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76189-56-5

76189-56-5

Identification

  • Product Name:Phosphine,1,1'-[(1S)-[1,1'-binaphthalene]-2,2'-diyl]bis[1,1-diphenyl-

  • CAS Number: 76189-56-5

  • EINECS:-0

  • Molecular Weight:622.686

  • Molecular Formula: C44H32P2

  • HS Code:HOSPHINO)-1,1'-BINAPHTHYL PRODUCT IDENTIFICATION

  • Mol File:76189-56-5.mol

Synonyms:Phosphine,[1,1'-binaphthalene]-2,2'-diylbis[diphenyl-, (S)-;Phosphine,(1S)-[1,1'-binaphthalene]-2,2'-diylbis[diphenyl- (9CI);(S)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl;(S)-BINAP;(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl;(S)-(-)-BINAP;(1S)-[1,1'-Binaphthalene]-2,2'-diylbis[diphenylphosphine];(-)-BINAP;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi, HarmfulXn

  • Hazard Codes:Xi,Xn

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TCI Chemical
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl >98.0%(GC)
  • Packaging:1g
  • Price:$ 82
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl >98.0%(GC)
  • Packaging:5g
  • Price:$ 267
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
  • Packaging:100 g
  • Price:$ 634
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
  • Packaging:25 g
  • Price:$ 202
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
  • Packaging:5 g
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% (S)-(-)-BINAP
  • Packaging:1g
  • Price:$ 72
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% (S)-(-)-BINAP
  • Packaging:250mg
  • Price:$ 30
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% (S)-(-)-BINAP
  • Packaging:5g
  • Price:$ 288
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(S)-(?)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene 97%
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  • Price:$ 220
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(S)-BINAP
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Relevant articles and documentsAll total 42 Articles be found

The Trityl-Cation Mediated Phosphine Oxides Reduction

Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric

supporting information, p. 3035 - 3043 (2021/05/10)

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

One-pot synthesis of binaphthyl-based phosphines via direct modification of BINAP

Ye, Jing-Jing,Zhang, Jian-Qiu,Shimada, Shigeru,Han, Li-Biao

supporting information, (2021/11/18)

Herein reported is the convenient and efficient strategy for the preparation of binaphthyl-based phosphines through direct modification to the commercially available 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) with sodium. In the absence of 15-crown-5-ether, a cyclic sodium dinapthylphospholide intermediate is mainly generated. With 15-crown-5-ether, P-Ph bonds are selectively cleft by Na to produce binaphthyl-based disodium phosphides. The mechanism of selective formation of sodium dinapthylphospholide or binaphthyl-based disodium phosphides is proposed.

Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene

-

, (2020/09/12)

The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.

Synthetic method of 2,2'-double diphenyl phosphine-1,1'-dinaphthalene

-

Paragraph 0018; 0033; 0034, (2018/10/11)

The invention discloses a synthetic method of 2,2'-double diphenyl phosphine-1,1'-dinaphthalene. The method comprises the following steps: adding a lithium metal sheet, a ligand, 2,2'-diethoxy-1,1'-dinaphthalene and an ethers solvent are added in a reaction still, heating the materials to the temperature of 60-140 DEG C, reacting the materials for 6-12 hours, dropping chlorodiphenylphosphine at the temperature of 0 DEG C, heating the material to room temperature, and obtaining the product after the reaction is completed; equivalent water quenching is carried out, a product solution is concentrated and filtered, a filter cake is washed with methanol, and vacuum drying is carried out to obtain the product 2,2'-double diphenyl phosphine-1,1'-dinaphthalene (BINAP). The method has the advantages of high yield, low preparation cost, simple post-treatment, high product purity, and is suitable for process enlargement.

Chemoselective Reduction of Phosphine Oxides by 1,3-Diphenyl-Disiloxane

Buonomo, Joseph A.,Eiden, Carter G.,Aldrich, Courtney C.

supporting information, p. 14434 - 14438 (2017/10/23)

Reduction of phosphine oxides to the corresponding phosphines represents the most straightforward method to prepare these valuable reagents. However, existing methods to reduce phosphine oxides suffer from inadequate chemoselectivity due to the strength of the P=O bond and/or poor atom economy. Herein, we report the discovery of the most powerful chemoselective reductant for this transformation to date, 1,3-diphenyl-disiloxane (DPDS). Additive-free DPDS selectively reduces both secondary and tertiary phosphine oxides with retention of configuration even in the presence of aldehyde, nitro, ester, α,β-unsaturated carbonyls, azocarboxylates, and cyano functional groups. Arrhenius analysis indicates that the activation barrier for reduction by DPDS is significantly lower than any previously calculated silane reduction system. Inclusion of a catalytic Br?nsted acid further reduced the activation barrier and led to the first silane-mediated reduction of acyclic phosphine oxides at room temperature.

Process route upstream and downstream products

Process route

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene
130164-89-5,94041-16-4,94041-18-6,86632-33-9

2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With trichlorosilane; triethyl phosphite; In tetrahydrofuran; toluene; at 100 ℃; for 3h;
95%
With 1,3-diphenyl-disiloxane; In toluene; at 110 ℃; chemoselective reaction; Sealed tube;
94%
2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene; With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate; In toluene; at 85 ℃; for 20h;
With sodium hydroxide; water; In toluene; for 0.25h; Product distribution / selectivity;
91%
2,2’-bis(diphenylphosphinooxide)-1,1’-binaphthalene; With trityl tetrakis(pentafluorophenyl)borate; In (2)H8-toluene; at 20 ℃; Glovebox; Inert atmosphere;
With phenylsilane; In (2)H8-toluene; at 100 ℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;
23%
With [AlH3(triethylamine)]; In hexane; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;
96 %Chromat.
2,2'-bis(diphenyloxyphosphino)-1,1'-binaphthyl
1227058-20-9

2,2'-bis(diphenyloxyphosphino)-1,1'-binaphthyl

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With tributylphosphine; iodine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;
92%
(R)-2,2'-diethoxy-1,1'-binaphthyl
19491-17-9,109135-26-4,109135-27-5

(R)-2,2'-diethoxy-1,1'-binaphthyl

chloro-diphenylphosphine
1079-66-9,74391-44-9

chloro-diphenylphosphine

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
(R)-2,2'-diethoxy-1,1'-binaphthyl; With N,N,N,N,-tetramethylethylenediamine; lithium; In tetrahydrofuran; at 65 ℃; for 10h; Large scale;
chloro-diphenylphosphine; In tetrahydrofuran; at 0 ℃; Reagent/catalyst; Temperature; Solvent; Large scale;
97%
2,2'-dibromo-1,1'-binaphthyl
74866-28-7,86688-08-6,150024-49-0

2,2'-dibromo-1,1'-binaphthyl

diphenylphosphonium chloride

diphenylphosphonium chloride

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
2,2'-dibromo-1,1'-binaphthyl; With magnesium; In tetrahydrofuran; at 70 ℃; for 0.5h; Inert atmosphere; Large scale;
diphenylphosphonium chloride; In tetrahydrofuran; at -10 - 20 ℃; for 2h; Temperature; Large scale;
98.4%
binaphthol bis(nonafluoro-n-butanesulfonate)
232264-15-2,232266-05-6,253326-48-6

binaphthol bis(nonafluoro-n-butanesulfonate)

diphenylphosphane
829-85-6

diphenylphosphane

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
diphenylphosphane; With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride; In DMF (N,N-dimethyl-formamide); at 20 - 100 ℃; for 0.5h;
binaphthol bis(nonafluoro-n-butanesulfonate); With 1,4-diaza-bicyclo[2.2.2]octane; In DMF (N,N-dimethyl-formamide); at 100 ℃; for 48h;
77%
2-(diphenylphosphinyl)-2'-(diphenylphosphanyl)-1,1'-binaphthalene
204862-91-9,152646-80-5,183244-55-5

2-(diphenylphosphinyl)-2'-(diphenylphosphanyl)-1,1'-binaphthalene

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With sodium hydroxide; trichlorosilane; 2,3-Dimethylaniline; In toluene;
92%
With hydrogenchloride; sodium hydroxide; trichlorosilane; 2,3-Dimethylaniline; In water; toluene;
92%
C<sub>44</sub>H<sub>32</sub>P<sub>2</sub>S<sub>2</sub>

C44H32P2S2

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With diisobutylaluminium hydride; In toluene; at 100 ℃; for 4h;
80%
With [AlH3(triethylamine)]; In hexane; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;
88 %Chromat.
2,2'-dibromo-1,1'-binaphthyl
74866-28-7,86688-08-6,150024-49-0

2,2'-dibromo-1,1'-binaphthyl

chloro-diphenylphosphine
1079-66-9,74391-44-9

chloro-diphenylphosphine

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With tert.-butyl lithium; In tetrahydrofuran;
78%
With tert.-butyl lithium; Yield given. Multistep reaction; 1.) THF, pentane; -75 deg C, 1 h then -65 deg C, 30 min 2.) THF, pentane; 1 h, -65 deg C then r.t.;
sodium diphenylphosphide
4376-01-6

sodium diphenylphosphide

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With 15-crown-5; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere; Schlenk technique;
binaphthol bis(nonafluoro-n-butanesulfonate)
232264-15-2,232266-05-6,253326-48-6

binaphthol bis(nonafluoro-n-butanesulfonate)

chloro-diphenylphosphine
1079-66-9,74391-44-9

chloro-diphenylphosphine

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl
76144-87-1,76189-55-4,76189-56-5,136655-44-2,98327-87-8

2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl

Conditions
Conditions Yield
With 1,4-diaza-bicyclo[2.2.2]octane; nickel dichloride; zinc; at 100 ℃;

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