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86-29-3

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86-29-3 Usage

Chemical Properties

Diphenylacetonitrile is a white to creamy or faint yellow crystalline powder, Soluble in ethanol, ether. It is obtained by bromination and condensation of phenylacetonitrile.Diphenylacetonitrile is mainly used as an intermediate to manufacture API which deals in treatment of respiratory stimulant. It is used to manufacture APIs like stomach amine, Aminepentamide Sulphate, Diphenoxylate, Diphenylacetaldehyde, Doxapram, Loperamide, Methadone.

Uses

Mathadone (M225865) impurity. Used in synthesis of methadone, antispasmodics and other pharmaceuticals.Diphenylacetonitrile is used to synthesize isocyanate, which is further prepared into UV paint, PU paint, transparent elastomer and adhesive, etc. In addition, it is also used in polyamide and epoxy resin industries.

Preparation

Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride. Diphenylacetonitrile undergoes anhydrous condensation with ethyl-4-bromo-butyrate. This is followed by its hydrolysis in alkaline medium that is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.

Application

Diphenylacetonitrile undergoes anhydrous condensation with ethyl-4-bromo-butyrate. This is followed by its hydrolysis in alkaline medium that is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.

Reactions

Methadone is synthesised by alkylation of diphenylacetonitrile using 2-dimethylaminopropylchloride in the presence of sodamide.Dextromoramide is synthesised by alkylation of diphenylacetonitrile using 1-morpholinyl-2- chloropropane in the presence of sodamide.Diphenylacetonitrile in the presence of sodium amide is alkylated with 1-ethyl-3-chlorpyrrolidine, giving (1-ethyl-3-pyrrolidinyl) diphenylacetonitrile.Isopropamide, is synthesized by alkylating diphenylacetonitrile with di-isopropylaminoethylchloride in the presence of sodium amide, and the subsequent hydrolysis of the nitrile group of the resulting compound to an amide group.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 3253, 1970 DOI: 10.1021/jo00835a016

General Description

Diphenylacetonitrile can be prepared in good yield by the dehydration of the amide of diphenyl acetic acid with phosphorous oxychloride.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by subcutaneous route. Questionable carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits toxic fumes of NOx, and CN-. See also NITRILES.

Synthesis

Add the 250mL ethyl acetate in 500mL glass there-necked flask, open and stir, add the 150g phenylcarbinol, add sodium methylate 80g, 70 ℃ of stirring reactions 2 hours are down to room temperature, add benzyl cyanide 120ml.Be heated to 110 ℃, distillation reaction 10h.Reaction naturally cools to room temperature after finishing, and adds the extraction of 200ml ethyl acetate and 200ml water, tells lower aqueous layer.The upper strata ethyl acetate layer adds water, and washing once adds anhydrous sodium sulfate drying.Concentrating under reduced pressure is removed ethyl acetate.Then in oily matter, add a small amount of dehydrated alcohol crystallisation by cooling, the crystallized product oven dry.Yield 90%, purity 99.0% (GC).

Purification Methods

Crystallise the nitrile from EtOH or pet ether (b 90-100o). [Beilstein 9 H 674, 9 IV 2505.]

Check Digit Verification of cas no

The CAS Registry Mumber 86-29-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 86-29:
(4*8)+(3*6)+(2*2)+(1*9)=63
63 % 10 = 3
So 86-29-3 is a valid CAS Registry Number.
InChI:InChI=1/C14H11N/c15-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H

86-29-3 Well-known Company Product Price

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  • Alfa Aesar

  • (L02404)  Diphenylacetonitrile, 99%   

  • 86-29-3

  • 100g

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (L02404)  Diphenylacetonitrile, 99%   

  • 86-29-3

  • 500g

  • 840.0CNY

  • Detail

86-29-3SDS

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 Diphenylacetonitrile

1.2 Other means of identification

Product number -
Other names Benzeneacetonitrile, α-phenyl-

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:86-29-3 SDS

86-29-3Synthetic route

1,1-diphenyl-2,2-dinitroethylene
15795-74-1

1,1-diphenyl-2,2-dinitroethylene

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran for 2h; Ambient temperature;100%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

diphenylmethyl p-tolyl sulfone
5433-78-3

diphenylmethyl p-tolyl sulfone

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 25℃; for 1h; Inert atmosphere;100%
2,2-diphenylacetamide
4695-13-0

2,2-diphenylacetamide

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;99%
With bis(trichloromethyl) carbonate; triethylamine In chloroform at 50℃; for 2h;87%
With palladium diacetate; Selectfluor; acetonitrile at 20℃; for 18h;84%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

diphenylchloromethane
90-99-3

diphenylchloromethane

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iodine; lithium carbonate In dichloromethane at 35℃; for 5h;99%
With titanium tetrachloride In dichloromethane at 0℃; for 2h;93%
diphenyl-acetaldehyde-oxime
41401-03-0

diphenyl-acetaldehyde-oxime

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In dichloromethane; 1,2-dichloro-ethane for 0.0833333h; Ambient temperature;98%
With 4-nitro-1-((trifluoromethyl)sulfonyl)-1H-imidazole; triethylamine In acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Sealed tube;78%
2,2-diphenyl-pentanedinitrile
2997-21-9

2,2-diphenyl-pentanedinitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
IrH5(P-(i-Pr)3)2 In toluene at 150℃; for 12h;98%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iodine; lithium carbonate In dichloromethane at 35℃; for 5h;98%
With tris(pentafluorophenyl)borate In acetonitrile at 20℃; for 1h;93%
With zinc trifluoromethanesulfonate In nitromethane at 100℃; for 5.5h;90%
With 3-dodecyl-2-iodo-1-methyl-1H-imidazol-3-ium hexafluoroantimonate; iodine In nitromethane at 20℃; for 2h; Inert atmosphere;46%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzhydryl methyl ether
1016-09-7

benzhydryl methyl ether

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With gold(III) chloride In dichloromethane at 20℃; for 0.0833333h; Reagent/catalyst; Time; Inert atmosphere;96%
bromobenzene
108-86-1

bromobenzene

phenylacetonitrile
140-29-4

phenylacetonitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With P(i-BuNCH2CH2)3N; sodium hexamethyldisilazane; palladium diacetate In toluene at 100℃; for 6h;93%
With potassium phosphate; dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere; Sealed tube;89%
With potassium hydroxide In water at 45℃; for 17h;84%
With caesium carbonate; triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 2h; Phenylation;44%
3,3-Diphenylpropionic acid
606-83-7

3,3-Diphenylpropionic acid

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With trifluoroacetic acid; trifluoroacetic anhydride; sodium nitrite at 20℃; nitrosative cleavage;93%
Diphenylacetaldehyde
947-91-1

Diphenylacetaldehyde

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With ammonia; oxygen In tert-Amyl alcohol at 40℃; under 750.075 Torr; for 24h; Green chemistry;93%
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃;92%
Multi-step reaction with 3 steps
1: ammonia / water / 20 °C / Green chemistry
2: iodine / water / 20 °C / Green chemistry
3: ammonia / water / 20 °C / Green chemistry
View Scheme
phenylacetonitrile
140-29-4

phenylacetonitrile

chlorobenzene
108-90-7

chlorobenzene

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
Stage #1: phenylacetonitrile With tris-(dibenzylideneacetone)dipalladium(0); bis(proazaphosphatrane); potassium tert-butylate In toluene at 20℃; for 0.333333h; Schlenk technique; Inert atmosphere;
Stage #2: chlorobenzene In toluene at 80℃; for 4h; Inert atmosphere; Schlenk technique;
92%
With sodium hexamethyldisilazane; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane; palladium diacetate In toluene at 90℃; for 6h;91%
2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

diphenylchloromethane
90-99-3

diphenylchloromethane

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With potassium carbonate; 18-crown-6 ether In acetonitrile for 6h; Heating;91%
tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

2-(diphenylmethyloxy)tetrahydro-2H-pyran
79373-25-4

2-(diphenylmethyloxy)tetrahydro-2H-pyran

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 6.5h; Heating;90%
2,2-diphenylacetic acid
117-34-0

2,2-diphenylacetic acid

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With sodium azide; TEA; triethylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0℃; for 30h;90%
With sodium azide; triethylamine; triphenylphosphine; (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane; dimethyl sulfoxide at 0 - 20℃; for 0.833333h;88%
Multi-step reaction with 2 steps
1: diethyl ether; NH3 / 230 °C / im geschlossenen Rohr
2: PCl5; POCl3
View Scheme
Multi-step reaction with 3 steps
1: thionyl chloride
2: ammonia
3: thionyl chloride / 90 - 105 °C
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride / tetrahydrofuran / 1 h / 50 °C
1.2: 0.08 h / 0 °C
2.1: palladium diacetate; Selectfluor; acetonitrile / 18 h / 20 °C
View Scheme
phenylacetonitrile
140-29-4

phenylacetonitrile

benzyl alcohol
100-51-6

benzyl alcohol

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
Stage #1: benzyl alcohol With sodium methylate In ethyl acetate; acetonitrile at 70℃; for 2h; Industrial scale;
Stage #2: phenylacetonitrile at 110℃; for 10h; Concentration; Industrial scale;
90%
Diphenyl-acetonitrile N-oxide
85823-49-0

Diphenyl-acetonitrile N-oxide

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With acetic acid; zinc In methanol for 3h; Ambient temperature;89.3%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzhydryl acetate
954-67-6

benzhydryl acetate

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iron(III) trifluoromethanesulfonate In 1,2-dichloro-ethane at 50℃; for 1h;88%
toluene-4-sulfonic acid phenyl ester
640-60-8

toluene-4-sulfonic acid phenyl ester

phenylacetonitrile
140-29-4

phenylacetonitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With potassium phosphate; palladium diacetate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;87%
phenyl methanesulfonate
16156-59-5

phenyl methanesulfonate

phenylacetonitrile
140-29-4

phenylacetonitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; XPhos In dichloromethane; tert-butyl alcohol at 110℃; for 4h; Inert atmosphere; Schlenk technique; Sealed tube;86%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

nitromethane
75-52-5

nitromethane

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With trimethylsilyl cyanide; zinc trifluoromethanesulfonate at 100℃; for 6.5h; Time; Inert atmosphere; Schlenk technique;85%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

Bromodiphenylmethane
776-74-9

Bromodiphenylmethane

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With iodine; lithium carbonate In dichloromethane at 35℃; for 5h;85%
bromobenzene
108-86-1

bromobenzene

phenylacetonitrile
140-29-4

phenylacetonitrile

A

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

B

2,2,2-triphenylacetonitrile
6639-43-6

2,2,2-triphenylacetonitrile

Conditions
ConditionsYield
With ethoxyethoxyethanol; sodium amide In 1,2-dimethoxyethane 1.) 45 deg C, 2 h, 2.) 0 deg C, 0.5 h, 3.) 0 deg C, 2 h;A 84%
B 15%
With potassium phosphate; tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate In 1,4-dioxane; water at 100℃; for 12h; Inert atmosphere; Sealed tube;A 33%
B 45%
bromobenzene
108-86-1

bromobenzene

acetonitrile
75-05-8

acetonitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With P(i-BuNCH2CH2)3N; sodium hexamethyldisilazane; palladium diacetate In toluene at 100℃; for 16h;81%
Stage #1: acetonitrile With sodium hexamethyldisilazane In toluene at 25℃; for 0.166667h;
Stage #2: bromobenzene With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate In toluene at 100℃; for 16h; Further stages.;
68.4%
(η6-fluorobenzene)tricarbonylchromium
12082-05-2

(η6-fluorobenzene)tricarbonylchromium

phenylacetonitrile
140-29-4

phenylacetonitrile

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With potassium hydroxide; iodine In diethyl ether; dimethyl sulfoxide addn. of C6H5CH2CN to mixt. of Cr(CO)3-complex/powd. KOH in DMSO (stirring; 20°C, 1 h), diln. with aq. HCl, extn. with Et2O, treating with excess I2 (room temp., 3 h); distn. (reduced pressure); identification by GC and NMR;80%
bromobenzene
108-86-1

bromobenzene

acetonitrile
75-05-8

acetonitrile

A

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

B

phenylacetonitrile
140-29-4

phenylacetonitrile

Conditions
ConditionsYield
With ethoxyethoxyethanol; sodium amide In 1,2-dimethoxyethane 1.) 45 deg C, 2 h, 2.) -10 deg C, 2 h, 3.) -30 deg C, 14 h;A 17%
B 79%
(RS)-mandelonitrile
532-28-5, 613-88-7

(RS)-mandelonitrile

benzene
71-43-2

benzene

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With sulfuric acid at 40 - 45℃; for 1h;78%
With aluminium trichloride anschliessendes Erwaermen;
With phosphorus pentoxide
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

copper(l) cyanide

copper(l) cyanide

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
In tetrahydrofuran at 80℃; for 12h;75%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

potassium cyanide
151-50-8

potassium cyanide

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Conditions
ConditionsYield
With sulfuric acid In trifluoroacetic acid for 6h; Ambient temperature;71%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

2,2,3,3-tetraphenylsuccinonitrile
3122-21-2

2,2,3,3-tetraphenylsuccinonitrile

Conditions
ConditionsYield
With methanol; sodium bromide In tetrahydrofuran at 20℃; for 0.7h; Electrolysis;100%
With 2-chloro-2-methyl-3-(p-nitrophenyl)-3-propanone; potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1.5h;86%
With 2,6-diphenyl-4-methoxyphenoxyl radical In chlorobenzene at 110℃; for 0.75h;65%
formaldehyd
50-00-0

formaldehyd

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

α-hydroxymethyl-α-phenylbenzenacetonitrile
92552-36-8

α-hydroxymethyl-α-phenylbenzenacetonitrile

Conditions
ConditionsYield
With pyridine; N-benzyl-trimethylammonium hydroxide In water at 0 - 23℃;100%
With N-benzyl-trimethylammonium hydroxide In methanol; toluene at 20℃; for 2h;98%
With water; calcium oxide In tetrahydrofuran at 30℃;
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

allyl bromide
106-95-6

allyl bromide

2,2-diphenyl-pent-4-enenitrile
5558-71-4

2,2-diphenyl-pent-4-enenitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
100%
Stage #1: Diphenylacetonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #2: allyl bromide In tetrahydrofuran; hexane at 20℃; for 3h;
98%
Stage #1: Diphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: allyl bromide In N,N-dimethyl-formamide at 0 - 20℃;
93%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

3(S)-(4-methylphenylsulfonyloxy)-1-phenylmethyl pyrrolidine
26055-95-8

3(S)-(4-methylphenylsulfonyloxy)-1-phenylmethyl pyrrolidine

2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile
197964-14-0

2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With sodium hydride In toluene for 2h; Reflux;
Stage #2: 3(S)-(4-methylphenylsulfonyloxy)-1-phenylmethyl pyrrolidine In toluene for 3h; Reflux;
100%
2-acetoxy-3-butene
6737-11-7

2-acetoxy-3-butene

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

3-methyl-2,2-diphenylpent-4-enenitrile
60171-90-6

3-methyl-2,2-diphenylpent-4-enenitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Schlenk technique;
Stage #2: 2-acetoxy-3-butene With bis[(1,2,3-η)-2-butenyl]di(μ-chloro)palladium(II); tri-tert-butyl phosphine In tetrahydrofuran; mineral oil at 0 - 20℃; for 16h; Tsuji-Trost Allylation; Inert atmosphere; Schlenk technique; regioselective reaction;
100%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

benzophenone
119-61-9

benzophenone

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In toluene for 3h;99%
With tetrabutylammomium bromide; oxygen In N,N-dimethyl-formamide Hg cathode, Pt anode, -1.0 V vs SCE;95%
With oxygen; potassium carbonate In water; dimethyl sulfoxide Ambient temperature;95%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

methyl iodide
74-88-4

methyl iodide

2,2-diphenylpropionitrile
5558-67-8

2,2-diphenylpropionitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 85℃; for 2h; Inert atmosphere; Sealed tube;99%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;92%
With sodium amide 1.) benzene, reflux, 2 h, 2.) benzene, reflux, 2 h; Yield given. Multistep reaction;
Stage #1: Diphenylacetonitrile 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;
Stage #1: Diphenylacetonitrile With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃;
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

(3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine
116183-79-0

(3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine

2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile
197964-14-0

2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.08333h;
Stage #2: (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine In tetrahydrofuran at 0 - 40℃;
99%
With potassium tert-butylate In tetrahydrofuran at 0 - 40℃; for 16 - 26h;99%
Stage #1: Diphenylacetonitrile With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.08333h;
Stage #2: (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine In tetrahydrofuran at 0 - 40℃; for 15.0833 - 25.1667h;
99%
Stage #1: Diphenylacetonitrile With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.08333h;
Stage #2: (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine In tetrahydrofuran at 0 - 40℃; for 15.0833 - 25.1667h;
99%
Stage #1: Diphenylacetonitrile With potassium tert-butylate In tetrahydrofuran at 0℃; for 1.08333h;
Stage #2: (3S)-3-<(4-tolylsulfonyl)oxy>-1-(phenylmethyl)pyrrolidine In tetrahydrofuran at 0 - 40℃; for 15 - 25h;
99%
[((CH3)2CHCH2)4Al2H(C3HN2(C6H5)2)]

[((CH3)2CHCH2)4Al2H(C3HN2(C6H5)2)]

Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

[((CH3)2CHCH2)4Al2(C3HN2(C6H5)2)NCHCH(C6H5)2]

[((CH3)2CHCH2)4Al2(C3HN2(C6H5)2)NCHCH(C6H5)2]

Conditions
ConditionsYield
In hexane at ambient temp.; XRD;99%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

bromopentene
1119-51-3

bromopentene

2,2-diphenyl-6-heptenenitrile
342819-91-4

2,2-diphenyl-6-heptenenitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 85℃; for 2h; Inert atmosphere; Sealed tube;99%
Stage #1: Diphenylacetonitrile With lithium dimethylamide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: bromopentene In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #1: Diphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;
Stage #2: bromopentene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 12h; Inert atmosphere;
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

allyl alcohol
107-18-6

allyl alcohol

2,2-diphenyl-pent-4-enenitrile
5558-71-4

2,2-diphenyl-pent-4-enenitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); carbon dioxide In dimethyl sulfoxide at 80℃; under 760.051 Torr; for 14h; Reagent/catalyst; Sealed tube;99%
With potassium carbonate In toluene at 80℃; for 18h; Catalytic behavior; Green chemistry;94%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In methanol at 80℃; Sealed tube; Schlenk technique; Inert atmosphere;94%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

1-Bromo-2-butyne
3355-28-0

1-Bromo-2-butyne

2,2-diphenylhex-4-ynenitrile

2,2-diphenylhex-4-ynenitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;
Stage #2: 1-Bromo-2-butyne In tetrahydrofuran; toluene; mineral oil at 20℃;
99%
Stage #1: Diphenylacetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h;
Stage #2: 1-Bromo-2-butyne In tetrahydrofuran at -78 - 0℃;
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

3-ethylethynyl-metyl carbonate
196882-96-9

3-ethylethynyl-metyl carbonate

C19H17N

C19H17N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;99%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

C8H10O3

C8H10O3

C20H17N

C20H17N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;99%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

C10H14O3

C10H14O3

C22H21N

C22H21N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;99%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

C11H16O3

C11H16O3

C23H23N

C23H23N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;99%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

2,2-Diphenylethylamine
3963-62-0

2,2-Diphenylethylamine

Conditions
ConditionsYield
With triethylamine alane In tetrahydrofuran for 1h; Ambient temperature;98.5%
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;90%
With lithium aluminium tetrahydride; diethyl ether
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Diphenylmethane
101-81-5

Diphenylmethane

Conditions
ConditionsYield
With PEG-400; sodium hydroxide for 0.0333333h; microwave irradiation;98%
With potassium hydroxide at 150℃; for 2h;80%
With sodium azide; acetic acid In 1-methyl-pyrrolidin-2-one; water at 220℃; for 0.266667h;73%
Multi-step reaction with 2 steps
1: sodium azide; acetic acid / 1-methyl-pyrrolidin-2-one; water / 0.27 h / 220 °C / Microwave irradiation
2: acetic acid / 1-methyl-pyrrolidin-2-one; water / 240 °C
View Scheme
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Methyl 2-butynoate
23326-27-4

Methyl 2-butynoate

(E)-methyl 4-cyano-3-methyl-4,4-diphenylbut-2-enoate
946617-85-2

(E)-methyl 4-cyano-3-methyl-4,4-diphenylbut-2-enoate

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide In 1,4-dioxane; methanol for 2h; Heating;98%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

propargyl bromide
106-96-7

propargyl bromide

2,2-diphenyl-4-pentynenitrile
21599-40-6

2,2-diphenyl-4-pentynenitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran at 20℃; for 1h;
Stage #2: propargyl bromide In tetrahydrofuran at 20℃; for 12h;
97%
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;
Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil at 20℃;
94%
Stage #1: Diphenylacetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h;
Stage #2: propargyl bromide In tetrahydrofuran; toluene; mineral oil
94%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

2-Bromoethyl methyl ether
6482-24-2

2-Bromoethyl methyl ether

4-methoxy-2,2-diphenylbutanenitrile

4-methoxy-2,2-diphenylbutanenitrile

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran; mineral oil at 85℃; for 2h; Inert atmosphere; Sealed tube;97%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

Carbonic acid dec-2-ynyl ester methyl ester
104846-77-7

Carbonic acid dec-2-ynyl ester methyl ester

C24H27N

C24H27N

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 2-(dicyclohexylphosphino)-2'-methylbiphenyl In N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube; regioselective reaction;97%
Diphenylacetonitrile
86-29-3

Diphenylacetonitrile

2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

3-(2-iodophenyl)-2,2-diphenylpropanenitrile

3-(2-iodophenyl)-2,2-diphenylpropanenitrile

Conditions
ConditionsYield
Stage #1: Diphenylacetonitrile With sodium hydride In N,N-dimethyl-formamide; benzene at 0℃; for 0.5h;
Stage #2: 2-Iodobenzyl bromide In N,N-dimethyl-formamide; benzene at 0 - 20℃; Further stages.;
96%

86-29-3Relevant articles and documents

-

Ginsburg,Baizer

, p. 2254 (1949)

-

Radical trifunctionalization of hexenenitrile via remote cyano migration

Chang, Chenyang,Wu, Xinxin,Zhang, Huihui,Zhu, Chen

supporting information, p. 1005 - 1008 (2022/02/01)

A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken

Synthesis of Succinonitrile Derivatives by Homocoupling from Cyanohydrin Derivatives with a Low-Valent Titanium Reagent

Endo, Ryusei,Kishida, Atsushi,Matsunaga, Kazuma,Nagasawa, Kokoro,Takatori, Kazuhiko

, (2022/02/07)

A method is described for synthesizing succinonitrile derivatives bearing alkyl or aryl substituents from cyanohydrin derivatives using low-valent titanium. The active species in this reaction is proposed to be a resonance hybrid of the TiIV nitrile enolate and TiIII alkyl radical.

Palladium-Catalyzed Direct α-Arylation of Arylacetonitriles with Aryl Tosylates and Mesylates

Yuen, On Ying,Chen, Xiangmeng,Wu, Junyu,So, Chau Ming

supporting information, p. 1912 - 1916 (2020/03/13)

The first general palladium-catalyzed α-arylation of arylacetonitriles with aryl and heteroaryl sulfonates are reported. Pd(OAc)2 associated with XPhos serves as the effective catalyst to facilitate this reaction. A broad range of electron-rich, -neutral, -deficient, and sterically hindered aryl/heteroaryl tosylates and mesylates are coupled with arylacetonitriles bearing different substituents to give the corresponding products in good to excellent yields. Catalyst loading down to 0.1 mol-% Pd was achieved, and 22 unprecedented compounds were synthesized from 43 demonstrated examples using this method. Its applicability with the modification of biological phenolic compounds was successfully demonstrated. The Pd/XPhos system catalyzed the α-arylation and followed by alkylation in one-pot sequential conditions, resulting in the direct synthesis of compounds containing quaternary center- and deuterium-containing compounds in good to excellent yields.

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