis  Staudinger Appel reactions)
InChI:InChI=1/C18H15P.BrH/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15H;1H

603-35-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma-Aldrich (T84409)  Triphenylphosphine  ReagentPlus®, 99% 603-35-0 T84409-1KG 1,832.22CNY Detail
Sigma-Aldrich (T84409)  Triphenylphosphine  ReagentPlus®, 99% 603-35-0 T84409-500G 970.52CNY Detail
Sigma-Aldrich (T84409)  Triphenylphosphine  ReagentPlus®, 99% 603-35-0 T84409-100G 198.90CNY Detail
Sigma-Aldrich (T84409)  Triphenylphosphine  ReagentPlus®, 99% 603-35-0 T84409-25G 122.85CNY Detail
Sigma-Aldrich (T84409)  Triphenylphosphine  ReagentPlus®, 99% 603-35-0 T84409-1G 117.00CNY Detail
Sigma-Aldrich (93092)  Triphenylphosphine  ≥95.0% (GC) 603-35-0 93092-1KG 2,176.20CNY Detail
Sigma-Aldrich (93092)  Triphenylphosphine  ≥95.0% (GC) 603-35-0 93092-250G 775.71CNY Detail
Alfa Aesar (14112)  Triphenylphosphine, 99+%    603-35-0 500g 1325.0CNY Detail
Alfa Aesar (14112)  Triphenylphosphine, 99+%    603-35-0 100g 401.0CNY Detail
Alfa Aesar (14112)  Triphenylphosphine, 99+%    603-35-0 25g 180.0CNY Detail
Alfa Aesar (L02502)  Triphenylphosphine, powder, 99%    603-35-0 1000g 2524.0CNY Detail
Alfa Aesar (L02502)  Triphenylphosphine, powder, 99%    603-35-0 250g 728.0CNY Detail

603-35-0SDS

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 Triphenylphosphine

1.2 Other means of identification

Product number -
Other names PP-360

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:603-35-0 SDS

603-35-0Synthetic route

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 5h;100%
With aluminium hydride*tetrahydrofuran100%
With titanium(IV) isopropylate; 1,1,3,3-Tetramethyldisiloxane In methyl cyclohexane at 80℃; for 14h;100%
methanol
67-56-1

methanol

dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

bromure de methoxyvinyltriphenylphosphonium
56351-16-7

bromure de methoxyvinyltriphenylphosphonium

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature;A 86%
B 100%
dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

bromure de methoxyvinyltriphenylphosphonium
56351-16-7

bromure de methoxyvinyltriphenylphosphonium

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium cyanide In dimethyl sulfoxide for 22h; Ambient temperature;A 86%
B 100%
triphenylphosphinediiodogermylene
97939-92-9

triphenylphosphinediiodogermylene

phenyllithium
591-51-5

phenyllithium

A

iodobenzene
591-50-4

iodobenzene

B

biphenyl
92-52-4

biphenyl

C

triphenylgermane
2816-43-5

triphenylgermane

D

tetraphenylgermane
1048-05-1

tetraphenylgermane

E

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:4 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 10%
B 13%
C 39%
D 36%
E 100%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:1 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 2.9%
B 2.9%
C 1.9%
D 14%
E 82%
In diethyl ether under N2, to suspn. of Ph3PGeI2 in ether PhLi added dropwise (1:2 molarratio), stirred for 5 d under reflux, hydrolyzed; dried, analyzed by gas chromy.;A 7.7%
B 9.6%
C 1.3%
D 19%
E 79%
methanol
67-56-1

methanol

triphenylphosphine borane
2049-55-0

triphenylphosphine borane

A

Trimethyl borate
121-43-7

Trimethyl borate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
at 120℃; Inert atmosphere; Microwave irradiation;A n/a
B 99%
benzonitrile
100-47-0

benzonitrile

(trimethylsilyl)diphenylphosphine
17154-34-6

(trimethylsilyl)diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With cis-[NiCl2(PPh3)2]; potassium tert-butylate In 1,4-dioxane at 90℃; for 10h; Inert atmosphere;99%
fluorobenzene
462-06-6

fluorobenzene

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 15-crown-5 In tetrahydrofuran at 25℃; for 16h; Reagent/catalyst; Inert atmosphere;99%
dichlorotriphenylphosphorane
2526-64-9

dichlorotriphenylphosphorane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With tributylphosphine98%
With sodium
With bis(2-methylphenyl)disulfide; triethylamine In chloroform for 7h; Heating;
2-[2-Oxo-1-(triphenyl-λ5-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one
103748-75-0

2-[2-Oxo-1-(triphenyl-λ5-phosphanylidene)-propyl]-1,2-dihydro-indazol-3-one

A

2-acetyl-4-oxo-dihydroquinazoline
17244-28-9

2-acetyl-4-oxo-dihydroquinazoline

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In toluene at 95℃; for 2h;A 98%
B n/a
iodobenzene
591-50-4

iodobenzene

diphenylphosphane
829-85-6

diphenylphosphane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With potassium acetate; 5percent Pd on charcoal In N,N-dimethyl-formamide at 190℃; for 0.05h; microwave irradiation;98%
With caesium carbonate In toluene at 115℃; for 24h; Inert atmosphere;90%
With potassium acetate In N,N-dimethyl acetamide at 130℃; for 3h; Reagent/catalyst; Solvent; Temperature; Schlenk technique; Inert atmosphere;86%
With rongalite; potassium hydroxide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;65%
chlorobenzene
108-90-7

chlorobenzene

potassium diphenylphosphine
15475-27-1, 4346-39-8

potassium diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 25 - 67℃; for 74.4h;98%
phenyl sodium
1623-99-0

phenyl sodium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With phosphorus tribromide97.3%
With anhydrous phosphorus trichloride In toluene
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

cyclenphosphorane
64317-97-1

cyclenphosphorane

cis-((H2cyclen)P)PtCl2PPh3}Cl
108148-25-0

cis-((H2cyclen)P)PtCl2PPh3}Cl

{(eta.2-cyclenphosphorane)PtClPPh3}
108148-24-9

{(eta.2-cyclenphosphorane)PtClPPh3}

C

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran under N2, mixt. of phosphorane and Pt complex in THF was stirred for 12h, pptn.; volatiles removed in vac., residue washed (10 times hexane, 10 times THF (to dissolve the η2-complex), residue (cis complex) and washing (η2.-complex) pumped dry separately, each heated to 90°C under vac., elem. anal.;A 96%
B 97%
C 97%
chlorobenzene
108-90-7

chlorobenzene

sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 15-crown-5 In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; for 3h; Reagent/catalyst; Inert atmosphere;97%
Diphenylphosphonigsaeure-trimethylsilylester
13683-01-7

Diphenylphosphonigsaeure-trimethylsilylester

phenyllithium
591-51-5

phenyllithium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃; for 2h;97%
benzylpotassium
3605-36-5

benzylpotassium

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
96.6%
triphenylphosphine sulfide
3878-45-3

triphenylphosphine sulfide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 1h; Product distribution; Further Variations:; Reaction partners; reaction times;96%
With n In tetrahydrofuran at 60℃; for 3h;95%
Stage #1: triphenylphosphine sulfide With oxalyl dichloride In toluene at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 20℃; for 0.5h; Inert atmosphere;
88%
2-methyl-2-(triphenylphosphonio)dithiopropionate betaine
69491-12-9

2-methyl-2-(triphenylphosphonio)dithiopropionate betaine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

A

2-isopropylidene-4,5-dimethoxycarbonyl-1,3-dithiole
85072-91-9

2-isopropylidene-4,5-dimethoxycarbonyl-1,3-dithiole

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In acetonitrile for 24h; Ambient temperature;A 96%
B 67%
Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 80℃; for 2h;96%
{Fe(C5H4S)2}Pt(P(C6H5)3)2

{Fe(C5H4S)2}Pt(P(C6H5)3)2

{Fe(C5H4S)2}Pt(P(C6H5)3)*C6H6

{Fe(C5H4S)2}Pt(P(C6H5)3)*C6H6

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In chloroform soln. of educt in CHCl3 heated to 60°C and stirred for 0.5 h under N2, cooled; concd. in vac., chromd. (SiO2, C6H6), 1st colorless fraction contained PPh3, red 2nd fraction collected, concd.;A 96%
B n/a
sodium methylate
124-41-4

sodium methylate

dibromure de vinylene-1,2 bis-triphenylphosphonium

dibromure de vinylene-1,2 bis-triphenylphosphonium

A

triphenylphosphine
603-35-0

triphenylphosphine

B

2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide

2-triphenylphosphoniumacetaldehyde dimethyl acetal bromide

Conditions
ConditionsYield
In methanol for 0.75h; Ambient temperature;A 95%
B 89%
ethanol
64-17-5

ethanol

triphenylphosphine borane
2049-55-0

triphenylphosphine borane

A

triethyl borate
150-46-9

triethyl borate

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 95%
triphenylphosphine borane
2049-55-0

triphenylphosphine borane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 96h; Inert atmosphere; Molecular sieve; Reflux;95%
With diisopropylamine In toluene at 30℃; Kinetics; Equilibrium constant; Reagent/catalyst; Solvent;
S-(4-linoleyloxybutyl)thioacetate

S-(4-linoleyloxybutyl)thioacetate

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 4.5h; Inert atmosphere; Cooling with ice;95%
3,3,4,4-tetramethyl-1,2-dioxetane
35856-82-7

3,3,4,4-tetramethyl-1,2-dioxetane

2,2-Dihydro-4,4,5,5-tetramethyl-2,2,2-triphenyl-1,3,2-dioxaphospholane
49595-63-3

2,2-Dihydro-4,4,5,5-tetramethyl-2,2,2-triphenyl-1,3,2-dioxaphospholane

A

3,3-dimethyl-butan-2-one
75-97-8

3,3-dimethyl-butan-2-one

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In benzene-d6 at 23.9℃; Kinetics; Rate constant; Thermodynamic data; other temperatures, Ea, ΔS(excit);A 6%
B 94%
iodobenzene
591-50-4

iodobenzene

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride at 120℃; for 0.5h; Inert atmosphere;93%
With nickel tetrafluoroborate; lithium chloride In acetonitrile electrolysis; var. supporting electrolytes, other aryl and alkyl halides;80%
With pyridine; tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 20h; Heating;
2-{[(Toluene-4-sulfonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-azo}-benzaldehyde
103748-72-7

2-{[(Toluene-4-sulfonyl)-(triphenyl-λ5-phosphanylidene)-methyl]-azo}-benzaldehyde

A

2-p.tosyl-4-oxo-dihydroquinazoline
103748-77-2

2-p.tosyl-4-oxo-dihydroquinazoline

B

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
In toluene at 70℃; for 5h;A 93%
B n/a
chlorobenzene
108-90-7

chlorobenzene

(trimethylsilyl)diphenylphosphine
17154-34-6

(trimethylsilyl)diphenylphosphine

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; potassium tert-butylate In 1,4-dioxane at 90℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere;93%
1-(benzoyl)piperidine-2,6-dione

1-(benzoyl)piperidine-2,6-dione

diphenylphosphane
829-85-6

diphenylphosphane

triphenylphosphine
603-35-0

triphenylphosphine

Conditions
ConditionsYield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); sodium carbonate In 1,4-dioxane at 160℃; for 48h; Reagent/catalyst; Inert atmosphere; Schlenk technique;93%
1,3-propanesultone
1120-71-4

1,3-propanesultone

triphenylphosphine
603-35-0

triphenylphosphine

3-(triphenylphosphonio)propane-1-sulfonate
116154-22-4

3-(triphenylphosphonio)propane-1-sulfonate

Conditions
ConditionsYield
In toluene for 12h; Reflux;100%
In tetrahydrofuran at 25℃;95%
In toluene for 24h; Reflux;43%
benzyl bromide
100-39-0

benzyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

Conditions
ConditionsYield
In xylene for 0.00833333h; Heating; microwave irradiation;100%
In toluene for 12h; Reflux;100%
at 100℃; for 0.0333333h; Irradiation;99%
chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

triphenylphosphine
603-35-0

triphenylphosphine

(methoxymethyl)triphenylphosphonium chloride
4009-98-7

(methoxymethyl)triphenylphosphonium chloride

Conditions
ConditionsYield
In dichloromethane Reflux;100%
In toluene at 95℃; for 16h;97.3%
In neat (no solvent) at 80℃; for 4h; Solvent; Temperature; Time; Inert atmosphere; Schlenk technique;93%
1-dodecylbromide
143-15-7

1-dodecylbromide

triphenylphosphine
603-35-0

triphenylphosphine

dodecyltriphenylphosphonium bromide
15510-55-1

dodecyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 48h;96.1%
In tetrahydrofuran for 12h; sealed tube, bath temperature 250 deg C;88%
bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

triphenylphosphine
603-35-0

triphenylphosphine

(methyloxycarbonylmethyl)triphenylphosphonium bromide
1779-58-4

(methyloxycarbonylmethyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In ethyl acetate at 20℃; for 17h;100%
In ethyl acetate97%
In benzene at 20℃; for 4h;97%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

triphenylphosphine
603-35-0

triphenylphosphine

triphenylphenacylphosphonium bromide
6048-29-9

triphenylphenacylphosphonium bromide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;100%
at 20℃; for 24h;100%
In toluene for 4h; Reflux;99%
p-methoxy-phenylazide
2101-87-3

p-methoxy-phenylazide

triphenylphosphine
603-35-0

triphenylphosphine

4-methoxy-N-(triphenylphosphoran-ylidene)-aniline
14796-89-5

4-methoxy-N-(triphenylphosphoran-ylidene)-aniline

Conditions
ConditionsYield
In toluene at 60℃; for 16h; Schlenk technique; Inert atmosphere;100%
In diethyl ether at 20℃; for 2h;88%
triphenylphosphine
603-35-0

triphenylphosphine

1,3-dibromo-propane
109-64-8

1,3-dibromo-propane

3-bromopropyltriphenylphosphonium bromide
3607-17-8

3-bromopropyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene at 110℃; for 16h;100%
In toluene for 24h; Reflux;99%
In toluene Inert atmosphere; Reflux;98%
triphenylphosphine
603-35-0

triphenylphosphine

Phenyl azide
622-37-7

Phenyl azide

N-phenyltriphenyliminophosphorane
2325-27-1

N-phenyltriphenyliminophosphorane

Conditions
ConditionsYield
In toluene at 20℃; for 2h; Condensation;100%
In diethyl ether for 2h; Heating;100%
In diethyl ether at 20℃; for 2h;79%
triphenylphosphine
603-35-0

triphenylphosphine

hexadecanyl bromide
112-82-3

hexadecanyl bromide

(1-hexadecyl)triphenylphosphonium bromide
14866-43-4

(1-hexadecyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
In toluene at 90℃; for 48h;79%
In acetonitrile for 36h; Heating;68%
triphenylphosphine
603-35-0

triphenylphosphine

diazodiphenylmethane
908093-98-1

diazodiphenylmethane

diphenyldiazomethane triphenylphosphazine
1109-01-9

diphenyldiazomethane triphenylphosphazine

Conditions
ConditionsYield
In benzene at 30℃; for 0.00333333h;100%
In acetonitrile at 30℃; Rate constant;
In acetonitrile at 30℃; Kinetics; Thermodynamic data; effect of 4,4'-disubstitution on the reactivity;
triphenylphosphine
603-35-0

triphenylphosphine

methyl iodide
74-88-4

methyl iodide

methyl-triphenylphosphonium iodide
2065-66-9

methyl-triphenylphosphonium iodide

Conditions
ConditionsYield
for 0.00833333h; Heating; microwave irradiation;100%
In toluene at 0℃; for 4h; Reflux;100%
In dichloromethane at 20℃; Inert atmosphere;100%
triphenylphosphine
603-35-0

triphenylphosphine

9-diazofluorenone
832-80-4

9-diazofluorenone

9-fluorenone triphenylphosphazine
751-35-9

9-fluorenone triphenylphosphazine

Conditions
ConditionsYield
In benzene at 30℃; for 0.00333333h;100%
With benzene
In acetonitrile
In acetonitrile Yield given;
triphenylphosphine
603-35-0

triphenylphosphine

Triphenylphosphine selenide
3878-44-2

Triphenylphosphine selenide

Conditions
ConditionsYield
With selenium In toluene for 6h; Heating;100%
With 4-phenyl-1,2,3-selenadiazole In benzene for 1h; Heating;100%
With selenium In chloroform-d1 at 20℃;100%
triphenylphosphine
603-35-0

triphenylphosphine

triphenylphosphine diiodide
6396-07-2

triphenylphosphine diiodide

Conditions
ConditionsYield
With iodine In diethyl ether at 20℃; for 1h;100%
With iodine In diethyl ether; toluene96%
With iodine
With 1,2-Diiodoethane In acetonitrile at 60℃; for 0.5h;
With iodine In dichloromethane at 0℃; for 2h;
triphenylphosphine
603-35-0

triphenylphosphine

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

Conditions
ConditionsYield
With CuO2H In acetonitrile at 70℃; for 6h;100%
With CuO2H In acetonitrile at 70℃; for 6h;100%
With periodate form of Amberlyst A26 In chloroform at 25℃; for 2h;100%
p-Methoxybenzyl bromide
2746-25-0

p-Methoxybenzyl bromide

triphenylphosphine
603-35-0

triphenylphosphine

((4-methoxyphenyl)methyl)triphenylphosphonium bromide
1530-38-7

((4-methoxyphenyl)methyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature;100%
In toluene at 110℃;99%
In toluene for 10h; Inert atmosphere; Reflux;98%
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%
4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

triphenylphosphine
603-35-0

triphenylphosphine

(4-methylbenzyl)triphenylphosphonium chloride
1530-37-6

(4-methylbenzyl)triphenylphosphonium chloride

Conditions
ConditionsYield
In acetonitrile for 4.5h; Reflux;100%
In acetonitrile for 4.5h; Reflux;100%
In xylene for 18h; Heating;86%
1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

triphenylphosphine
603-35-0

triphenylphosphine

4-bromobenzyl triphenylphosphonium bromide
51044-13-4

4-bromobenzyl triphenylphosphonium bromide

Conditions
ConditionsYield
In chloroform for 4h; Heating / reflux;100%
In acetonitrile for 4.5h; Reflux;100%
In acetone at 20℃; for 12h;99%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

triphenylphosphine
603-35-0

triphenylphosphine

but-3-en-1-yltriphenylphosphonium bromide
16958-42-2

but-3-en-1-yltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 24h; Inert atmosphere; Reflux;100%
In N,N-dimethyl-formamide for 3h; Heating;84%
In acetonitrile at 23℃; for 23h; Reflux; Inert atmosphere;81%
triphenylphosphine
603-35-0

triphenylphosphine

prenyl bromide
870-63-3

prenyl bromide

(3-methylbut-2-enyl)triphenylphosphonium bromide
1530-34-3

(3-methylbut-2-enyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene at 110℃; Inert atmosphere;100%
In benzene at 20℃; for 20h;96%
In toluene Ambient temperature;93%
[14C]methyl iodide
16170-82-4

[14C]methyl iodide

triphenylphosphine
603-35-0

triphenylphosphine

-methyltriphenylphosphonium iodide
1560-52-7

-methyltriphenylphosphonium iodide

Conditions
ConditionsYield
In benzene at 22℃; for 37h;100%
In diethyl ether Methylation;95%
In benzene for 24h;90%
(E)-1-bromo-2-hexene
73881-10-4

(E)-1-bromo-2-hexene

triphenylphosphine
603-35-0

triphenylphosphine

<(E)-hex-2-enyl>triphenylphosphonium bromide
88517-93-5

<(E)-hex-2-enyl>triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 5h; Heating;100%
1-bromo-hexane
111-25-1

1-bromo-hexane

triphenylphosphine
603-35-0

triphenylphosphine

hexyltriphenylphosphonium bromide
4762-26-9

hexyltriphenylphosphonium bromide

Conditions
ConditionsYield
In toluene for 8h; Reflux;100%
In acetonitrile for 16h; Heating;95.6%
In toluene for 120h; Heating;92%
iodomethane-d3
865-50-9

iodomethane-d3

triphenylphosphine
603-35-0

triphenylphosphine

(methyl-d3)triphenylphosphonium iodide
1560-56-1

(methyl-d3)triphenylphosphonium iodide

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Reflux;100%
In tetrahydrofuran for 1h; Schlenk technique; Reflux;99%
In tetrahydrofuran for 1h; Schlenk technique; Inert atmosphere; Reflux;99%
1-bromo-octane
111-83-1

1-bromo-octane

triphenylphosphine
603-35-0

triphenylphosphine

n-octyltriphenylphosphoniumbromide
42036-78-2

n-octyltriphenylphosphoniumbromide

Conditions
ConditionsYield
In chlorobenzene for 48h; Heating;100%
In toluene Reflux;100%
In o-xylene Heating;98.7%
1-Bromotetradecane
112-71-0

1-Bromotetradecane

triphenylphosphine
603-35-0

triphenylphosphine

(n-tetradecyl)triphenylphosphonium bromide
25791-20-2

(n-tetradecyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In toluene Reflux;100%
at 140℃; for 7h;92%
In benzene for 48h; Substitution; Heating;92%
6-bromohexanoic acid
4224-70-8

6-bromohexanoic acid

triphenylphosphine
603-35-0

triphenylphosphine

(5-carboxypentyl)triphenylphosphonium bromide
50889-29-7

(5-carboxypentyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In acetonitrile for 16h; Heating;100%
at 100℃; for 4h;100%
In acetonitrile for 24h; Heating;99%

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