Phenylacetonitrile

log Kow = 1.56

1.56

1.47

1.0214 at 59 °F (EPA, 1998) - Denser than water; will sink

1.0205

1.0214 @ 15°C

less than 1 mg/mL at 63 °F (NTP, 1992)

Miscible with oxygenated solvents.

SOL IN ALL PROP IN ALC, ETHER; SOL IN ACETONE

In water, 100 mg/L at 25 °C

0.1 mg/mL at 25 °C

215 °F (NTP, 1992)

102 °C

102 °C (closed cup)

235 °F (113 °C) (Open cup)

451.4 °F at 760 mmHg (EPA, 1998)

233.5 °C

233.00 to 234.00 °C. @ 760.00 mm Hg

233.5 °C @760 [mm Hg]

-10.8 °F (EPA, 1998)

-23.8 °C

-23.8 °C

-23.8 °C

Danger

H301 (88%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1715 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Chemical: Benzeneacetonitrile

List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)

Benzeneacetonitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzeneacetonitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 15-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/10522

Benzyl cyanide: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

When heated to decomposition, it emits very toxic fumes of cyanide and nitrogen oxides. Container may explode in heat of fire. Runoff from fire control water may give off poisonous gases. Avoid sodium hypochlorite. (EPA, 1998)

· Combustible material: may burn but does not ignite readily.

Poisonous. May be fatal if inhaled, swallowed, or absorbed through skin. Contact may cause burns to skin and eyes. (EPA, 1998)

· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.

The following chemicals have been specifically designated by the Administrator of the Drug Enforcement Administration as the listed chemicals subject to the provisions of this part and parts 1309 and 1313 of this chapter. Each chemical has been assigned the DEA Chemical Code Number set forth opposite it. Benzyl cyanide (DEA Code: 8735) is included on this list.

Phenylacetonitrile, liquid

UN2470

Div 6.1 Poisonous materials (49 eCFR § 173.132)

PG III: the degree of danger presented by the material is minor

Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Warning: Benzyl cyanide may be fatal if inhaled, swallowed, or absorbed through skin or mucous membranes. Caution is advised.

General First Aid:

...Combustion in an approved incinerator for a chemical waste.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]:

Immediate precautionary measure

0.39 [mg/m3]

4.3 [mg/m3]

15 [mg/m3]

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.56(2) and a regression-derived equation(3), indicates that benzyl cyanide is expected to have moderate mobility in soil(SRC). Volatilization of benzyl cyanide from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.4X10-4 atm-cu m/mole(4) derived from its vapor pressure, 8.9X10-2 mm Hg(5), and water solubility, 100 mg/L(6). Benzyl cyanide is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 8.9X10-2 mm Hg(SRC), determined from a fragment constant method(5). A 77% theoretical BOD in 2 weeks using an activated sludge inoculum and the MITI test(6) indicates that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.56(2) and a regression-derived equation(3), indicates that benzyl cyanide may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.4X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4) derived from its vapor pressure, 8.9X10-2 mm Hg(5), and water solubility, 100 mg/L(6). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5.7 hours and 6.4 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 9(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 77% theoretical BOD in 2 weeks using an activated sludge inoculum and the MITI test(6) indicates that biodegradation may be an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzyl cyanide , which has a vapor pressure of 8.9X10-2 mm Hg at 25 °C(SRC)(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzyl cyanide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7.8 days(SRC), calculated from its rate constant of 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Benzyl cyanide does not contain chromophores that would be expected to absorb light at wavelengths >290 nm and would not be expected to be susceptible to direct photolysis by sunlight(SRC).

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

The Koc of benzyl cyanide is estimated as 170(SRC), using a log Kow of 1.56(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzyl cyanide is expected to have moderate mobility in soil.

The following chemicals have been specifically designated by the Administrator of the Drug Enforcement Administration as the listed chemicals subject to the provisions of this part and parts 1309 and 1313 of this chapter. Each chemical has been assigned the DEA Chemical Code Number set forth opposite it. Benzyl cyanide (DEA Code: 8735) is included on this list.

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzyl cyanide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.

Groups of 3 male rats were administered once by gavage (58.6, 152.3, 210.9 mg/kg bw) and by ip injection (15.2, 22.3, 30..5 mg/kg bw). Cyanide was slowly liberated from the dosed nitrile and excreted as cyanide and thiocyanate... .

Benzyl cyanide is...metabolized into benzoic acid and thiocyanate, probably via hydroxylation to mandelonitrile. Hydrolysis of cyanide group to give phenylacetic acid...occurs as minor pathway.

Benzyl cyanide is oxidized by mouse liver microsomes to benzaldehyde and cyanide ion...

Benzyl cyanide can be metabolized by rat nasal tissue enzymes to cyanide. However, the cyanide produced could be metabolized efficiently to the less toxic thiocyanate in the nasal cavity.

... Benzyl cyanide (150 mg/kg) administered orally to rats led to markedly increased urinary thiocyanate levels; for male rats this was equivalent to 54% of the dose and for females this was 65% over a period of 3 days. When adjusted for incomplete recoveries of the marker, thiocyanate, these values equated to 61 and 89%, respectively.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Used in organic synthesis; as a chemical intermediate for pharmaceutical drugs; with esters for perfumes and flavors; in the synthesis of optical bleaches for fibers; in the production of insecticides; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Organic synthesis; especially penicillin precursors

Chemical intermediate for amphetamines, phenobarbital, the stimulant, methyl phenidylacetate, esters as perfumes & flavors

Phenylacetonitrile is used as an intermediate in the production of synthetic penicillins or barbiturates, in the synthesis of optical bleaches for fibers, in the production of insecticides, and for perfumes and flavors (via phenylacetic acid to "honey-type" ester compounds).

Benzyl cyanide is an intermediate to the production of phenobarbital, methylphenidate, and many amphetamines. (L589)

(1972) No Data

(1975) No Data

(1975) 3.0X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1976) 2.14X10+7 GRAMS (PRINCPL CUSTMS DISTS)

2023: 50,000 - <250,000 lb

(1972) GREATER THAN 1.82X10+6 GRAMS

(1975) GREATER THAN 9.08X10+5 GRAMS

Benzyl cyanide

Benzeneacetonitrile; Benzylnitrile; Phenylacetonitrile; Phenyl acetyl nitrile

IFRA_STD_112.pdf

38

IFRA 51st Amendment - Guidance for the use of IFRA Standards

Prohibition: This material should not be used as a fragrance ingredient_Restriction: This material should be used only in the limited quantity as stated in the Standard

Reaction of benzyl chloride with potassium cyanide

... Made from benzyl chloride, and sodium cyanide

Phenylacetonitrile is produced by the reaction of benzyl chloride with alkali cyanide in alcohol or aqueous solution under phase transfer catalysis with N,N-dialkylbenzylammonium chloride.

Benzyl cyanide

A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)