[ CAS No. 321921-71-5 ] {[proInfo.proName]}

Name: 321921-71-5|Di(adamantan-1-yl)(butyl)phosphine|97%
Brand: Ambeed
SKU: A516771
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Quality Control of [ 321921-71-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 321921-71-5 ]

SDS Specification

Alternatived Products of [ 321921-71-5 ]

Product Details of [ 321921-71-5 ]

CAS No. :	321921-71-5	MDL No. :	MFCD05861606
Formula :	C₂₄H₃₉P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTJWUNNIRKDDIV-UHFFFAOYSA-N
M.W :	358.54	Pubchem ID :	11371790
Synonyms :

Calculated chemistry of [ 321921-71-5 ]

Physicochemical Properties

Num. heavy atoms :	25
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	5
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	112.85
TPSA :	13.59 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.85 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.47
Log Po/w (XLOGP3) :	6.53
Log Po/w (WLOGP) :	7.21
Log Po/w (MLOGP) :	6.94
Log Po/w (SILICOS-IT) :	6.8
Consensus Log Po/w :	6.39

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.85
Solubility :	0.00051 mg/ml ; 0.00000142 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.61
Solubility :	0.0000875 mg/ml ; 0.000000244 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.68
Solubility :	0.000753 mg/ml ; 0.0000021 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	7.65

Safety of [ 321921-71-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	2811
Hazard Statements:	H301+H311+H331-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 321921-71-5 ]

* 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.

Upstream synthesis route of [ 321921-71-5 ]
Downstream synthetic route of [ 321921-71-5 ]

[ 321921-71-5 ] Synthesis Path-Upstream 1~7

1
[ 157282-19-4 ]
[ 321921-71-5 ]

Reference： [1] Patent: US2004/68131, 2004, A1,
[2] Patent: US2004/68131, 2004, A1,

2
[ 109-65-9 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Yield	Reaction Conditions	Operation in experiment
13 mmol, 85%	With n-butyllithium In toluene	4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 4.1 g (30 mmol) of 1-butyl bromide were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3*), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure. Yield: 4.6 g (13 mmol, 85percent) of di(1-adamantyl)-n-butylphosphine. The product can be recrystallized from di-n-butyl ether (m.p.: 102° C.). ³¹P{¹H} NMR (162.0 MHz, C₆D₆, 297 K): δ=24.6

Reference： [1] Patent: US2004/68131, 2004, A1,

3
[ 109-69-3 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Yield	Reaction Conditions	Operation in experiment
13 mmol, 85%	With n-butyllithium In toluene	4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 2.8 g (30 mmol) of 1-butyl chloride were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3*), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure. The product was purified by bulb tube distillation under fine vacuum. Yield: 4.6 g (13 mmol, 85percent) of di(1-adamantyl)-n-butylphosphine.

Reference： [1] Patent: US2004/68131, 2004, A1,

4
[ 542-69-8 ]
[ 131266-79-0 ]
[ 321921-71-5 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 23, p. 9727 - 9732

5
[ 542-69-8 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Reference： [1] Synthesis, 2004, # 6, p. 935 - 941

6
[ 109-72-8 ]
[ 157282-19-4 ]
[ 321921-71-5 ]

Reference： [1] Synlett, 2000, # 11, p. 1589 - 1592

7
[ 847616-85-7 ]
[ 321921-71-5 ]
[ 1375477-29-4 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16856 - 16868,13
[2] Journal of the American Chemical Society, 2012, vol. 134, # 40, p. 16856 - 16868

[ 321921-71-5 ] Synthesis Path-Downstream 1~46

1
[ 109-72-8 ]
[ 157282-19-4 ]
[ 321921-71-5 ]

Reference： [1]Synlett,2000,p. 1589 - 1592

2
[ 542-69-8 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Reference： [1]Synthesis,2004,p. 935 - 941

3
[ 5111-65-9 ]
[ 321921-71-5 ]
[ 63444-51-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate;	Example 82 Heck Coupling with Ethylene: 50 mmol of 6-methoxy-2-bromonaphthalene and 60 mmol of potassium carbonate are dissolved in 40 ml of NMP, and 0.001 mol % of Pd(OAc)2 and 0.004 mol % of butyldiadamantyl-phosphine are added. The mixture is placed under an ethylene pressure of 20 bar and stirred at 130 C. until conversion is complete. After filtration of the insoluble constituents, washing with alkaline solution and distillation, 92% of 6-methoxy-2-vinylnaphthalene is obtained.

Reference： [1]Patent: US2004/68131,2004,A1

4
[ 109-65-9 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Yield	Reaction Conditions	Operation in experiment
4.6 g (13 mmol, 85%)	With n-butyllithium; In toluene;	4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 4.1 g (30 mmol) of 1-butyl bromide were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3*), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure. Yield: 4.6 g (13 mmol, 85%) of di(1-adamantyl)-n-butylphosphine. The product can be recrystallized from di-n-butyl ether (m.p.: 102 C.). 31P{1H} NMR (162.0 MHz, C6D6, 297 K): delta=24.6

Reference： [1]Patent: US2004/68131,2004,A1

5
[ 109-69-3 ]
[ 131211-27-3 ]
[ 321921-71-5 ]

Yield	Reaction Conditions	Operation in experiment
4.6 g (13 mmol, 85%)	With n-butyllithium; In toluene;	4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 2.8 g (30 mmol) of 1-butyl chloride were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3*), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure. The product was purified by bulb tube distillation under fine vacuum. Yield: 4.6 g (13 mmol, 85%) of di(1-adamantyl)-n-butylphosphine.

Reference： [1]Patent: US2004/68131,2004,A1

6
[ 623-12-1 ]
[ 321921-71-5 ]
[ 768-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;Zinc chloride; palladium diacetate; In tetrahydrofuran;	Example 80 Coupling of Aryl Chlorides with Organozinc Compounds: 50 mmol of anhydrous zinc chloride (dissolved in 40 ml of THF) were added at 0 C to a suspension of 50 mmol of ethynyllithium-ethylenediamine complex in 40 ml of THF. After heating to RT for half an hour, the solution was again cooled to 0 C. and 40 mmol of 4-chloroanisole, 0.05 mol % of Pd(OAc)2 and 0.1 mol % of butyldiadamantylphosphine were added. The reaction mixture was stirred at 25 to 50 C. until conversion was complete. 2 M HCl solution was then added to the reaction solution. After extraction with ether, washing of the ether phase and distillation, 76% of p-methoxyphenylacetylene is obtained.

Reference： [1]Patent: US2004/68131,2004,A1

7
[ 157282-19-4 ]
[ 321921-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane;	Example 1 Di (1-adamantyl)-n-butylphosphine (n-BuPAd2) (Variant 1): 11 ml of a 1.6 M solution of n-butyllithium in hexane (18 mmol) were added dropwise to 5.0 g (15 mmol) of diadamantylchlorophosphine in 250 ml of absolute tetrahydrofuran. The solution was refluxed for 1 h. After removal of the solvent under vacuum, the residue was distilled under vacuum. 2.6 g (7.3 mmol, 49%) of diadamantyl-n-butylphosphine were obtained. Di(1-adamantyl)-n-butylphosphine (n-BuP(1-Ad)2) (Variant 2):
	With n-butyllithium; In tetrahydrofuran; hexane;	MS (E. I., 70 eV):. m/z: 358 (M+, 12%); 135 (Ad+, 100%) MS (C.I., isobutene): m/z: 359 (M++H, 100%) Di(1-adamantyl)-n-butylphosphine (n-BuP(1-Ad)2) (Variant 3): 1.5 g (4.5 mmol) of di(1-adamantyl)chlorophosphine were placed in 40 ml of absolute THF, and 5.ml of a 1.6 M solution of n-BuLi in hexane (8 mmol) were added using a syringe, with stirring. The mixture was refluxed for 2 h, the solvent was distilled off under reduced pressure and the residue was distilled in a bulb tube. Yield: 0.77 g (2.1 mmol, 48%) of di(1-adamantyl)-n-butylphosphine. Di(1-adamantyl)-n-butylphosphine (n-BuP(1-Ad)2) (Variant 4):

Reference： [1]Patent: US2004/68131,2004,A1
[2]Patent: US2004/68131,2004,A1

8
[ 88946-80-9 ]
[ 321921-71-5 ]
[(1,3,5-C₆H₃(i)Pr₃)RuCl₂(PAd₂Bu)] [ No CAS ]

Reference： [1]Organometallics,2005,vol. 24,p. 5792 - 5794

9
[ 88946-80-9 ]
[ 321921-71-5 ]
[RuCl₂(PAd₂Bu)]3 [ No CAS ]

Reference： [1]Organometallics,2005,vol. 24,p. 5792 - 5794

10
dichloro(1,5-cyclooctadiene)ruthenium(II) [ No CAS ]
[ 321921-71-5 ]
[RuCl₂(PAd₂Bu)]3 [ No CAS ]

Reference： [1]Organometallics,2005,vol. 24,p. 5792 - 5794

11
[ 52462-29-0 ]
[ 321921-71-5 ]
[RuCl₂(PAd₂Bu)]3 [ No CAS ]

Reference： [1]Organometallics,2005,vol. 24,p. 5792 - 5794

12
[ 1271-03-0 ]
[ 321921-71-5 ]
[ 1006871-91-5 ]

Reference： [1]Organometallics,2008,vol. 27,p. 297 - 300
[2]Journal of the American Chemical Society,2008,vol. 130,p. 15549 - 15563
[3]Organometallics,2008,vol. 27,p. 297 - 300

13
[ 39929-21-0 ]
[ 321921-71-5 ]
[ 866395-15-5 ]

Reference： [1]Inorganic Chemistry Communications,2008,vol. 11,p. 409 - 412
[2]Australian Journal of Chemistry,2014,vol. 67,p. 481 - 499

14
Pd₂Br₂(P(C₄H₉)(C₁₀H₁₅)2)2(C₆H₄CF₃)2 [ No CAS ]
[ 321921-71-5 ]
[ 1071965-74-6 ]