16642-93-6|3-(3-Cyanophenyl)acrylic acid| Ambeed

CAS No. :	16642-93-6
Formula :	C₁₀H₇NO₂
M.W :	173.17
SMILES Code :	O=C(O)/C=C/C1=CC=CC(C#N)=C1
MDL No. :	MFCD00182407
InChI Key :	WEYFZKRRQZYAJI-SNAWJCMRSA-N
Pubchem ID :	13370798

Safety of [ 16642-93-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 16642-93-6 ]

* 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 [ 16642-93-6 ]

[ 16642-93-6 ] Synthesis Path-Downstream 1~54

1
[ 141-82-2 ]
[ 24964-64-5 ]
[ 16642-93-6 ]

Yield	Reaction Conditions	Operation in experiment
81%		General procedure: 3-Cyanobenzaldehyde (11a) or 4-cyanobenzaldehyde (11b) (15 mmol) and malonic acid (30 mmol) were dissolved in pyridine (30 mL). Piperidine (3.0 mmol) was added and the reaction was heated for 4 h at 100 C. The reaction was cooled to room temperature and 5 M HCl (25 mL) was added slowly. The resulting white precipitate was collected by filtration, washed with water and dried to give (E)-3-cyanocinnamic acid (12a) or (E)-4-cyanocinnamic acid (12b) in yields of 81% and 78%, respectively.

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 5162 - 5174.
[2]Journal of the American Chemical Society,1948,vol. 70,p. 1560.
[3]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.
[4]Patent: WO2006/123725,2006,A1 .Location in patent: Page/Page column 40.
[5]Organic Letters,2021,vol. 23,p. 9413 - 9418.

2
[ 16642-93-6 ]
[ 138611-02-6 ]

References: [1]Journal of the Chemical Society. Chemical communications,1991,p. 1702 - 1703.

3
[ 16642-93-6 ]
[ 42287-97-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;palladium on charcoal; In water;	(c) 3-(3-Cyanophenyl)propanoic acid A solution of 3-cyano-cinnamic acid (11.5 g) in water (200 ml) and 2M sodium hydroxide solution (35 ml) was hydrogenated at 60 psi over 10% palladium on charcoal for 1.5 hours. The catalyst was filtered off and the filtrate was acidified with 2M hydrochloric acid to precipitate the product as a white solid, m.p. 103 C.

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1519 - 1522.
[2]Patent: US4845110,1989,A .

4
[ 16642-93-6 ]
[ 138227-63-1 ]
4-{4-[3-(3-cyano-phenyl)-acryloylamino]-phenoxy}-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610.

5
[ 16642-93-6 ]
[ 264264-45-1 ]
trans-3-(2-(4-((3-(3-cyanophenyl)prop-2-enyl)carboxamido)cyclohexyl)ethyl)-7-methylsulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4952 - 4964.

6
[ 67-56-1 ]
[ 16642-93-6 ]
[ 193151-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid;Reflux;	General procedure: According to method I [2a, 3a, 6a, 9a,10a,12a,13a]: 15 mmols ofcinnamic acid were dissolved in 20 ml of dried methanol and 0.5 mlof concentrated sulfuric acid was added. Mixturewas refluxed from7 to 17 h. Next, the solvent was evaporated, residue was extractedwith 40 ml of ethyl acetate and washed with 0.5% NaOH and brine.Organic layer was dried with anhydrous sodium sulfate and solventwas evaporated again. When necessary, product was crystallizedfrom ethanol with addition of active carbon.

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.
[2]European Journal of Medicinal Chemistry,2015,vol. 103,p. 238 - 251.

7
[ 16642-93-6 ]
3-((1S,2R)-2-Amino-cyclopropyl)-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.

8
[ 16642-93-6 ]
(1S,2S)-2-(3-Cyano-phenyl)-cyclopropanecarboxylic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.

9
[ 16642-93-6 ]
(1S,2S)-2-(3-Cyano-phenyl)-cyclopropanecarboxylic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.

10
[ 16642-93-6 ]
[(1S,2R)-2-(3-Cyano-phenyl)-cyclopropyl]-carbamic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.

11
[ 16642-93-6 ]
N⁶-[trans-2-(3-cyanophenyl)cyclopropyl]adenosine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2021 - 2034.

12
[ 16642-93-6 ]
4-(4-[3-(3-cyano-phenyl)-acryloyl]-ethoxycarbonylmethyl-amino}-phenoxy)-piperidine-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610.

13
[ 16642-93-6 ]
[(E)-3-(3-Carbamimidoyl-phenyl)-acryloyl]-[4-(piperidin-4-yloxy)-phenyl]-amino}-acetic acid ethyl ester; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610.

14
[ 16642-93-6 ]
([(E)-3-(3-Carbamimidoyl-phenyl)-acryloyl]-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-amino)-acetic acid; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610.

15
[ 16642-93-6 ]
([(E)-3-(3-Carbamimidoyl-phenyl)-acryloyl]-{4-[1-(1-imino-ethyl)-piperidin-4-yloxy]-phenyl}-amino)-acetic acid ethyl ester; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2597 - 2610.

16
[ 16642-93-6 ]
[ 193151-11-0 ]