80151-33-3|3-(3-Chlorophenyl)prop-2-yn-1-ol| Ambeed

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Quality Control of [ 80151-33-3 ] Purity: 95% SDS Specification

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NMR

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Product Details of [ 80151-33-3 ]

CAS No. :	80151-33-3
Formula :	C₉H₇ClO
M.W :	166.60
SMILES Code :	OCC#CC1=CC=CC(Cl)=C1
MDL No. :	MFCD04039064
InChI Key :	JSWQDMZGLWMJEG-UHFFFAOYSA-N
Pubchem ID :	4074324

Safety of [ 80151-33-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 80151-33-3 ]

* 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 [ 80151-33-3 ]

[ 80151-33-3 ] Synthesis Path-Downstream 1~35

1
[ 50-00-0 ]
[ 766-83-6 ]
[ 80151-33-3 ]

References: [1]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 954 - 959.
[2]Journal of Organic Chemistry,2017,vol. 82,p. 9066 - 9074.
[3]European Journal of Organic Chemistry,2021,vol. 2021,p. 6777 - 6780.

2
[ 80151-33-3 ]
[ 41412-81-1 ]

References: [1]Bulletin of the Chemical Society of Japan,1973,vol. 46,p. 954 - 959.

3
[ 80151-33-3 ]
[ 1026840-30-1 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1084 - 1091.
[2]Journal of the American Chemical Society,2012,vol. 134,p. 12751 - 12757.

4
[ 625-99-0 ]
[ 107-19-7 ]
[ 80151-33-3 ]

Yield	Reaction Conditions	Operation in experiment
>= 99%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine; at 20℃;Inert atmosphere;	General procedure: A round-bottomed flask containing a magentic stirbar and iodobenzene (911.5 mg, 4.468 mmol,1.0 equiv) was added with PdCl2(PPh3)2 (62.9 mg, 0.0896 mmol, 0.02 equiv), CuI (34.9 mg, 0.183mmol, 0.04 equiv) and 5.0 mL of Et3N. The resulted mixture was thoroughly degassed by a steadystream of argon for 15 min before propargyl alcohol (0.14 mL, 270.2 mg, 4.820 mmol, 1.1 equiv)was added via syringe. Ther resulted reaction mixture was allowed to stir at room temperatureunder argon overnight. The reaction mixture was diluted with saturated aqueous NH4Cl and theseparated aqueous layer was extracted with 3xEtOAc. Combined organic phases were washed withsaturated aqueous NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to givea crude material. The crude material was purified by SiO2 column chromatography eluting with10% EtOAc-hexane to give the desired product 1a as a brown oil (451.5 mg, 76%);.

References: [1]Synlett,2022.
[2]Journal of the American Chemical Society,2012,vol. 134,p. 12751 - 12757.
[3]Journal of the American Chemical Society,2010,vol. 132,p. 11881 - 11883.
[4]Journal of Medicinal Chemistry,1998,vol. 41,p. 2524 - 2536.
[5]Journal of Medicinal Chemistry,1998,vol. 41,p. 1084 - 1091.
[6]Chemistry - A European Journal,2014,vol. 20,p. 5910 - 5913.
[7]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3878 - 3882.
[8]Angewandte Chemie - International Edition,2018,vol. 57,p. 8734 - 8738.
Angew. Chem.,2018,vol. 130,p. 8870 - 8874,5.
[9]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1108 - 1116.
[10]Organic Letters,2020,vol. 22,p. 3765 - 3769.
[11]European Journal of Organic Chemistry,2021,vol. 2021,p. 1553 - 1558.
[12]New Journal of Chemistry,2021,vol. 45,p. 16430 - 16433.

5
[ 524-38-9 ]
[ 80151-33-3 ]
2-[3-(3-Chloro-phenyl)-prop-2-ynyloxy]-isoindole-1,3-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2524 - 2536.

6
[ 80151-33-3 ]
[ 198143-17-8 ]
[ 198143-40-7 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1999 - 2006.

7
[ 108-37-2 ]
[ 107-19-7 ]
[ 80151-33-3 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1999 - 2006.

8
[ 80151-33-3 ]
[ 124-63-0 ]
[ 227954-24-7 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1999 - 2006.

9
[ 80151-33-3 ]
1-{4-[3-(3-chloro-phenyl)-prop-2-ynylsulfanyl]-[1,2,5]thiadiazol-3-yl}-4-aza-tricyclo[2.2.1.0^2,6]heptane [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1999 - 2006.

10
[ 80151-33-3 ]
1-<3-<3-(3-chlorophenyl)-2-propyn-1-yloxy>-1,2,5-thiadiazol-4-yl>-4-azatricyclo<2,2,1,0^2,6>heptane 4-oxide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1999 - 2006.

11
[ 80151-33-3 ]
[ 754159-80-3 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2524 - 2536.

12
[ 80151-33-3 ]
5-Benzenesulfonyl-5-[3-(3-chloro-phenyl)-prop-2-ynyl]thiazolidine-2,4-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1084 - 1091.

13
[ 80151-33-3 ]
5-[3-(3-Chloro-phenyl)-prop-2-ynyl]-5-(toluene-4-sulfonyl)-thiazolidine-2,4-dione [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1084 - 1091.

Yield	Reaction Conditions	Operation in experiment
80%		(a) 1-(3-Chlorophenyl)-1-propyn-3-ol (yield 80% of theory), with use of 3-bromochlorobenzene. 1 H-NMR Spectrum, 100 MHz (CDCl3, TMS) δ in ppm: 2.2-2.4(s); 4.45(s); 7.2-7.5(m) in the ratio of 1:2:4.

15
[ 80151-33-3 ]
[ 1232144-31-8 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 11881 - 11883.
[2]Chemistry - A European Journal,2014,vol. 20,p. 5910 - 5913.
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1108 - 1116.
[4]New Journal of Chemistry,2021,vol. 45,p. 16430 - 16433.
[5]European Journal of Organic Chemistry,2021,vol. 2021,p. 6777 - 6780.

16
[ 80151-33-3 ]
3-(but-3-enyl)-6-(1-(3-chlorophenyl)propa-1,2-dienyl)-6-methyltetrahydro-2H-pyran-2-one [ No CAS ]