2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
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2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
structure -
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CAS No:
657408-07-6
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Formula:
C26H35O2P
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Chemical Name:
2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
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Synonyms:
Phosphine,dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)-;Dicyclohexyl(2′,6′-dimethoxy[1,1′-biphenyl]-2-yl)phosphine;2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl;2-(Dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl;Dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine;S-Phos;(2,6-Dimethoxy-1,1′-biphenyl-2-yl)dicyclohexylphosphine;(2′,6′-Dimethoxy-[1,1′-Biphenyl]-2-yl)dicyclohexylphosphine
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CAS No:
2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Basic Attributes
410.53
410.53
2017-001-1
XI1MQ32186
DTXSID90460730
2922299090
Characteristics
18.5
6.7
white crystal
125-127 °C @ Solvent: Acetone
513.3°C at 760 mmHg
330.7±27.6 °C
Refrigerated.
Safety Information
NONH for all modes of transport
3
40
24/25-36/37
Xn
P281
H351
|Warning|H302+H312+H332 (11.11%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 10 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Use and Manufacturing
To a solution of 1, 3-dimethoxybenzene (2 ml, 15.30 mmol) in anhydrous THF (35 ml) at 0° C., nBuLi (6.2 ml, 15.50 mmol) is added to the dropping funnel for 5 min.B) methyl 5-(4-(1H-pyrazol-1-yl)benzyl)-2-amino-3-fluoro-4-methylbenzoate Under a nitrogen stream, lithium chloride (0.32 g), zinc powder (0.50 g) and a stirrer bar were added to a reaction container, and the mixture was heated under reduced pressure at 180 C. for 15 min. After cooling to room temperature, the reaction container was filled with nitrogen, THF (2 mL) and 1, 2-dibromoethane (0.04 g) were added and the mixture was heated until air bubbles were developed. To the mixture was added trimethylsilyl chloride (0.02 g) and the mixture was stirred at 70 C. for 15 min. To the mixture was added 1-(4-(chloromethyl)phenyl)-1H-pyrazole (0.96 g) at room temperature and the mixture was stirred at 70 C. for 2 hr. The reaction mixture was cooled at room temperature, a mixture of palladium acetate (0.02 g), 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (0.06 g) and methyl 2-amino-5-bromo-3-fluoro-4-methylbenzoate (1.0 g) in THF (5 mL) was added dropwise, and the mixture was stirred under a nitrogen atmosphere at 70 C. for 1 hr and then at room temperature overnight. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (1.2 g). MS: [M+H]+ 340.2Synthesis of ethyl (E)-3-(thieno[3, 2-b]thiophen-3-yl)acrylate To a 500 mL sealed tube was added 3-bromothieno[3, 2-b]thiophene (13 g, 59.3 mmol), ethyl acrylate (7.13 g, 71.2 mmol), triethylamine (66.2 mL, 475 mmol), Pd(OAc)2 (0.666 g, 2.97 mmol), dicyclohexyl(2', 6'-dimethoxy-[1, 1'-biphenyl]-2-yl)phosphane (0.244 g, 0.593 mmol) and dimethylformamide (DMF) (100 mL). The mixture was sparged with N2 for about 15 minutes. The resulting mixture was stirred and heated in oil bath at 130 C. for 16 hours. Upon completion, the DMF was removed and the crude product was dissolved in water (100 mL) and DCM (100 mL). The aqueous layers were further extracted with DCM (2*300 mL) and the combined DCM fractions were passed through small pad of silica and concentrated. The resulting product was used in the next reaction without further purification.
suzuki reaction
Computed Properties
Molecular Weight:410.5
XLogP3:6.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:410.23746735
Monoisotopic Mass:410.23746735
Topological Polar Surface Area:18.5
Heavy Atom Count:29
Complexity:441
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl
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