[ CAS No. 20893-30-5 ] {[proInfo.proName]}

Name: 20893-30-5|2-(Thiophen-2-yl)acetonitrile|95%
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SKU: A100651
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Quality Control of [ 20893-30-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 20893-30-5 ]

CAS No. :	20893-30-5	MDL No. :	MFCD00005453
Formula :	C₆H₅NS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CLSHQIDDCJTHAJ-UHFFFAOYSA-N
M.W :	123.18	Pubchem ID :	72880
Synonyms :

Calculated chemistry of [ 20893-30-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.84
TPSA :	52.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.16 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.52
Log Po/w (XLOGP3) :	1.26
Log Po/w (WLOGP) :	1.81
Log Po/w (MLOGP) :	0.75
Log Po/w (SILICOS-IT) :	2.8
Consensus Log Po/w :	1.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.79
Solubility :	1.98 mg/ml ; 0.0161 mol/l
Class :	Very soluble
Log S (Ali) :	-1.95
Solubility :	1.38 mg/ml ; 0.0112 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.11
Solubility :	0.952 mg/ml ; 0.00773 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 20893-30-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501	UN#:	3276
Hazard Statements:	H301-H311-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 20893-30-5 ]

* 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 [ 20893-30-5 ]
Downstream synthetic route of [ 20893-30-5 ]

[ 20893-30-5 ] Synthesis Path-Upstream 1~4

1
[ 20893-30-5 ]
[ 39098-97-0 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1949, p. 847,851

2
[ 20893-30-5 ]
[ 1918-77-0 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With sodium hydroxide In water for 5 h; Reflux	An aqueous solution of 150 g of 30percent sodium hydroxide was heated to reflux,Then, 113 g of 2-thiophene acetonitrile was slowly added dropwise,And then reflux reaction 5 hours (the reaction process a large number of ammonia gas generated).After the reaction is complete,Cooling to 20-30 ,The impurities were then extracted three times with 200 mL of ethyl acetate.After extraction,Cooling to 10-20 ,Add 30percent hydrochloric acid to adjust the pH value to 1-2,200 g of dichloromethane was added twice.The combined methylene chloride layer was charged with 5 g of activated carbon,Stirring for 20-30 minutes,After filtering,The filtrate was concentrated to a paste,300 mL of n-hexane was added,Cooling to 0-5 ,Crystallization for 3 hours,filter,Dried to give 121.8 g of 2-thiopheneacetic acid,Yield 93.4percent. HPLC area normalized content of 99.4percent.

Reference： [1] Patent: CN106518839, 2017, A, . Location in patent: Paragraph 0006; 0013; 0014
[2] Journal of Organic Chemistry, 1958, vol. 23, p. 1289,1290
[3] Bulletin de la Societe Chimique de France, 1949, p. 847,851
[4] Journal of the American Chemical Society, 1941, vol. 63, p. 2945
[5] Journal of Organic Chemistry, 1950, vol. 15, p. 81,87

3
[ 20893-30-5 ]
[ 71637-37-1 ]

Reference： [1] Journal of Nanoscience and Nanotechnology, 2011, vol. 11, # 7, p. 5876 - 5882
[2] Macromolecules, 2004, vol. 37, # 14, p. 5265 - 5273
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 5, p. 1119 - 1128
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 16, p. 4782 - 4786[5] Angew. Chem., 2015, vol. 127, # 16, p. 4864 - 4868,5

4
[ 20893-30-5 ]
[ 298-12-4 ]
[ 912368-67-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate In methanol for 2 h; Heating / reflux	Example 1; 2-phenvI-4-f(3S)-piperidin-3-vIaminolthieno[3,2-c1pyridine-7-carboxamide; Step 1:(2Z)-3-cyano-3-(2-thienyl)acrylic acid; To a stirred solution of 2-thienylacetonitrile (24.8 g,0.20 mol) in MeOH (300 mL) is added glyoxylic acid monohydrate (18.5 g, 0.20 mol) and potassium carbonate (25.5 g, 0.20 mol). The reaction slurry is placed under a nitrogen atmosphere and heated to reflux. After 2h the reaction mixture is cooled to rt and the product is obtained by filtration. The filter cake is washed with a large amount of MeOH and then dried in a vacuum oven overnight to give 43.1 g (99percent) of the title compound as a white crystalline potassium salt. ¹H NMR δ 7.95 (d, 3H), 7.75 (d, IH), 7.30 (dd, IH), 7.05 (s, IH), 3.0-4.0 (br s, IH). LCMS (ES, M+H=180, M-H=I 78).

Reference： [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 3, p. 1061 - 1073
[2] Patent: WO2006/106326, 2006, A1, . Location in patent: Page/Page column 53

[ 20893-30-5 ] Synthesis Path-Downstream 1~87

1
[ 20893-30-5 ]
[ 26421-44-3 ]
3c-(2,5-dimethyl-[3]thienyl)-2-[2]thienyl-acrylonitrile [ No CAS ]

Reference： [1]Journal of the Chemical Society,1950,p. 2130,2134

2
[ 20893-30-5 ]
[ 5381-20-4 ]
3c(?)-benzo[b]thiophen-3-yl-2-[2]thienyl-acrylonitrile [ No CAS ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1951,vol. 232,p. 238
[2]Journal of the Chemical Society,1951,p. 255

3
[ 20893-30-5 ]
[ 459-57-4 ]
[ 347-52-4 ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 2-cyanomethylthiophene With sodium In methanol at 20℃; for 0.333333h; Stage #2: 4-fluorobenzaldehyde In methanol for 4h; Reflux;	4.1.2. General method for the synthesis of compounds 6-11 General procedure: Sodiumwas dissolved in 10 mL of absolute methanol and benzylcyanide or 2-(thiophen-2-yl)acetonitrile was added. The mixturewas stirred at room temperature for 20 min, after that the appropriatealdehyde was added and heated at reflux. The cooled reactionmixture was filtered and, if necessary, recrystallized from theappropriate solvent.
51%	With potassium <i>tert</i>-butylate In ethanol at 20℃;
	With potassium hydroxide

Reference： [1]Gupta, Chhedi Lal; Hranjec, Marijana; Juričić, Štefica; Klobučar, Marko; Malod-Dognin, Noël; Pavelić, Sandra Kraljević; Perin, Nataša; Pržulj, Nataša; Rep, Valentina; Selgrad, Danijel; Sović, Irena [European Journal of Medicinal Chemistry, 2019]
[2]Quiroga, Jairo; Cobo, Debora; Insuasty, Braulio; Abonia, Rodrigo; Nogueras, Manuel; Cobo, Justo; Vasquez, Yelkaira; Gupta, Mahabir; Derita, Marcos; Zacchino, Susana [Archiv der Pharmazie, 2007, vol. 340, # 11, p. 603 - 606]
[3]Buu-Hoi et al. [Journal of the Chemical Society, 1952, p. 4590,4593]

4
[ 20893-30-5 ]
[ 100-52-7 ]
[ 89986-24-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium methylate In methanol at 30℃; ΔE, Σ, A;
92%	With sodium ethanolate In ethanol for 2.5h; Heating;
65%	With potassium <i>tert</i>-butylate In ethanol at 20℃;

46%	Stage #1: 2-cyanomethylthiophene With sodium In methanol at 20℃; for 0.333333h; Stage #2: benzaldehyde In methanol for 4h; Reflux;	4.1.2. General method for the synthesis of compounds 6-11 General procedure: Sodiumwas dissolved in 10 mL of absolute methanol and benzylcyanide or 2-(thiophen-2-yl)acetonitrile was added. The mixturewas stirred at room temperature for 20 min, after that the appropriatealdehyde was added and heated at reflux. The cooled reactionmixture was filtered and, if necessary, recrystallized from theappropriate solvent.
	With sodium ethanolate at 20℃; Behandeln bei Siedetemperatur;
	With potassium hydroxide at 20℃; Behandeln bei Siedetemperatur;

Reference： [1]Alberghina, Gaetano; Amato, Maria Emanuela; Corsaro, Antonio; Fisichella, Salvatore; Scarlata, Giuseppe [Journal of the Chemical Society. Perkin transactions II, 1985, p. 353 - 356]
[2]Stuart, John G.; Quast, Michael J.; Martin, Gary E.; Lynch, Vincent M.; Simonsen, Stanley H.; et al. [Journal of Heterocyclic Chemistry, 1986, vol. 23, p. 1215 - 1234]
[3]Quiroga, Jairo; Cobo, Debora; Insuasty, Braulio; Abonia, Rodrigo; Nogueras, Manuel; Cobo, Justo; Vasquez, Yelkaira; Gupta, Mahabir; Derita, Marcos; Zacchino, Susana [Archiv der Pharmazie, 2007, vol. 340, # 11, p. 603 - 606]
[4]Gupta, Chhedi Lal; Hranjec, Marijana; Juričić, Štefica; Klobučar, Marko; Malod-Dognin, Noël; Pavelić, Sandra Kraljević; Perin, Nataša; Pržulj, Nataša; Rep, Valentina; Selgrad, Danijel; Sović, Irena [European Journal of Medicinal Chemistry, 2019]
[5]Crowe; Nord [Journal of Organic Chemistry, 1950, vol. 15, p. 1177,1182]
[6]Cagniant [Bulletin de la Societe Chimique de France, 1949, p. 847,851]

5
[ 20893-30-5 ]
[ 120-14-9 ]
(2E)-3-(3,4-dimethoxyphenyl)-2-(2-thienyl)prop-2-enenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.433333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).
78%	With potassium <i>tert</i>-butylate In ethanol at 20℃; for 1.16667h;
	With potassium hydroxide; ethanol

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]
[2]Soudan; Lucas; Hoang Ang Ho; Jobin; Breau; Belanger [Journal of Materials Chemistry, 2001, vol. 11, # 3, p. 773 - 782]
[3]Buu-Hoi et al. [Journal of the Chemical Society, 1950, p. 2130,2134]

6
[ 20893-30-5 ]
[ 100-10-7 ]
[ 142518-79-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.416667h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).
	With piperidine; ethanol

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]
[2]Buu-Hoi et al. [Journal of the Chemical Society, 1950, p. 2130,2134]

7
[ 20893-30-5 ]
[ 1918-77-0 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With sodium hydroxide; In water; for 5h;Reflux;	An aqueous solution of 150 g of 30% sodium hydroxide was heated to reflux,Then, 113 g of 2-thiophene acetonitrile was slowly added dropwise,And then reflux reaction 5 hours (the reaction process a large number of ammonia gas generated).After the reaction is complete,Cooling to 20-30 ,The impurities were then extracted three times with 200 mL of ethyl acetate.After extraction,Cooling to 10-20 ,Add 30% hydrochloric acid to adjust the pH value to 1-2,200 g of dichloromethane was added twice.The combined methylene chloride layer was charged with 5 g of activated carbon,Stirring for 20-30 minutes,After filtering,The filtrate was concentrated to a paste,300 mL of n-hexane was added,Cooling to 0-5 ,Crystallization for 3 hours,filter,Dried to give 121.8 g of 2-thiopheneacetic acid,Yield 93.4%. HPLC area normalized content of 99.4%.

Reference： [1]Patent: CN106518839,2017,A .Location in patent: Paragraph 0006; 0013; 0014
[2]Organic Letters,2019,vol. 21,p. 8805 - 8809
[3]Journal of Organic Chemistry,1958,vol. 23,p. 1289,1290

8
[ 4461-29-4 ]
[ 20893-30-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With allyl bromide; 1,1'-carbonyldiimidazole In acetonitrile 1.) 0.5 h, RT; 2.) 2 h, reflux;
84%	With phosgene In tetrahydrofuran; toluene at 25℃; for 4h; Inert atmosphere;
83%	at 225℃; for 1h;	A Nitrile Product Preparation Example A General procedure: Following the amide intermediate Preparation Example A. The reaction vessel is closed (when the amide intermediate has a boiling point at normal pressure equal to or lower than the reaction temperature TB described below) or the reaction vessel is kept open (when the amide intermediate has a boiling point higher than the normal pressure When the reaction temperature is TB), stirring is continued (600 r/min), the reaction temperature is changed to TB, and after the reaction temperature TB is maintained for TD hours, the reaction is substantially completed. Then, the reaction vessel was sealed and connected to a vacuum pump so that the degree of vacuum in the reaction vessel reached 20-50 mbar (according to the type of nitrile product) and the distillate was used as the nitrile product. The yield of the nitrile product was calculated and sampled for nuclear magnetic resonance and elemental analysis to characterize the nitrile product obtained. Specific reaction conditions and characterization results are shown in Tables A-7, A-8, A-9, A-10, A-11 and A-12 below. These characterization results show that the nitrile product obtained has an extremely high purity (above 99%).In these nitrile product preparation examples, 10 g of phosphorus pentaoxide is preferably added to the reaction vessel as a catalyst at one stage, optionally at the beginning of the reaction.

74%	Stage #1: 2-(thiophen-2-yl)acetamide With C₃₉H₄₅N₂ In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere; Stage #2: With phenylsilane In acetonitrile at 80℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
	With phosphorus pentoxide

Reference： [1]Kamijo, Tetsuhide; Harada, Hiromu; Iizuka, Kinji [Chemical and pharmaceutical bulletin, 1984, vol. 32, # 7, p. 2560 - 2564]
[2]Bobal, Pavel; Otevrel, Jan; Svestka, David [RSC Advances, 2020, vol. 10, # 42, p. 25029 - 25045]
[3]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN104557610, 2018, B Location in patent: Paragraph 0153; 0154; 0155; 0164; 0165
[4]Ahmed, Jasimuddin; Hota, Pradip Kumar; Maji, Subir; Mandal, Swadhin K.; Rajendran, N. M. [Chemical Communications, 2020, vol. 56, # 4, p. 575 - 578]
[5]Dann; Distler [Chemische Berichte, 1954, vol. 87, p. 365,372]

9
[ 20893-30-5 ]
[ 20265-35-4 ]
[ 22018-90-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1968,p. 3223 - 3233

10
[ 20893-30-5 ]
[ 36321-73-0 ]
[ 144061-55-2 ]

Reference： [1]Heterocycles,1992,vol. 34,p. 1239 - 1249

11
[ 20893-30-5 ]
[ 67-56-1 ]
[ 19432-68-9 ]

Reference： [1]Journal of Chemical Research, Miniprint,1983,p. 2201 - 2218

12
[ 20893-30-5 ]
[ 67-56-1 ]
methyl 2-(thiophen-2-yl)acetimidate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogenchloride In diethyl ether at 0 - 5℃;
87%	With acetyl chloride In diethyl ether at 0℃; for 1h; Inert atmosphere;	4.1.4. Methyl 2-(thiophen-2-yl)acetimidate Hydrochloride (6) Acetyl chloride (8.0 mL, 8.8 g, 101.3 mmol) was added dropwise over 10 min to a cold (0 °C) well-stirred solution of 2-thiopheneacetonitrile (5) (3.4 mL, 4.0 g, 32.4 mmol) and dry methanol (6.6 mL, 5.2 g, 162.9 mmol) in dry diethyl ether (30mL) under nitrogen. After the addition, the reaction mixture was stirred at 0 °C for an additional hour, then was closed well and kept in the cold (4 °C) without stirring. Colorless crystals precipitated after 3 days. The crystals were filtered via a glass sinter, washed with dry ether (60 mL), and then dried in vacuum to generate 5.44 g (87%) of a highly hydroscopic solid imidate salt 6. 1H NMR (400 MHz, CDCl3): = 12.90 (br. s, 1H, HaHbN+=), 11.94 (br. s, 1 H, HaHbN+=), 7.30-7.28 (m, 1 H,5-HTh), 7.20 (d, J = 3.6 Hz, 1 H, 3-HTh), 7.02-7.00 (m, 1 H, 4-HTh), 4.33 (s, 5 H, CH2 + OCH3) ppm. 13C NMR (100 MHz,CDCl3): = 177.0 (OC=N+H2), 130.9 (2-CTh), 129.0 (3-HCTh),127.5 (4-HCTh), 126.5 (5-HCTh), 61.2 (OCH3), 33.2 (CH2)ppm.

Reference： [1]Leschke, Christian; Elz, Sigurd; Garbarg, Monique; Schunack, Walter [Journal of Medicinal Chemistry, 1995, vol. 38, # 8, p. 1287 - 1294]
[2]Trifonov, Lena; Afri, Michal; Korshin, Edward E.; Gruzman, Arie; Palczewski, Krzysztof [Medicinal Chemistry, 2018, vol. 14, # 7, p. 688 - 694]

13
[ 20893-30-5 ]
[ 1732-26-9 ]
5-(2-thienylmethyl)-4-pyrenecarbonitrile [ No CAS ]

Reference： [1]Synthesis,1995,p. 827 - 830

14
[ 20893-30-5 ]
[ 23667-06-3 ]
6-methyl-3-N,N-dimethylamino-2-(2-thienyl)methylbenzonitrile [ No CAS ]

Reference： [1]Synthesis,1996,p. 59 - 63

15
[ 20893-30-5 ]
[ 90-02-8 ]
[ 91805-18-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide In water for 0.333333h; Sonication; Green chemistry;	2.2.1.1 3-(thiophen-2-yl)-2H-chromen-2-one (3a) 2-hydroxybenzaldehyde and 2-thiopheneacetonitrile; the catalytic amount of potassium hydroxide were mixed in round bottom flask containing 15mL of distilled Water. The reaction mixture was subjected to ultrasonication for 15min and then, acidified by adding drop by drop 10N HCl (8-10mL) with continued ultrasonication for 5min, obtained crude product was precipitated, filtered and then purified by column chromatography. Appearance: White solid; yield: 85 %; mp: 142°C; IR (KBr) (vmax/cm-1): 3065(C-H), 1753(O-C=O), 1439(C=C), 1250(C-S),; 1H NMR (400MHz, CDCl3) δ (ppm): 8.0 (s, 1H), 7.45 (d, J=3.2Hz, 1H), 7.5 (dd, J=10.4.Hz,2H), 7.4 (d, J=4.8Hz, 1H), 7.3 (d, J=8Hz, 1H), 7.29(t, J=7.6Hz, 1H), 7.1(t, J=4Hz, 1H),; Mass spectra: theoretical: 228.23, obtained: 228.98.
	With hydrogenchloride; sodium hydroxide; cetyltrimethylammonim bromide 1.) H₂O (pH 12.4) 90 deg C, 6 h, 2.) H₂O, 90 deg C, 1 h; Yield given. Multistep reaction;

Reference： [1]Alghamdi, Abdulaziz Ali; Kumar, Naveen; Mahadevan, K. M.; Nagaraju, G.; Udayabhanu [Journal of Molecular Structure, 2021, vol. 1223]
[2]Brufola, Gianluca; Fringuelli, Francesco; Piermatti, Oriana; Pizzo, Ferdinando [Heterocycles, 1996, vol. 43, # 6, p. 1257 - 1266]

16
[ 20893-30-5 ]
[ 925252-42-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol at 80℃; for 4h;	2 Example 2, (S)-1-(4,4-Dimethyl-1-oxo-1-(((3-(thiophen-2-ylmethyl)-1,2,4-oxadiazole -5-yl)methyl)amino)pent-3-yl)-2-(1H-indazol-6-yl)-N-methyl-1H-benzo[d]imidazole-6-carboxamide (compound 2) Preparation of compound 2-2 Combine the compound 2-(thiophen-2-yl)acetonitrile (2-1) (8.0g, 64.95mmol), N,N-diisopropylethylamine (13.4g, 103.92mmol) and hydroxylamine hydrochloride (6.8g) at room temperature , 97.42mmol) was dissolved in ethanol (150mL). The reaction solution was heated to 80°C and stirred for 4 hours. LCMS detected the completion of the reaction. The reaction solution was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent gradient: dichloromethane to dichloromethane: methanol = 80:1) to obtain the target product (Z)-N'-hydroxy-2-(thiophen-2-yl)acetamidine (2-2) (6.6 g, yield: 65.0%) Properties: yellow solid.
40%	With hydroxylamine hydrochloride; sodium carbonate In ethanol; water Heating;
1.07 g	With hydroxylamine In methanol for 48h; Heating;

Reference： [1]Current Patent Assignee: JIANGSU SIMCERE PHARM - CN113004252, 2021, A Location in patent: Paragraph 0116-0119
[2]Lessel; Herfs [Pharmazie, 2000, vol. 55, # 1, p. 22 - 26]
[3]Moloney, Gerard P.; Angus, James A.; Robertson, Alan D.; Stoermer, Martin J.; Robinson, Michael; Wright, Christine E.; McRae, Ken; Christopoulos, Arthur [European Journal of Medicinal Chemistry, 2008, vol. 43, # 3, p. 513 - 539]

17
[ 20893-30-5 ]
[ 771-15-3 ]
11-amino-5H-anthra[2,3-b]thiophen-10-one [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3149 - 3153

18
[ 20893-30-5 ]
[ 7048-04-6 ]
[ 116247-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; water;	Example 10 N-(2'-thienylacetyl)-D,L-cysteine 24.6 g (0.2 mole) thiophene-2-acetonitrile, 35.2 g (0.2 mole) D,<strong>[7048-04-6]L-cysteine hydrochloride monohydrate</strong> and 27.6 g (0.2 mole) potassium carbonate were heated in 500 ml methanol and 250 ml water for 6 hours at the boiling point. Then the solvent was removed under reduced pressure, the residue taken up in 200 ml water and adjusted with concentrated hydrochloric acid to pH 4. 40.8 g (83% of theory) colorless product with a melting point of 138-140 C. precipitated.

Reference： [1]Patent: US4918223,1990,A

19
[ 20893-30-5 ]
[ 151903-52-5 ]
(2E)-3-(4-formyl-2,5-dihexyloxyphenyl)-2-(2-thienyl)prop-2-enenitrile [ No CAS ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 5193 - 5198

20
[ 20893-30-5 ]
[ 115662-09-4 ]
[ 865087-23-6 ]

Reference： [1]Journal of Materials Chemistry,2012,vol. 22,p. 15379 - 15387
[2]New Journal of Chemistry,2003,vol. 27,p. 783 - 785

21
[ 20893-30-5 ]
[ 204905-77-1 ]
1-cyano-2-(2-(3,4-ethylenedioxythienyl))-1-(2-thienyl)vinylene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 16440 - 16450

22
[ 20893-30-5 ]
[ 86-81-7 ]
(E)-2-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.5h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).
70%	With potassium <i>tert</i>-butylate In ethanol Heating;
70%	With potassium <i>tert</i>-butylate In ethanol at 20℃;

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]
[2]Cobo, Debora; Quiroga, Jairo; De La Torre, Jose M.; Cobo, Justo; Low, John N.; Glidewell, Christopher [Acta Crystallographica, Section C: Crystal Structure Communications, 2006, vol. 62, # 9, p. o550-o553]
[3]Quiroga, Jairo; Cobo, Debora; Insuasty, Braulio; Abonia, Rodrigo; Nogueras, Manuel; Cobo, Justo; Vasquez, Yelkaira; Gupta, Mahabir; Derita, Marcos; Zacchino, Susana [Archiv der Pharmazie, 2007, vol. 340, # 11, p. 603 - 606]

23
[ 20893-30-5 ]
[ 71637-37-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 26h;Inert atmosphere; Darkness;	To a stirred solution of 2-(thiophen-2- yl)acetonitrile 1 (15g, 121.7 mmol) in DMF (110 mL), NBS (22.7g, 127.8 mmol) was added portion wise for 2 h. The reaction mixture was stirred in the dark under nitrogen for 24 h. Diethyl ether (100 mL) was added to the reaction mixture and washed with water (50 mL) and brine (30 mL). Organic layer was concentrated and purified by column chromatography (silica gel 100-200 mesh, 5% ethyl acetate in pet ether) to afford compound 2 (15g, 86%) as a pale yellow solid. NMR (400MHz, CDCh,): 6.95(d, J = 4.1 1H), 6.84(m, 1H), 3.84 (s, 2H).

Reference： [1]Patent: WO2019/43642,2019,A1 .Location in patent: Paragraph 0053; 0055
[2]Journal of Nanoscience and Nanotechnology,2011,vol. 11,p. 5876 - 5882
[3]Macromolecules,2004,vol. 37,p. 5265 - 5273
[4]Journal of Polymer Science, Part A: Polymer Chemistry,2011,vol. 49,p. 1119 - 1128
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 4782 - 4786
Angew. Chem.,2015,vol. 127,p. 4864 - 4868,5
[6]Journal of Materials Chemistry C,2019,vol. 7,p. 11457 - 11464

24
[ 20893-30-5 ]
[ 416887-49-5 ]
3-[3-methoxy4-(2-nitro-4-trifluoromethyl-phenoxy)-phenyl]-2-thiophen-2-yl-acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydroxide In ethanol at 0 - 20℃; for 0.5h;	25 To a solution of 3-methoxy-4-(2-nitro-4-trifluoromethyl-phenoxy)benzaldehyde (0.15 g, 0.44 mmol) and thiophen-2-yl-acetonitrile (0.047 mL, 0.44 mmol) in absolute ethanol (1.5 mL) at 0° C. was added 50% KOH (0.2 mL). The mixture was slowly warmed to rt and stirred for 30 min. After addition of water the solid product was filtered. Recrystallization from Et2O yielded a colorless crystalline product (0.098 g, 55%). 1H NMR (CDCl3): 3.80 (s, 3H), 6.95 (d, 1H), 7.11 (m, 1H), 7.22 (d, 1H), 7.38 (m, 4H), 7.71 (m, 2H), 8.27 (d, 1H). LCMS (ESI): RT 2.06 min, purity 100%, [M+H2O] 464.

Reference： [1]Current Patent Assignee: JOHNSON & JOHNSON INC - US2006/14812, 2006, A1 Location in patent: Page/Page column 18

25
[ 20893-30-5 ]
[ 89487-92-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 50℃; for 0.166667h; Green chemistry; regioselective reaction;	Monoiodothiophenes 2, 5, 7, 10, 13; General Procedure General procedure: The thiophene derivative (1 mmol, 1 equiv) was dissolved in EtOH (2mL) at the temperature indicated in Tables 1-5. Then, NIS (1 or 1.1 equiv, see Tables 1-5) was added followed by PTSA (10% mol). The mixture was stirred for 10 min, then sat. Na2S2O3 (2 mL) was added. The mixture was diluted with EtOAc (3 mL). After phase separation, the organic phase was washed with 1 M Na2CO3 solution, dried (MgSO4), filtered through cotton, and evaporated to give the iodinated thiophene derivative.
60%	With sulfuric acid; iodine; iodic acid; acetic acid In tetrachloromethane; water at 20℃; for 20h;	P4 A mixture of 15.4 g (0.125 mol) of 2-thienyl-acetonitrile, 40 ml of acetic acid, 15 [ML] of water, 7 ml of concentrated sulfuric acid, 10 [ML] of carbon [TETRACHLORIDE,] 10.2 g (0.04 mol) of iodine and 4.1 g (0.023 mol) of iodic acid [(HL03)] is, in analogy to J. Med. Chem. 42 (18), 3557 (1999), stirred at [20°C] for 20 hours. Gas chromatography analysis shows that about 90% of the starting materials have reacted. After further addition of carbon tetrachloride, the organic phase is separated off and the aqueous phase is extracted with ethyl acetate. The organic phases are combined and washed with sodium thiosulfate solution and sodium chloride solution. After concentration of the dried organic phase, the crude product obtained is stirred in diethyl ether/hexane. The desired title compound is obtained in a yield of 18.5 g (60% of theory) in the form of light-brown crystals. [H-NMR] [(CDCI3)] : 8 (ppm) =3.88 (s, 2H); 6.75 (d, 1H) ; 7.15 (d, 1H).

Reference： [1]Grolleau, Jérémie; Frère, Pierre; Gohier, Frédéric [Synthesis, 2015, vol. 47, # 24, p. 3901 - 3906]
[2]Current Patent Assignee: Syngenta (in: Sinochem Holdings); SINOCHEM HOLDINGS CORPORATION LTD - WO2004/2981, 2004, A2 Location in patent: Page 31

26
[ 20893-30-5 ]
[ 5197-95-5 ]
[ 106-93-4 ]
1-(thiophen-2-yl)cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane; water;	a 1-Thiophen-2-ylcyclopropanecarbonitrile A stirred mixture of 2-thiopheneacetonitrile (2.5 g, 20 mmol), <strong>[5197-95-5]benzyltriethylammonium bromide</strong> (0.54 g, 2.0 mmol), dichloromethane (20 mL), and 50% aqueous sodium hydroxide solution (8 g, 200 mmol) was cooled to 0 C. and treated dropwise with 1,2-dibromoethane (2.07 mL, 24 mmol). The mixture was allowed to warm to room temperature and stir for two days. After diluting with dichloromethane (20 mL) and water (30 mL), the aqueous layer was extracted with dichloromethane (3*40 mL) and the combined organics were washed with water (30 mL), brine (30 mL), dried with sodium sulfate and concentrated in vacuo. The dark residual oil was purified by flash chromatography (10/90 ethyl acetate/hexane) to give the title compound as a light brown oil (1.40 g). 1H NMR (200 MHz, CDCl3) delta 7.40 (dd, 1H), 7.20 (dd, 1H), 6.95 (dd, 1H), 1.55 (m, 2H), 1.45 (m, 2H).

Reference： [1]Patent: US2003/114666,2003,A1

27
[ 20893-30-5 ]
[ 118753-70-1 ]
tert-butyl 4-cyano-4-(thiophen-2-yl)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	Stage #1: 2-cyanomethylthiophene With sodium amide In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: N-(tert-butyloxycarbonyl)bis(2-chloroethyl)amine In N,N-dimethyl-formamide at 20℃; for 96.3333h;	110.1 To a solution of thiophen-2-yl-acetonitrile (700 mg, 5.69 mmol) at 0° C. in DMF (30 mL) was added NaNH2 (665 mg, 17.0 mmol) carefully over 10 min and N-tert-butoxycarbonyl-bis(2-chloroethyl)amine (4.12 g, 10 mmol) in DMF was added slowly for 20 min. The resulting suspension was stirred at room temperature for 96 hours. The reaction mixture was cooled and quenched with ice-water (100 mL) and the mixture was extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by column chromatography on silica gel (20% EtOAc/hexanes) to yield the BOC-protected piperidine (31% yield). 1H NMR (d6-DMSO, 300 MHz) δ 1.47 (m, 9H), 1.96 (m, 2H), 2.24 (m, 2H), 3.20 (m, 2H), 4.25 (m, 2H), 7.01 (m, 1H), 7.15 (m, 1H), 7.30 (m, 1H); MS (ESI) m/z=293 (MH+).
		58.1 58.1 58.1 Synthesis of 1-tert-butoxycarbonyl-4-cyano-4-(thiophen-2-yl)-piperidine Prepare by the method of example 30.2 using 2-thiopheneacetonitrile (10 mmol) and 2-chloro-N-(2-chloroethyl)-N-tert-Butoxycarbonyl-ethanamine (11 mmol). Purify to give the title compound.
		58 58.1 Synthesis of 1-tert-butoxycarbonyl-4-cyano-4-(thiophen-2-yl)-piperidine 58.1 Synthesis of 1-tert-butoxycarbonyl-4-cyano-4-(thiophen-2-yl)-piperidine Prepare by the method of example 30.2 using 2-thiopheneacetonitrile (10 mmol) and 2-chloro-N-(2-chloroethyl)-N-tert-Butoxycarbonyl-ethanamine (11 mmol). Purify to give the title compound.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2010/204265, 2010, A1 Location in patent: Page/Page column 135
[2]Current Patent Assignee: SANOFI - US5635510, 1997, A
[3]Current Patent Assignee: SANOFI - US5824690, 1998, A

28
[ 20893-30-5 ]
[ 298-12-4 ]
[ 912368-67-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In methanol; for 2.0h;Heating / reflux;	Example 1; 2-phenvI-4-f(3S)-piperidin-3-vIaminolthieno[3,2-c1pyridine-7-carboxamide; Step 1:(2Z)-3-cyano-3-(2-thienyl)acrylic acid; To a stirred solution of 2-thienylacetonitrile (24.8 g,0.20 mol) in MeOH (300 mL) is added glyoxylic acid monohydrate (18.5 g, 0.20 mol) and potassium carbonate (25.5 g, 0.20 mol). The reaction slurry is placed under a nitrogen atmosphere and heated to reflux. After 2h the reaction mixture is cooled to rt and the product is obtained by filtration. The filter cake is washed with a large amount of MeOH and then dried in a vacuum oven overnight to give 43.1 g (99%) of the title compound as a white crystalline potassium salt. 1H NMR δ 7.95 (d, 3H), 7.75 (d, IH), 7.30 (dd, IH), 7.05 (s, IH), 3.0-4.0 (br s, IH). LCMS (ES, M+H=180, M-H=I 78).

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 1061 - 1073
[2]Patent: WO2006/106326,2006,A1 .Location in patent: Page/Page column 53

29
[ 20893-30-5 ]
[ 7335-25-3 ]
β-(2-chlorophenyl)-β-hydroxy-α-(2-thienyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In ethanol;	1) 1.12 g of sodium was added to 25 ml of dry ethanol, followed by heating to a reflux temperature. Then, a mixture comprising 5.0 g of 2-thiopheneacetonitrile, 7.49 g of <strong>[7335-25-3]ethyl 2-chlorobenzoate</strong> and 25 ml of dry ethanol, was dropwise added. After completion of the dropwise addition, the mixture was reacted for 1 hour under reflux. After completion of the reaction, the reaction mixture was cooled and put into water, and the aqueous layer washed with methylene chloride was weakly acidified with hydrochloric acid and extracted with methylene chloride. The obtained extracted layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.6 g of beta-(2-chlorophenyl)-beta-hydroxy-alpha-(2-thienyl)acrylonitrile having a melting point of from 164 to 167 C. The NMR spectrum data of this compound were as follows. 1H-NMR deltappm (Solvent: CDCl3/400 MHz)

Reference： [1]Patent: US6187944,2001,B1

30
[ 20893-30-5 ]
[ 74-88-4 ]
[ 90222-97-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.05h; Stage #2: methyl iodide In tetrahydrofuran; toluene for 0.25h;	1a To a solution of 2-(thiophen-2-yl) acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF, KHMDS (24.4 mmol, 48.9 ml, 0.5M in toluene) was added at 0° C. The mixture was allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) was added slowly over a period of 10 minutes. The mixture was stirred for 5 minutes and monitored by TLC. Upon completion, the reaction was quenched with aqueous ammonium chloride. The organic phase was separated with ethyl acetate and dried over sodium sulfate. The product was purified via vacuum distillation. (bp 42° C. at 1 torr) Yield: 89%. 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 ppm (d, 1H), 7.2 ppm (t, 1H), 7.0 ppm (d, 1H), 1.9 ppm (s, 6H).
89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 0.05h; Stage #2: methyl iodide In tetrahydrofuran for 0.25h;	1a Example 1a 2-Methyl-2-(thiophen-2-yl)propanenitrile (1a)-To a solution of 2-(thiophen-2-yl) acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF, KHMDS (24.4 mmol, 48.9 ml, 0.5M in toluene) was added at 0° C. The mixture was allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) was added slowly over a period of 10 minutes. The mixture was stirred for 5 minutes and monitored by TLC. Upon completion, the reaction was quenched with aqueous ammonium chloride. The organic phase was separated with ethyl acetate and dried over sodium sulfate. The product was purified via vacuum distillation (bp 42° C. at 1 torr) Yield: 89%. 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 ppm (d, 1H), 7.2 ppm (t, 1H), 7.0 ppm (d, 1H), 1.9 ppm (s, 6H).
89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; Stage #2: methyl iodide In tetrahydrofuran; toluene for 0.25h;	1a Example 1a; 2-Methyl-2-(thiophen-2-yl)propanenitrile-To a solution of 2-(thiophen-2-yl) acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF, KHMDS (24.4 mmol, 48.9 ml, 0.5M in toluene) was added at 0° C. The mixture was allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) was added slowly over a period of 10 minutes. The mixture was stirred for 5 minutes and monitored by TLC. Upon completion, the reaction was quenched with aqueous ammonium chloride. The organic phase was separated with ethyl acetate and dried over sodium sulfate. The product was purified via vacuum distillation. (bp 42° C. at 1 torr) Yield: 89%. 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 ppm (d, 1H), 7.2 ppm (t, 1H), 7.0 ppm (d, 1H), 1.9 ppm (s, 6H).

89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0℃; for 0.05h; Stage #2: methyl iodide In tetrahydrofuran; toluene for 0.25h;	2a Example 2a 2-Methyl-2-(thiophen-2-yl)propanenitrile-To a solution of 2-(thiophen-2-yl) acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF, KHMDS (24.4 mmol, 48.9 ml, 0.5M in toluene) was added at 0° C. The mixture was allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) was added slowly over a period of 10 minutes. The mixture was stirred for 5 minutes and monitored by TLC. Upon completion, the reaction was quenched with aqueous ammonium chloride. The organic phase was separated with ethyl acetate and dried over sodium sulfate. The product was purified via vacuum distillation (bp 42° C. at 1 torr) Yield: 89%. 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 ppm (d, 1H), 7.2 ppm (t, 1H), 7.0 ppm (d, 1H), 1.9 ppm (s, 6H).
89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 0.05h; Stage #2: methyl iodide In tetrahydrofuran for 0.25h;	1 Example 1Ia[0065] 2-Methyl-2-(thiophen-2-yl)propanenitrile - To a solution of 2-(thiophen-2-yl)acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF,KHMDS (24.4 mmol, 48.9 ml, 0.5 M in toluene) is added at 0 0C. The mixture is allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) is added slowly over a period of 10 minutes. The mixture is stirred for another 5 minutes and monitored by TLC. Upon completion, the reaction is quenched with aqueous ammonium chloride. The organic phase is separated with ethyl acetate and dried over sodium sulfate. The product is purified via vacuum distillation (bp 42 0C at 1 torr). Yield 89%; 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 (d, IH), 7.2 (t, IH), 7.0 (d, IH), 1.9 (s, 6H).
89%	Stage #1: 2-cyanomethylthiophene With potassium hexamethylsilazane In tetrahydrofuran at 0℃; for 0.05h; Stage #2: methyl iodide In tetrahydrofuran for 0.25h;	1 Example 1Ia[0069] 2-Methyl-2-(thiophen-2-yl)propanenitrile - To a solution of 2-(thiophen-2-yl)acetonitrile (1 g, 8.13 mmol) in 4 ml anhydrous THF,KHMDS (24.4 mmol, 48.9 ml, 0.5 M in toluene) is added at 0 0C. The mixture is allowed to stir for 3 minutes, after which a solution of 16.26 mmol iodomethane (1.13 ml in 26 ml anhydrous THF) is added slowly over a period of 10 minutes. The mixture is stirred for another 5 minutes and monitored by TLC. Upon completion, the reaction is quenched with aqueous ammonium chloride. The organic phase is separated with ethyl acetate and dried over sodium sulfate. The product is purified via vacuum distillation (bp 42 0C at 1 torr). Yield 89%; 1H NMR (500 MHz, CDCl3): δ (ppm) 7.4 (d, IH), 7.2 (t, IH), 7.0 (d, IH), 1.9 (s, 6H). [0070] In a similar fashion the following compounds are synthesized.
58.6%	Stage #1: 2-cyanomethylthiophene With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran for 1.5h; Inert atmosphere;	185 EXAMPLE 185: Compound 442B: 5-(1-cyano-1-methylethyl)-N-[3-(4-[(3S,4R)-3-fluoro-1- methylpiperidin-4-yl]amino}-1-(2,2,2-trifluoroethyl)-1H-indol-2-yl)-1,2,4-oxadiazol-5- yl]methyl}thiophene-2-carboxamide To a mixture of 2-(2-thienyl)acetonitrile (5 g, 40.6 mmol, 4.31 mL, 1 eq) in THF (7 mL) was added sodium hydride (4.87 g, 121.8 mmol, 60% purity, 3 eq) in one portion 0 °C under nitrogen. The mixture was stirred at 0 °C for 30 min, followed by addition of iodomethane (122 mmol, 7.6 mL, 3 eq), then the reaction was heated to 20 °C and stirred for 1.5 h. The residue was poured into ammonium chloride (saturated, 30 mL). The aqueous phase was extracted with EA (3x20 mL). The combined organic phase was washed with brine (3x20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100-200 mesh silica gel, PE/EA=99/1, 91/19) to afford the product (3.6 g, 58.6% yield) as white oil.1H NMR (400 MHz, CHCl3-d) δ = 7.28 (d, J=0.86 Hz, 1H), 7.27 (d, J=1.10 Hz, 1H), 7.12 (dd, J=3.55, 0.98 Hz, 1H), 6.99 (dd, J=5.01, 3.67 Hz, 1H), 1.82 (s, 6H).
	With sodium hydride In dimethyl sulfoxide at 25℃; for 3.08333h;	27 Method 27; 2-Methyl-2-(2-thienyr)propanenitrile; A solution of NaH (0.974 g, 24.36 mmol) in DMSO (30 ml) was treated with 2- thienylacetonitrile (1.00 g, 8.12 mmol) by dropwise addition. After stirring for 5 min at 25 0C, methyl iodide (6.91 g, 48.72 mmol) was added to the reaction mixture via syringe. The resulting solution was stirred at 25 0C for 3 h before being diluted with H2O (100 ml). The resulting solution was extracted with EtOAc. The organics were washed with NaCl(sat) and dried with MgSO4(s). The organics were removed under reduced pressure, and the residue was purified by column chromatography utilizing an ISCO system (EtOAc-Hexane) to give 1.0 g of (81 %) a pale yellow oil; m/z 152.
	Stage #1: 2-cyanomethylthiophene With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran at 0 - 20℃; for 13h; Inert atmosphere;

Reference： [1]Current Patent Assignee: UNIVERSITY OF TENNESSEE - US2009/286815, 2009, A1 Location in patent: Page/Page column 5-6
[2]Current Patent Assignee: UNIVERSITY OF TENNESSEE - US2009/286810, 2009, A1 Location in patent: Page/Page column 4; 5
[3]Current Patent Assignee: UNIVERSITY OF TENNESSEE - US2009/286824, 2009, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: UNIVERSITY OF TENNESSEE - US2009/286818, 2009, A1 Location in patent: Page/Page column 4; 7
[5]Current Patent Assignee: UNIVERSITY OF TENNESSEE - WO2011/22692, 2011, A2 Location in patent: Page/Page column 11; 18-19
[6]Current Patent Assignee: UNIVERSITY OF TENNESSEE - WO2011/22694, 2011, A2 Location in patent: Page/Page column 11; 19
[7]Current Patent Assignee: PMV PHARMACEUTICALS INC - WO2021/231474, 2021, A1 Location in patent: Paragraph 0949
[8]Current Patent Assignee: ASTRAZENECA PLC - WO2007/71963, 2007, A2 Location in patent: Page/Page column 51
[9]Takamatsu, Kazutaka; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro [Journal of Organic Chemistry, 2015, vol. 80, # 6, p. 3242 - 3249]

31
[ 20893-30-5 ]
[ 13304-62-6 ]
[ 1201921-14-3 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 18252 - 18253

32
[ 20893-30-5 ]
[ 207129-05-3 ]
[ 1219686-69-7 ]

Yield	Reaction Conditions	Operation in experiment
88.2%	at 25 - 30℃; for 0.5h; Deep eutectic solvent;
68.5%	With potassium <i>tert</i>-butylate In methanol at 20 - 50℃; for 12h;	2.3 2.2.3 Synthesis of (2E,2′E)-3,3′-(9-hexyl-9H-carbazole-3,6-diyl)bis(2-(thiophen-2-yl)acrylonitrile) (1c) General procedure: Freshly distilled methanol (100 ml) was taken in a 250 ml single neck round bottom flask. The compound 1b (3 g, 1eq) and thiophene-2-acetonitrile (2.65 g, 2.2eq) were added to the methanol. A catalytic amount of potassium tert-butoxide was added into this mixture at room temperature. The reaction mixture was stirred for 12 h at 50 °C. It was monitored by TLC. A bright yellow solid was filtered after 12 h. It was recrystallized in dichloromethane and methanol to give the product 2.6 g (yield = 52%).(0009)1H NMR (CDCl3, ppm): δ 8.60-8.50 (m, 2H), 8.12-8.09 (m, 2H), 7.51-7.45 (m, 2H), 7. 42-7.38 (m, 2H), 7.26 (s, 2H), 7.13-7.10 (m, 2H), 7.04-7.00 (m, 2H), 4.32 (t, 2H, J = 7.2 Hz), 1.93-1.55 (m, 2H), 1.39-1.25 (m, 6H), 0.89-0.87 (m, 3H). 13C NMR (CDCl3, ppm): δ 142.22, 140.77, 140.08, 128.21, 127.42, 126.47, 125.63, 125.60, 123.32, 122.93, 117.91, 109.87, 103.17, 43.79, 31.64, 29.14, 27.05, 22.66, 14.13.
68.5%	With potassium <i>tert</i>-butylate In methanol at 50℃; for 12h;	Synthesis of (2E, 2′E)-3, 3′-(9-hexyl-9H-carbazole-3,6-diyl) bis (2-(thiophen-2-yl) acrylonitrile) (1c) [23] General procedure: Freshly distilled methanol (100mL) was taken in a 250mL single neck round bottom flask. The compound 1b (3g, 1eq) and thiophene-2-acetonitrile (2.65g, 2.2eq) were added to the methanol. A catalytic amount of potassium tert-butoxide was added into this mixture at room temperature. Then the reaction mixture was stirred for 12h at 50°C. It was monitored by TLC. A bright yellow solid was filtered after 12h. It was recrystallized in dichloromethane and methanol to give the product

Reference： [1]Sonawane, Yogesh A.; Phadtare, Sunanda B.; Borse, Bhushan N.; Jagtap, Amit R.; Shankarling, Ganapati S. [Organic Letters, 2010, vol. 12, # 7, p. 1456 - 1459]
[2]Ramkumar, Sekar; Anandan, Sambandam [Dyes and Pigments, 2013, vol. 97, # 3, p. 397 - 404]
[3]Reddy, Gachumale Saritha; Ramkumar, Sekar; Asiri, Abdullah M.; Anandan, Sambandam [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 145, p. 531 - 539]

33
[ 20893-30-5 ]
[ 262291-69-0 ]
[ 1427737-33-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium <i>tert</i>-butylate In methanol at 20 - 50℃; for 12h;	2.3 2.2.3 Synthesis of (2E,2′E)-3,3′-(9-hexyl-9H-carbazole-3,6-diyl)bis(2-(thiophen-2-yl)acrylonitrile) (1c) Freshly distilled methanol (100 ml) was taken in a 250 ml single neck round bottom flask. The compound 1b (3 g, 1eq) and thiophene-2-acetonitrile (2.65 g, 2.2eq) were added to the methanol. A catalytic amount of potassium tert-butoxide was added into this mixture at room temperature. The reaction mixture was stirred for 12 h at 50 °C. It was monitored by TLC. A bright yellow solid was filtered after 12 h. It was recrystallized in dichloromethane and methanol to give the product 2.6 g (yield = 52%).(0009)1H NMR (CDCl3, ppm): δ 8.60-8.50 (m, 2H), 8.12-8.09 (m, 2H), 7.51-7.45 (m, 2H), 7. 42-7.38 (m, 2H), 7.26 (s, 2H), 7.13-7.10 (m, 2H), 7.04-7.00 (m, 2H), 4.32 (t, 2H, J = 7.2 Hz), 1.93-1.55 (m, 2H), 1.39-1.25 (m, 6H), 0.89-0.87 (m, 3H). 13C NMR (CDCl3, ppm): δ 142.22, 140.77, 140.08, 128.21, 127.42, 126.47, 125.63, 125.60, 123.32, 122.93, 117.91, 109.87, 103.17, 43.79, 31.64, 29.14, 27.05, 22.66, 14.13.
52%	With potassium <i>tert</i>-butylate In methanol at 50℃; for 12h;	Synthesis of (2E, 2′E)-3, 3′-(9-hexyl-9H-carbazole-3,6-diyl) bis (2-(thiophen-2-yl) acrylonitrile) (1c) [23] Freshly distilled methanol (100mL) was taken in a 250mL single neck round bottom flask. The compound 1b (3g, 1eq) and thiophene-2-acetonitrile (2.65g, 2.2eq) were added to the methanol. A catalytic amount of potassium tert-butoxide was added into this mixture at room temperature. Then the reaction mixture was stirred for 12h at 50°C. It was monitored by TLC. A bright yellow solid was filtered after 12h. It was recrystallized in dichloromethane and methanol to give the product 2.6g (yield=52%). 1H NMR (CDCl3, ppm): δ 8.60-8.50 (m, 2H), 8.12-8.09 (m, 2H), 7.51-7.45 (m, 2H), 7.42-7.38 (m, 2H), 7.26 (s, 2H), 7.13-7.10 (m, 2H), 7.04-7.00 (m, 2H), 4.32 (t, 2H, J=7.2Hz), 1.93-1.55 (m,2H), 1.39-1.25 (m, 6H), 0.89-0.87 (m, 3H). 13C NMR (CDCl3, ppm): δ 142.22, 140.77, 140.08, 128.21, 127.42, 126.47, 125.60, 123.32, 122.93, 117.91, 109.87, 103.17, 43.79, 31.64, 29.14, 27.05, 22.66, 14.13.

Reference： [1]Ramkumar, Sekar; Anandan, Sambandam [Dyes and Pigments, 2013, vol. 97, # 3, p. 397 - 404]
[2]Reddy, Gachumale Saritha; Ramkumar, Sekar; Asiri, Abdullah M.; Anandan, Sambandam [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 145, p. 531 - 539]

34
[ 20893-30-5 ]
[ 772-31-6 ]
[ 1429308-59-7 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3351 - 3353

35
[ 20893-30-5 ]
[ 6640-25-1 ]
[ 1429308-60-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h;

Reference： [1]Huang, Huawen; Ji, Xiaochen; Wu, Wanqing; Jiang, Huanfeng [Chemical Communications, 2013, vol. 49, # 32, p. 3351 - 3353]

36
[ 20893-30-5 ]
[ 77972-87-3 ]
[ 1429308-65-5 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 3351 - 3353

37
[ 20893-30-5 ]
[ 5228-49-9 ]
[ 1472056-53-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide; In methanol; at 20℃; for 24h;	General procedure: Compound 1a or 1b (10 mmol) and thiophene-2-acetonitrile 2 (12 mmol) were added to a stirred solution of KOH (20 g, 357 mmol) in methanol (50 mL). The mixture was stirred at ambient temperature for 24 h. The solvent was distilled off under reduced pressure, and the precipitate was collected by filtration, washed with water and EtOH, dried in air, and crystallised from EtOH. The following compounds were prepared by this method.

Reference： [1]Journal of Chemical Research,2013,vol. 37,p. 438 - 440

38
[ 20893-30-5 ]
[ 5228-51-3 ]
[ 1472056-54-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium hydroxide In methanol at 20℃; for 24h;	Synthesis of 3a and 3b; general procedure General procedure: Compound 1a or 1b (10 mmol) and thiophene-2-acetonitrile 2 (12 mmol) were added to a stirred solution of KOH (20 g, 357 mmol) in methanol (50 mL). The mixture was stirred at ambient temperature for 24 h. The solvent was distilled off under reduced pressure, and the precipitate was collected by filtration, washed with water and EtOH, dried in air, and crystallised from EtOH. The following compounds were prepared by this method.

Reference： [1]Hoseini-Hesar, Toktam; Pordel, Mehdi; Roshani, Mina; Shams, Alireza [Journal of Chemical Research, 2013, vol. 37, # 7, p. 438 - 440]

39
[ 20893-30-5 ]
[ 5447-02-9 ]
C₂₇H₂₁NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; <i>tert</i>-butyl alcohol for 2h;	7.i Compound 6 To a stirred solution of the compound 5 (1 g, 3.1 mmol) and 2-thiopheneacetonitrile (Aldrich, 0.39 g, 3.1 mmol) in t-butanol and THF mixture (10 mL:2 mL), tetrabutylammonium hydroxide (TBAH) solution (0.34 mL, 0.3 mmol) was slowly added. (Compound 5 was prepares according to the method described in C. C. Li et al, J. Org. Chem. 2003, 68, 8500.) After 2 hours, the mixture was poured into the water, and extracted with dichloromethane (200 mL). After the solvent was removed by rotary evaporation, the crude product was purified by column chromatography on silica gel column (ethyl acetate: petroleum ether=1:3) to provide 1.0 g (yield=75%). 1H-NMR (400 MHz, CDCl3) δ (ppm) 7.62 (s, 1H), 7.50 (d, 2H, J=8.0 Hz), 7.45 (d, 2H, J=8.0 Hz), 7.41-7.24 (m, 10H), 7.05 (t, 1H), 6.95 (d, 1H, J=8.0 Hz), 5.25 (s, 2H), 5.24 (s, 2H). EI MS calcd for C27H21NO2S 423.53 m/z, found (+NH4+ (18 m/z)): 441.16 m/z

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF QUEENSLAND - US8598350, 2013, B2 Location in patent: Page/Page column 49; 50

40
[ 20893-30-5 ]
[ 1613810-53-9 ]
[ 1613810-63-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium <i>tert</i>-butylate In butan-1-ol at 80℃; for 1h;	4.9. General procedure for the Knoevenagel condensation ofdialdehydes 5a,b with 2-(hetaryl)acetonitriles General procedure: KOt-Bu (1.5 mmol, 120 mg) was added to a solution of the appropriate dialdehyde 5 (0.15 mmol) and 2-(hetaryl)acetonitrile (3 mmol, 370 mg-2-(thiophen-2-yl)acetonitrile; 520 mg-2-(benzo[d]thiazol-2-yl)acetonitrile) in anhydrous n-butanol (10 ml) with stirring at 80 °C. The mixture was stirred at the same temperature for 1 h, then the reaction mixture was neutralized byaddition of excess glacial acetic acid (1 ml). The precipitate was filtered,washed with hot methanol and dried at 110 °C to afford the compounds 9a,b or 10 in analytical pure form.

Reference： [1]Irgashev, Roman A.; Teslenko, Anton Yu.; Zhilina, Ekaterina F.; Schepochkin, Aleksandr V.; El'Tsov, Oleg S.; Rusinov, Gennady L.; Charushin, Valery N. [Tetrahedron, 2014, vol. 70, # 31, p. 4685 - 4696]

41
[ 20893-30-5 ]
[ 1613810-54-0 ]
[ 1613810-64-2 ]
C₄₆H₄₃N₃OS₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium <i>tert</i>-butylate In butan-1-ol at 80℃; for 1h;	4.9. General procedure for the Knoevenagel condensation ofdialdehydes 5a,b with 2-(hetaryl)acetonitriles General procedure: KOt-Bu (1.5 mmol, 120 mg) was added to a solution of the appropriate dialdehyde 5 (0.15 mmol) and 2-(hetaryl)acetonitrile (3 mmol, 370 mg-2-(thiophen-2-yl)acetonitrile; 520 mg-2-(benzo[d]thiazol-2-yl)acetonitrile) in anhydrous n-butanol (10 ml) with stirring at 80 °C. The mixture was stirred at the same temperature for 1 h, then the reaction mixture was neutralized byaddition of excess glacial acetic acid (1 ml). The precipitate was filtered,washed with hot methanol and dried at 110 °C to afford the compounds 9a,b or 10 in analytical pure form.

42
[ 20893-30-5 ]
C-phenyl-N-methylnitrone [ No CAS ]
[ 79271-56-0 ]
3-(methyl((triethylsilyl)oxy)amino)-3-phenyl-2-(thiophen-2-yl)propanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine In 1,2-dichloro-ethane at -30℃; for 0.5h; Inert atmosphere;	General procedure for addition of nitrile to nitrone General procedure: To a mixture of (Z)-N-benzylidenemethanamine oxide 10 (54.1 mg, 0.40 mmol),2-phenylpropanenitrile 13 (53 μL, 0.40 mmol) and Et3N (112 μL, 0.80 mmol) in DCE (2 mL) was added TESOTf (181 μL, 0.80 mmol) at -30 °C, and the reaction mixture was stirred at this temperature for 30 min. Saturated aqueous sodium bicarbonate (1 mL) was added to the mixture,and the product was extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography(SiO2, hexane-Et2O = 15:1) afforded O-TES β-hydroxyamino nitrile 14c (143.5 mg, 0.377mmol, 94%) as an inseparable 55:45 mixture of diastereomers.

Reference： [1]Yoshimura, Fumihiko; Abe, Taiki; Tanino, Keiji [Synlett, 2014, vol. 25, # 13, p. 1863 - 1868]

43
[ 20893-30-5 ]
[ 183718-76-5 ]
3-(1-hexyl-1H-indol-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium methylate In methanol at 20℃; for 6h; Inert atmosphere;	2.2.2. Synthesis of 3-(1-hexyl-1H-indol-3-yl)-2-(thiophen-2-yl)acrylonitrile (2) To a freshly prepared solution of sodium methoxide (0.132 g, 5.76 mmol of sodium in 10 mL of methanol), 1-hexyl-1H-indole-3-carbaldehyde (1, 1.1 g, 4.8 mmol) was added slowly while stirring. Thiophene-2-acetonitrile (0.709 g, 5.76 mmol) was then added to reaction mass. Stirring was continued for 6 h at room temperature. The precipitated yellow solid was collected by filtration, washed with methanol and finally recrystallized from chloroform. Yellow solid, yield 65%, m.p. 91-93 C. (ATR, cm-1): 3103 (-C-H aromatic stretching); 2974 (-C-H aliphatic stretching); 2207 (-CN stretching). 1H NMR (400 MHz, DMSO-d6): δ (ppm) 8.31 (s, 1H), 8.00 (d, J = 7.6 Hz, 1H), 7.96 (s, 1H), 7.61 (d, J = 8 Hz, 1H), 7.58 (d, J = 4.8 Hz,1H), 7.40 (s, 1H), 7.30 (t, J = 7.2 Hz, 1H), 7.23 (t, J = 7.6 Hz, 1H), 7.15 (s, 1H), 4.31 (t, J = 6.8 Hz, 2H), 1.78 (s, 2H), 1.27 (s, 6H), 0.83 (t,J = 6.4 Hz, 3H). Anal. Calcd. for C21H22N2S: C,75.41; H,6,63; N, 8.38 found: C 73.21; H, 6.69; N, 8.43.

Reference： [1]Babu, Dickson D.; Gachumale, Saritha Reddy; Anandan, Sambandam; Adhikari, Airody Vasudeva [Dyes and Pigments, 2015, vol. 112, p. 183 - 191]

44
[ 20893-30-5 ]
[ 17754-90-4 ]
[ 117850-52-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With piperidine In acetic acid; N,N-dimethyl-formamide
74%	With piperidine; acetic acid In N,N-dimethyl-formamide Reflux; Inert atmosphere;	7-(Diethylamino)-3-(thiophen-2-yl)-coumarin (2) A mixture of 1 (5.0 g, 25.87 mmol) and 2-(thiophen-2-yl)acetonitrile (3.5 g, 28.46 mmol) in DMF (38 ml) and AcOH (20 ml) was added with piperidine (10.24 ml, 103.49 mmol). The reaction mixture was stirred at reflux under N2 for 24 h. After being cooled to room temperature, water (100 ml) was added and the mixture was extracted with CH2Cl2 (70 ml x 3). The combined organic phase was washed with water (100 ml), brine solution (100 ml), dried over anhydrous Na2SO4, filtered, and the solvents were removed to dryness. Purification by column chromatography over silica gel eluting with a mixture of CH2Cl2 and hexane (1:3) followed by recrystallization with a mixture of CH2Cl2 and methanol gave 2 (4.74 g, 64%) as a yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.22 (6H, t, J = 6.9 Hz), 3.42 (4H, q, J = 7.1 Hz), 6.54 (1H, s), 6.59 (1H, d, J = 8.7 Hz), 7.08 (1H, t, J = 4.8 Hz), 7.31-7.34 (2H, m), 7.65 (1H, d, J = 3.9 Hz), 7.89 (1H, s) ppm; MALDI-TOF (m/z) calcd for C17H17NO2S 299.0980 [M+]; found 299.1101
4.74 g	With piperidine In acetic acid; N,N-dimethyl-formamide for 24h; Reflux; Inert atmosphere;

	Stage #1: 2-cyanomethylthiophene; 4-(Diethylamino)salicylaldehyde With piperidine Stage #2: With hydrogenchloride
	With piperidine; acetic acid

Reference： [1]Kotchapradist, Palita; Prachumrak, Narid; Sunonnam, Thitiya; Tarsang, Ruangchai; Namuangruk, Supawadee; Sudyoadsuk, Taweesak; Keawin, Tinnagon; Jungsuttiwong, Siriporn; Promarak, Vinich [Dyes and Pigments, 2015, vol. 112, p. 227 - 235]
[2]Kochapradist, Palita; Sunonnam, Thitiya; Prachumrak, Narid; Namuangruk, Supawadee; Keawin, Tinnagon; Jungsuttiwong, Siriporn; Sudyoadsuk, Taweesak; Promarak, Vinich [Tetrahedron Letters, 2014, vol. 55, # 49, p. 6689 - 6693]
[3]Kotchapadist, Palita; Prachumrak, Narid; Sunonnam, Thitiya; Namuangruk, Supawadee; Sudyoadsuk, Taweesak; Keawin, Tinnagon; Jungsuttiwong, Siriporn; Promarak, Vinich [European Journal of Organic Chemistry, 2015, vol. 2015, # 3, p. 496 - 505]
[4]Yu, Tianzhi; Zhu, Zeyang; Bao, Yanjun; Zhao, Yuling; Liu, Xiaoxiao; Zhang, Hui [Dyes and Pigments, 2017, vol. 147, p. 260 - 269]
[5]Bhagwat, Archana A.; Avhad, Kiran C.; Patil, Dinesh S.; Sekar, Nagaiyan [Photochemistry and Photobiology, 2019, vol. 95, # 3, p. 740 - 754]

45
[ 20893-30-5 ]
[ 613-84-3 ]
5-methyl-2-(thiophen-2-yl)benzofuran-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium methylate; copper diacetate In dimethyl sulfoxide at 100℃; for 15h; Green chemistry;
66%	With sodium methylate; copper diacetate In acetonitrile at 100℃;	8 Example 8 Room temperature (20-35 deg.] C) under the reaction flask were sequentially added 5-methyl-salicylaldehyde (0.5mmol), Cu (OAc) 2 (0.1mmol), 2- thiophene acetonitrile (0.75mmol), sodium methoxide (2mmol) and DMSO (2ml), then stirred and heated to 100 deg.] C until the reaction of 5-methyl salicylaldehyde reaction was complete. After completion of the reaction, the reaction solution was cooled to room temperature and 20ml of water was added, extracted with methylene chloride three times with dichloromethane 10ml, separated on silica gel column, evaporated under reduced pressure, yield 66%

Reference： [1]Zhang, Lianpeng; Peng, Zhixing; Wen, Qiaodong; Li, Xihui; Lu, Ping; Wang, Yanguang [Organic Letters, 2016, vol. 18, # 4, p. 728 - 731]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN105399710, 2016, A Location in patent: Paragraph 0036; 0037

46
[ 20893-30-5 ]
1-hexyl-5-nitro-1H-indole-3-carbaldehyde [ No CAS ]
3-(1-hexyl-5-nitro-1H-indol-3-yl)-2-(thiophene-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium methylate In methanol at 20℃; for 9h; Inert atmosphere;	2.2.3. Synthesis of 3-(1-hexyl-5-nitro-1H-indol-3-yl)-2-(thiophene-2-yl)acrylonitrile (3) To a freshly prepared solution of sodium methoxide (0.060 g, 2.62 mmol of sodium in 10 mL of methanol), thiophene-2-acetonitrile (0.323 g, 2.62 mmol) was added slowly while stirring. 1-Hexyl-5-nitro-1H-indole-3-carbaldehyde (2, 0.6 g, 2.18 mmol) was then added to reaction mass. Stirring was continued for 9 h at room temperature. The precipitated yellow solid was collected by filtration, washed with methanol and finally recrystallized from chloroform. Yellow solid, yield 69%. 1H NMR (400 MHz DMSO-d6,ppm): δ 9.14 (s, 1H), 8.48 (s, 1H), 8.17 (d, J = 24 Hz, 2H), 7.84 (s, 1H),7.64 (s, 1H), 7.53 (s, 1H), 7.17 (d, 1H), 4.40 (s, 2H), 1.79 (s, 2H), 1.27 (s,6H), 0.83 (t, 3H). Anal. Calcd. for C21H21N3O2S: C, 66.47; H,5.58; N,11.07 found: C, 66.31; H, 5.61; N, 11.15. ESI-MS (+ve mode) m/zCalcd for C21H21N3O2S: 379.14. Found: 380.14 [M+H]+.

Reference： [1]Babu, Dickson D.; Elsherbiny, Dalia; Cheema, Hammad; El-Shafei, Ahmed; Adhikari, Airody Vasudeva [Dyes and Pigments, 2016, vol. 132, p. 316 - 328]

47
[ 20893-30-5 ]
[ 35486-42-1 ]
6,8-dibromo-3-(thiophen-2-yl)imidazo[1,2-a]pyridin-2-amine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 7617 - 7622

48
[ 20893-30-5 ]
[ 35486-42-1 ]
C₁₁H₉Br₂N₃S [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 7617 - 7622

49
[ 20893-30-5 ]
[ 17422-74-1 ]
(E)-3-(4-oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.333333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o). 4.4 Spectral Characterization4.4.1 (E)-3-(4-Oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile (3a)Yellow crystalline solid, yield 96 %, m.p. 213-214 °C,Analytical cal. C16H9NO2S: C, 68.80; H, 3.25; N, 5.01;found: C, 68.77; H, 3.26; N, 5.03. IR (KBr cm-1): 2219(C≡N), 1652 (C=Oγ-pyrone), 1612 (C=Cγ-pyrone), 1560, 1462(C=Caromatic). 1H NMR (400 MHz, DMSO-d6, δ, ppm):7.25(s, 1H, H-2), 8.01 (d, 1H, H-5), 7.45 (m, 1H, H-6), 7.58 (m,1H, H-7), 7.58 (d, 1H, H-8), 7.40 (s, 1H, =CHolifinic), 7.38(d, 1H, H-3), 7.20 (m, 1H, H-4), 7.70 (d, 1H, H-5). 13CNMR (100 MHz, DMSO-d6, δ, ppm): 150.12 (C-2), 118.50(C-3), 178.45 (C-4), 124.82 (C-5), 123.83 (C-6), 135.51(C-7), 116.82 (C-8), 125.54 (C-4a), 152.44 (C-8a), 136.05(C-2), 127.42 (C-3), 127.15 (C-4), 131.51 (C-5), 110.45(C-1), 152.84 (C-2), 178.50 (C=O), 117.91 (CN). MS(EI): (m/z) 279.04 [M+·].

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

50
[ 20893-30-5 ]
[ 42059-81-4 ]
(E)-3-(6-methyl-4-oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.4h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

51
[ 20893-30-5 ]
[ 69155-76-6 ]
(E)-3-(6-fluoro-4-oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With silica bonded N-(propylcarbamoyl)sulfamic acid; In neat (no solvent); at 80℃; for 0.333333h;Green chemistry;	General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Catalysis Letters,2016,vol. 146,p. 1687 - 1705

52
[ 20893-30-5 ]
[ 52817-12-6 ]
(E)-3-(6-bromo-4-oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.366667h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

53
[ 20893-30-5 ]
[ 61424-76-8 ]
(E)-3-(2-amino-4-oxo-4H-chromen-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.416667h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

54
[ 20893-30-5 ]
[ 99-61-6 ]
(E)-3-(3-nitrophenyl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.333333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

55
[ 20893-30-5 ]
[ 555-16-8 ]
(E)-3-(4-nitrophenyl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.333333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

56
[ 20893-30-5 ]
[ 13677-79-7 ]
(E)-2-(thiophen-2-yl)-3-(3,4,5-trihydroxyphenyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.433333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

57
[ 20893-30-5 ]
[ 708-06-5 ]
(E)-3-(2-hydroxynaphthalen-1-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.5h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

58
[ 20893-30-5 ]
[ 487-89-8 ]
(E)-3-(1H-indol-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With silica bonded N-(propylcarbamoyl)sulfamic acid In neat (no solvent) at 80℃; for 0.333333h; Green chemistry;	4.3 General Procedure for the Synthesisof Acrylonitrile Derivatives General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 °C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Parveen, Mehtab; Azaz, Shaista; Ahmad, Faheem; Malla, Ali Mohammed; Alam, Mahboob [Catalysis Letters, 2016, vol. 146, # 9, p. 1687 - 1705]

59
[ 20893-30-5 ]
[ 52562-50-2 ]
(E)-3-(5-methyl-1H-indol-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With silica bonded N-(propylcarbamoyl)sulfamic acid; In neat (no solvent); at 80℃; for 0.366667h;Green chemistry;	General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Catalysis Letters,2016,vol. 146,p. 1687 - 1705

60
[ 20893-30-5 ]
[ 3414-19-5 ]
(E)-3-(5-hydroxy-1H-indol-3-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With silica bonded N-(propylcarbamoyl)sulfamic acid; In neat (no solvent); at 80℃; for 0.4h;Green chemistry;	General procedure: To a mixture of substituted aromatic aldehydes 1(a-o) (2 mmol) and 2-thiopheneacetonitrile 2 (2 mmol), 80 mgof SBPCSA was added and the reaction mixture was heatedon an oil bath at 80 C for (20-30 min) with stirring. Aftercompletion of the reaction as evident from thin layerchromatography (TLC), the reaction mixture was dilutedwith ethanol and filtered off to recover the catalyst forfurther use in catalytic cycles. The filtrate was evaporatedunder reduced pressure to obtain the product. The crudeproduct was further purified by crystallization fromappropriate solvent to afford the pure product 3(a-o).

Reference： [1]Catalysis Letters,2016,vol. 146,p. 1687 - 1705

61
[ 20893-30-5 ]
[ 3029-19-4 ]
(E)-3-(pyren-1-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.1%	With potassium <i>tert</i>-butylate In methanol at 20 - 65℃; for 12h;	4.1 2.4.1 Synthesis of (E)-3-(pyren-1-yl)-2-(thiophen-2-yl)acrylonitrile (2) Freshly distilled methanol (30 mL) was taken in a 100 mL single neck round bottom flask. The compound 1 (pyrene-1-carbaldehyde) (0.5 g, 1 eq) and thiophene-2-acetonitrile (0.375 g, 1.4 eq) were added to the methanol. A catalytic amount of potassium tert-butoxide was added into this mixture at room temperature. Then the reaction mixture was stirred for 12 h at 65 °C. It was monitored by TLC. A bright yellow solid was filtered after 12 h. It was recrystallized in dichloromethane and methanol to give the product 0.423 g (yield = 58.1%). 1H NMR (500 MHz, CDCl3, ppm): δ 8.63 (d, 1H, J = 10 Hz), 8.42 (s, 1H), 8.24-8.05 (m, 8H), 7.52 (s, 1H), 7.40 (s, 1H), 7.15 (s, 1H). 13C NMR (CDCl3, ppm): δ 140.11, 139.47, 137.54, 134.75, 132.79, 132.36, 131.25, 130.90, 130.48, 129.75, 129.00, 128.49, 127.93, 127.39, 126.25, 124.97, 124.54, 123.34, 122.39, 118.76, 117.15, 112.05, 108.79. IR (KBr, cm-1): 2219. Chemical Formula: C23H13NS Molecular Weight: 335.42, Found: 335.12.

Reference： [1]Saritha, Gachumale; Wu, Jerry J.; Anandan, Sambandam [Organic electronics, 2016, vol. 37, p. 326 - 335]

62
[ 20893-30-5 ]
[ 766-47-2 ]
C₁₅H₁₃NS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide; <i>tert</i>-butyl alcohol at 80℃; for 12h; Inert atmosphere; stereoselective reaction;	18 The reaction bottle by adding 0.3 millimoles ofOrtho-methyl phenylacetylene0.3 millimoles of2 - thiophene acetonitrile, 0.3 millimoles of bi Potassium,0.3 millimolar t-butanol, 1 ml of dimethylsulfoxide, and the mixture was stirred for 12 hours under the protection of nitrogen at 80 ° C. After heating and Stirring, cooled to the room temperature. The reaction solution with 15 ml water washing, and then the extraction The ethyl ester three times (once for each 10 ml), the combined organic phase is dried over anhydrous sodium sulfate, the solvent is removed by distillation under reduced pressure, and then purified by column chromatography to obtain the desired product. The column chromatography eluant is the Volume ratio of 100: 1 of the mixed solvent of hexane and yield of 83%.

Reference： [1]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN106116998, 2016, A Location in patent: Paragraph 0150-0151

63
[ 20893-30-5 ]
2-thiophenylethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With boron trifluoride In tetrahydrofuran at 45 - 50℃;	3 Embodiment 3: synthesis of 2-thiophene-ethylamine The 1L to four bottle 500 ml tetrahydrofuran (THF), then adding 210-215g2-thiophene acetonitrile, 40-45g nabh, then slowly dropping 85-90g boron trifluoride ether solution, after dripping, the temperature rising to 45-50 °C and thermal insulation 4-8h, heat insulating end of the reaction after cooling to room temperature, then poured into the quality of the volume of the same concentration is 8-12% in the hydrochloric acid, stir, re-used for quality concentration is 25-35% NaOH solution of, regulating pH=9-10, then using an appropriate amount of toluene extraction 2-4 time, organic layer saturated salt water for washing after concentrated under reduced pressure to remove toluene, to dry to obtain 220g2-thiophene ethylamine, yield 98%, purity 98.3% (GC).

Reference： [1]Current Patent Assignee: GNSG ANHUI HONG SIFANG; CHINESE ACADEMY OF SCIENCES - CN104447679, 2016, B Location in patent: Paragraph 0041-0042

64
[ 20893-30-5 ]
[ 5813-89-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With oxygen; ammonium chloride; copper(l) chloride In 1,2-dichloro-ethane; toluene at 70℃; Sealed tube;	11 Synthesis Example 11 Synthesis of 2-thiophenecarboxamide In the reaction vessel was added 10mol% CuCl, the reaction tube was evacuated, filled with oxygen,In an oxygen atmosphere, 0.2 mmol of 2-thiopheneacetonitrile, 0.4 mmol of ammonium chloride, 1 ml of toluene and 1 ml of 1,2-dichloroethane were added, the reaction vessel was sealed, and reacted at 70 ° C,After the reaction was completed, it was washed with water, extracted with chloroform, dried and concentrated by evaporation under reduced pressure to remove the solvent. The crude product was separated by column chromatography to give the desired product in a yield of 80%.
63%	With copper(I) oxide; oxygen; ammonium chloride; sodium hydroxide In acetonitrile at 120℃; for 30h; Schlenk technique;

Reference： [1]Current Patent Assignee: HUBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN106478442, 2017, A Location in patent: Paragraph 0055; 0056; 0057
[2]Chen, Xiuling; Peng, Yanhong; Li, Yan; Wu, Minghu; Guo, Haibing; Wang, Jian; Sun, Shaofa [RSC Advances, 2017, vol. 7, # 30, p. 18588 - 18591]

65
[ 765-50-4 ]
[ 75-86-5 ]
[ 20893-30-5 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With triethylamine In ethanol at 60 - 65℃; for 10h;	3.1 Synthesis of 2-thiopheneacetonitrile 102.6 g of acetone cyanohydrin,Ethanol 150 mL,8.3 g of triethylamine was placed in a flask,Heating up to 60-65 ,133.3 g of 2-chloromethylthiophene,Methyl isobutyl ketone 200mL mixture slowly dripping,After the dripping reaction was completed for 10 hours,After adding 250 mL of purified water,After cooling slightly, the organic phase was separated;The organic phase was distilled off under reduced pressure to remove the organic solvent,Further distillation gave 113.3 g of 2-thiophene acetonitrile,Yield 92.1%.

Reference： [1]Current Patent Assignee: LUDONG UNIVERSITY - CN106518839, 2017, A Location in patent: Paragraph 0006; 0013

66
[ 20893-30-5 ]
[ 110677-45-7 ]
(E)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; In ethanol; water; acetonitrile; at 50℃;	General procedure: Ten mmol of the acetonitrile derivate and 10 mmol of N-(4-formylphenyl) carbazole are placed ina 50-mL flask, 25 mL of ethanol are added. Then the mixture is stirred for 5 min, after that, 3 dropsof an aqueous solution 10% of potassium hydroxide is added to the mixture, the reaction is stirredand heat up to 50 C, and was monitored by thin layer chromatography until was completed, then themixture is cool down to 0 C. The formation of a crystalline precipitate is observed, it is filtered andwashed using cold EtOH. The solid is recovered and purified by recrystallization process using assolvent a mixture of acetone/EtOH 40:60.(E)-3-(4-(9H-carbazol-9-yl)phenyl)-2-(thiophen-2-yl)acrylonitrile (CZ-2): Yellow solid, Yield: 90%, m.p.159-161 C. FTIR (ATR, cm-1) 2214 (CN), 1487 (CS). 1H NMR (500 MHz, THF-d6) λ (ppm): 8.07-8.21(4H, m), 7.62-7.77 (3H, m), 7.32-7.52 (6H, m), 7.16-7.26 (2H, m), 7.04-7.13 (1H, m); 13C NMR (125 MHz,THF-d6) λ (ppm): 140.2, 139.4, 139.2, 132.4, 130.6, 127.9, 127.1, 126.8, 126.7, 125.9, 123.8, 120.2, 120.1,116.4, 109.6, 106.1; HRMS-TOF (ESI, m/z): [M + H]+ Found: 377.11064 for C25H16N2S; [M + H]+ Calcd:377.11069; Error 0.1987 ppm.

Reference： [1]Molecules,2018,vol. 23

67
[ 20893-30-5 ]
diphenyl(vinyl)sulfonium trifluoromethanesulfonate [ No CAS ]
1-(thiophen-2-yl)cyclopropanecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h;	General Procedure B: for aryl / heteroaryl acetonitriles substrate’s cyclopropanation General procedure: To a 5 mL Schlenk tube were added aryl / heteroaryl acetonitriles 1 (1.0 mmol, 1.0 equiv.), vinyl diphenylsulfonium triflate (434.4 mg, 1.2 mmol, 1.2 equiv.), and DMSO (5 mL). The mixture was stirred at room temperature for 2 min and to the mixture DBU (456 mg, 3 mmol, 3.0 equiv.) was added. The mixture was stirred for 12 hours at room temperature, and then to the mixture was added saturated ammonium chloride solution (25 mL). The resulting mixture was extracted with EtOAc (3 x 150 mL). The combined organic layers were washed with H2O (2 x 30 mL), dried with anhydrous sodium sulfate. After concentration, product 2 was purified using silica gel column chromatography using an appropriate eluent.

Reference： [1]Zhou, Mingwei; Hu, Yimin; En, Ke; Tan, Xuefei; Shen, Hong C.; Qian, Xuhong [Tetrahedron Letters, 2018, vol. 59, # 14, p. 1443 - 1445]

68
[ 45438-73-1 ]
[ 7677-24-9 ]
[ 20893-30-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate In acetonitrile at 70℃; for 6h;	2 Example 2 Preparation of thiophene-2-acetonitrile(II) take 2-bromomethylthiophene, 175g, dissolved in 500 ml of acetonitrile, Add 150g of potassium carbonate and add 110g of trimethylsilyl cyanide in batches.The reaction system was heated to 70°C for 6 hours, after the reaction was completed,Cooled to room temperature, filtered, and the filtrate was evaporated under reduced pressure to acetonitrile. The residue was added with 300 ml of toluene. 200 ml of 1N NaOH solution was added to the system. The mixture was separated and 100 ml of a 1N NaOH solution was added to the organic layer. The mixture was separated and washed with water to neutrality. Dry with magnesium sulfate, filter, and recover the solution under reduced pressure.The residue was distilled under reduced pressure to give 119 g of a pale yellow liquid in a yield of 97%.

Reference： [1]Current Patent Assignee: JIANGSU COLLEGE OF ENGINEERING AND TECHNOLOGY - CN107540654, 2018, A Location in patent: Paragraph 0046; 0047

69
[ 765-50-4 ]
[ 7677-24-9 ]
[ 20893-30-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In acetonitrile at 70℃; for 10h;	1 Example 1 Preparation of Thiophene-2-acetonitrile (I) Take 2-chloromethyl thiophene 132g, dissolved in 500 ml of acetonitrile, add 150g of potassium carbonate, add 110g of trimethylsilyl cyanide in batches, after the addition, the reaction system was heated to 70 ° C reaction 10h, after the reaction was completed, cooled to At room temperature, the filtrate was filtered, the filtrate was recovered under reduced pressure in acetonitrile, the residue was added with 300 ml of toluene, and 200 ml of 1N NaOH solution was added to the system. The liquid was separated, and the organic layer was added to 1N.NaOH solution 100 ml, liquid separation, washed with water to neutrality, dried over anhydrous magnesium sulfate, filtered, and the filtrate was recovered under reduced pressure. The residue was distilled under reduced pressure to obtain 120 g of pale yellow liquid with a yield of 98%.

Reference： [1]Current Patent Assignee: JIANGSU COLLEGE OF ENGINEERING AND TECHNOLOGY - CN107698554, 2018, A Location in patent: Paragraph 0039; 0040

70
[ 20893-30-5 ]
C₁₆H₁₁NO [ No CAS ]
C₂₂H₁₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	Synthesis of 4 via Condensation of 3 with Aryl acetonitrile General procedure: To a mixture of aryl acetonitrile (0.10 mmol) and 3 (0.10 mmol) in ethanol (10 mL), sodium methoxide inmethanol (1 M, 5 mL) was added and stirred for 10 min at room temperature under air. The reaction mixturewas diluted with ethanol (10 mL), and then filtered to remove solid. The solid was washed with an ethanol(10 mL) and a large amount of methanol (100 mL), and dried under vacuum to give as a powder.

Reference： [1]Hayashi, Shotaro; Hirai, Ryosuke; Yamamoto, Shin-ichi; Koizumi, Toshio [Chemistry Letters, 2018, vol. 47, # 8, p. 1003 - 1005]

71
[ 20893-30-5 ]
[ 81172-89-6 ]
C₁₄H₉NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 2-cyanomethylthiophene; terephthalaldehyde mono(diethylacetal) With sodium methylate In methanol at 20℃; for 0.166667h; Stage #2: With hydrogenchloride In chloroform; water Reflux;	Synthesis of 3 General procedure: To a mixture of aryl acetonitrile (1.0 mmol) and terepthalaldehyde mono(diethyl acetal) (2.08 g, 1.0 mmol)in methanol (10 mL), sodium methoxide in methanol (1 M, 10 mL) was added and stirred for 10 min atroom temperature under air. The reaction mixture was diluted with methanol (30 mL), and then filtered toremove yellow solid. The filtrate was poured into a large amount of water (100 mL). The solid was collectedby filtration, and then washed with a small amount of methanol (5 mL). The solid was dissolved inchloroform (30 mL). To the solution, concentrated HCl solution (10 mL) was added and stirred by refaxconditions. Chloroform phase was extracted, evaporated, and dried under vacuum to give as a powder.

Reference： [1]Hayashi, Shotaro; Hirai, Ryosuke; Yamamoto, Shin-ichi; Koizumi, Toshio [Chemistry Letters, 2018, vol. 47, # 8, p. 1003 - 1005]

72
[ 20893-30-5 ]
[ 623-27-8 ]
DTCS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	Synthesis of s-4 via Condensation of p-Terephthalaldehyde with Aryl acetonitrile General procedure: To a mixture of aryl acetonitrile (0.10 mmol) and p-terephthalaldehyde (0.050 mmol) in ethanol (5 mL),sodium methoxide in methanol (1 M, 5 mL) was added and stirred for 10 min at room temperature under air.The reaction mixture was diluted with a large amount of methanol (100 mL), and then filtered to removesolid. The solid was washed with an ethanol (10 mL), and dried under vacuum to give as a powder..

Reference： [1]Hayashi, Shotaro; Hirai, Ryosuke; Yamamoto, Shin-ichi; Koizumi, Toshio [Chemistry Letters, 2018, vol. 47, # 8, p. 1003 - 1005]

73
[ 20893-30-5 ]
C₁₅H₁₀N₂O [ No CAS ]
C₂₁H₁₃N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	Synthesis of 4 via Condensation of 3 with Aryl acetonitrile General procedure: To a mixture of aryl acetonitrile (0.10 mmol) and 3 (0.10 mmol) in ethanol (10 mL), sodium methoxide inmethanol (1 M, 5 mL) was added and stirred for 10 min at room temperature under air. The reaction mixturewas diluted with ethanol (10 mL), and then filtered to remove solid. The solid was washed with an ethanol(10 mL) and a large amount of methanol (100 mL), and dried under vacuum to give as a powder.

Reference： [1]Hayashi, Shotaro; Hirai, Ryosuke; Yamamoto, Shin-ichi; Koizumi, Toshio [Chemistry Letters, 2018, vol. 47, # 8, p. 1003 - 1005]

74
[ 20893-30-5 ]
C₁₄H₉NOS [ No CAS ]
DTCS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	Synthesis of 4 via Condensation of 3 with Aryl acetonitrile General procedure: To a mixture of aryl acetonitrile (0.10 mmol) and 3 (0.10 mmol) in ethanol (10 mL), sodium methoxide inmethanol (1 M, 5 mL) was added and stirred for 10 min at room temperature under air. The reaction mixturewas diluted with ethanol (10 mL), and then filtered to remove solid. The solid was washed with an ethanol(10 mL) and a large amount of methanol (100 mL), and dried under vacuum to give as a powder.

Reference： [1]Hayashi, Shotaro; Hirai, Ryosuke; Yamamoto, Shin-ichi; Koizumi, Toshio [Chemistry Letters, 2018, vol. 47, # 8, p. 1003 - 1005]

75
[ 98-03-3 ]
[ 20893-30-5 ]
2,3-di-thiophen-2-yl-acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.3%	With potassium <i>tert</i>-butylate In ethanol at 20℃; for 2h;	4.2 2.4.2 Preparation of 2,3-di-thiophen-2-yl-acrylonitrile (4) Potassium tert-butoxide (6g, 53.49mmol) was added to a stirred solution of 5-thiophene acetonitrile (3) (5.49g, 44.58mmol) which dissolved in ethanol. To this Thiophene 2-carbaldehyde (1) (5g, 44.58mmol) was added dropwise and stirred at room temperature for 2h. The formed yellow color precipitate was filtered and dried. Yield: 8g, 83.3%. Mp: 110°C. FT-IR (KBr, ν/cm-1): 2208.5 (-CN- stretch), 3080.3 (aromatic C-H stretch), 3097.6 (=C-H stretch). 1H NMR (400MHz, CDCl3, δ δ ppm): 7.61 (d, 1H), 7.53 (d, 1H), 7.49 (s, 1H, cyano-vinylene H), 7.34 (d, 1H), 7.29 (d, 1H), 7.14 (t, 1H), 7.06 (t, 1H). 13 C NMR (100MHz, CDCl3, δ δ ppm): 138.7, 137.5, 132.1, 132.0, 129.9, 128.2, 127.9, 126.9 (8C, thiophene C) 125.9 (1C, vinylene C), 116.9 (1C, -CN), 103.1 (1C, vinylene C). GC-MS GC-MS calculated for C11H7NS2 (m/z)=217, found, 217.31.

Reference： [1]Mahesh; Karpagam; Putnin, Thitirat; Le, Huong; Bui, Thanh-Tuân; Ounnunkad, Kontad; Goubard, Fabrice [Journal of Photochemistry and Photobiology A: Chemistry, 2019, vol. 371, p. 238 - 247]

76
[ 20893-30-5 ]
[ 73183-34-3 ]
2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; Inert atmosphere;	I.288.b b) 2-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)acetonitrile A mixture of 2-thiopheneacetonitrile (199 mg, 1.57 mmol), bis(pinacolato)diboron (244 mg, 0.941 mmol), (1,5-cyclooctadiene)(methoxy)iridium(l) dimer (5.5 mg, 0.0083 mmol) and 4,4'-di-tert-butyl-2,2'-dipyridyl (5.5 mg, 0.0205 mmol) in THF (7.5 mL) is degassed with a nitrogen stream for 15 min and then stirred at 80°C overnight. It is then cooled to RT, concentrated under reduced pressure and the residue is purified by FC (Hept to Hept EtOAc 9:1) to obtain the expected product as a colourless oil, which crystallizes upon standing (300 mg, 77%). LC-MS B: tR = 0.94 min; no ionization. 1H NMR (500 MHz, d6-DMSO) δ: 7.45 (d, J = 3.5 Hz, 1H), 7.17 (d, J = 3.5 Hz, 1H), 4.36 (d, J = 0.7 Hz, 2 H), 1.29 (s, 12 H).

Reference： [1]Current Patent Assignee: IDORSIA PHARMACEUTICALS LTD - WO2018/210994, 2018, A1 Location in patent: Page/Page column 176

77
[ 20893-30-5 ]
[ 120-21-8 ]
(E)-3-(4-(diethylamino)phenyl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium hydroxide In ethanol at 20℃; for 24h;	3.1. Synthesis of (E)-3-(4-(diethylamino)phenyl)-2-(thiophen-2-yl)acrylonitrile The aromatic aldehyd 4-(diethylamino)benzaldehyde, NaOH,EtOH, 2-(thiophen-2-yl)acetonitrile were obtained from (SigmaAldrich, India). The (E)-3-(4-(diethylamino)phenyl)-2-(thiophen-2-yl)acrylonitrile was synthesized by Knoevenagel condensation reaction[5e8].Fig. 1 and Table 1 show the reaction scheme of synthesisof our title compound (DPTA) single crystal.The 2-(thiophen-2-yl) acetonitrile (2 g, 0.0162mmole), 4-(diethylamino) benzaldehyde (2.8 g, 0.0162mmole), 2.5 g of 40%NaOH was dissolved in ethanol (30 ml) and stirred at room temperaturefor 24 h. The reactor was monitored by TLC analysis. Afterthe completion of the reaction, the crude mass was allowed to bepurified by various fractions in column chromatography techniquesusing the mixture of 20% of Hexane: EtOAc as the mobile phasesolvent. The complete reaction and total synthesized derivatives ofcompounds are shown in Fig. 2 (a) and (b).

Reference： [1]Sathyamoorthy; Vinothkumar; IrshadAhamed; MuraliManohar; Priya; Liu, Jinghe [Journal of Molecular Structure, 2019, vol. 1192, p. 241 - 251]

78
[ 20893-30-5 ]
[ 3779-31-5 ]
[ 74-88-4 ]
2-methyl-2-(thiophen-2-yl)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 2-cyanomethylthiophene With methylmagnesium bromide; lithium chloride In tetrahydrofuran; diethyl ether at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-dibenzylmalononitrile In tetrahydrofuran; diethyl ether at 80℃; for 6h; Inert atmosphere; Stage #3: methyl iodide In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	4.2.3. General procedure A: synthesis of malononitriles fromprimary nitriles using MeMgBr General procedure: Step 1: To an 8-mL culture tube with stir bar was added lithium chloride (1.1 equiv) and the flask was flame-dried under vacuum and cooled under an atmosphere of N2. THF (1.0 M) was added, followed by the appropriate nitrile (1.0 equiv). While stirring, methylmagnesium bromide (1.1 equiv of a solution in Et2O) was added dropwise at r.t., and the solutionwas stirred at r.t. for 30 min under an atmosphere of N2. A 1.1M stock solution of dimethylmanononitrile (DMMN) or dibenzylmalononitrile (DBMN) inTHF was prepared and added at r.t. (1.1 equiv of a 1.1M solution inTHF, reaction volume 0.50M with respect to nitrile starting material). The reaction was stirred at 80 C for 6 h under an atmosphere of N2. Step 2: The reaction was cooled to r.t. and DMF was added to bring the reaction solvent to a 1:1 THF/DMF ratio (0.25Mof a 1:1 THF/DMF mixture with respect to nitrile starting material). The desired electrophile (1.2 equiv) was added in a single portion. Ifthe electrophile was a solid, it was added with the DMF as a 0.60Mstock solution. The reaction was stirred at 80 C for 16 h, or until complete conversion was achieved as judged by TLC. The reaction was cooled to r.t., opened to air, quenched with 1M aq. HCl, and extracted with EtOAc (3). The organic fractions were combined,dried over MgSO4, and concentrated. The crude residue was purified by flash column chromatography to yield the desired malononitrile.

Reference： [1]Mills, L. Reginald; Rousseaux, Sophie A.L. [Tetrahedron, 2019, vol. 75, # 32, p. 4298 - 4306]

79
[ 20893-30-5 ]
[ 119072-55-8 ]
[ 42872-83-3 ]
C₁₉H₁₉N₃S [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 7076 - 7081

80
[ 20893-30-5 ]
[ 119072-55-8 ]
[ 57381-37-0 ]
C₁₈H₁₆ClN₃S [ No CAS ]

Reference： [1]Chemical Science,2019,vol. 10,p. 7076 - 7081

81
[ 20893-30-5 ]
[ 27892-81-5 ]
4,5-diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	Preparation of 4,5-Diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole In Dioxane solvent (1 mL) [Rh (COD) Cl] 2 (4.93 mg, 0.01 mmol) and (S, S) -DIOP (12.0 mg, 0.024 mmol), 4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol ) And 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol) were added and reacted at 100 oC for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. The column (Ether: DCM: Haxane = 1: 1: 20) is processed to4,5-diphenyl-3- (thiophen-2-ylmethyl) -1,2-selenazole (68.2 g, 90%) was obtained.
90%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	Preparation of 4,5-diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole [Rh(COD)Cl]2 (4.93 mg, 0.01 mmol) and (S,S)-DIOP (12.0 mg, 0.024 mmol) in Dioxane solvent (1 mL),After adding 4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol), react at100 °C for 6 hours. After completion of the reaction, the solvent is removed using an evaporator. Then, proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to obtain the desired compound, 4,5-diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole (68.2 g, 90%).
90%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	2 Preparation of 4,5-Diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole [Rh(COD)Cl]2(4.93 mg, 0.01 mmol) and (S,S)-DIOP (12.0 mg, 0.024 mmol) in dioxane solvent (1 mL),4,5-diphenyl-1,2,3-selenadiazole (57.04 mg, 0.2 mmol) andAfter adding 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol), react at 100oC for 6 hours. After completion of the reaction, the solvent is removed using an evaporator. And column (Ether: DCM: Haxane = 1: 1: 20)4,5-diphenyl-3-(thiophen-2-ylmethyl)-1,2-selenazole (68.2 g, 90%) was obtained.

Reference： [1]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR102037409, 2019, B1 Location in patent: Paragraph 0501; 0502; 0504
[2]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR102111278, 2020, B1 Location in patent: Paragraph 0502-0503; 0505
[3]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR2020/102325, 2020, A Location in patent: Paragraph 0478-0480; 0501-0504

82
[ 20893-30-5 ]
[ 35676-30-3 ]
3-(thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	Preparation of 3-(thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole In Dioxane solvent (1 mL) [Rh (COD) Cl] 2 (4.93 mg, 0.01 mmol) and (S, S) -DIOP (12.0 mg, 0.024 mmol), 4,5,6,7-tetrahydrobenzo [d] [1,2,3] Selenadiazole (37.42 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol) were added, followed by reaction at 100 oC for 6 hours. After the reaction is completed, the solvent is removed using an evaporator. Then, the column (Ether: DCM: Haxane = 1: 1: 20) was subjected to 3- (thiophen-2-ylmethyl) -4,5,6,7-tetrahydrobenzo [d] [1,2] as a desired compound.selenazole (52.4 g, 93%) was obtained.
93%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	Preparation of 3-(thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole [Rh(COD)Cl]2 (4.93 mg, 0.01 mmol) and (S,S)-DIOP (12.0 mg, 0.024 mmol) in Dioxane solvent (1 mL),After adding 4,5,6,7-tetrahydrobenzo[d][1,2,3]selenadiazole (37.42 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol), react for 6 hours at 100 °C. . After completion of the reaction, the solvent is removed using an evaporator. Then, proceed to the column (Ether: DCM: Haxane = 1: 1: 20) to obtain the desired compound 3-(thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole ( 52.4 g, 93%).
93%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h;	2 Preparation of 3-(Thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole [Rh(COD)Cl]2(4.93 mg, 0.01 mmol) and (S,S)-DIOP (12.0 mg, 0.024 mmol) in dioxane solvent (1 mL),4,5,6,7-tetrahydrobenzo[d][1,2,3]selenadiazole (37.42 mg, 0.2 mmol) and 2-thiopheneacetonitrile (0.21 mL, 2.0 mmol) was added, and then reacted at 100oC for 6 hours. After completion of the reaction, the solvent is removed using an evaporator. Then proceed to the column (Ether: DCM: Haxane = 1: 1: 20), 3-(thiophen-2-ylmethyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole (52.4 g, 93%) was obtained.

Reference： [1]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR102037409, 2019, B1 Location in patent: Paragraph 0591; 0592; 0594
[2]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR102111278, 2020, B1 Location in patent: Paragraph 0592-0593; 0595
[3]Current Patent Assignee: KANGWON NATIONAL UNIVERSITY - KR2020/102325, 2020, A Location in patent: Paragraph 0478-0480; 0591-0594

83
[ 20893-30-5 ]
[ 540-88-5 ]
N-(tert-butyl)-2-(thiophen-2-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With BF₃ immobilized on β-cyclodextrine functionalized silica coated CoFe₂O₄ magnetic nanoparticles In neat (no solvent) at 20℃; for 1h;	2.4. General procedure for the modified-Ritter reaction catalyzed byCoFe2O4(at)SiO2-PrNH-βCDs-BF3 General procedure: A mixture of tertbutyl acetate (2.5 mmol), nitirle (1 mmol), andCoFe2O4SiO2-NH-βCDs-BF3 (0.08 g) was stirred in neat conditiontill completion of the reaction (monitored by TLC). After reactioncompletion, CH2Cl2 was added to the reaction mixture and theorganic layer was simply decanted by means of an external magnet.Then, the reaction mixture was extracted with CH2Cl2, driedover Na2SO4, concentrated under vacuum and the pure productwas obtained. This was further purified by recrystallization withsuitable solvent (EtOAc/hexane). Melting point, 1H NMR, 13CNMR and FT-IR spectra were consistent with the assigned structuresin literature [43,62,63].

Reference： [1]Hamadi, Hosein; Zanjani, Zohreh; Yadollahi, Mahtab [Polyhedron, 2020, vol. 175]

84
[ 20893-30-5 ]
[ 4265-16-1 ]
(E)-3-(benzofuran-2-yl)-2-(thiophen-2-yl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium hydroxide In ethanol; water at 20℃; for 24h;	General Synthesis of (TACNBNF)compound was depicted schematicallyin Scheme 1. The 2-(thiophen-2-yl) acetonitrile (1 g, 8.118mmole), benzofuran-2-carbaldehyde (1.2 g, 8.118 mmol), and 2 g ofNaOH were dissolved in 45 ml of ethanol. Then, these reactionmixtures were stirred vigorously at normal room temperature for24 h. The improvement of the reactionwas monitored by TLC. Aftercompletion of the reaction, the mixtures were poured into ice coldwater. The solid product was filtered, washed with cold ethanol toremove excess benzofuran-2-carbaldehyde, and dried in a vacuumchamber to collect the green colouredcrude product. The precipitatewas allowed to purify by column chromatography techniqueusing the mixture of Hexane: Ethyl Acetate (2/8): eluent. Rectangularslabsof green colour crystals (yield was 88%) of the TACNBNFwas grown using slow evaporation method by DCM (2 ml) andmethanol (1 ml) mixture solvents.

Reference： [1]Ahamed, J. Irshad; Priya; Vinothkumar; Sathyamoorthy; MuraliManohar; Liu, Jinghe; Valan [Journal of Molecular Structure, 2020, vol. 1202]

85
[ 20893-30-5 ]
[ 105-07-7 ]
(E)-4-(2-cyano-2-(thiophen-2-yl)vinyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: 2-cyanomethylthiophene With sodium In methanol at 20℃; for 0.333333h; Stage #2: 4-cyanobenzaldehyde In methanol for 4h; Reflux;	4.1.2. General method for the synthesis of compounds 6-11 General procedure: Sodiumwas dissolved in 10 mL of absolute methanol and benzylcyanide or 2-(thiophen-2-yl)acetonitrile was added. The mixturewas stirred at room temperature for 20 min, after that the appropriatealdehyde was added and heated at reflux. The cooled reactionmixture was filtered and, if necessary, recrystallized from theappropriate solvent.

86
[ 20893-30-5 ]
[ 7570-45-8 ]
(E)-3-(9-ethyl-9H-carbazol-3-yl)-2-(thiophen-2-yl) acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium <i>tert</i>-butylate In ethanol for 0.25h; Reflux;	3.1.1 (E)-3-(9-Ethyl-9H-carbazol-3-yl)-2-(thiophen-2-yl) acrylonitrile (2A) To the solution of 1A, 0.2g (89.6mmol) and 2-(thiophen-2-yl) acetonitrile (0.11g 89.6mmol) add the catalytic amount of potassium tertiary butoxide in 20ml ethanol. The mixture was refluxed for 15min and allow to cool the reaction mixture. The yellow colored solid was obtained which was filtered and washed with a small amount of ethanol, recrystallized with ethanol The crude product was purified with 2% Ethyl acetate Hexane mixture to get a pure yellow colored product. Yield: 0.23g 85%. Melting point-120-122°C. NMR-1H NMR (500MHz, CDCl3) δ 8.58 (d, J=8.5Hz, 1H), 8.16 (d, J=7.5Hz, 1H), 8.10 (d, J=8.5Hz, 1H), 7.57 (d, J=8.5Hz, 1H), 7.51 (d, J=8.5Hz, 1H), 7.45 (dd, J=7.5, 1.5Hz,2H), 7.37 (dd, J=8.2 7.5Hz, 1H), 7.30 (m, J=7.5,1.5Hz,2H), 7.08 (dd, J=7.5, 7.5Hz, 1H), 4.39 (q, J=8Hz,2H), 1.47 (t, J=8Hz, 3H). 13C NMR (125MHz, CDCl3) δ 141.2, 128.0, 126.8, 126.5, 125.9, 125.1, 122.5, 120.8, 119.8, 108.9, 37.7, 13.8. Elemental Analysis Expected- C-76.80 H-4.91 N8.53 Chemical Formula: C21H16N2S Found C 76.84 H 4,90N 8.54.
	With sodium In methanol at 20℃;

Reference： [1]Bhalekar, Sulochana; Avhad, Kiran; Sekar, Nagaiyan [Journal of Photochemistry and Photobiology A: Chemistry, 2020, vol. 391]
[2]Babu, Dickson D.; Keremane, Kavya S.; Naik, Praveen [Journal of Molecular Liquids, 2020, vol. 310]

87
[ 20893-30-5 ]
[ 124-38-9 ]
5-(cyanomethyl)thiophene-2-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate In dimethyl sulfoxide at 25℃; for 18h; Irradiation; Sealed tube; regioselective reaction;	General Procedure for the Carboxylation of Arenes - GP2b (no glovebox) General procedure: To a dry flat-bottomed crimp vial (5 mL) equipped with stirring bar, was added the arene (if solid)(0.1 mmol) and 2,3,6,7-tetramethoxyanthracen-9(10H)-one (6.3 mg, 0.02 mmol, 20 mol %). Cs2CO3 (98 mg,3 equiv.) was quickly added and the vial was sealed with a Supelco aluminium crimp seal with septum(PTFE/butyl). The vial was then evacuated and refilled with N2 (3×) via syringe needle. The reaction mixturewas dissolved in DMSO (1 mL, dry and degassed by bubbling with N2) and the arene (0.1 mmol) (if liquid)was added via syringe. The reaction mixture then had gaseous CO2 (22 cm3) added via a gastight Hamiltonsyringe, into the head space of the vial. The vial was then irradiated from the bottom side with blue lightand a constant reaction temperature (25°C) was maintained by employing a water-cooling circuit connected to a thermostat. After the designated time the reactions were extracted via an acid base wash. The combinedorganic layers were dried over Na2SO4, filtered and concentrated in vacuo.

Reference： [1]Bergonzini, Giulia; Brandt, Peter; Fricke, Florian; Johansson, Magnus J.; König, Burkhard; Schmalzbauer, Matthias; Svejstrup, Thomas D. [Chem, 2020, vol. 6, # 10, p. 2658 - 2672]

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P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 20893-30-5 ] {[proInfo.proName]}

Quality Control of [ 20893-30-5 ]

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[ 20893-30-5 ] Synthesis Path-Upstream 1~4

[ 20893-30-5 ] Synthesis Path-Downstream 1~87

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Nitriles

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[ 20893-30-5 ]