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Benzoic acid(CAS No. 65-85-0)

Benzoic acid C7H6O2 (cas 65-85-0) Molecular Structure

65-85-0 Structure

Identification and Related Records

【Name】
Benzoic acid
【CAS Registry number】
65-85-0
【Synonyms】
Melting point standard benzoic acid
Benzoic-12C7 acid, 13C-depleted
Benzoic acid, USP Grade
4-Carboxypolystyrene
【EINECS(EC#)】
200-618-2
【Molecular Formula】
C7H6O2 (Products with the same molecular formula)
【Molecular Weight】
122.12
【Inchi】
InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
【Canonical SMILES】
C1=CC=C(C=C1)C(=O)O
【MOL File】
65-85-0.mol

Chemical and Physical Properties

【Appearance】
white crystals or powder
【Density】
1.08
【Melting Point】
121-123℃
【Boiling Point】
249℃
【Refractive Index】
1.504
【Flash Point】
121℃
【Water】
Slightly soluble. 0.34 g/100 mL
【Solubilities】
Slightly soluble. 0.34 g/100 mL in water
【Color/Form】
Monoclinic tablets, plates, leaflets
White scales or needle crystals
【Stability】
Stable. Combustible. Incompatible with strong bases, strong oxidizing agents, alkalies.
【Storage temp】
Store at RT.
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 227 NM (LOG E= 4.06); SADTLER REF NUMBER: 779 (IR, PRISM); 162 (IR, GRATING)
IR: 6994 (Coblentz Society Spectral Collection)
UV: 252 (Sadtler Research Laboratories Spectral Collection)
1H NMR: 57 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 230(Johnson and Jankowski, Carbon13 NMR Spectra, John wiley and Sons, New York)
Raman: 6 (Sadtler Research Laboratories Spectral Collection)
MASS: 61193 (NIST/EPA/MSDC Mass Spectral Database 1990 Version)
Intense mass spectral peaks: 77 m/z, 105 m/z, 122 m/z
Index of refraction = 1.504 at 132 deg C/D
【Computed Properties】
Molecular Weight:122.12134 [g/mol]
Molecular Formula:C7H6O2
XLogP3:1.9
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:1
Exact Mass:122.036779
MonoIsotopic Mass:122.036779
Topological Polar Surface Area:37.3
Heavy Atom Count:9
Formal Charge:0
Complexity:104
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Feature 3D Ring Count:1
Effective Rotor Count:1
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/37/38;R42/43
【Safety Statements 】
S22;S24;S26;S37/39;S45
【Hazard Note】
Harmful
【Safety】

Hazard Codes: Xn,T
Risk Statements: 22-36-42/43-36/37/38-40-63-43-23/24/25-45
22:  Harmful if swallowed 
36:  Irritating to the eyes 
42/43:  May cause sensitization by inhalation and skin contact 
36/37/38:  Irritating to eyes, respiratory system and skin 
40:  Limited evidence of a carcinogenic effect 
63:  In case of accident by inhalation, remove casualty to fresh air and keep at rest 
43:  In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water) 
23/24/25:  Toxic by inhalation, in contact with skin and if swallowed 
45:  May cause cancer 
41:  Risk of serious damage to eyes 
37/38:  Irritating to respiratory system and skin 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 26-45-37/39-24-22-36/37-24/25-23-53
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
37/39:  Wear suitable gloves and eye/face protection 
24:  Avoid contact with skin 
22:  Do not breathe dust 
36/37:  Wear suitable protective clothing and gloves 
24/25:  Avoid contact with skin and eyes 
23:  Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 
53:  Avoid exposure - obtain special instruction before use 
36:  Wear suitable protective clothing
RIDADR: UN 3077 9/PG 3
WGK Germany: 1
RTECS: DG0875000
F: 21
Hazard Note: Harmful

【PackingGroup 】
Z01
【Skin, Eye, and Respiratory Irritations】
Dust irritating to nose and throat if inhaled; solid irritating to skin and eyes. At elevated temp, fumes may cause irritation of eyes, resp system, and skin.
Mildly irritating to mucous membranes
【Cleanup Methods】
Cover with soda ash or sodium bicarbonate. Mix and add water.
Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be contained with a flexible impermeable membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
【Transport】
UN 9094
【Fire Fighting Procedures】
If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
【Fire Potential】
Slight, when exposed to heat or flame; can react with oxidizing materials.
Benzoic acid is burned in oxygen as primary thermochemical standard to calibrate oxygen bomb calorimeters used in... determination of calorific value of liquid hydrocarbon fuels. If the benzoic acid is powdered (rather than pelleted...), very rapid combustion occurs and flame front may burn through the non-metallic... seals on valve seats and the bomb may be destroyed.
【Formulations/Preparations】
GRADES: Technical, CP, USP, FCC.
Industrial grade, 97.5%; Technical grade, 99.0%; United States Pharmacopeia/Food Chemicals Codex , 99.5-100.5%. /From table/
Industrial and technical grades of benzoic acid are available in molten as well as solid forms (called flakes or chips). USP/FCC grade is available in solid form either as crystals or powder.
【Exposure Standards and Regulations】
Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Benzoic acid is included in topical antifungal drug products.
【Reactivities and Incompatibilities】
The powder burns rapidly in oxygen.
Can react with oxidizing materials.
【Other Preventative Measures】
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary.
Personnel protection: Avoid breathing vapors or dusts. ... Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Bureau of mines dust respirator; when melted material present, use eye protection and organic respirator for fumes.
Wear rubber gloves, a mask, coveralls, a body shield and self-contained respirator.
Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles.
【Specification】

 Benzoic acid , its cas register number is 65-85-0. It also can be called Benzenecarboxylic acid ; Benzeneformic acid ; Benzenemethonic acid ; Carboxybenzene ; Oracylic acid ; phenyl carboxylic acid ; Phenylformic acid .It is a white crystals or powder and slightly soluble in water. At high temperature it can react with oxidizing reagents.Dust may be irritating to nose and eyes. At elevated temperatures, fumes may cause irritation of eyes, respiratory system, and skin.

【Octanol/Water Partition Coefficient】
log Kow = 1.87
【Disposal Methods】
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.
The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: biological treatment.
Incineration: Waste material can be burned in an approved incinerator with an afterburner, as a soln in a flammable solvent or as a solid packaged in paper, plastic or cardboard.
The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: activated carbon.
The following wastewater treatment technologies have been investigated for benzoic acid: concentration process: resin adsorption.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Decarboxylation of phthalic anhydride in the presence of catalysts; chlorination of toluene to yield benzotrichloride, which is hydrolyzed to benzoic acid; oxidation of toluene; from benzoin resin.
Benzoic acid is manufactured by treating molten phthalic anhydride with steam in the presence of a zinc oxide catalyst, by the hydrolysis of benzotrichloride, or by the oxidation of toluene with nitric acid or sodium bichromate or with air in the presence of a transition metal salt catalyst.
Benzoic acid is almost exclusively manufactured by the cobalt catalyzed liquid-phase air oxidation of toluene.
The USP/FCC grade of benzoic acid is usually produced by extraction and crystallization, although distillation has also been used. In the extraction-crystallization process, toluene, water, and methanol have all been used and each is capable of producing a high quality benzoic acid product.
U.S. Exports

(1972) 2.9X10+8 G
(1975) 8.67X10+8 G
U.S. Imports

(1972) NEGLIGIBLE
(1975) 6.04X10+7 G
(1984) 3.87X10+8 g /Summation of two report items for Benzoic Acid/
U.S. Production

(1972) 7.06X10+10 G
(1975) 2.87X10+10 G
(1983) 3.22X10+10 g (est)
(1991) 2.68x10+8 lb
Consumption Patterns

CHEMICAL PROFILE: Benzoic Acid. Phenol, 55%; benzoate plasticizers, 22%; sodium and potassium benzoate, 8%; benzoylchloride, 7%; alkylated resins, 3%; others, including butyl benzoate, sucrose benzoate, USP applications and exports, 5%.
CHEMICAL PROFILE: Benzoic acid. Demand: 1986: 160 million lb; 1987: 163 million lb; 1991 /projected/: 175 million lb.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods.
【Therapeutic Uses】
Antifungal Agents; Food Preservatives
... Used in combination with salicylic acid, as in Whitfield's ointment ... It is used especially in the treatment of athlete's foot and to lesser extent for management of ringworm.
Medication (vet): has been used with salicylic acid as topical antifungal
EXPTL Use: Process for controlling waste nitrogen accumulation diseases in humans by administering at least 1 compound selected from group of benzoic acid, phenylacetic acid and their salts is disclosed. Sodium benzoate, (6.2 g/day) given to female patient with carbophosphate synthetase deficiency Increased total urinary nitrogen excretion 58%.
【Biomedical Effects and Toxicity】
Benzoic acid and sodium benzoate are rapidly absorbed from the gastrointestinal tract of mammals and conjugated with glycine in the liver. The resulting hippuric acid is excreted in the urine rapidly (75% to 100% of the dose is excreted within 6 hours; the remaining dose is excreted within 2 to 3 days).
/Investigators/ reported that 42.6% +/-16.5% of a dermally applied [14C]-Benzoic acid dose (4 ug/sq cm; in acetone)was excreted in the urine within 24 hours. When applied in petrolatum, 60.5% of the dose was absorbed.
By quantifying 24-hour urine excretion, /investigators/ demonstrated that dermal application of 1000 nmol [14C]-Benzoic acid (1.0X10-3 Ci/nmol) produced the following penetration scale: forehead > abdomen > thigh > chest > arm > back. The 4-day penetration through the forehead (27.65 +/- 3.61 nmol/sq cm) was three times greater than absorption through the back (8.55+/- 1.32 nmol/sq cm). Benzoic Acid had been applied to two sites of each body area; one site was tape stripped to determine the amount of test material in the stratum corneum. The quantified values from the urine were comparable to predicted values estimated from the tape stripping.
In a study investigating the effects of aging on dermal absorption, /investigators/ applied [14C]-Benzoic acid (in acetone) to the forearm of two groups of panelists, "young" (22 to 40 years) and "old" (>65 years). A 24-hour protective patch was placed on the skin and the site was washed after patch removal. A second protective patch was then applied and remained in place until day 7. Analysis of 7-day urine excretion indicated that 36.2% +/-4.6% of the applied dose was absorbed by the young panelists, whereas 19.5% +/-1.6% was absorbed by the old panelists. The difference was statistically significant ( p
No statistical difference (p > .05) was found /for/ the percutaneous absorption of benzoic acid by Asian, Black, and Caucasian panelists. [14C]-Benzoic acid (1 umol/sq cm) was applied to two sites of the upper arm and the sites were washed after 30 minutes of contact. (The two applications occurred on contralateral arms and were made 48 hours apart.) Urine was collected for 24 hours and one site was tape stripped to measure benzoic acid in the stratum corneum. Amounts absorbed were 1.43% +/-0.27% by Asian skin, 1.07% +/-0.17% by Black skin, and 1.2% +/-0.19% by Caucasian skin.
(14)C was excreted at different rates from various species following oral dose of (14)C-benzoic acid. In 24-hr urine, man excreted 100%, hamster 99%, dog 94%, guinea pigs 79%, ferret 69%, rabbit 60%, mouse 55%, pig 50% & squirrel monkey 48%. Man received one-fiftieth of dose (52 + or - 4 mg/kg) given to other species.
Biliary excretion ... in different species. Percent of dose excreted in 3 hr: rat 1.2, guinea pig 1.7, rabbit 0.7, dog 0.8, cat 1.2, hen 0.5.
The transdermal absorption of benzoic acid was studied in excised human skin and compared to absorption in living man. In equivalent time, the total absorption (% of applied dose) was 42.6% (in vivo) or 44.9 (in vitro).
The percutaneous absorption and the excretion of benzoic acid were tested in female weanling Yorkshire swine (approximately 20 kg) after topical and intravenous administration. After iv injection of 200 ug (10 uCi)/pig 84.5% of 14C-activity were excreted with urine and 4.6% in feces within 6 days; the radiolabel recovery in carcass was 0.1%. After topical application of the same dose the radiolabel recovery within 6 days (% of applied does) was in urine 20%, feces 2.9%, carcass 0.8%, border 40.2%, dosed skin 12.2% and adjacent skin 9.1%.
The percutaneous absorption of 14C-labelled benzoic acid was studied in the Mexican hairless dog and compared to human data. Total absorption and maximum absorption rates were greater in humans than in hairless dogs. Surface counting experiments showed that benzoic acid persisted on the dog skin far longer than on human skin (no further information).
The percutaneous absorption of increasing topical doses of benzoic acid was determined in the Rhesus monkey and humans (dosage: 4, 40, 2000 ug/sq cm; dose absorbed: monkey 59.2%, 3.6%, 17.4%; human 42.6%, 25.7%, 14.4%). In vivo percutaneous absorption was similar, also the dose-response curve was similar in the two species (no further information).
The percutaneous absorption and metabolism of benzoic acid was determined through hairless guinea pig skin in vitro. The absorption within 48 hr was greater through nonviable skin (60.1% of applied dose) than through viable skin (49.5%). 6.9% of absorbed dose (2 ug/sq cm) were conjugated with glycine to form hippuric acid.
Damaging the skin (tape stripping, irritation, delipidization) increased absorption of benzoic acid dissolved in acetone (200 ug/mL, 50 uCi; topical application: 4 ug/sq cm) in hairless guinea pigs: 71.1/73.4/94.1% vs 34.2% absorbed in the group with intact skin.
In humans, the peak plasma concentration is reached within 1-2 hr /afetr oral ingestion/.
Benzoic acid is not completely absorbed by the dermal route. In a study with 6 human subjects, /investigators/ found an uptake of 36% of the applied dose (14C-labelled benzoic acid dissolved in acetone; 4 ug/sq cm; circular area of 13 sq cm; ventral surface of the forearm; non-occlusive) within 12 hr. The total uptake within 5 days was 43%. In a second study with 6-7 subjects (comparable method; application of 3, 400 or 2000 ug/sq cm), the percent absorption decreased from 35% to 14% within 24 hr. However, the total uptake per sq cm increased from 1 to 288 ug.
Hippuric acid is rapidly excreted in urine. In humans, after oral /benzoic acid/ doses of up to 160 mg/kg bw, 75-100% of the applied dose is excreted as hippuric acid within 6 hr after administration, and the rest within 2-3 days.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.87(2) and a regression-derived equation(3), indicates that benzoic acid is expected to have moderate mobility in soil(SRC). A pKa of 4.19(4) indicates benzoic acid will exist almost entirely in the ionized form at pH values of 5 to 9 and therefore, volatilization from moist soil surfaces is not expected to be an important fate process. Benzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.00X10-4 mm Hg(5). Mineralization half-life in Captina silt loam for benzoic acid in solution was 4.5 hr after a 30 min lag(6) and complete degradation occurring in 1 day with a Niagra silt loam inoculum(7), suggesting that biodegradation of benzoic acid maybe an important fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.87(2) and a regression-derived equation(3), indicates that benzoic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.19(4) indicates benzoic acid will exist almost entirely as an anion at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5) and BCF values of 10 for algae and 5 for fish(6) suggest that bioconcentration in aquatic organisms is low(SRC). Biodegradation half-lives of 0.85 and 3.6 days using inoculum from a polluted river and a reservoir, respectively(7), suggest that biodegradation in water may be an important fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzoic acid, which has a vapor pressure of 7X10-4 mm Hg at 25 deg C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzoic acid 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 13 days(SRC), calculated from its rate constant of 1.2X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Benzoic acid does not absorb light at wavelengths >290 nm(2) and therefore should not be expected to be susceptible to direct photolysis by sunlight(SRC).

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