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Quality Control of Phenylpropiolic acid Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Phenylpropiolic acid

CAS No. :	637-44-5
Formula :	C₉H₆O₂
M.W :	146.14
SMILES Code :	O=C(O)C#CC1=CC=CC=C1
MDL No. :	MFCD00004361
InChI Key :	XNERWVPQCYSMLC-UHFFFAOYSA-N
Pubchem ID :	69475

Safety of Phenylpropiolic acid

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

Application In Synthesis of Phenylpropiolic acid

* 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 [ 637-44-5 ]
Downstream synthetic route of [ 637-44-5 ]

[ 637-44-5 ] Synthesis Path-Upstream 1~4

1
[ 150-76-5 ]
[ 637-44-5 ]
[ 40547-03-3 ]
[ 26964-24-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With trifluoroacetic acid In chlorobenzene at 100℃; Inert atmosphere	General procedure: A mixture of Phenol derivatives (1) (1.0 mmol), trifluoromethanesulfonic acid (1.0 mmol) and propiolic acid (2a) (0.5 mmol) in PhCl (3.0 mL) was stirred at 100 °C for 1 h. After completion of reaction as indicated by TLC, the reaction mixture was poured into H₂O, neutralized with NaHCO₃solution and extracted CH₂Cl₂. The organic layer was washed with 2M NaOH, dried over anhydrous MgSO₄. The solvent was removed in vaccum, and the products were purified by silica gel columnchromatography (EtOAc-Hex) to give the desired product 3.
48%	With trifluorormethanesulfonic acid In chlorobenzene at 100℃; for 3 h;	The title compound was synthesized in the same manner as in Example 1, except that 4-methoxyphenol was used instead of phenol, 3-phenylpropiolic acid was used instead of propiolic acid, and the reaction time was 3 hours

References: [1] Tetrahedron Letters, 2016, vol. 57, # 32, p. 3600 - 3603.
[2] Patent: KR101656876, 2016, B1, . Location in patent: Paragraph 0160; 0161.

2
[ 672-13-9 ]
[ 637-44-5 ]
[ 26964-24-9 ]

References: [1] Organic Letters, 2017, vol. 19, # 24, p. 6606 - 6609.

3
[ 95062-66-1 ]
[ 637-44-5 ]
[ 26964-24-9 ]

References: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 6, p. 1218 - 1231.

4
[ 637-44-5 ]
[ 26964-24-9 ]

References: [1] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436.
[2] Journal of Organic Chemistry, 1986, vol. 51, # 23, p. 4432 - 4436.

[ 637-44-5 ] Synthesis Path-Downstream 1~25

1
[ 136-77-6 ]
[ 637-44-5 ]
6-Hexyl-7-hydroxy-4-phenyl-chromen-2-one [ No CAS ]

References: [1]Journal of Chemical Research - Part S,1998,p. 392 - 393.

2
[ 20651-67-6 ]
[ 637-44-5 ]
[ 19165-51-6 ]

References: [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2827 - 2832.

3
[ 589-87-7 ]
[ 637-44-5 ]
[ 13667-12-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; potassium carbonate; triphenylphosphine; In dimethyl sulfoxide; at 100℃; for 24h;Inert atmosphere;	General procedure: Aryl halide (0.5 mmol), alkynoic acid (0.6 mmol), CuI (2 mol %), PPh3 (4 mol %) and K2CO3 (1.0 mmol) were added to a screw-capped test tube. The tube was then evacuated and backfilled with argon (3 cycles). H2O (3 mL) was added by syringe at room temperature. The tube was again evacuated and backfilled with argon (3 cycles). The mixture was heated to 100 C and stirred for 24 h. After cooling to room temperature, the mixture was diluted with water, and the combined aqueous phases were extracted three times with ethyl acetate. The organic layers were combined, dried over Na2SO4 and concentrated to yield the crude product, which was further purified by silica gel chromatography, using petroleum ether and ethyl acetate as eluent to provide the desired product.
87%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 90℃; for 12h;	General procedure: Pd-CNT (237 mg, 0.15 mmol of Pd), aryl alkynyl carboxylic acid (3.3 mmol), aryl iodide (3.0 mmol) and DBU (913.4 mg, 6.0 mmol) were stirred in DMSO (10.0 mL) at 90 C for 12 h. The resulting crude mixture was filtered. The filtrated organic solution was poured into 20 mL of saturated aqueous ammonium chloride and extracted with Et2O (3 × 20 mL). The combined ether extracts were washed with brine (60 mL), dried over MgSO4, and filtered. The solvent was removed under vacuum. The crude product was purified by flash chromatography (5% ethyl acetate in hexane).

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 6938 - 6942.
[2]Tetrahedron,2012,vol. 68,p. 6413 - 6419.
[3]Journal of Organometallic Chemistry,2013,vol. 724,p. 271 - 274.
[4]Chemical Communications,2010,vol. 46,p. 9049 - 9051.
[5]RSC Advances,2016,vol. 6,p. 109296 - 109300.
[6]Advanced Synthesis and Catalysis,2011,vol. 353,p. 2731 - 2738.

4
[ 5467-74-3 ]
[ 637-44-5 ]
[ 13667-12-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine; copper(II) choride dihydrate; triethylamine; p-benzoquinone; In dichloromethane; at 20℃; for 12h;Schlenk technique;	1-Bromo-4-(phenylethynyl)benzene (3aj).8 The reaction of CuCl2.2H2O (2.14 mg,0.0125 mmol), 1,4-benzoquinone (27 mg, 0.25 mmol), 4-bromophenylboronic acid 1a(36.5 mg, 0.25 mmol) and phenylboronic acid 2j (100 mg, 0.5 mmol), Et3N (51 mg,0.5 mmol), pyridine (40 mg, 0.5 mmol) in DCM (3 mL), afforded 34.2 mg of 3aj(53%).

References: [1]Tetrahedron Letters,2013,vol. 54,p. 1951 - 1955.

5
[ 480452-05-9 ]
[ 637-44-5 ]
[ 1431960-45-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; HATU; In tetrahydrofuran; at 25℃; for 12h;	PP-2-2A FC-1 -4A To a stirred solution of phenylpropiolic acid (156 mg, 1 .1 mmol) in THF (2 mL) was added N-(tert-butoxycarbonyl)-2-methyl-1 , 3-diaminopropane (200 mg, 1.1 mmol), HATU (613 mg, 1 .6 mmol) and TEA (0.3 mL). The reaction mixture was stirred at 25 C for 12 hrs. The analysis of LCMS showed completion of reaction and formation of desired product, it was quenched by addition of H20 (20 mL), extracted with EtOAc (2 x 50 mL), the organic layer was washed with H20, brine dried over Na2S04 and concentrated. The residue was purified by column chromatography on silica gel (DCM/MeOH = 10:1 ) to afford the product as a white solid (0.28 g, yield: 82%).

References: [1]Patent: WO2013/62945,2013,A1 .Location in patent: Page/Page column 100.

6
[ 31739-56-7 ]
[ 119072-55-8 ]
[ 2393-23-9 ]
[ 637-44-5 ]
[ 1604835-53-1 ]

References: [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 2084 - 2091.

7
[ 57297-29-7 ]
[ 637-44-5 ]
[ 651043-20-8 ]

References: [1]New Journal of Chemistry,2014,vol. 38,p. 3062 - 3070.

8
[ 924869-17-0 ]
[ 637-44-5 ]
methyl 2-(phenylethynyl)benzoxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With Pd(II)(N-(3-(1-hydroxy-3-phenylpropan-2-yl carbamoyl)benzylidene)-2-methylpropan-2-amineoxide(-2H)); silver(l) oxide; In N,N-dimethyl-formamide; at 80℃;	General procedure: To an oven dried 25 mL round bottom flask, palladium complex (7 mg, 3 mol %), silver(I) oxide (229 mg, 1 mmol) and aryl propiolic acid (1 mmol), under air, were added. Azole substrate (0.5 mmol) in DMF (4 mL) was added to the reaction mixture. The reaction mixture was stirred at 80 C for 6-8 h. The reaction mixture was diluted with EtOAc then filtered through filter paper. The filtrate was quenched with Ice cold water and then, aqueous layer was extracted with EtOAc. The organic phase was washed with NaCl (satd aq), dried with Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

References: [1]Tetrahedron,2015,vol. 71,p. 1975 - 1981.

9
[ 30309-80-9 ]
[ 637-44-5 ]
2-(di-o-tolylphosphoryl)-1-phenylethanone [ No CAS ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 4335 - 4338.

10
[ 119072-55-8 ]
[ 53903-49-4 ]
[ 104-87-0 ]
[ 637-44-5 ]
C₃₀H₂₉F₃N₂O₃ [ No CAS ]