[ CAS No. 77876-39-2 ] {[proInfo.proName]}

Name: 77876-39-2|(2S,4S)-Pentane-2,4-diylbis(diphenylphosphine)|98%
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SKU: A943826
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Quality Control of [ 77876-39-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 77876-39-2 ]

Product Details of [ 77876-39-2 ]

CAS No. :	77876-39-2	MDL No. :	MFCD00058923
Formula :	C₂₉H₃₀P₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CTYPJIUQROQJBG-DQEYMECFSA-N
M.W :	440.50	Pubchem ID :	2734567
Synonyms :

Safety of [ 77876-39-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 77876-39-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 77876-39-2 ]

[ 77876-39-2 ] Synthesis Path-Downstream 1~7

1
[ 77876-39-2 ]
[ 74-88-4 ]
[ 77876-41-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	In ethanol at 25℃; for 12h;

Reference： [1]MacNeil, Patricia A.; Roberts, Nicholas K.; Bosnich, B. [Journal of the American Chemical Society, 1981, vol. 103, # 9, p. 2273 - 2280]

2
[ 850346-91-7 ]
[ 77876-39-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene for 20h; Heating / reflux;	7 The complex cis-RuCl2(PPh3)2[2-(H2NCH2)CSH4N] (5) (303 mg, 0.377 mmol) and (S,S)-(-)-Skewphos (166 mg, 0.377 mmol) were suspended in 5 ml toluene. The mixture is refluxed for 20 hours; the solution volume is then reduced to one half and the complex is precipitated by adding 2 ml of pentane. The solid obtained is filtered off, and dried under reduced pressure. Yield: 200 mg (74%). Elemental analysis (%) calculated for C35H38Cl2N2P2Ru: C, 58.34; H, 5.32 ; N, 3.89; found: C, 58.06; H, 5.17; N, 3.63. ¹H NMR (200.1 MHz, CDCl3, 20 °C, TMS) : δ 8.78 (d, J (HH) 3.1 Hz, 1 H; ortho-C5H4N), 7.95-6.69 (m, 23H; aromatic protons), 4.20 (wide s, 1 H; NH), 3.61 (d, J (HH) 15.6 Hz, 1 H; CHN), 3.37 (m, 1 H; PCH), 3.07 (m, 1 H; PCH), 2.81 (wide s, 1 H; CHN), 2.33-1.63 (m, 2H; CH2), 1.25 (wide s, 1H; NH), 1.16 (dd, J (HP), = 7.2, 13.6 Hz, 3H; CH3), 0.76 (dd, J (HP), = 7.0,11.6, 3H; CH3). ¹3C {¹H} NMR (50.3 MHz, CDCl3, 20 °C, TMS) : δ 158.4 (s, NCCH2), 149.6 (s, NCH), 139.8-119.3 (m, aromatic C), 51.5 (s, CH2N), 37.8 (s; CH2), 33.5 (d, J (CP) 27.2 Hz; CHP), 20.3 (d, J (CP) 32.1 Hz; CHP), 18.9 (d, J (CP) 6.6 Hz; CH3), 17.7 (d, J (CP) 1.6 Hz; CH3). 3¹P {¹H} NMR (81.0 MHz, CDCl3, 20 °C, H3PO4) : δ 64.8 (d, J (PP) 44.7 Hz), 45.3 (d, J (PP) 44.7 Hz).

Reference： [1]Current Patent Assignee: UNIVERSITY OF UDINE - WO2005/105819, 2005, A1 Location in patent: Page/Page column 15

3
[ 850346-91-7 ]
[ 77876-39-2 ]
[ 850346-95-1 ]

Yield	Reaction Conditions	Operation in experiment
74%	In toluene for 20h; Heating / reflux;	7 The complex cis-RuCl2(PPh3)2[2-(H2NCH2)C5H4N] (5) (303 mg, 0.377 mmol) and (S,S)-(-)-Skewphos (166 mg, 0.377 mmol) were suspended in 5 ml toluene. The mixture is refluxed for 20 hours; the solution volume is then reduced to one half and the complex is precipitated by adding 2 ml of pentane. The solid obtained is filtered off, and dried under reduced pressure.Yield: 200 mg (74%). Elemental analysis (%) calculated for C35H38Cl2N2P2Ru: C, 58.34; H, 5.32; N, 3.89; found: C, 58.06; H, 5.17; N, 3.63. 1H NMR (200.1 MHz, CDCl3, 20° C., TMS): δ 8.78 (d, J(HH)=3.1 Hz, 1H; ortho-C5H4N), 7.95-6.69 (m, 23H; aromatic protons), 4.20 (wide s, 1H; NH), 3.61 (d, J(HH)=15.6 Hz, 1H; CHN), 3.37 (m, 1H; PCH), 3.07 (m, 1H; PCH), 2.81 (wide s, 1H; CHN), 2.33-1.63 (m, 2H; CH2), 1.25 (wide s, 1H; NH), 1.16 (dd, J(HP), J(HH)=7.2, 13.6 Hz, 3H; CH3), 0.76 (dd, J(HP), J(HH)=7.0, 11.6, 3H; CH3). 13C{1H} NMR (50.3 MHz, CDCl3, 20° C., TMS): δ 158.4 (s, NCCH2), 149.6 (s, NCH), 139.8-119.3 (m, aromatic C), 51.5 (s, CH2N), 37.8 (s; CH2), 33.5 (d, J(CP)=27.2 Hz; CHP), 20.3 (d, J(CP)=32.1 Hz; CHP), 18.9 (d, J(CP)=6.6 Hz; CH3), 17.7 (d, J(CP)=1.6 Hz; CH3). 31P{1H} NMR (81.0 MHz, CDCl3, 20° C., H3PO4): δ 64.8 (d, J(PP)=44.7 Hz), 45.3 (d, J(PP)=44.7 Hz).

Reference： [1]Current Patent Assignee: UNIVERSITY OF UDINE - US2008/249308, 2008, A1 Location in patent: Page/Page column 6

4
[ CAS Unavailable ]
[ 77876-39-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With silver tetrafluoroborate In methanol at 20℃; for 24h; Darkness; Inert atmosphere; Schlenk technique; Glovebox;	2.2.1. Chiral organometallic complexes General procedure: Both commercial and in house prepared chiral organometallic Ru, Rh and Ir complexes (Table 1 and Scheme 1) were used. Ir based complexes IrCl(COD)-(S,S)-BDPP (A, Table 1 and Scheme 1) and [IrCl-(S)-BINAP]2 (B, Table 1 and Scheme 1) were synthesized as reported elsewhere [45,46]. For IrCl(COD)-BDPP, A: a mixture of di-μ-chloro-1.5 (COD) di-iridium (0.004 mmol), (S,S)- BDPP (0.008 mmol) and AgBF4 (0.009 mmol) in 5 mL of methanol was stirred at room temperature for 24 h in the absence of light. The resulting AgCl was removed by filtration and the mixture reduced under vacuum to yield a bright red solid precipitate. The obtained precipitate was recrystallized in 30 mL of diethyl ether, washed three times with 3 mL of diethyl ether and dried overnight under vacuum. [IrCl(S)-BINAP]2 B: the active complex was made prior to hydrogenation by mixing the iridium complex IrCl(COD) (0.004 mmol) with BINAP (0.008 mmol) in methylene chloride at 25 °C for 10 min. RuCl(p-cymene)[(S,S)-Ts-DPEN] (C, Table 1 and Scheme 1) was purchased from Sigma-Aldrich while RuOTf(pcymene)[(S,S)-Ts-DPEN] (D, Table 1 and Scheme 1) complex was prepared as follows: [RuCl2(p-cymene)]2 (0.5 mmol), (S,S)-TsDPEN (1 mmol) and 7 mL CH2Cl2 were charged in a Schlenk and stirred for 5 min at room temperature, then 7 mL of water was added. The resulting layers were separated and the CH2Cl2 layer was dried with CaCl2, filtered and the CH2Cl2 removed under reduced pressure. The resulting solid (0.34 mmol) was reacted with CF3SO3H (TfOH, triflic acid) (0.34 mmol) in 3 mL THF within a Schlenk tube on stirring for 1 h. The precipitate was filtered and washed with THF. [Rh(COD)(S,S)-DIPAMP][BF4] (E, Table 1 and Scheme 1) and [Rh(COD)(R,R)-Me-DuPHOS][BF4] (F, Table 1 and Scheme 1) complexes were purchased from Strem Chemicals.

Reference： [1]Podolean, Iunia; Hardacre, Christopher; Goodrich, Peter; Brun, Nicolas; Backov, Rénal; Coman, Simona M.; Parvulescu, Vasile I. [Catalysis Today, 2013, vol. 200, # 1, p. 63 - 73]

5
[ 1097204-17-5 ]
[ 77876-39-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: (2S,4S)-2,4-bis(diphenylphosphino)pentane With tris(triphenylphosphine)ruthenium(II) chloride In toluene for 2h; Reflux; Inert atmosphere; Stage #2: 1-(benzo[h]quinolin-2-yl)methanamine With triethylamine In isopropyl alcohol at 110℃; for 2h; Inert atmosphere;	12 Example 12: Synthesis of the complex RuCl[(S,S)-(-)-Skewphos](CNN) (14) (mixture of two diastereomers in a 1:0.23 ratio) The complex RuCl2(PPh3)3 (4) (0.150 g, 0.156 mmol) was reacted with (S,S)-(-)-Skewphos (89 mg, 0.202 mmol) in 3 ml of toluene. The suspension was refluxed for 2 hours, toluene was evaporated, and HCNN-H (1) (36 mg, 0.172 mmol), triethylamine (0.22 ml, 1.58 mmol) and 2-propanol (2 ml) were added. The mixture was then heated again under reflux (110 C) for 2 hours. The precipitate obtained by addition of pentane was filtered off, and washed with pentane (3 x 3 ml). The solid was suspended in dichloromethane (0.5 ml) and kept at -20 C overnight. After filtration, the solution volume was reduced to one half and pentane was added (2 ml). The precipitate was filtered off, washed with pentane (1 x 2 ml) and dried under reduced pressure. Yield 70mg (57%). Elemental analysis (%) calculated for C43H41ClN2P2Ru: C, 65.85; H, 5.27; N, 3.57; Found C, 66.06; H, 5.37; N, 3.63. 1H NMR (200.1 MHz, CD2Cl2, 20 °C TMS): δ 8.31-5.80 (m, 27H; aromatic protons), 4.42 (s), 4.20 (d, J(HH) = 3.4 Hz), 3. 68 (s broad), 3.37 (m), 3. 03 (m), 2.78 (s broad), 2.36 (q, J(HH) = 13.5 Hz), 2. 00-1.40 (m), 1.35 (t, J(HH) = 7.4 Hz), 1.29 (dd, J(HP), J(HH) = 14.5, 7.3 Hz), 0.91 (m broad), 0.76 (s broad), 0.55 (dd, J(HP), J(HH) = 6.9, 11.4 Hz). 13C{1H) NMR (50.3 MHz, CD2Cl2, 20 °C): δ 178.5 (m; CRu), 159.3-116.2 (m; aromatic carbons), 51.3 (d, J(CP) = 1.5 Hz; CH2N), 37.9 (m; CH2), 33.0 (m; PCH), 32.6 (m; PCH), 20.1 (s; CH3), 19.5 (d, J(CP) = 6.1 Hz; CHCH3) 17.5 (d, J(CP) = 6.5 Hz; CHCH3). 31P{1H} NMR (81.0 MHz, CD2Cl2, 20 °C, H3PO4): δ 66.2 (d, J(PP) = 46.1 Hz), 47.8 (d, J(PP) = 46.2 Hz), principal product; 64.4 (d, J(PP) = 48.7 Hz), 53.3 (d, J(PP) = 48.7 Hz).

Reference： [1]Current Patent Assignee: UNIVERSITY OF UDINE - EP2178843, 2013, B1 Location in patent: Paragraph 0073

6
[ 1637241-10-1 ]
[ 77876-39-2 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: cis-[RuCl₂((S)-8-amino-5,6,7,8-tetrahydroquinoline)(PPh₃)₂]; (2S,4S)-2,4-bis(diphenylphosphino)pentane In dichloromethane at 20℃; for 0.5h; Stage #2: In toluene at 110℃; for 24h;	c-[RuCl₂((S)-CAMPY) ((2R,4R)-(-)-2,4-bis-(diphenylphosphine)pentane)] ((S),(R,R)-8) General procedure: Complex 3 (50 mg, 0.059 mmol) was added into a solution of ((2R,4R)-(-)-2,4-Bis-(diphenylphosphine)pentane) (BDPP) in dichloromethane (0.059mmol in 8ml). After stirring at room temperature for 30min, solvent was evaporated under reduced pressure. Toluene (8ml) was added to the solid and the yellow solution was heated to 110°C for 24h. A yellow solid was obtained upon partially elimination of the solvent under reduced pressure to about 2ml and by adding 10ml of degassed hexane (40mg; yield 88%). 31P NMR (121.5MHz, CDCl3, 298K): δ ppm 65.05 (d, J=44.5Hz, 1P, Pβ), 45.30 (d, J=44.5Hz, 1P, Pα). 1H NMR (400.1MHz, CDCl3, 298K): δ ppm 8.71 (m, 1H, H2N), 7.69 (m, 5H, PhPα), 7.60-7.49 (m, 5H, PhPα), 7.47-7.37 (m, 5H, PhPβ), 7.18 (t, J=7.90Hz, 1H, H4N), 7.12-7.04 (m, 5H, PhPβ), 6.74 (t, J=6.60Hz, 1H, H3N), 3.74 (t, J=10.8Hz, 1H, NH2N), 3.50-3.34 (m, 1H, CHPβ), 3.16-3.01 (m, 1H, CHPα), 2.91-2.78 (m, 1H, H8N), 2.66-2.59 (m, 2H, CH2N), 2.30-2.26 (m, 1H, CH2P), 1.83-1.74 (m, 2H, CH2N, CH2P), 1.60-1.50 (m, 2H, CH2N),1.30-1.25 (m, 2H, CH2N, NH2N), 1.19 (dd, J=13.6, 7.2Hz, 3H, CH3Pα), 0.83 (dd, J=11.6, 7.0Hz, 3H, CH3Pβ). 13C NMR (100.6MHz, CDCl3, 298K): δ ppm 148.8, 136.2-123.9 (aromatic carbons), 59.6, 38.3, 34, 27.57, 22.1, 20.5, 19.3, 18.2. C38H42Cl2N2P2Ru, PM 760, calc. C 60.00H 5.57 N 3.68; found C 59.87 H 5.52 N 3.60.

Reference： [1]Zerla, Daniele S.; Rimoldi, Isabella; Cesarotti, Edoardo; Facchetti, Giorgio; Pellizzoni, Michela; Fusè, Marco [Journal of Organometallic Chemistry, 2014, vol. 771, p. 2 - 8]

7
[ CAS Unavailable ]
[ 77876-39-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With diethylamine In toluene at 60℃; for 5h; Inert atmosphere; Schlenk technique;	6 Example 6 Synthesis of (S,S)-Skewphos Under an argon atmosphere, into a 50 mL Schlenk flask were added (2S,4S)-Skewphos-BH3 (1.00 g) [mw. 468.17, 2.14 mmol] and diethylamine (23 mL) [d=0.70, mw. 73.14, 220.1 mmol], and the mixture was stirred at 60° C. for 5 hr. After cooling in an ice bath, methanol (23 mL) was added, and the mixture was stirred in an ice bath for 20 min. The mixture was concentrated under reduced pressure, dehydrated methanol for organic synthesis (23 mL) was added, and the mixture was suspended by stirring in an ice bath for 1 hr. After filtration under reduced pressure, the crystals were washed with cold methanol and dried at room temperature under normal pressure to give the object compound. White crystalline powder, 506.5 mg, yield 54%, 1H-NMR (500 MHz, CDCl3, TMS) δ 0.99 (dd, J=15.3 Hz, 6.8 Hz, 6H), 1.30-1.41 (m, 2H), 2.43-2.56 (m, 2H), 7.24-7.34 (m, 8H), 7.37-7.50 (m, 8H). 13C-NMR (125 MHz, CDCl3, CDCl3) δ15.61-15.74 (m), 27.17-27.34 (m), 36.31-36.61 (m), 128.25-128.35 (m), 128.50-128.90 (m), 133.18-133.92 (m), 136.38-137.57 (m). 31P-NMR (202 MHz, CDCl3, H3PO4) 5-0.36 (s).
	With 1,4-diaza-bicyclo[2.2.2]octane In toluene at 90℃; for 18h;

Reference： [1]Current Patent Assignee: ASTENA HOLDINGS CO LTD - US2015/51416, 2015, A1 Location in patent: Paragraph 0297
[2]Wang, Guangzhu; Shen, Chaoren; Ren, Xinyi; Dong, Kaiwu [Chemical Communications, 2022, vol. 58, # 8, p. 1135 - 1138]

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[ 77876-39-2 ]

A713973[ 96183-46-9 ]

(2R,4R)-Pentane-2,4-diylbis(diphenylphosphine)

Reason: Optical isomers

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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H240	Heating may cause an explosion
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 77876-39-2 ] {[proInfo.proName]}

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[ 77876-39-2 ] Synthesis Path-Downstream 1~7

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