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

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

 EINECS N/A
CAS No. 64896-28-2 Density N/A
PSA 27.18000 LogP 6.02920
Solubility N/A 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 N/A 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;

Article Data 6

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

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

64896-28-2

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

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

triphenylphosphine

81495-76-3

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

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;
1079-66-9

chloro-diphenylphosphine

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
65567-06-8, 4541-02-0

lithium diphenylphosphide

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
64896-27-1

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

65567-06-8, 4541-02-0

lithium diphenylphosphide

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

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

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;
41593-58-2

diphenylphosphineborane

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)

193265-35-9

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

64896-28-2

(2S,3S)-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%
1116524-79-8

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

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

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%

(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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