Product Name

  • Name

    (2S,3S)-(-)-Bis(diphenylphosphino)butane

  • EINECS
  • CAS No. 64896-28-2
  • Article Data6
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 108-110 °C
  • Formula C28H28P2
  • Boiling Point 529.19 °C at 760 mmHg
  • Molecular Weight 426.478
  • Flash Point 291.15 °C
  • Transport Information
  • Appearance White granular powder
  • Safety 37/39-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 64896-28-2 ((2S,3S)-(-)-Bis(diphenylphosphino)butane)
  • Hazard Symbols IrritantXi
  • Synonyms (2S,3S)-(?)-2,3-Bis(diphenylphosphino)butane;(2S,3S)-Butane-2,3-diylbis(diphenylphosphane);(S,S)-Chiraphos;
  • PSA 27.18000
  • LogP 6.02920

Synthetic route

(3S,4S,5R)-3,4-Bis-diphenylphosphanyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one

(3S,4S,5R)-3,4-Bis-diphenylphosphanyl-5-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-dihydro-furan-2-one

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
Yield given. Multistep reaction;
triphenylphosphine
603-35-0

triphenylphosphine

(2R,3R)-butane-2,3-diyl dimethanesulfonate
81495-76-3

(2R,3R)-butane-2,3-diyl dimethanesulfonate

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
With sodium cyanide; tertiary butyl chloride; sodium thiocyanide; lithium; nickel(II) nitrate Yield given. Multistep reaction;
chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) THF, hexane, -90 deg C, 1.5 h, 2. a) from -90 deg C to RT, 3 h, b) RT, 16 h
View Scheme
lithium diphenylphosphide
65567-06-8, 4541-02-0

lithium diphenylphosphide

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) THF, hexane, -90 deg C, 1.5 h, 2. a) from -90 deg C to RT, 3 h, b) RT, 16 h
View Scheme
-2,3-butandiol di-(4-methylbenzolsulfonat)
64896-27-1

-2,3-butandiol di-(4-methylbenzolsulfonat)

lithium diphenylphosphide
65567-06-8, 4541-02-0

lithium diphenylphosphide

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
In tetrahydrofuran at -4 - 20℃;
Stage #1: -2,3-butandiol di-(4-methylbenzolsulfonat); lithium diphenylphosphide With nickel(II) perchlorate hexahydrate In tetrahydrofuran Inert atmosphere;
Stage #2: With sodium thiocyanate In ethanol Inert atmosphere;
Stage #3: With sodium cyanide In ethanol Inert atmosphere;
[Ni((S,S)-chiraphos)2NCS]NCS

[Ni((S,S)-chiraphos)2NCS]NCS

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
With sodium cyanide In ethanol; water Inert atmosphere;
With sodium cyanide In ethanol; water Inert atmosphere; Heating;
C28H34B2P2

C28H34B2P2

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 110℃; for 1h; Inert atmosphere;
diphenylphosphineborane
41593-58-2

diphenylphosphineborane

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: tert-butylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Sonication
1.2: 20 h / 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 1 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: tert-butylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Sonication
1.2: 20 h / 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 1 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: tert-butylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Sonication
1.2: 20 h / 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 1 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: allylmagnesium bromide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
1.2: 20 h / 20 °C / Inert atmosphere; Sonication
2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 1 h / 110 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
1.2: 20 h / 20 °C / Inert atmosphere
2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 1 h / 110 °C / Inert atmosphere
View Scheme
tris(dibenzylideneacetone)dipalladium (0)

tris(dibenzylideneacetone)dipalladium (0)

[10-bromo-5,15-diphenylporphyrinato]-magnesium(II)
193265-35-9

[10-bromo-5,15-diphenylporphyrinato]-magnesium(II)

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

[PdBr(10,20-diphenylporphyrinatonickel(II))((S,S)-2,3-bis(diphenylphosphino)butane)]

[PdBr(10,20-diphenylporphyrinatonickel(II))((S,S)-2,3-bis(diphenylphosphino)butane)]

Conditions
ConditionsYield
In toluene (Ar); Schlenk technique; P ligand was added to hot (105°C) toluene; Pd compd. was added; stirred for 5 min; Ni complex was added; stirredat 105°C for 2 h; TLC monitoring; cooled to room temp.; concd. (vac.); hexane added; filtered; washed (hexane); dried (vac.); elem. anal.;99%
...Expand
(Pd((CH3)2NC2H4N(CH3)2)(CH3C6H4CHN(CH2C6H5)COC7H7))(1+)*CF3SO3(1-)=(Pd((CH3)2NC2H4N(CH3)2)(C7H7CHN(C7H7)COC7H7))CF3SO3
1116524-79-8

(Pd((CH3)2NC2H4N(CH3)2)(CH3C6H4CHN(CH2C6H5)COC7H7))(1+)*CF3SO3(1-)=(Pd((CH3)2NC2H4N(CH3)2)(C7H7CHN(C7H7)COC7H7))CF3SO3

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

(Pd(((C6H5)2PCHCH3)2)(CH3C6H4CHN(CH2C6H5)COCH2C6H5))(1+)*CF3SO3(1-)=(Pd(((C6H5)2PCHCH3)2)(CH3C6H4CHN(C7H7)COC7H7))CF3SO3

(Pd(((C6H5)2PCHCH3)2)(CH3C6H4CHN(CH2C6H5)COCH2C6H5))(1+)*CF3SO3(1-)=(Pd(((C6H5)2PCHCH3)2)(CH3C6H4CHN(C7H7)COC7H7))CF3SO3

Conditions
ConditionsYield
In dichloromethane under Ar atm. soln. Pd complex and (2S,3S)-bis(diphenylphosphino)butane in CH2Cl2 was stirred for 3.5 h at r.t.; solvent was removed in vacuo, flash chromy. on silica (CH2Cl2-MeOH 19:1); elem. anal.;99%
[bis(μ-chloro[(R)-N,N-dimethyl(α-methylbenzyl)amino-2-C,N]palladium(II))]

[bis(μ-chloro[(R)-N,N-dimethyl(α-methylbenzyl)amino-2-C,N]palladium(II))]

silver trifluoromethanesulfonate
2923-28-6

silver trifluoromethanesulfonate

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

[((R)-(+)-N,N-dimethyl-1-phenylethylamine-N,C)Pd((2S,3S)-2,3-bis(diphenylphosphino)butane)][CF3SO3]

[((R)-(+)-N,N-dimethyl-1-phenylethylamine-N,C)Pd((2S,3S)-2,3-bis(diphenylphosphino)butane)][CF3SO3]

Conditions
ConditionsYield
In dichloromethane (N2) to 1 equiv of Pd-complex were added 2 equiv of diphosphine and 2 equiv of CF3SO3Ag in CH2Cl2, the mixt. was stirred at 25°C for 3 h; sepd., reduced in vac.; elem. anal.;98%
...Expand
methylidenetricobalt nonacarbonyl
15664-75-2

methylidenetricobalt nonacarbonyl

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

[Co3(μ3-CH)(CO)7((2S,3S)-(-)-bis(diphenylphosphino)butane)]

[Co3(μ3-CH)(CO)7((2S,3S)-(-)-bis(diphenylphosphino)butane)]

Conditions
ConditionsYield
In hexane under Ar or N2; a soln. of Co-contg. compd. (22.6E-6 mol) and a ligand (23.5E-6 mol) was heated slowly to reflux under stirring; monitoring by spot TLC (eluent: hexane-CH2Cl2 (2:1 v/v)); the compd. wasconcd. and dried under vac.;98%
trans-bis(triphenylphosphino)Pt(CF3)Cl
71581-10-7

trans-bis(triphenylphosphino)Pt(CF3)Cl

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

(chiraphos)Pt(CF3)Cl

(chiraphos)Pt(CF3)Cl

Conditions
ConditionsYield
In toluene suspn. of Pt-complex and chiraphos was stirred for 24 h at room temp. under N2 (Schlenk flask); concd., Et2O added, ppt. was filtered off, washed with Et2O, recrystd. from CH2Cl2-Et2O; elem. anal.;96%
trans-[(Pt(PPh2)2)2(3,5-(CCC(CPh2)CC)2-C5H3N)2]

trans-[(Pt(PPh2)2)2(3,5-(CCC(CPh2)CC)2-C5H3N)2]

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

cis-[Pt(S,S-chiraphos)(3,5-(CCC(CPh2)CC)2-C5H3N)2Pt(S,S-chiraphos)]

cis-[Pt(S,S-chiraphos)(3,5-(CCC(CPh2)CC)2-C5H3N)2Pt(S,S-chiraphos)]

Conditions
ConditionsYield
In dichloromethane at room temp. for 14 h;96%
Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane)

Pt(N,N′-dicyclohexylimidazol-2-ylidene)(divinyltetramethylsiloxane)

iodine
7553-56-2

iodine

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

(N,N'-dicyclohexylimidazolylidene)Pt((S,S)-Chiraphos)I2

(N,N'-dicyclohexylimidazolylidene)Pt((S,S)-Chiraphos)I2

Conditions
ConditionsYield
In toluene under Ar atm. soln. I2 in toluene was added at 0°C to soln. Pt complex in toluene, soln. ligand in toluene was added at 0°C and stirred at room temp. overnight;96%
...Expand
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)
32993-05-8

chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II)

hexane
110-54-3

hexane

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

toluene
108-88-3

toluene

[Ru(C5H5)Cl((C6H5)2PCH(CH3)CH(CH3)P(C6H5)2)]*0.3C6H14*0.3C7H8

[Ru(C5H5)Cl((C6H5)2PCH(CH3)CH(CH3)P(C6H5)2)]*0.3C6H14*0.3C7H8

Conditions
ConditionsYield
In toluene byproducts: PPh3; (Ar); std. Schlenk technique; soln. of Ru complex and ligand in toluene was stirred at 90°C for 16 h; cooled to room temp.; chromd. (silica gel, toluene, EtOAc); concd. (vac.); petroleum ether added; elem. anal.;96%
...Expand
tris(propionitrile)tricarbonylmolybdenum(0)
103933-26-2

tris(propionitrile)tricarbonylmolybdenum(0)

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

(Mo(CO)3(2(S),3(S)-bis(diphenylphosphino)butane)(NCEt))

(Mo(CO)3(2(S),3(S)-bis(diphenylphosphino)butane)(NCEt))

Conditions
ConditionsYield
In further solvent(s) (Mo(CO)3(NCEt)3) and chir were suspender in propionitrile, immersed for 5 min into ultrasonic bath and stirred for 1 h at 20°C; Et2O was added, ppt. was filtered off, washed with Et2O and dried under vac.; elem. anal.;95%
[(η5-C5H4COCH3)(PPh3)2RuCl]

[(η5-C5H4COCH3)(PPh3)2RuCl]

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

[(η5-C5H4COCH3)((2S,3S)-(-)-Ph2PCMeCHMePPh2)RuCl]

[(η5-C5H4COCH3)((2S,3S)-(-)-Ph2PCMeCHMePPh2)RuCl]

Conditions
ConditionsYield
In benzene thermal reaction, C6H6, 4 h (N2); recrystd. from n-hexane-CH2Cl2; elem. anal.;95%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

bis(methanol)-tetra-μ-benzoato(O,O')-diruthenium(II,III) hexafluorophosphate

bis(methanol)-tetra-μ-benzoato(O,O')-diruthenium(II,III) hexafluorophosphate

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

Δ-(benzoato-O,O′)-bis(S,S-1,2-bis(diphenylphosphino)butane-P,P')ruthenium(II) hexafluorophosphate

Δ-(benzoato-O,O′)-bis(S,S-1,2-bis(diphenylphosphino)butane-P,P')ruthenium(II) hexafluorophosphate

Conditions
ConditionsYield
Stage #1: bis(methanol)-tetra-μ-benzoato(O,O')-diruthenium(II,III) hexafluorophosphate; (2S,3S)-2,3-bis(diphenylphosphino)butane In methanol for 12h; Inert atmosphere; Reflux;
Stage #2: ammonium hexafluorophosphate at -10℃; Inert atmosphere; diastereoselective reaction;		95%
...Expand
dichloro(1,5-cyclooctadiene)platinum(ll)
12080-32-9

dichloro(1,5-cyclooctadiene)platinum(ll)

(2S,3S)-2,3-bis(diphenylphosphino)butane
64896-28-2

(2S,3S)-2,3-bis(diphenylphosphino)butane

PtCl2((2S,3S)-2,3-bis(diphenylphosphino)butane)(II)

PtCl2((2S,3S)-2,3-bis(diphenylphosphino)butane)(II)

Conditions
ConditionsYield
In dichloromethane dissolving of Pt-complex and S,S-chiraphos in CH2Cl2, stirring for 30 min; addn. of MeOH, evapn. of CH2Cl2 under vac., elem. anal.;94%
In dichloromethane N2-atmosphere; 20°C;

(2S,3S)-(-)-Bis(diphenylphosphino)butane Specification

The (2S,3S)-(-)-Bis(diphenylphosphino)butane with CAS registry number of 64896-28-2 is also known as (S,S)-Chiraphos. The systematic name is (2S,3S)-Butane-2,3-diylbis(diphenylphosphane). It belongs to product categories of Asymmetric Synthesis; Phosphine Ligands; Synthetic Organic Chemistry. In addition, the formula is C28H28P2 and the molecular weight is 426.47. This chemical is a white granular powder and should be sealed in cool, dry place away from oxidant.

Physical properties about (2S,3S)-(-)-Bis(diphenylphosphino)butane are: (1)ACD/LogP: 7.56; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9; (4)ACD/LogD (pH 7.4): 9; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 3216258; (8)ACD/KOC (pH 7.4): 3216258; (9)#Freely Rotating Bonds: 7; (10)Flash Point: 291.15 °C; (11)Enthalpy of Vaporization: 77.395 kJ/mol; (12)Boiling Point: 529.19 °C at 760 mmHg.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. SMILES: P(c1ccccc1)(c2ccccc2)[C@H]([C@@H](P(c3ccccc3)c4ccccc4)C)
2. InChI: InChI=1/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1
3. InChIKey: FWXAUDSWDBGCMN-ZEQRLZLVBA
4. Std. InChI: InChI=1S/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1
5. Std. InChIKey: FWXAUDSWDBGCMN-ZEQRLZLVSA-N

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