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104-85-8

Basic Information
CAS No.: 104-85-8
Name: Benzonitrile,4-methyl-
Article Data: 814
Molecular Structure:
Molecular Structure of 104-85-8 (Benzonitrile,4-methyl-)
Formula: C8H7N
Molecular Weight: 117.15
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;
EINECS: 203-244-8
Density: 0.981 g/cm3
Melting Point: 26-28 ºC(lit.)
Boiling Point: 218.389 ºC at 760 mmHg
Flash Point: 85.636 ºC
Solubility: water: <0.1 g/100 mL at 17 °C
Appearance: beige solid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38-43
Safety: 26-36/37
PSA: 23.79000
LogP: 1.86668
Synthetic route
589-18-4

4-Methylbenzyl alcohol

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

A

methyl 4-amino(d-2)benzoate

B

104-85-8

para-methylbenzonitrile

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

4-methyl-benzaldehyde

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%
619-55-6

para-methylbenzamide

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%
7175-47-5

4-methylphenyl isocyanide

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.
104-84-7

para-methylbenzylamine

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%
106-38-7

para-bromotoluene

557-19-7

nickel cyanide

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%
118474-36-5

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

A

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

B

104-85-8

para-methylbenzonitrile

C

triethylammonium tetraphenylborate

Conditions
ConditionsYield
With triethylamine In dichloromethane not isolated; IR spectroscopy;A 99%
B n/a
C n/a
118474-34-3

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

A

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

B

104-85-8

para-methylbenzonitrile

C

triethylammonium tetraphenylborate

Conditions
ConditionsYield
With triethylamine In dichloromethane not isolated; IR spectroscopy;A 99%
B n/a
C n/a
10254-13-4

N-(Diphenylmethylen)-p-toloylsaeureamid

104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
With chlorotriphenoxyphosphonium chloride; triethylamine In chloroform at -30 - 20℃; von Braun degradation;99%
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Consensus Reports

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

Standards and Recommendations

CONTENT: 99.0% min
MOISTURE: 0.1% max

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.