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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 11487Generated: October 23, 2026

Diphenylamine

DPA · DFA · N-PHENYLANILINE · Diphenylamin · Benzenamine,N-phenyl- · Diphenylaniline · Diphenylamine, synthesis grade · Z-876

https://huagongshe.com/en/chemical/11487

Diphenylamine molecular structure

Identifiers & Physical Properties

CAS No.122-39-4
Molecular formulaC12H11N
Average molar mass169.22 g/mol
Monoisotopic mass169.08914935 g/mol
SMILESc1ccc(Nc2ccccc2)cc1
InChIKeyDMBHHRLKUKUOEG-UHFFFAOYSA-N
PubChem CID11487
ChEMBLCHEMBL38688
ChEBICHEBI:4640
EC No.204-539-4
DTXSIDDTXSID4021975

Chemical & Physical Properties

XLogP3.5
Topological polar surface area12
Hydrogen bond donors1
Hydrogen bond acceptors1
Rotatable bonds2
Heavy atoms13
Formal charge0
Complexity116
Chemical classesDye
PolymersNitrogen Compounds -> Amines, Polyaromatic
SpringerMaterials PropertiesAngular frequency
FragrancesFragrance substance (Diphenylamine) -> IFRA amendment 38
PesticidesPesticide -> EPA IRISPlant Growth RegulatorsActive substance -> EU Pesticides database: Not approvedPesticide (Diphenylamine (DPA)) -> USDA PDB
LogP (partition coefficient)log Kow = 3.503.57
OdorPleasant, floral odor.
Density1.068 at 141.8 °F (USCG, 1999) - Denser than waterwill sink1.161.2 g/cm³1.158 @ 22°C
Color/FormMonoclinic leaflets from dilute alcoholCrystalsColorless, tan, amber, or brown crystalline solid.
Solubilityless than 1 mg/mL at 61 °F (NTP, 1992)1 g dissolves in 2.2 ml of alcohol, 4 ml propyl alcoholFreely sol in benzene, ether, glacial acetic acid, carbon disulfide.Very sol in ethanol, acetone, benzene, carbon tetrachloride, pyridine, ethyl acetatesol in ether, acetic acidslightly sol in chloroformSoluble in oxygenated and aromatic solventsIn water, 53 mg/liter @ 20 °C0.053 mg/mL at 20 °Calcohol: passes testSlightly soluble. 0.03 g/100 mL
Flash point307 °F (NTP, 1992)153 °C OC153 °C c.c.
Human DrugsPharmaceuticals
Melting point52 °C
Boiling point302 °C(lit.)
Bulk density610kg/m3
Vapor density5.82 (vs air)
Vapor pressure1 mm Hg ( 108 °C)
Refractive index1.5785 (estimate)
Storage conditionsStore below +30°C.
Physical statecrystalline
pKa (acidity coefficient)0.79(at 25℃)
Colortan
SensitivityAir & Light Sensitive
Merck14,3317
BRN508755
Henry's law constant3.7×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Exposure limitsPC-TWA:10 mg/m3
Dielectric constant3.3(11℃)
StabilityStablemay discolour on exposure to light. Incompatible with strong acids, strong oxidizing agents.
InChI1S/C12H11N/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H
InChIKeyDMBHHRLKUKUOEG-UHFFFAOYSA-N
SMILESN(c1ccccc1)c2ccccc2
LogP (partition coefficient)3.82 at 20.2℃
CAS DataBase Reference122-39-4(CAS DataBase Reference)
Indirect Additives used in Food Contact SubstancesDIPHENYLAMINE
FDA 21 CFR175.105175.300176.170176.180177.2600
EWG's Food Scores3-6
FDA UNII9N3CBB0BIQ
NIST Chemistry ReferenceDiphenylamine(122-39-4)
EPA Substance Registry SystemDiphenylamine (122-39-4)
Pesticides Freedom of Information Act (FOIA)Diphenylamine
UNSPSC Code77101502
NACRESNA.24
GHS pictogramGHS05,GHS06,GHS08,GHS09
Signal wordDanger
GHS hazard statementsH301+H311+H331-H318-H361-H372-H370-H317-H410
GHS precautionary statementsP501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P391-P308+P311-P361+P364-P333+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338+P310-P403+P233-P405
Target organsKidney,Liver,spleen
Personal protective equipment (PPE)dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard symbolsT,N,F
Risk statements (R)23/24/25-33-50/53-52/53-39/23/24/25-11-51/53
Safety statements (S)28-36/37-45-60-61-28A-16-7
Occupational exposure band (OEB)B
Occupational exposure limit (OEL)TWA: 10 mg/m3
UN transport numberUN 3077 9/PG 3
Water hazard class (WGK)3
RTECS numberJJ7800000
F8-10-23
Autoignition temperature630 °C DIN 51794
TSCA inventory statusTSCA listed
Customs code2921 44 00
Hazard class6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
Packing groupIII
Storage class6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazardous substances data122-39-4(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 1120 mg/kg LD50 dermal Rabbit > 5000 mg/kg
REACH registrationsActive
Limited quantities5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & Regulations

GHS classificationDangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301+H311+H331 (10.1%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P337+P317, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Regulatory informationChemical: Benzenamine, N-phenyl-Hazard Traits - CarcinogenicityCommission Regulation (EC) No 33/2008Benzenamine, N-phenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N-phenyl- 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)Diphenylamine is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2009/859/EC, Reg. (EU) No 578/2012
Other safety informationEvaluation - Benzenamine, N-phenyl-
DOT labelPoison
Fire hazardsSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.
Fire potentialCombustible when exposed to heat or flame.
Health hazardsInhalation may irritate mucous membranes. Overexposure, including ingestion of solid or skin contact, may cause fast pulse, hypertension, and bladder trouble. Contact with dust irritates eyes. (USCG, 1999)
Hazards summaryThe toxicity of diphenylamine is similar to that of aniline. Hepatotoxic effects have been demonstrated in animals. It can cause bladder irritation and induce methemoglobinemia in workers. As a skin sensitizer it cross-reacts with p-phenylene diamine. [ACGIH] May have effects on the kidneys and bloodA skin, eye, and respiratory tract irritant[ICSC]
Reactive groupAmines, Aromatic
EC classificationSymbol: T, NR: 23/24/25-33-50/53S: (1/2)-28-36/37-45-60-61
UN classificationUN Hazard Class: 9UN Pack Group: IIIUN Pack Group: II
TSCA requirementsPursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Diphenylamine is included on this list.Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.
FIFRA requirementsAs the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Diphenylamine is found on List B. Case No: 2210Pesticide type: fungicide, herbicideCase Status: RED Approved 9/1997OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .Active ingredient (AI): diphenylamineData Call-in (DCI) Date(s): 01/10/1991, 10/13/1995AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI.Tolerances for residues of the plant growth regulator diphenylamine are established in or on the following commodities: Apple, wet pomaceapple from preharvest or postharvest use, including use of impregnated wrapscattle, fatcattle, livercattle, meat byproducts, except livergoat, fatgoat, livergoat, meat byproducts, except liverhorse, fathorse, liverhorse, meat byproducts, except livermilksheep, fatsheep, liversheep, meat byproducts, except liverand sheep, meat.A time-limited tolerance is established for the indirect or inadvertent residues of diphenylamine in or on the following commodity: pear (Expiration/Revocation Date: 12/1/01).
Fire fightingFire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.Use water spray, powder, alcohol-resistant foam, carbon dioxide.
First aid measuresFresh air, rest.Rinse and then wash skin with water and soap.Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. Give one or two glasses of water to drink.
First aidEYES: 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.(General first aid procedures)
Safe storageProvision to contain effluent from fire extinguishing. Separated from strong acids and oxidants. Store in an area without drain or sewer access.
Exposure control and personal protectionBiological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]5.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire fighting proceduresFoam, dry chemical, carbon dioxide. ...Water or foam may cause frothing
Storage conditionsIn general, materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well-ventilated place, out of direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected... Incompatible materials should be isolated from each other.Keep protected from light./Store/ separated from strong acids, oxidants.
Cleanup methodsSweep spilled substance into containersif appropriate, moisten first to prevent dusting, then remove to safe place
Nonfire spill responseSMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a 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.
Disposal methodsSRP: 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Burn in admixture with flammable solvent in furnace equipped with afterburner and scrubber. Recommendable methods: Incineration ... .
Spillage disposalPersonal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Then store and dispose of according to local regulations.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.The worker should wash daily at the end of each work shift.Work clothing that becomes wet or significantly contaminated should be removed and replaced.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
InteractionsDiphenylamine (5 mg) together with sodium nitrite (15 mg) fed to rats greatly decreased growth of animals. Kidney and liver toxicities and papillomatous hyperplasia of bladder observed in rats fed diphenylamine and sodium nitrite.The toxicity of halogenated hydrocarbons such as carbon tetrachloride, hexachlorophene, and bithionol sulfoxide, used in veterinary medicine was diminished by the prior or simultaneous administration of diphenylamine (0.1-10% of the admin hydrocarbon)....Dimethyl sulfoxide lessened the incidence of papillary lesions from diphenylamine.
Target organsHepaticEyes, skin, respiratory system, cardiovascular system, blood, bladder, reproductive systemKidney,Liver,spleen
Ecotoxicity valuesLC50 Brachydanio rerio (Zebrafish) 2.2 mg/L/48 hr /Conditions of bioassay not specified/LC50 Oryzias latipes (Japanese medaka) 5.1 mg/L/48 hr /Conditions of bioassay not specified/LC50 Pimephales promelas (Fathead minnow, 31 day old) 3.79 mg/L/96 hr @ 24.9 °C (95% CI: 3.47-4.14 mg/L)flow through, dissolved oxygen 7.3 mg/L, hardness 48.0 mg/L as calcium carbonate, alkalinity 43.1 mg/L as calcium carbonate, pH 7.8 /99+% pure/EC50 Pimephales promelas (Fathead minnow, 31 day old) affected fish lost schooling behavior, were hypoactive, swam near the tank bottom and were darly colored. 3.63 mg/L/96 hr @ 24.9 °C (95% CI: 3.31-3.99 mg/L)
Environmental fateTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.50(2) and a regression-derived equation(3), indicates that N,N-diphenylamine is expected to have low mobility in soil(SRC). Volatilization of N,N-diphenylamine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 6.7X10-4 mm Hg(4), and water solubility, 53 mg/liter(5). N,N-Diphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). N,N-Diphenylamine is not expected to biodegrade in soil based on aqueous screening tests(6). N,N-Diphenylamine, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge innoculum at 100 mg/l and the Japanese MITI test(6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,900(SRC), determined from a log Kow of 3.50(2) and a regression-derived equation(3), indicates that N,N-diphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.7X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 6.70X10-4 mm Hg(4), and water solubility, 53 mg/l(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9.4 and 107 days, respectively(SRC). According to a classification scheme(6), BCFs ranging from 51 to 253(7), suggests bioconcentration in aquatic organisms is moderate(SRC). N,N-Diphenylamine was found to be not readily biodegradable in aqueous screening tests(7). N,N-Diphenylamine, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge innoculum at 100 mg/l and the Japanese MITI test(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diphenylamine, which has a vapor pressure of 6.7X10-4 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase N,N-diphenylamine 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 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
Food survey valuesN,N-Diphenylamine was found in domestic and imported apples at avg concns of 0.275 ppm (max, 8.1 ppmdetections, 223 out of 769) and 0.232 ppm (max, 5.9 ppmdetections, 402 out of 1,062), respectively(1). N,N-Diphenylamine was detected in fruits and vegetables (15 of 3,962 sample) at concns between <0.01 and <5 ug/g from samples collected in Ontario, Canada between the years 1991 to 1995(2). As part of the Danish Pesticide Monitoring Program conducted between the years 1995-96, N,N-diphenylamine was detected in 5 of 96 apples and 1 of 33 pear samples(3). In selected agricultural commodities available in Canada, the concn of N,N-diphenylamine ranged from <0.05 to 2.0 ppm in 16 of 676 samples analyzed(4).
Adverse effectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure routesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact
Toxicity summaryDiphenylamine uncouples mitochondrial oxidative phosphorylation, resulting in a decrease in hepatocellular ATP content and consequently hepatocyte injury (A15350). Short-term and long-term exposure in animal models results in altered haematological parameters, splenic erythropoiesis, splenic congestion and haemosiderosis (L2078).
Average Daily IntakeBased on a FDA Total Diet Study analysis conducted between the years 1986 to 1991, the avg daily intake of N,N-diphenylamine was determined for eight age groups as follows (all ug/kg body wt/day): 6-11 month old (0.0034), 2 year old (0.0410), 14-16 year old female (0.0073), 14-16 year old male (0.0099), 25-30 female (0.0074), 25-30 male (0.0051), 60-65 year old female (0.0079), and 60-65 year old male (0.0065)(1,2).
Signs and SymptomsCough. Sore throat.Redness.irritation eyes, skin, mucous membraneeczematachycardia, hypertensioncough, sneezingmethemoglobinemiaincreased blood pressure, heart rateproteinuria, hematuria (blood in the urine), bladder injuryIn Animals: teratogenic effects
Effluent ConcentrationsN,N-Diphenylamine had been detected as a volatile organic compound released from textile floor coverings(1). N,N-Diphenylamine was detected in 3 samples of municipal landfill leachate from Gryta, Vasteras, Sweden at concns of 2.3, 3.5, and <2 ug/liter (quantification limit = 2 ug/liter)(2).
ICSC Environmental DataThe substance is toxic to aquatic organisms. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment.
Atmospheric standardsThis action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Diphenylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
State drinking water guidelines(ME) MAINE 175 ug/l(FL) FLORIDA 175 ug/l
Federal drinking water guidelinesEPA 200 ug/l
F8-10-23
Occupational exposure band (OEB)B
Occupational exposure limit (OEL)TWA: 10 mg/m3
Personal protective equipment (PPE)dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Water hazard class (WGK)3
TSCA inventory statusTSCA listed
RTECS numberJJ7800000
UN transport numberUN 3077 9/PG 3
Customs code2921 44 00
ToxicityLD50 orally in Rabbit: 1120 mg/kg LD50 dermal Rabbit > 5000 mg/kg
Risk statements (R)23/24/25-33-50/53-52/53-39/23/24/25-11-51/53
Signal wordDanger
GHS pictogramGHS05,GHS06,GHS08,GHS09
Hazard symbolsT,N,F
Safety statements (S)28-36/37-45-60-61-28A-16-7
Hazard class6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1STOT RE 2
Storage class6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Packing groupIII
GHS hazard statementsH301+H311+H331-H318-H361-H372-H370-H317-H410
Limited quantities5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted quantitiesMax Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH registrationsActive
Autoignition temperature630 °C DIN 51794
GHS precautionary statementsP501-P273-P272-P260-P270-P202-P201-P271-P264-P280-P391-P308+P311-P361+P364-P333+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338+P310-P403+P233-P405
Hazardous substances data122-39-4(Hazardous Substances Data)

Applications & Uses

Description

Solutions of diphenylamine are used to treat apples a few days before harvest. Residue on apples’ surfaces of 10 ppm is permitted by regulation in Australia, Canada, and the United States.

Uses

Diphenylamine is used in the manufactureof dyes, as a stabilizer for nitrocelluloseexplosives, and as an analytical reagent forcolorimetric tests for nitrate and chlorate.Other applications of this compoundinclude preventing postharvest deteriorationof apple and peer crops; as an antioxidant inrubber and elastomer industry and in the per fumery. As a stabilizer for propellants andexplosives, it binds their degradation prod ucts thus prolonging the storage time of suchpropellants.

Uses

Diphenylamine is used post-harvest to prevent superficial scald in apples in cold store.

Uses

Diphenylamine is an aromatic amine that was shown to exhibit antioxidant activities and is now used as an anti-scald agent. It is also used in the manufacture of a variety of substances, for instance, dye stuffs and their intermediates, pesticides, anthelmintic drugs, and as reagents in analytical chemistry laboratories.

General Description

Light tan to brown solid with a pleasant odor. Sinks in water.