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o-Tolunitrile

o-Tolunitrile structure

o-Tolunitrile 

structure
  • CAS No:

    529-19-1

  • Formula:

    C8H7N

  • Chemical Name:

    o-Tolunitrile

  • Synonyms:

    O-CYANO TOLUENE;o-toluic nitrile;O-TOLUNITRILE;o-toluonitrile;o-Tolylnitrile;O-TOLYL CYANIDE;O-METHYLBENZONITRILE;2-methyl-benzonitril

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

clear colorless to slightly yellow liquid


o-Tolyl Cyanide, is a versatile intermediate, used in the synthesis of various pharmaceutical and biologically active compounds. It can be used in the preparation of highly efficient triarylene conjugated dyes for sensitized solar cells


O-tolunitrile is a light blue clear liquid. (NTP, 1992)


O-tolunitrile is a light blue clear liquid. (NTP, 1992)


Fractionally distil the nitrile, wash it with conc HCl or 50% H2SO4 at 60o until the smell of isonitrile has gone (this also removes any amines), then wash it with saturated NaHCO3 and dilute NaCl solutions, then dry it with K2CO3 and redistil it. [Beilstein 9 IV 1703.]

o-Tolunitrile Basic Attributes

117.15

117.15

1857417

208-451-7

3048F2A3KT

66549

1759

TSCA listed

DTXSID6022050

Clear colorless to slightly yellow

29269095

Characteristics

23.8

2.12

Clear colorless to slightly yellow Liquid

0.989 g/mL at 25 °C(lit.)

-13 °C

205 °C(lit.)

184 °F

n20/D1.5279(lit.)

<0.1 g/100 mL at 17 ºC

Store below +30°C.

0.45 mmHg

Oral-rat LD50: 3200 mg/kg; Abdominal cavity-mouse LD50: 700 mg/kg

Open flame is flammable; burning produces toxic nitrogen oxides and cyanide fumes

1.1-6.7%(V)

7 (H2O, 20℃)

7.6×10-1mol/(m3Pa) at 25℃, Schüürmann (2000)

Insoluble in water.

Nitriles

Nitriles, such as o-Tolunitrile, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Store below +30°C.

Safety Information

I; II

3276

2

Xi

61-37-36-26-24/25

XV0600000

Xi

The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

Stable at room temperature in closed containers under normal storage and handling conditions.

P273

38-52/53-36/37/38

3276

o-Tolunitrile is combustible.

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P321, P332+P313, P362, and P501|Aggregated GHS information provided by 131 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicity

moderately toxic

NIOSH: IDLH 25 mg/m3

Drug Information

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

o-tolunitrile

o-Tolunitrile Use and Manufacturing

Uses

Used as medicine and dye intermediate


o-Tolyl Cyanide, is a versatile intermediate, used in the synthesis of various pharmaceutical and biologically active compounds. It can be used in the preparation of highly efficient triarylene conjugated dyes for sensitized solar cells

Benzonitrile, 2-methyl-: ACTIVE

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Van Den Dool and Kratz RI, polar column, temperature ramp Capillary DB-Wax 1912. temperature ramp 60. m/0.25 mm/0.25 μm, 2. K/min; Tstart: 50. C; Tend: 230. C Shimoda, M.Shigematsu, H.Shiratsuchi, H.Osajima, Y.Comparison of the odor concentrates by SDE and adsorptive column method from green tea infusionJ. Agric. Food Chem.1995, 43, 6, 1616-1620.
Van Den Dool and Kratz RI, polar column, temperature ramp Capillary DB-Wax 1912. temperature ramp 60. m/0.25 mm/0.25 μm, He, 2. K/min; Tstart: 50. C; Tend: 230. C Shimoda, M.Shigematsu, H.Shiratsuchi, H.Osajima, Y.Comparison of volatile compounds among different grades of green tea and their relations to odor attributesJ. Agric. Food Chem.1995, 43, 6, 1621-1625.
Van Den Dool and Kratz RI, polar column, temperature ramp Capillary HP-5 172.6 temperature ramp 30. m/0.3 mm/0.25 μm, He, 50. C @ 5. min, 5. K/min, 200. C @ 15. min Shao, X.Wang, G.Sun, Y.Zhang, R.Xie, K.Liu, H.Determination and Characterization of the Pyrolysis Products of Isoprocarb by GC-MSJ. Chromatogr. Sci.2006, 44, 3, 141-147.

Computed Properties

Molecular Weight:117.15
XLogP3:2.2
Hydrogen Bond Acceptor Count:1
Exact Mass:117.057849228
Monoisotopic Mass:117.057849228
Topological Polar Surface Area:23.8
Heavy Atom Count:9
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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