Product Name

  • Name

    Benzonitrile,4-methyl-

  • EINECS 203-244-8
  • CAS No. 104-85-8
  • Article Data814
  • CAS DataBase
  • Density 0.981 g/cm3
  • Solubility water: <0.1 g/100 mL at 17 °C
  • Melting Point 26-28 ºC(lit.)
  • Formula C8H7N
  • Boiling Point 218.389 ºC at 760 mmHg
  • Molecular Weight 117.15
  • Flash Point 85.636 ºC
  • Transport Information
  • Appearance beige solid
  • Safety 26-36/37
  • Risk Codes 36/37/38-43
  • Molecular Structure Molecular Structure of 104-85-8 (Benzonitrile,4-methyl-)
  • Hazard Symbols IrritantXi
  • Synonyms 1-Cyano-4-methylbenzene;4-Cyanotoluene;4-Methylbenzonitrile;4-Methylcyanobenzene;4-Methylphenyl cyanide;4-Toluenitrile;4-Tolyl cyanide;NSC 70985;p-Cyanotoluene;p-Methylbenzonitrile;p-Toluenenitrile;p-Tolylcyanide;
  • PSA 23.79000
  • LogP 1.86668

Synthetic route

4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 20℃; for 24h;100%
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 130℃; under 3750.38 Torr; for 24h;100%
Stage #1: 4-Methylbenzyl alcohol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;		99%
C8H7(2)H2N

C8H7(2)H2N

A

methyl 4-amino(d-2)benzoate

methyl 4-amino(d-2)benzoate

B

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With methyl 4-azidobenzoate at 70℃; for 2h; Inert atmosphere;A 94%
B 100%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; periodic acid; potassium iodide at 60℃; for 65745h; Sealed tube; Green chemistry;99%
With ammonium sulfate; sodium carbonate; sulfur In dimethyl sulfoxide at 120℃; for 12h; Reagent/catalyst; Solvent; Time; Temperature;99%
With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In dichloromethane at 23℃; for 24h; Inert atmosphere;98%
para-methylbenzamide
619-55-6

para-methylbenzamide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; copper(l) chloride In toluene at 100℃; for 24h;99%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide for 13h; Ambient temperature;95%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide for 13h; Product distribution; Ambient temperature; also in (C2H5O)3PO, other temperature, other time;95%
4-methylphenyl isocyanide
7175-47-5

4-methylphenyl isocyanide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
at 520 - 550℃; under 0.01 Torr;99%
In 1,3,5-trimethyl-benzene Thermodynamic data; ΔG(excit.), ΔH(excit.), ΔS(excit.), t1/2;
With 1,1-Diphenylethylene In various solvent(s) at 210℃; Rate constant; Thermodynamic data; ΔG(excit.) <250 deg C>; ΔH(excit.), ΔS(excit.);100 % Chromat.
para-methylbenzylamine
104-84-7

para-methylbenzylamine

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With oxygen In acetone at 20℃; for 3.8h; Electrochemical reaction;99%
With trichloroisocyanuric acid; ammonia In water at 20 - 60℃;98%
With C22H22Cl2FeN2O8(2-)*2C16H36N(1+); oxygen In neat (no solvent) at 100℃; under 760.051 Torr; for 0.5h; Green chemistry;98%
para-bromotoluene
106-38-7

para-bromotoluene

nickel cyanide
557-19-7

nickel cyanide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one; water at 200℃; under 10343 Torr; for 0.166667h; Product distribution; Further Variations:; Solvents; Reaction partners; Temperatures; reaction times; absence of microwave irradiation; microwave irradiation;99%
{cis-Fe(4-MeC6H4N2H)(4-MeC6H4CN)(P(OEt)3)4}(BPh4)2
118474-36-5

{cis-Fe(4-MeC6H4N2H)(4-MeC6H4CN)(P(OEt)3)4}(BPh4)2

A

Fe(CH3C6H4N2)(P(OC2H5)3)4(1+)

Fe(CH3C6H4N2)(P(OC2H5)3)4(1+)

B

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

C

triethylammonium tetraphenylborate

triethylammonium tetraphenylborate

Conditions
ConditionsYield
With triethylamine In dichloromethane not isolated; IR spectroscopy;A 99%
B n/a
C n/a
...Expand
{cis-Fe(4-MeC6H4N2H)(4-MeC6H4CN)(PPh(OEt)2)4}(BPh4)2
118474-34-3

{cis-Fe(4-MeC6H4N2H)(4-MeC6H4CN)(PPh(OEt)2)4}(BPh4)2

A

Fe(CH3C6H4N2)(C6H5P(OC2H5)2)4(1+)

Fe(CH3C6H4N2)(C6H5P(OC2H5)2)4(1+)

B

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

C

triethylammonium tetraphenylborate

triethylammonium tetraphenylborate

Conditions
ConditionsYield
With triethylamine In dichloromethane not isolated; IR spectroscopy;A 99%
B n/a
C n/a
...Expand
N-(Diphenylmethylen)-p-toloylsaeureamid
10254-13-4

N-(Diphenylmethylen)-p-toloylsaeureamid

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With chlorotriphenoxyphosphonium chloride; triethylamine In chloroform at -30 - 20℃; von Braun degradation;99%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

methylzinc halide lithium chloride

methylzinc halide lithium chloride

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 20℃; for 0.5h; Negishi Coupling; Schlenk technique; Inert atmosphere;99%
p-methylbenzaldehyde oxime
3235-02-7, 3717-15-5, 3717-16-6, 140461-26-3, 140461-27-4

p-methylbenzaldehyde oxime

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
copper diacetate In acetonitrile for 4h; Heating;98%
With trichloro(trifluoromethanesulfonato)titanium(IV) at 80℃; for 10h; Dehydration;97%
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20℃;97%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

4-tolyl iodide
624-31-7

4-tolyl iodide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With copper (II) trifluoroacetate hydrate; palladium diacetate In dimethyl sulfoxide at 130℃; for 4h; Sealed tube; Inert atmosphere;98%
4-methylbenzoyl cyanide
14271-73-9

4-methylbenzoyl cyanide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In benzene at 120℃; for 12h;97%
4-Methylbenzyl chloride
104-82-5

4-Methylbenzyl chloride

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With ammonia; oxygen; VCrO; silica gel at 210℃; for 8h;97%
With sodium azide; palladium diacetate; triphenylphosphine In acetone at 80℃; for 36h; Schlenk technique;92%
With trichloroisocyanuric acid; ammonia In water at 20 - 60℃;90%
N-benzyl-4-methylbenzamide
5436-83-9

N-benzyl-4-methylbenzamide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With bromotriphenoxyphosphonium bromide; triethylamine In chloroform at -60℃; von Braun degradation; Reflux;97%
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

ammonia
7664-41-7

ammonia

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [{Cu(NO3)}(μ-3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide)]2; oxygen; potassium carbonate at 50℃; for 24h;97%
4-tolyl iodide
624-31-7

4-tolyl iodide

potassium cyanide
151-50-8

potassium cyanide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; tributyltin chloride; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;96%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In various solvent(s) at 60℃; for 4h;94%
Methyl-(4-oxo-5-phenyl-2-p-tolyl-4H-4λ4-[1,4,3]oxathiazin-6-yl)-phenyl-amine
131497-56-8

Methyl-(4-oxo-5-phenyl-2-p-tolyl-4H-4λ4-[1,4,3]oxathiazin-6-yl)-phenyl-amine

A

C15H13NO2S
131497-52-4

C15H13NO2S

B

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
for 24h; Ambient temperature;A 96%
B n/a
for 24h; Ambient temperature; other 1,4,3-oxathiazin-4-oxides;A 96%
B n/a
4-cyanobenzyl bromide
17201-43-3

4-cyanobenzyl bromide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With sodium tetrahydroborate; cetyltributylphosphonium bromide In dichloromethane; water at 18℃; for 0h; Product distribution;96%
With indium(III) chloride; lithium dimethylamino borohydride In tetrahydrofuran at 25℃; for 4h; Inert atmosphere; chemoselective reaction;70%
With Perbenzoic acid; tri-n-butyl-tin hydride In benzene at 90℃; for 12h; Mechanism; in the presence of α-bromotoluene (competitor), relative reactivity; other solvent (MeCN);
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

(CH3)2AlOC2H4N(CH3)2

(CH3)2AlOC2H4N(CH3)2

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In benzene at 80℃; for 6h; Substitution;96%
With tri-tert-butyl phosphine; [(CO)3Co]2(μ-CO)Pd[μ-(Ph2PCH2)2] In benzene at 120℃; for 2.5h;95 % Chromat.
4-cyanophenyl trifluoromethanesulfonate
66107-32-2

4-cyanophenyl trifluoromethanesulfonate

methyltriisopropoxytitanium(IV)
18006-13-8

methyltriisopropoxytitanium(IV)

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
bis(η3-allyl-μ-chloropalladium(II)); (R*)-(S*)-PPFA In tetrahydrofuran for 3h; Heating;96%
para-bromotoluene
106-38-7

para-bromotoluene

K4Fe(CN)6

K4Fe(CN)6

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With 1,8-bis(diisopropylphosphino)triptycene; potassium phosphate; palladium diacetate In N,N-dimethyl-formamide at 85℃; for 24h;96%
N-tert-butyl-4-methylbenzamide
42498-32-8

N-tert-butyl-4-methylbenzamide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With bromotriphenoxyphosphonium bromide; triethylamine In chloroform at -60 - 20℃; von Braun degradation;96%
4-tolyl iodide
624-31-7

4-tolyl iodide

potassium ferrocyanide

potassium ferrocyanide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst;96%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 5h; Reagent/catalyst; Solvent; Temperature;96%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 10h; Inert atmosphere;95%
tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

4-toluenediazonium o-benzenedisulfonimide

4-toluenediazonium o-benzenedisulfonimide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
In acetonitrile at 22℃; for 0.25h; Sandmeyer Reaction;96%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

4-tolyl perfluorobutanesulfonate
93131-73-8

4-tolyl perfluorobutanesulfonate

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate at 40℃; for 3h; Catalytic behavior; Time; Temperature; Green chemistry;96%
para-methylphenylmagnesium bromide
4294-57-9

para-methylphenylmagnesium bromide

pyridin-2-yl cyanate
175351-40-3

pyridin-2-yl cyanate

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.166667h;95%
p-tolylmethylenediacetate
2929-93-3

p-tolylmethylenediacetate

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With trimethylsilylazide; titanium tetrachloride In dichloromethane for 2h; Ambient temperature;95%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

p-toluamidoxime
19227-13-5

p-toluamidoxime

Conditions
ConditionsYield
With hydroxylamine In ethanol; water Reflux;100%
With hydroxylamine In ethanol; water at 25 - 78℃; for 18h; Reagent/catalyst; Temperature;100%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;96%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

p-methylselenobenzamide
67213-27-8

p-methylselenobenzamide

Conditions
ConditionsYield
With selenium; carbon monoxide; water; triethylamine In tetrahydrofuran at 100℃; under 3800 Torr; for 5h;100%
Stage #1: para-methylbenzonitrile With woollins’ reagent In toluene for 4h; Heating;
Stage #2: With water In toluene for 1h;		100%
With selenium; carbon monoxide; water In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 5h;96%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

4-methylbenzylamine hydrochloride
26177-45-7

4-methylbenzylamine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60℃; under 375.038 Torr; for 18h; Flow reactor;100%
Stage #1: para-methylbenzonitrile With [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; diethylphenylsilane at 20℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;		99%
Stage #1: para-methylbenzonitrile With [RhCl2(p-cymene)]2; dimethylamine borane In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; Sealed ampoule;
Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;		98%
Triethoxyvinylsilane
78-08-0

Triethoxyvinylsilane

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

C24H43NO6Si2

C24H43NO6Si2

Conditions
ConditionsYield
carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 24h; Addition;100%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

/PBGLH020--490/

/PBGLH020--490/

N-(4-Chloro-benzyl)-4-methyl-benzamidine

N-(4-Chloro-benzyl)-4-methyl-benzamidine

Conditions
ConditionsYield
In tetrahydrofuran at 55℃; for 3h;100%
dichlorine monoxide

dichlorine monoxide

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

p-cyanobenzo trichloride
2179-45-5

p-cyanobenzo trichloride

Conditions
ConditionsYield
In tetrachloromethane100%
ammonium hexafluorophosphate

ammonium hexafluorophosphate

C32H31FeP2(1+)*I(1-)

C32H31FeP2(1+)*I(1-)

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

(SFe,RC)-[(η5-cyclopentadienyl)[bis(diphenylphosphanyl)propane-κP](4-methylbenzonitrile)iron]hexafluorophosphate

(SFe,RC)-[(η5-cyclopentadienyl)[bis(diphenylphosphanyl)propane-κP](4-methylbenzonitrile)iron]hexafluorophosphate

Conditions
ConditionsYield
In chloroform at 20℃; for 2h; Inert atmosphere;100%
...Expand
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

terephthalonitrile
623-26-7

terephthalonitrile

Conditions
ConditionsYield
Stage #1: para-methylbenzonitrile With hydrogen bromide; dihydrogen peroxide In tetrachloromethane; water at 20℃; for 1h; Irradiation;
Stage #2: With ammonia; iodine In tetrachloromethane; water; acetonitrile at 20 - 60℃; for 18h;		99%
With 1,10-Phenanthroline; ammonium acetate; dihydrogen peroxide; oxygen In N,N-dimethyl acetamide at 180℃; under 11400.8 Torr; for 24h; Autoclave;66%
With tert.-butylnitrite; N-hydroxyphthalimide; palladium diacetate In acetonitrile at 80℃; for 24h; Inert atmosphere; Sealed tube;64%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

para-methylbenzamide
619-55-6

para-methylbenzamide

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In ethanol at 20℃; for 2.5h;99%
With water; tricyclohexylphosphine; {Rh(OMe)(cod)}2 In isopropyl alcohol at 25℃; for 24h;99%
With cobalt(II,III) oxide; water at 140℃; for 24h;99%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

para-methylbenzylamine
104-84-7

para-methylbenzylamine

Conditions
ConditionsYield
With hydrogen; silica gel; nickel In methanol; ammonia at 120℃; under 7600 Torr; for 6h;99%
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); potassium tert-butylate; hydrogen bromide; hydrogen; 2-((di-iso-propylphosphino)methyl)-1-methyl-1H-imidazole In tetrahydrofuran; water; acetone; toluene at 20℃; under 37503.8 Torr; for 5.5h; Inert atmosphere; Schlenk technique; Autoclave;99%
With C19H34Cl2CoN2P; hydrogen; sodium ethanolate; sodium triethylborohydride In benzene at 135℃; under 22502.3 Torr; for 36h; Autoclave;99%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

p-cyanobenzo trichloride
2179-45-5

p-cyanobenzo trichloride

Conditions
ConditionsYield
With hypochlorous anhydride In tetrachloromethane at 25℃;99%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

5-(4-methylphenyl)-2H-tetrazole
24994-04-5

5-(4-methylphenyl)-2H-tetrazole

Conditions
ConditionsYield
Stage #1: para-methylbenzonitrile With α,α,α-trifluorotoluene; tris(2-perfluorohexylethyl)tin azide at 80℃; for 12h; Cyclization;
Stage #2: With hydrogenchloride In diethyl ether at 25℃; for 12h; Hydrolysis;		99%
With sodium azide; acetic acid In butan-1-ol for 96h; Heating;90%
With sodium azide; zinc(II) chloride In water for 24h; Heating;82%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

5-(p-tolyl)-1H-tetrazole
24994-04-5

5-(p-tolyl)-1H-tetrazole

Conditions
ConditionsYield
Stage #1: para-methylbenzonitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;		99%
With sodium azide; acetic acid In 1-methyl-pyrrolidin-2-one; water at 220℃; under 5250.53 Torr; for 0.0833333h; Microwave irradiation;98%
With sodium azide; gold In N,N-dimethyl-formamide at 80℃; for 1.5h; Reagent/catalyst; Inert atmosphere;98%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

4,4,5,5-tetramethyl-N-(4-methylbenzyl)-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolan-2-amine

4,4,5,5-tetramethyl-N-(4-methylbenzyl)-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolan-2-amine

Conditions
ConditionsYield
With C37H59AlN2 In neat (no solvent) at 60℃; for 1.5h; Inert atmosphere;99%
With silver hexafluoroantimonate at 60℃; for 12h; Inert atmosphere; Glovebox;99%
With manganese(II) triflate bis-acetonitrile solvate; potassium tert-butylate In benzene-d6 at 20℃; for 3h; Inert atmosphere; Glovebox;99%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

N-benzyl-3-phenylprop-2-en-1-amine
107175-80-4

N-benzyl-3-phenylprop-2-en-1-amine

1,4-dibenzyl-2-(p-tolyl)-4,5-dihydro-1H-imidazole

1,4-dibenzyl-2-(p-tolyl)-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)ytterbium(III) In toluene at 25℃; for 12h; Inert atmosphere; Glovebox; Schlenk technique;99%
With tris(bis(trimethylsilyl)amido)ytterbium(III) In toluene at 22℃; for 12h; Inert atmosphere;80%
ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate
60474-27-3

ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

ethyl 5-phenyl-3-(p-tolyl)isothiazole-4-carboxylate

ethyl 5-phenyl-3-(p-tolyl)isothiazole-4-carboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In chlorobenzene at 130℃; for 2h; Glovebox;99%
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

C22H28OSi

C22H28OSi

Conditions
ConditionsYield
Stage #1: para-methylbenzonitrile; 2,3-dimethyl-buta-1,3-diene; dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With tris(3,5-dimethylphenyl)phosphine; copper diacetate In toluene at 20℃; for 19h; Inert atmosphere; Schlenk technique; Glovebox;
Stage #2: With hydrogenchloride In water; toluene at 20℃; for 1h; Inert atmosphere; Schlenk technique; Glovebox;		99%
...Expand
benzaldehyde
100-52-7

benzaldehyde

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

N-benzyl-1-(p-tolyl)methanaminium chloride

N-benzyl-1-(p-tolyl)methanaminium chloride

Conditions
ConditionsYield
Stage #1: benzaldehyde; para-methylbenzonitrile With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether		99%

p-Tolunitrile Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

p-Tolunitrile Standards and Recommendations

CONTENT: 99.0% min
MOISTURE: 0.1% max

p-Tolunitrile Specification

The CAS registry number of p-Tolunitrile is 104-85-8. Its EINECS registry number is 203-244-8. The IUPAC name is 4-Methylbenzonitrile. In addition, the molecular formula is C8H7N and the molecular weight is 117.15. It is also called 1-Cyano-4-methylbenzene. What's more, it is a kind of beige solid and belongs to the classes of Benzene Derivatives; Aromatic Nitriles; Phenyls & Phenyl-Het; Nitriles; Benzonitriles (Building Blocks for Liquid Crystals); Functional Materials. Besides, it should be stored in sealed container, and put in a cool and dry place. The storage place must stay away from oxidant.

Physical properties about this chemical are: (1)ACD/LogP: 2.37; (2)ACD/LogD (pH 5.5): 2.371; (3)ACD/LogD (pH 7.4): 2.371; (4)ACD/BCF (pH 5.5): 37.348; (5)ACD/BCF (pH 7.4): 37.348; (6)ACD/KOC (pH 5.5): 464.564; (7)ACD/KOC (pH 7.4): 464.564; (8)#H bond acceptors: 1; (9)Polar Surface Area: 23.79 Å2; (10)Index of Refraction: 1.531; (11)Molar Refractivity: 35.943 cm3; (12)Molar Volume: 116.115 cm3; (13)Polarizability: 14.249×10-24cm3; (14)Surface Tension: 39.609 dyne/cm; (15)Density: 1.009 g/cm3; (16)Flash Point: 85.636 °C; (17)Enthalpy of Vaporization: 45.478 kJ/mol; (18)Boiling Point: 218.389 °C at 760 mmHg; (19)Vapour Pressure: 0.126 mmHg at 25 °C.

Preparation of p-Tolunitrile: it can be prepared by 3,6,6-Trimethyl-4-[(4-methyl-benzylidene)-amino]-4,6-dihydro-1H-cyclopenta[e][1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester. The other product is 4-methyl-benzaldehyde. This reaction will need reagent MeONa and solvent ethanol. The reaction time is 3 hours by heating. The yield is about 89 %.

p-Tolunitrile can be prepared by 3,6,6-trimethyl-4-[(4-methyl-benzylidene)-amino]-4,6-dihydro-1H-cyclopenta[e][1,2,4]triazine-5,7-dicarboxylic acid dimethyl ester. The other product is 4-methyl-benzaldehyde

Uses of p-Tolunitrile: it can be used as pharmaceutical and dye intermediates. And it can be used to get 2,4,6-tri-p-tolyl-[1,3,5]triazine and 2,4,5-tri-p-tolyl-1H-imidazole. This reaction will need reagent NaH of nanometric size and solvent tetrahydrofuran. The reaction time is 7 hours by heating. The yield is about 22 %.

p-Tolunitrile can be used to get 2,4,6-tri-p-tolyl-[1,3,5]triazine and 2,4,5-tri-p-tolyl-1H-imidazole

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. And it may cause sensitization by skin contacting. When you are using it, you should wear suitable protective clothing and gloves. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc1ccc(cc1)C#N
(2)InChI: InChI=1/C8H7N/c1-7-2-4-8(6-9)5-3-7/h2-5H,1H3
(3)InChIKey: VCZNNAKNUVJVGX-UHFFFAOYAI

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1300mg/kg (1300mg/kg)   Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. Vol. 19, Pg. 225, 1969.
rabbit LDLo subcutaneous 1080mg/kg (1080mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Archives Internationales de Pharmacodynamie et de Therapie. Vol. 5, Pg. 161, 1899.
rat LD50 oral 3800mg/kg (3800mg/kg)   Zentralblatt fuer Arbeitsmedizin und Arbeitsschutz. Vol. 19, Pg. 225, 1969.

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