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[ CAS No. 873-73-4 ] {[proInfo.proName]}

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Chemical Structure| 873-73-4
Chemical Structure| 873-73-4
Structure of 873-73-4 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ; DOI:

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C?H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

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Product Details of [ 873-73-4 ]

CAS No. :873-73-4 MDL No. :MFCD00191917
Formula : C8H5Cl Boiling Point : -
Linear Structure Formula :- InChI Key :LFZJRTMTKGYJRS-UHFFFAOYSA-N
M.W : 136.58 Pubchem ID :70118
Synonyms :

Calculated chemistry of [ 873-73-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.39
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 3.21
Log Po/w (WLOGP) : 2.4
Log Po/w (MLOGP) : 3.44
Log Po/w (SILICOS-IT) : 3.11
Consensus Log Po/w : 2.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.2
Solubility : 0.0857 mg/ml ; 0.000627 mol/l
Class : Soluble
Log S (Ali) : -2.88
Solubility : 0.179 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.118 mg/ml ; 0.000861 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 873-73-4 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P210-P240-P241-P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P405-P501 UN#:1325
Hazard Statements:H228-H315-H319-H335 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 873-73-4 ]

* 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 [ 873-73-4 ]

[ 873-73-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 873-73-4 ]
  • [ 4016-63-1 ]
  • 2-Amino-8-(4-chloro-phenylethynyl)-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one [ No CAS ]
  • 2
  • [ 873-73-4 ]
  • [ 7681-65-4 ]
  • [ 63558-65-6 ]
  • [ 393857-01-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;dichlorobis(triphenylphosphine)palladium[II]; In dichloromethane; EXAMPLE 3 Preparation of 4-chloro-5-(4-chlorophenylethynyl)pyrimidine A mixture of 0.6 g of 1-chloro-4-ethynylbenzene, 1.44 g of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong> (J. Chem. Soc. Perkins Trans. I, 1977,621, Allen et al), 7.0 cc of triethylamine, 58 mg of copper iodide and 108 mg of dichlorobis(triphenylphosphine)palladium II was stirred at room temperature under nitrogen for 18 hours. The reaction mixture was evaporated in vacuo. The resulting tan solid was partitioned between water and dichloromethane and the organic extracts washed twice with water, dried over sodium sulfate and evaporated to give a dark brown solid, 1.57 g. The solid was redissolved in dichloromethane and hexanes added to give 120 mg of a beige powder after filtration. The filtrate was purified by column chromatography on silica gel using 1:1 ethyl acetate/dichloromethane as the eluant. The middle rf spot fractions (silica gel TLC in 1:1) were pooled and evaporated to give 0.8 g of a yellow solid, 4-chloro-5-(4-chlorophenylethynyl)-pyrimidine
  • 3
  • [ 873-73-4 ]
  • [ 263351-43-5 ]
  • C20H20ClNO2 [ No CAS ]
  • 6
  • [ 873-73-4 ]
  • [ 154237-70-4 ]
  • 4-(4-chlorophenylethynyl)-3-cyanopyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% General procedure: 4-Bromo-3-cyanopyridine 27 (92 mg, 0.5 mmol) in THF (5 mL)was added to CuI (9.6 mg, 50 lmol), (Ph3P)4Pd (29 mg, 25 lmol)and Na ascorbate (9.9 mg, 50 lmol) in Et3N (5 mL) under Ar. Themixture was stirred at 40 C for 30 min. Phenylethyne 21a(76.5 mg, 0.75 mmol) was added and the mixture was stirred at40 C for 10 h. Evaporation and chromatography (petroleumether/EtOAc 3:1) gave 28a (80 mg, 78%) as an off-white powder.
  • 7
  • [ 873-73-4 ]
  • [ 74-96-4 ]
  • [ 124-38-9 ]
  • [ 20026-96-4 ]
  • 8
  • [ 873-73-4 ]
  • [ 108-95-2 ]
  • [ 42019-78-3 ]
  • 10
  • [ 873-73-4 ]
  • [ 19591-17-4 ]
  • N-(2-((4-chlorophenyl)ethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In acetonitrile; at 20℃;Inert atmosphere; <strong>[19591-17-4]N-(2-iodophenyl)acetamide</strong> (100.0 mg, 0.38 mmol, 1.0 equiv) in CH3CN (5.0 mL) was added sequentially with PdCl2(PPh3)2 (5.4 mg, 0.01 mmol, 0.02 equiv), Ph3P (4.0 mg, 0.02 mmol, 0.04equiv), 1-chloro-4-ethynylbenzene (57.6 mg, 0.42 mmol, 1.1 equiv). The resulting solution was degassed by passing through a steady stream of argon for 30 min (flask 1). In the meantime in another flask, a mixture of CuI (3.0 mg, 0.02 mmol, 0.04 equiv) in Et3N was also degassed bypassing through a steady stream of argon for 30 min (flask 2). After degassing, the mixture ofCuI in Et3N in flask 2 was transferred into the solution in flask 1 using a syringe with wide-boarneedle which resulted in the reaction solution turning yellow and giving white precipitates. The reaction mixture was allowed to stir at room temperature overnight and was quenched byaddition with sat. aq. NH4Cl. The separated aqueous phase was extracted with EtOAc (3x times).The combined organic phases were washed with sat. aq. NaCl, dried over anh. Na2SO4 and concentrated under reduced pressure. The crude material was purified by SiO2 column chromatography eluting with 30-50% EtOAc-hexane to yield 114.6 mg of compound 1d (>99%)as a white solid.
  • 11
  • [ 873-73-4 ]
  • [ 34883-46-0 ]
  • 1-((4-chlorophenyl)ethynyl)-2-phenoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; for 10h;Inert atmosphere; (1)To <strong>[34883-46-0]1-iodo-2-phenoxybenzene</strong> (2g, 6.8mmol)a solution of triethylamine (20 mL) added to 4-chlorophenylacetylene(1.1g, 8.1mmol),Pd(PPh3)2Cl2 (95 mg, 135 mumol), CuI (26 mg, 135 mumol).Under argon protection conditions,After the reaction was carried out for 10 hours,Triethylamine was removed under reduced pressure.The residue was extracted with ethyl acetate (20 mL×3).Then use water (10mL)Wash twice with saturated brine (10 mL) and dry over anhydrous sodium sulfate.Filter and remove the solvent under pressure.The residue was purified by silica gel column chromatography eluting elut1-((4-Chlorophenyl)ethynyl)-2-phenoxybenzene(1.9 g, 92% yield).
  • 12
  • [ 873-73-4 ]
  • [ 6638-05-7 ]
  • C17H16ClN3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With potassium fluoride; sodium azide; silver carbonate; In N,N-dimethyl-formamide; at 50℃; for 6.0h; General procedure: to a solution of phenylacetylene (1a)(0.055 mL, 0.5 mmol), 2,6-di-tert-butyl-4-methylphenol(BHT) (2a) (133 mg, 0.6 mmol), NaN3 (39 mg, 0.6 mmol)and KF (58 mg, 1.0 mmol) in DMF (1 mL) at 50 C, Ag2CO3(41 mg, 0.15 mmol) was added. The reaction mixture wasthen stirred for 6 h when TLC conformed that substrate 1a was consumed. The resulting reaction mixture was cooled toroom temperature and extracted by dichloromethane(3×15 mL). The organic layer was washed with brine(3×40 mL), dried over MgSO4 and concentrated. Purificationof the crude product via flash column chromatography (silicagel; petroleum ether) and concentratinon in vacuo affordedthe desired product of 3a-N2/3a-N1 in 91% yield.
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