p-Tolunitrile

Base Information

• Chemical Name: p-Tolunitrile
• CAS No.: 104-85-8
• Molecular Formula: C8H7N
• Molecular Weight: 117.15
• Hs Code.: 29269095
• European Community (EC) Number: 203-244-8
• NSC Number: 70985
• UN Number: 3273
• UNII: H20555V8NO
• DSSTox Substance ID: DTXSID6026169
• Nikkaji Number: J10.115J
• Wikidata: Q27279529
• ChEMBL ID: CHEMBL1386404
• Mol file: 104-85-8.mol

Synonyms:p-Tolunitrile;4-METHYLBENZONITRILE;104-85-8;4-Cyanotoluene;Benzonitrile, 4-methyl-;4-Tolunitrile;p-Methylbenzonitrile;p-Cyanotoluene;p-Toluonitrile;p-Tolylnitrile;p-Tolunitril;p-Toluenenitrile;p-Toluic nitrile;4-methylbenzenecarbonitrile;1-Methyl-4-cyanobenzene;4-Methylcyanobenzene;4-Toluenkarbonitril;Nitril kyseliny p-toluylove;4-methyl-benzonitrile;p-Tolunitril [Czech];Nitril kyseliny p-toluylove [Czech];4-Toluenkarbonitril [Czech];NSC 70985;CCRIS 4737;1-Cyano-4-methylbenzene;P-TOLUNITRILE-D7;EINECS 203-244-8;MFCD00001827;UNII-H20555V8NO;AI3-14826;CHEMBL1386404;DTXSID6026169;H20555V8NO;NSC-70985;EC 203-244-8;1219804-01-9;para-toluonitrile;p-Tolunitrile, 98%;PARA TOLUNITRILE;TOLUNITRILE, P-;CYANOTOLUENE, P-;P-TOLUNITRILE [MI];WLN: NCR D1;SCHEMBL46818;DTXCID206169;SCHEMBL10729751;HMS1766A03;NSC70985;STR00267;Tox21_200947;BDBM50037786;LS-381;STL169108;AKOS000120771;AC-7209;NCGC00091204-01;NCGC00091204-02;NCGC00258500-01;CAS-104-85-8;p-Tolunitrile, purum, >=98.0% (GC);TS-03564;AM20050255;FT-0658815;T0307;EN300-17589;Q-200493;Q27279529;Z56965882;F0001-0091

Chemical Property of p-Tolunitrile

Chemical Property:

• Appearance/Colour: beige solid
• Vapor Pressure: 0.126mmHg at 25°C
• Melting Point: 26-28 ºC(lit.)
• Refractive Index: 1.5285-1.5305
• Boiling Point: 218.389 ºC at 760 mmHg
• Flash Point: 85.636 ºC
• PSA: 23.79000
• Density: 0.981 g/cm³
• LogP: 1.86668
• Storage Temp.: Store below +30°C.
• Solubility.: alcohol: very soluble
• Water Solubility.: <0.1 g/100 mL at 17℃
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 117.057849228
• Heavy Atom Count: 9
• Complexity: 123
• Transport DOT Label: Flammable Liquid Poison

Purity/Quality:

99% ^*data from raw suppliers

p-?Tolunitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi:Irritant
• Statements: R36/38:
• Safety Statements: S37:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C#N
• Uses: p-?Tolunitrile is a reagent used in the preparation of 1H-Indazoles from imidates and nitrosobenzenes.

Technology Process of p-Tolunitrile

There total 561 articles about p-Tolunitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-methylthiobenzamide (2362-62-1) + benzyl chloride (100-44-7) → dibenzyl sulfide (538-74-9) + para-methylbenzonitrile (104-85-8)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In water; benzene; at 30 ℃; for 2h; Product distribution;

Reference yield: 88.0%

p-methylbenzaldehyde oxime (3235-02-7,3717-15-5,3717-16-6,140461-26-3,140461-27-4) + dimethylbromosulphonium bromide (50450-21-0) → dimethyl sulfoxide (67-68-5,8070-53-9) + para-methylbenzonitrile (104-85-8)

Guidance literature:

In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2009.07.100

Reference yield: 82.0%

para-methylbenzylamine (104-84-7) → para-methylbenzonitrile (104-85-8) + para-methylbenzamide (619-55-6)

Guidance literature:

With water; oxygen; at 140 ℃; for 10h; under 3800.26 Torr;

DOI:10.1002/anie.200802464

upstream raw materials:

pyridine

p-methylbenzaldehyde oxime benzoyl ester

pyridine hydrochloride

tetrachloromethane

Downstream raw materials:

N,N'-methylenebis(4-methylbenzamide)

pyridin-3-yl(p-tolyl)methanone

N-[2]pyridyl-p-toluamidine

5-methoxy-2-p-tolyl-oxazole

Refernces

• 1、 Donga, Zhongmin,Yea, Zhibin. "Reusable, highly active heterogeneous palladium catalyst by convenient self-encapsulation cross-linking polymerization for multiple carbon-carbon cross-coupling reactions at ppm to ppb palladium loadings". . p. 3401 - 3414. Retrieved 2014.
• 2、 Gelman,Schumann,Blum. "Dichlorobis(triphenylphosphine)nickel-catalyzed cross-coupling of aryl chlorides with intramolecularly stabilized group 13 metal alkylating reagents". . p. 7555 - 7558. Retrieved 2000.
• 3、 Liu, Lixin,Dong, Jianyu,Zhang, Yaxing,Zhou, Yongbo,Yin, Shuang-Feng. "Cu-mediated nitrogen atom transfer via C≡N bond cleavage". . p. 9948 - 9952. Retrieved 2015.
• 4、 Kazemi, Foad,Kiasat, Ali Reza,Fadavipoor, Elham. "A versatile method for the conversion of aldoximes to nitriles using silica gel/thionyl chloride". . p. 433 - 436. Retrieved 2004.
• 5、 Gonzalez, Carlos M.,Pincock, James A.. "Activation energies for the singlet excited state processes of substituted benzenes: Para, meta, and ortho isomers of methylbenzonitrile and methylanisole in acetonitrile". . p. 8870 - 8871. Retrieved 2004.
• 6、 Jang, Wonseok,Kim, Se Eun,Yang, Cheol Mo,Yoon, Sungwoo,Park, Myunghwan,Lee, Junseong,Kim, Youngjo,Kim, Min. "Cobalt/nitrophenolate-catalyzed selective conversion of aldoximes into nitriles or amides". . p. 120 - 123. Retrieved 2015.
• 7、 Andrieux, Claude P.,Combellas, Catherine,Kanoufi, Fredéric,Savéant, Jean-Michel,Thiébault, André. "Dynamics of bond breaking in ion radicals. Mechanisms and reactivity in the reductive cleavage of carbon-fluorine bonds of fluoromethylarenes". . p. 9527 - 9540. Retrieved 1997.
• 8、 Coleman et al.. "-". . p. 738. Retrieved 1970.
• 9、 Zhang, Guo-Ying,Yu, Jin-Tao,Hu, Mao-Lin,Cheng, Jiang. "Palladium-catalyzed cyanation of aryl halides with CuSCN". . p. 2710 - 2714. Retrieved 2013.
• 10、 Koo, Ja Seo,Lee, Jae In. "2-pyridyl cyanate: A useful reagent for the preparation of nitriles". . p. 3709 - 3713. Retrieved 1996.