CAS 135139-00-3 (R)-(+)-2,2'-Bis(di(3,5-xylyl)phosphino)-1,1'-binaphthyl (HCID 4189905)

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Basic information

CAS: 135139-00-3
Standard SMILES: Cc1cc(C)cc(P(c2cc(C)cc(C)c2)c2ccc3ccccc3c2-c2c(P(c3cc(C)cc(C)c3)c3cc(C)cc(C)c3)ccc3ccccc23)c1
InChIKey: MXGXXBYVDMVJAO-UHFFFAOYSA-N
Molecular formula: C52H48P2
Average molar mass: 734.9 g/mol
Monoisotopic mass: 734.3231248

Names & identifiers

Preferred name: (R)-(+)-2,2'-Bis(di(3,5-xylyl)phosphino)-1,1'-binaphthyl
IUPAC: [1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane
English name: (S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl
Molecular formula: C52H48P2
Molecular weight: 734.89

Names & synonyms

135139-00-3137219-86-4(R)-(+)-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL(R)-(+)-2,2'-Bis(di(3,5-xylyl)phosphino)-1,1'-binaphthyl1,1'-Binaphthalene-2,2'-diylbis(bis(3,5-dimethylphenyl)phosphine)1,1'-Binaphthalene-2,2'-diylbis[bis(3,5-dimethylphenyl)phosphine]RefChem:406967681-146-8681-153-6(R)-DM-BINAP145416-77-9(S)-DM-BINAP

Show more names

XylbinapRAC-XYLYL-BINAP(S)-3,5-XYLYL-BINAP(S)-(-)-2,2'-bis(di-(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl(S)-(-)-XyL98% (S)-XylBINAP(S)-(-)-XylBINAP(S)-3,5-Xyl-BINAPRAC-3,5-Xylyl-Binap

(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl(R)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthylDM-BINAP[1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphaneMFCD01630821(R)-(+)-XYLBINAP(R)-2,2'-Bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthalene

Properties

Computed structural properties

XLogP: 14.3
Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 7
Heavy atoms: 54
Formal charge: 0
Complexity: 999

Physicochemical properties

Melting point: 203 · 203-206°C
alpha: -172 · -172 º (c=1 in chloroform)
Boiling point: 825.3 · 825.3±65.0 °C(Predicted)
storage temp.: Inert atmosphere,Room Temperature
Water Solubility: Insoluble in water
form: crystal
color: white to pale yellow
optical activity: -172 °, · [α]/D -172°, 20, c =1 in chloroform
InChIKey: MXGXXBYVDMVJAO-UHFFFAOYSA-N
SMILES: C1(C2C=CC=CC=2C=CC=1P(C1=CC(=CC(C)=C1)C)C1=CC(=CC(C)=C1)C)C1C2C=CC=CC=2C=CC=1P(C1=CC(=CC(C)=C1)C)C1=CC(=CC(C)=C1)C
UNSPSC Code: 12352005 · 12352005
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

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 6 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

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

Hazard information

Hazard Classes and Categories · 3 items

Skin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: WGK 3
tsca: No
hs_code: 2931.90.6000
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-37
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Chemistry & industry

Applications · 1 item

UsesCatalyst for:Asymmetric hydrogenation of benzophenoneRegio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives in the presence of chiral biaryl bisphosphine ligandsRegiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolatesLigand controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids to form regioisomeric arylcyclopentenolsPlatinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperatureStereoselective preparation of chiral N,O-biaryls via Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes