Welcome to LookChem.com Sign In|Join Free

CAS

  • or

13781-53-8

Post Buying Request

13781-53-8 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

13781-53-8 Usage

Chemical Properties

clear yellow to brown liquid

Uses

3-Thiopheneacetonitrile was used in the synthesis of:(E)-3-phenyl-2-(3-thienyl) acrylonitrile(Z)-3-(4-methylphenyl)-2-(3-thienyl) acrylonitrile

Check Digit Verification of cas no

The CAS Registry Mumber 13781-53-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,8 and 1 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13781-53:
(7*1)+(6*3)+(5*7)+(4*8)+(3*1)+(2*5)+(1*3)=108
108 % 10 = 8
So 13781-53-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H5NS/c7-3-1-6-2-4-8-5-6/h2,4-5H,1H2

13781-53-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A12805)  3-Thiopheneacetonitrile, 98%   

  • 13781-53-8

  • 5g

  • 848.0CNY

  • Detail
  • Alfa Aesar

  • (A12805)  3-Thiopheneacetonitrile, 98%   

  • 13781-53-8

  • 25g

  • 3834.0CNY

  • Detail
  • Aldrich

  • (219193)  3-Thiopheneacetonitrile  96%

  • 13781-53-8

  • 219193-5G

  • 1,262.43CNY

  • Detail
  • Aldrich

  • (219193)  3-Thiopheneacetonitrile  96%

  • 13781-53-8

  • 219193-25G

  • 4,361.76CNY

  • Detail

13781-53-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Cyanomethylthiophene

1.2 Other means of identification

Product number -
Other names Thiophene-3-acetonitrile

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13781-53-8 SDS

13781-53-8Synthetic route

3-chlorothiophene
17249-80-8

3-chlorothiophene

sodium cyanoacetate
1071-36-9

sodium cyanoacetate

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(η3-allyl-μ-chloropalladium(II)) In 1,3,5-trimethyl-benzene at 20 - 140℃; for 5.16667h; Inert atmosphere; Sealed tube; chemoselective reaction;78%
Thien-3-ylboronic acid
6165-69-1

Thien-3-ylboronic acid

chloroacetonitrile
107-14-2

chloroacetonitrile

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; Sealed tube;53%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,4-dioxane; water at 60℃; for 12h; Inert atmosphere; Sealed tube;
3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

sodium cyanide
143-33-9

sodium cyanide

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
tetrabutylammomium bromide In dichloromethane; water Heating / reflux;44%
With ethanol
3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

potassium cyanide

potassium cyanide

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water28%
3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

potassium cyanide
151-50-8

potassium cyanide

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With ethanol
3-thiophene carboxaldehyde
498-62-4

3-thiophene carboxaldehyde

[(p-methylphenyl)sulfonylmethyl]isonitrile
38622-91-2, 36635-61-7

[(p-methylphenyl)sulfonylmethyl]isonitrile

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With potassium tert-butylate 1.) THF, -20 deg C, 30 min, 2.) THF, -20 deg C, 30 min; Yield given. Multistep reaction;
Methyl 2-cyano-2-(3-thienyl)acetate
81344-59-4

Methyl 2-cyano-2-(3-thienyl)acetate

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With water; triethylamine Product distribution;
3-Methylthiophene
616-44-4

3-Methylthiophene

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / Reflux
2: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: N-Bromosuccinimide; dibenzoyl peroxide
2: N-benzyl-N,N,N-triethylammonium chloride / water
View Scheme
3-Bromomethylthiophene
34846-44-1

3-Bromomethylthiophene

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 0 - 20℃; Inert atmosphere;4.06 g
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(Z)-3-Dimethylamino-2-thiophen-3-yl-acrylonitrile

(Z)-3-Dimethylamino-2-thiophen-3-yl-acrylonitrile

Conditions
ConditionsYield
With 2,4-dichlorophenoxyacetic acid dimethylamine In toluene Heating;100%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

methanol
67-56-1

methanol

2-Thiophen-3-yl-acetimidic acid methyl ester; hydrochloride

2-Thiophen-3-yl-acetimidic acid methyl ester; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0 - 5℃;99%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

3-(3'-Thienyl)-2-(2''-tolyl)propenenitrile

3-(3'-Thienyl)-2-(2''-tolyl)propenenitrile

Conditions
ConditionsYield
With sodium ethanolate In ethanol98%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-(3-thienyl)ethylamine
59311-67-0

2-(3-thienyl)ethylamine

Conditions
ConditionsYield
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 4h; Inert atmosphere;97%
With diisobutylaluminum borohydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;71%
With indium(III) chloride; sodium tetrahydroborate In tetrahydrofuran at 25℃; for 16h; Inert atmosphere;67%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-amino-benzenethiol
137-07-5

2-amino-benzenethiol

2-((thiophen-3-yl)methyl)benzo[d]thiazole
1427180-57-1

2-((thiophen-3-yl)methyl)benzo[d]thiazole

Conditions
ConditionsYield
With copper diacetate; triethylamine In ethanol at 70℃; for 6h;97%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

(Z)-3-Thiophen-2-yl-2-thiophen-3-yl-acrylonitrile
13781-61-8

(Z)-3-Thiophen-2-yl-2-thiophen-3-yl-acrylonitrile

Conditions
ConditionsYield
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; ΔE*, Σ*, A;95%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

benzaldehyde
100-52-7

benzaldehyde

(E)-3-phenyl-2-(3-thienyl)acrylonitrile
13781-54-9

(E)-3-phenyl-2-(3-thienyl)acrylonitrile

Conditions
ConditionsYield
With sodium methylate In methanol at 30℃; Kinetics; Thermodynamic data; ΔE*, Σ*, A;95%
With sodium ethanolate In ethanol94%
With potassium tert-butylate In ethanol Heating;60%
With potassium tert-butylate In ethanol at 20℃; Knoevenagel condensation;60%
With sodium ethanolate In ethanol at 4℃; for 8h;51%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

4-Octyne
1942-45-6

4-Octyne

(Z)-2-propyl-3-(3-thienylmethyl)-2-hexenenitrile
1180490-30-5

(Z)-2-propyl-3-(3-thienylmethyl)-2-hexenenitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); dimethylaluminum chloride; 2-dicyclohexylphosphino-2',4',6'-trimethylbiphenyl In hexane; toluene at 80℃; for 2h; Inert atmosphere; stereoselective reaction;95%
With bis(1,5-cyclooctadiene)nickel (0); dimethylaluminum chloride; 2-dicyclohexylphosphino-2',4',6'-trimethylbiphenyl In hexane; tetradecane; toluene at 80℃; for 2h; Inert atmosphere; regioselective reaction;95%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-(thiophen-3-yl) ethanamine hydrochloride
34843-84-0

2-(thiophen-3-yl) ethanamine hydrochloride

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With borane-dimethyl sulfide complex In tetrahydrofuran for 16h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.333333h;
94%
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 16h; Heating / reflux;
Stage #2: With methanol In tetrahydrofuran
94%
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 16h; Heating / reflux;
Stage #2: With hydrogenchloride; methanol at 20℃; for 0.333333h;
94%
Stage #1: (thiophen-3-yl)acetonitrile With dimethylsulfide borane complex In tetrahydrofuran for 12h; Reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran for 0.5h;
78.5%
Stage #1: (thiophen-3-yl)acetonitrile With borane-THF In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;
Stage #2: With methanol In tetrahydrofuran
Stage #3: With hydrogenchloride In 1,4-dioxane; methanol
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

5-(thiophen-3-ylmethyl)-1H-1,2,3,4-tetrazole

5-(thiophen-3-ylmethyl)-1H-1,2,3,4-tetrazole

Conditions
ConditionsYield
With sodium azide; triethylamine hydrochloride In toluene at 110℃; for 16h; Inert atmosphere;93%
With aluminium trichloride; sodium azide In tetrahydrofuran for 48h; Heating;61%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

4,4-bis(methylthio)but-3-en-2-one
17649-86-4

4,4-bis(methylthio)but-3-en-2-one

(E)-3-Methylsulfanyl-5-oxo-2-thiophen-3-yl-hex-3-enenitrile

(E)-3-Methylsulfanyl-5-oxo-2-thiophen-3-yl-hex-3-enenitrile

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; benzene for 0.25h; Metallation;
Stage #2: 4,4-bis(methylthio)but-3-en-2-one In N,N-dimethyl-formamide at 20℃; Substitution;
93%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

ethanol
64-17-5

ethanol

ethyl 2-(thiophen-3-yl)acetimidate hydrochloride

ethyl 2-(thiophen-3-yl)acetimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0℃; Pinner reaction;93%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

bis(acetonitrile)diiodotricarbonyltungsten(II)
113350-36-0, 102382-37-6

bis(acetonitrile)diiodotricarbonyltungsten(II)

triphenylphosphine
603-35-0

triphenylphosphine

WI2(CO)3(thiophene-3-acetonitrile)(PPh3)
211744-19-3

WI2(CO)3(thiophene-3-acetonitrile)(PPh3)

Conditions
ConditionsYield
In dichloromethane N2-atmosphere; stirring W-complex with equimolar amt. of PPh3 for 3 min,filtration into equimolar amt. of ligand soln., stirring for 30 min; solvent removal (vac.); elem. anal.;93%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-(2,5-diiodothiophen-3-yl)acetonitrile

2-(2,5-diiodothiophen-3-yl)acetonitrile

Conditions
ConditionsYield
With N-iodo-succinimide; toluene-4-sulfonic acid In ethanol at 50℃; for 0.166667h; Green chemistry; regioselective reaction;93%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

Glyoxilic acid
298-12-4

Glyoxilic acid

(2Z)-3-cyano-3-(3-thienyl)acrylic acid
1076169-87-3

(2Z)-3-cyano-3-(3-thienyl)acrylic acid

Conditions
ConditionsYield
With potassium carbonate In methanol for 3h; Knoevenagel Condensation; Reflux;90%
With potassium carbonate In methanol for 3h; Heating / reflux;90%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

methyl iodide
74-88-4

methyl iodide

rac-2-(thiophen-2-yl)propanenitrile
88701-59-1

rac-2-(thiophen-2-yl)propanenitrile

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
90%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

cyclopropyl(4-fluorophenyl)methanone
772-31-6

cyclopropyl(4-fluorophenyl)methanone

9a-(4-fluorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
1429308-76-8

9a-(4-fluorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one

Conditions
ConditionsYield
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation;90%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

bis(acetonitrile)diiodotricarbonyltungsten(II)
113350-36-0, 102382-37-6

bis(acetonitrile)diiodotricarbonyltungsten(II)

WI2(CO)3(thiophene-3-acetonitrile)2
211744-17-1

WI2(CO)3(thiophene-3-acetonitrile)2

Conditions
ConditionsYield
In dichloromethane N2-atmosphere; stirring W-complex with 2 equiv. of ligand (warm water bath, 90 min, then room temp., 1 h); filtration, solvent removal (vac.); elem. anal.;89%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

2-(thiophene-3-yl) acetamide
13781-66-3

2-(thiophene-3-yl) acetamide

Conditions
ConditionsYield
With water at 130℃; for 1h; Microwave irradiation;88%
With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In nitromethane; water at 20 - 100℃; for 3h;75%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

methyl (4-methoxyphenyl)carbodithioate
5874-09-9

methyl (4-methoxyphenyl)carbodithioate

2-(4-methoxyphenyl)thieno[2,3-b]thiophene-3-carbonitrile

2-(4-methoxyphenyl)thieno[2,3-b]thiophene-3-carbonitrile

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With potassium tert-butylate In 1,4-dioxane at 0℃; for 0.166667h;
Stage #2: methyl (4-methoxyphenyl)carbodithioate In 1,4-dioxane at 0 - 20℃; for 1h;
Stage #3: With iodine In 1,4-dioxane at 90℃;
87%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

α,α'-dichloroazo compound
57908-42-6

α,α'-dichloroazo compound

6,7,8,9-tetrahydro-2-(thiophene-3-yl)methyl-5H-[1,2,4]triazolo[1,5-a]azepine

6,7,8,9-tetrahydro-2-(thiophene-3-yl)methyl-5H-[1,2,4]triazolo[1,5-a]azepine

Conditions
ConditionsYield
With antimonypentachloride In dichloromethane at -60 - 23℃; for 2.16667h;86%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

formic acid ethyl ester
109-94-4

formic acid ethyl ester

3-hydroxy-2-(thien-3-yl)acrylonitrile sodium salt

3-hydroxy-2-(thien-3-yl)acrylonitrile sodium salt

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Heating;85%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

allyl bromide
106-95-6

allyl bromide

2-allyl-2-(thiophen-3-yl)pent-4-enenitrile
62716-51-2

2-allyl-2-(thiophen-3-yl)pent-4-enenitrile

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In dimethyl sulfoxide at 20℃; for 0.5h; Inert atmosphere;
Stage #2: allyl bromide In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere;
85%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

4-chlorophenyl cyclopropyl ketone
6640-25-1

4-chlorophenyl cyclopropyl ketone

9a-(4-chlorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
1429308-77-9

9a-(4-chlorophenyl)-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one

Conditions
ConditionsYield
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation;84%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

cyclopropyl phenyl ketone
3481-02-5

cyclopropyl phenyl ketone

9a-phenyl-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one
1429308-75-7

9a-phenyl-7,8,9,9a-tetrahydrothieno[3,2-g]indolizin-5(4H)-one

Conditions
ConditionsYield
With tributylphosphine; boron trifluoride diethyl etherate; copper(I) bromide In nitromethane at 90℃; for 18h; Ritter Amidation;84%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

N-Hydroxy-2-thiophen-3-yl-acetamidine
925252-85-3, 155601-61-9

N-Hydroxy-2-thiophen-3-yl-acetamidine

Conditions
ConditionsYield
With potassium carbonate; ammonium chloride In methanol at 60℃; for 12h;83%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

bis-(1-chloro-1-methyl-ethyl)-diazene
29540-62-3

bis-(1-chloro-1-methyl-ethyl)-diazene

1,5-dimethyl-3-((thiophene-3-yl)methyl)-1H-1,2,4-triazole

1,5-dimethyl-3-((thiophene-3-yl)methyl)-1H-1,2,4-triazole

Conditions
ConditionsYield
With antimonypentachloride In dichloromethane at -60 - 23℃; for 2.16667h;83%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

methyl 4-bromocrotonate
1117-71-1

methyl 4-bromocrotonate

methyl 5-(dimethylamino)thiophene-2-carbodithioate

methyl 5-(dimethylamino)thiophene-2-carbodithioate

2-(5-(dimethylamino)thiophen-2-yl)-3-(thiophen-3-yl)thieno[3,2-b]pyridin-5(4H)-one

2-(5-(dimethylamino)thiophen-2-yl)-3-(thiophen-3-yl)thieno[3,2-b]pyridin-5(4H)-one

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: methyl 5-(dimethylamino)thiophene-2-carbodithioate In tetrahydrofuran at 0℃; for 0.5h;
Stage #3: methyl 4-bromocrotonate In tetrahydrofuran at 0 - 20℃; for 8.5h;
82%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

hexachlorobenzene
118-74-1

hexachlorobenzene

α-(3-Thiophene-yl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile

α-(3-Thiophene-yl)-α-(2,3,4,5,6-pentachlorophenyl)acetonitrile

Conditions
ConditionsYield
With n-butyllithium In diethyl ether 1.) -70 deg C, 2 h, 2.) -70 deg C to r.t.; r.t., overnight;80%
(thiophen-3-yl)acetonitrile
13781-53-8

(thiophen-3-yl)acetonitrile

methyl fluorobenzenedithiocarboxylate
5969-47-1

methyl fluorobenzenedithiocarboxylate

2-(4-fluorophenyl)thieno[2,3-b]thiophene-3-carbonitrile

2-(4-fluorophenyl)thieno[2,3-b]thiophene-3-carbonitrile

Conditions
ConditionsYield
Stage #1: (thiophen-3-yl)acetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h;
Stage #2: methyl fluorobenzenedithiocarboxylate In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h;
Stage #3: With tetrabutylammomium bromide; copper diacetate; palladium diacetate In N,N-dimethyl-formamide; mineral oil at 90℃;
80%
Stage #1: (thiophen-3-yl)acetonitrile With potassium tert-butylate In 1,4-dioxane at 0℃; for 0.166667h;
Stage #2: methyl fluorobenzenedithiocarboxylate In 1,4-dioxane at 0 - 20℃; for 1h;
Stage #3: With iodine In 1,4-dioxane at 90℃;
77%

13781-53-8Relevant articles and documents

I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond

Wang, Sheng,Zhang, Xiaowei,Cao, Chengyao,Chen, Chao,Xi, Chanjuan

supporting information, p. 4515 - 4519 (2017/10/13)

A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.

The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.

supporting information, p. 50 - 53 (2015/07/28)

The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei

supporting information; experimental part, p. 4470 - 4474 (2011/06/24)

Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 13781-53-8