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76189-55-4 - (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98% - (R)-(+)-BINAP - B23785 - Alfa Aesar

B23785 (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%

CAS Number
76189-55-4
Synonyms
(R)-(+)-BINAP

Size Price ($) Quantity Availability
250mg 26.92
1g 77.04
5g 362.40
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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl, 98%

MDL
MFCD00010805

Chemical Properties

Formula
C44H32P2
Formula Weight
622.69
Melting point
239-241°
Sensitivity
Air Sensitive
Solubility
Insoluble in water.

Applications

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthy is used as a chiral ligand for metal mediated asymmetric catalysis.

Notes

Air sensitive. Incompatible with oxidizing agents.

Literature References

Chiral chelating ligand which is the basis of a number of homogeneous catalysts which promote hydrogenation reactions with very high enantiomeric excesses. Rh complexes catalyze the asymmetric hydrogenation of ɑ-acylaminoacrylic acids: J. Am. Chem. Soc., 102, 7932 (1980), and the isomerization of allylamines to chiral enamines: J. Chem. Soc., Chem. Commun., 600 (1982); Synthesis, 665 (1991). Asymmetric hydrogenation of ß-keto esters is achieved with a Ru based catalyst: J. Org. Chem., 57, 6691 (1992). For preparation of a cycloocta-1,5-diene Rh complex and use in enantioselective hydrogenation reaction, see: Org. Synth. Coll., 8, 183 (1993). For a review of the use of Ru BINAP complexes in asymmetric hydrogenation, see: Acta Chem. Scand., 50, 380 (1996).

Reviews: BINAP catalysis: Acc. Chem. Res., 23, 345 (1990); binaphthylic derivatives as chiral auxiliaries: Synthesis, 503 (1992); advances in biaryl-type biphosphne ligands: Tetrahedron, 61, 5405 (2005).

Shuto, Y.; Yamamura, T.; Tanaka, S.; Yoshimura, M.; Kitamura, M. Asymmetric NaBH4 1,4-Reduction of C3-Disubstituted 2-Propenoates Catalyzed by a Diamidine Cobalt Complex. ChemCatChem 2015, 7 (10), 1547-1550.

Tani, Y.; Kuga, K.; Fujihara, T.; Terao, J.; Tsuji, Y. Copper-catalyzed C-C bond-forming transformation of CO2 to alcohol oxidation level: selective synthesis of homoallylic alcohols from allenes, CO2, and hydrosilanes. Chem. Commun. 2015, 51 (65), 13020-13023.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,1223
Beilstein
4914063
Harmonized Tariff Code
2931.90
TSCA
No

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