(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthyl

HCID 4189906

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Basic information

CAS: 100165-88-6
Standard SMILES: Cc1ccc(P(c2ccc(C)cc2)c2ccc3ccccc3c2-c2c(P(c3ccc(C)cc3)c3ccc(C)cc3)ccc3ccccc23)cc1
InChIKey: IOPQYDKQISFMJI-UHFFFAOYSA-N
Molecular formula: C48H40P2
Average molar mass: 678.8 g/mol
Monoisotopic mass: 678.26052454

Names & identifiers

Preferred name: (S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthyl
IUPAC: [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane
English name: (S)-(-)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL
Molecular formula: C48H40P2
Molecular weight: 678.78

Names & synonyms

100165-88-62,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl153305-67-0RefChem:407671(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1, 1'-binaphthyl623-900-0680-944-399646-28-3(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl(R)-Tol-BINAP(S)-Tol-BINAP(S)-2,2'-BIS(DI-P-TOLYLPHOSPHINO)-1,1'-BINAPHTHYL

Show more names

(S)-T-BINAP(S)-(−(S)-4-Me-BINAP98% (S)-TolBINAP(S)-T-BINAP(S)-(-)-2,2'-Bis(di-p-toLBis(diphenylphosphinothiazide)BisdiptolylphosphinobinaphthylSTolBI

(R)-(+)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl(R)-(+)-TolBINAP(R)-2,2'-bis(di-p-tolylphosphino)-1,1'-binaphthaleneMFCD01311709[1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphaneR-tol-BinapS-tol-Binap(S)-Tol BINAP

Database identifiers

CAS: 100165-88-6、153305-67-0、99646-28-3
PubChem CID: 4189906
DTXSID: DTXSID501379641
EC Number: 623-900-0、677-521-0、680-944-3
Nikkaji: J1.058.034J、J1.783.418E、J134.981C

Properties

Computed structural properties

XLogP: 12.9
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 7
Heavy atoms: 50
Formal charge: 0
Complexity: 897

Physicochemical properties

Melting point: 252 · 252-256 °C
alpha: -160 ° · -160° (c 0.5, C6H6)
Boiling point: 754.4 · 754.4±60.0 °C(Predicted)
storage temp.: Inert atmosphere,Room Temperature
form: Powder
color: White
optical activity: 20 · [α]20/D -156°, c = 0.5 in benzene
Water Solubility: Insoluble in water.
InChIKey: IOPQYDKQISFMJI-UHFFFAOYSA-N
SMILES: P(C1C=CC(C)=CC=1)(C1C=CC(C)=CC=1)C1C=CC2=CC=CC=C2C=1C1C2=CC=CC=C2C=CC=1P(C1C=CC(C)=CC=1)C1C=CC(C)=CC=1
CAS DataBase Reference: 100165 · 100165-88-6(CAS DataBase Reference)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36/37/39
WGK Germany: 3 · 3
TSCA: No
HS Code: 29333990 · 29333990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H228 (16.7%): Flammable solid [Danger Flammable solids]

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Flam. Sol. 2 (16.7%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
tsca: No
hs_code: 29333990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36/37/39
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 2 items

Uses(S)-(-)-2,2'-Bis(di-p-tolylphosphino)-1,1'-binaphthyl is chiral ligand widely used in asymmetric synthesis. It also used as excellent catalysts for asymmetric hydrogenation of alkenes and some cyclic anhydrides. BINAP is used in organic synthesis for enantioselective transformations catalyzed by its complexes of ruthenium, rhodium, and palladium

Uses(S)-T-BINAP reacts with silver nitrate to form (S)-Tol-BINAP·AgNO3, which can catalyze the enantioselective allylation reaction of aldehydes to form enantiopure secondary alcohols. It may be used as a chiral ligand in the palladium catalyzed asymmetric double carbohydroamination of iodoarenes to form α-aminoamides. It can also catalyze the asymmetric N-allylation reaction of ortho-tert-butylanilide derivatives with diallyl carbonate to form chiral N-allyl ortho-tert-butylanilides.