23152-99-0|1-Ethynyl-4-isopropylbenzene| Ambeed

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Quality Control of [ 23152-99-0 ] Purity: 97% SDS Specification

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Product Citations

Transition Metal‐Free Catalytic C− H Silylation of Terminal Alkynes with bis (Trimethylsilyl) acetylene Initiated by KHMDS

Krzysztof Kuciński ; Grzegorz Hreczycho ;

DOI: 10.1002/cctc.202200794 ChemCatChem,2022,14(18):e202200794.

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.

Purchased from AmBeed: 768-60-5 ; 40307-11-7 ; 171290-52-1 ; 766-83-6 ; 886363-40-2 ; 62452-73-7 ; 1945-84-2 ; 29079-00-3 ; 766-97-2 ; 705-31-7 ; 23152-99-0 ; 14630-40-1 ; 766-47-2 ; 873-73-4 ; 2510-23-8 ; 704-41-6 ; 67237-53-0 ; 160542-02-9 ; 766-49-4 ; 769-26-6

Product Details of [ 23152-99-0 ]

CAS No. :	23152-99-0
Formula :	C₁₁H₁₂
M.W :	144.21
SMILES Code :	C#CC1=CC=C(C(C)C)C=C1
MDL No. :	MFCD03839988
InChI Key :	CODCGGILXPHCLE-UHFFFAOYSA-N
Pubchem ID :	637501

Safety of [ 23152-99-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 23152-99-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.27
Num. rotatable bonds	1
Num. H-bond acceptors	0.0
Num. H-bond donors	0.0
Molar Refractivity	48.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	0.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.7
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	4.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.46
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.54

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.58
Solubility	0.038 mg/ml ; 0.000264 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.68
Solubility	0.03 mg/ml ; 0.000208 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.28
Solubility	0.0759 mg/ml ; 0.000526 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	Low
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-4.35 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	1.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<2.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.6

Application In Synthesis of [ 23152-99-0 ]

* 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 [ 23152-99-0 ]

[ 23152-99-0 ] Synthesis Path-Downstream 1~35

1
α,β-dichloro-4-isopropyl-styrene [ No CAS ]
[ 23152-99-0 ]

References: [1]Chemische Berichte,1900,vol. 33,p. 3261.

2
[ 667-49-2 ]
[ 23152-99-0 ]
[ 75599-92-7 ]
[ 75599-95-0 ]

References: [1]Journal of Organic Chemistry,1981,vol. 46,p. 144 - 147.
[2]Journal of Organic Chemistry,1981,vol. 46,p. 144 - 147.

3
[ 667-49-2 ]
[ 23152-99-0 ]
1,4,4-Trifluoro-2-(4-isopropyl-phenyl)-cyclobut-2-enecarbonyl fluoride [ No CAS ]
2,2,3,4-Tetrafluoro-6-(4-isopropyl-phenyl)-2H-pyran [ No CAS ]

References: [1]Journal of Organic Chemistry,1981,vol. 46,p. 144 - 147.

4
[ 23152-99-0 ]
[ 99255-51-3 ]
[ 99255-60-4 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 630 - 636.

5
[ 23152-99-0 ]
[ 90-02-8 ]
[ 109619-10-5 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1658 - 1663.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1847 - 1853.

6
[ 23152-99-0 ]
[ 35672-49-2 ]

References: [1]Journal of Organic Chemistry,1972,vol. 37,p. 3749 - 3750.

7
[ 23152-99-0 ]
[ 128217-88-9 ]
p-HS-C₆H₄-X (X=Br or F) [ No CAS ]
4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-[4-(4-isopropyl-phenylethynyl)-benzenesulfonyl]-butyric acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3096 - 3100.

8
[ 926008-95-9 ]
[ 23152-99-0 ]
C₂₁H₁₈N₃Cl [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605.

9
[ 23152-99-0 ]
[ 544-92-3 ]
3-(4-isopropylphenyl)propynenitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1533 - 1538.

10
[ 17356-09-1 ]
[ 23152-99-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 1586 - 1605.
[2]Journal of Medicinal Chemistry,2003,vol. 46,p. 5249 - 5257.

11
[ 23152-99-0 ]
[ 109619-13-8 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1658 - 1663.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1847 - 1853.

12
[ 23152-99-0 ]
[ 92831-11-3 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1658 - 1663.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1847 - 1853.
[2]Journal of Organic Chemistry USSR (English Translation),1986,vol. 22,p. 1658 - 1663.
Zhurnal Organicheskoi Khimii,1986,vol. 22,p. 1847 - 1853.

13
[ 23152-99-0 ]
4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-[4-(4-isopropyl-phenylethynyl)-benzenesulfonyl]-butyric acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3096 - 3100.

14
[ 23152-99-0 ]
4,6-diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5249 - 5257.

15
[ 23152-99-0 ]
4-amino-5,6-(bis-4-(2-propyl)phenyl)-7-(4-dimethylaminophenyl)pyrido[2.3-d]pyrimidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 5249 - 5257.

16
[ 23152-99-0 ]
C₁₉H₁₈NS⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 1023 - 1027.

17
[ 122-03-2 ]
[ 23152-99-0 ]

References: [1]Arzneimittel-Forschung/Drug Research,2000,vol. 50,p. 1023 - 1027.

18
[ 23152-99-0 ]
[ 54290-22-1 ]
[ 79135-52-7 ]

Yield	Reaction Conditions	Operation in experiment
11.40 g (87%)	dichlorobis(triphenylphosphine)palladium[II]; copper(I) iodide; In triethylamine;	The crude 4-isopropylphenylacetylene was dissolved in triethylamine (100 mL). 4-iodoisopropylbenzene (12.3 g, 50 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.70 g, 1 mmol), and copper(I) iodide (1.5 g) were added. The reaction was stirred at room temperature for 2 days, heated to reflux for 1 hour, cooled, diluted with hexanes, and filtered. The filtrate was evaporated under reduced pressure. The residue was filtered through a pad of silica gel with hexanes, and the solvent was evaporated to give 11.40 g (87%) of 1,2-bis(4-(2-propyl)phenyl)acetylene.

References: [1]Patent: US6030969,2000,A .

19
[ 1118-02-1 ]
[ 23152-99-0 ]
N-hydroxy-N-[4-[4-(1-methylethyl)phenyl]-3-butyn-2-yl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 22 Preparation of N-Hydroxy-N-[4-[4-(1-methylethyl)phenyl]-3-butyn-2-yl]urea The title compound was prepared according to the procedure of Example 15 using p-isopropylphenylacetylene instead of p-bromophenylacetylene in step (a), and using trimethylsilyl isocyanate instead of methyl isocyanate in step (d). m.p. 154-156 C.; NMR (300 MHz, DMSO-d6), 1.18 (6H, d, J=7 Hz), 1.35 (3H, d, J=7 Hz), 2.89 (1H, m), 5.12 (1H, q, J=7 Hz), 6.55 (2H, s), 7.22 (2H, d, J=7 Hz), 7.31 (2H, d, J=7 Hz), 9.31 (1H, s); MS (M+1)+ 247, (M+NH4)+ 264. Analysis calc'd for C14 H18 N2 O2: C, 68.26; H, 7.36; N, 11.37. Found: C, 67.80, H, 7.27; N, 11.17.

References: [1]Patent: US5476873,1995,A .

20
[ 14221-06-8 ]
[ 23152-99-0 ]
{Mo₂((CH₃)2CHC₆H₄CCH)(O₂CCH₃)((H₂NCH₂)2)4}⁽³⁺⁾*3{O₂CCH₃}^(1-)*2((H₂NCH₂)2) [ No CAS ]

References: [1]Inorganic Chemistry,1991,vol. 30,p. 156 - 158.

21
C₁₂H₁₄Br₂O₂ [ No CAS ]
[ 23152-99-0 ]

References: [1]Chinese Journal of Chemistry,2011,vol. 29,p. 2350 - 2354.

22
[ 3368-21-6 ]
[ 23152-99-0 ]

References: [1]Chinese Journal of Chemistry,2011,vol. 29,p. 2350 - 2354.

23
[ 23152-99-0 ]
[ 21047-57-4 ]
[ 1392492-90-8 ]

References: [1]Organic Letters,2012,vol. 14,p. 4070 - 4073.

24
[ 21047-57-4 ]
[ 122-03-2 ]
[ 23152-99-0 ]

References: [1]Organic Letters,2012,vol. 14,p. 4070 - 4073.

25
[ 23152-99-0 ]
[ 698-02-2 ]
[ 1401560-07-3 ]

References: [1]Journal of Organic Chemistry,2012,vol. 77,p. 9163 - 9170.

26
[ 76334-36-6 ]
[ 23152-99-0 ]
[ 1459714-34-1 ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6707 - 6712.

27
[ 586-61-8 ]
[ 23152-99-0 ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6707 - 6712.

28
[ 57529-04-1 ]
[ 23152-99-0 ]
C₁₅H₁₉ClS₂ [ No CAS ]

References: [1]Chemistry - A European Journal,2015,vol. 21,p. 14328 - 14331.

29
[ 6590-65-4 ]
[ 23152-99-0 ]
C₂₅H₂₅NO₃S [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 5563 - 5568.
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 7737 - 7741.
Angew. Chem.,2016,vol. 128,p. 7868 - 7872,5.
[3]Organic Letters,2019.

30
[ 23152-99-0 ]
4-(3-(4-isopropylphenyl)propioloyl)-3-(4-methylphenylsulfonamido)phenyl 4-methylbenzenesulfonate [ No CAS ]