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アクリジン

Acridine

HCID 9215
ノートを作成反応を作成見積依頼を出す
印刷プレビュー
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
260-94-6
標準SMILES
c1ccc2nc3ccccc3cc2c1
InChIKey
DZBUGLKDJFMEHC-UHFFFAOYSA-N
分子式
C13H9N
平均分子量
179.22 g/mol
単同位体質量
179.07349929

概要

Small colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion.

名称と識別子

優先名称
Acridine
IUPAC
acridine
現地名
アクリジン
英語名
Acridine
分子式
C13H9N
分子量
179.22

名称と別名

ACRIDINE260-94-69-Azaanthracene10-Azaanthracene2,3-BenzoquinolineAcrydineAkridinDibenzo[b,e]pyridineBenzo(b)quinolineDibenzo(b,e)pyridine2,3,5,6-DibenzopyridineBenzo[b]quinoline
名称をさらに表示
アクリジンアクリジン標準品アクリジン, 98+%アクリジン, 50 µg/mL in TolueneAceridineAcridine >ACRIDINE 97%
Akridin [Czech]NSC 3408NSC-3408CCRIS 1636HSDB 634EINECS 205-971-6UNII-42NI1P5Q1XUN2713

データベース識別子

CAS
260-94-6、39327-16-7
PubChem CID
9215
DTXSID
DTXSID8059766
ChEMBL
CHEMBL39677
ChEBI
CHEBI:36420
UNII
42NI1P5Q1X
EC Number
205-971-6
Nikkaji
J2.978E

物性

構造計算による物性

XLogP
3.4
極性表面積
12.9 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
0
重原子数
14
形式電荷
0
複雑度
181

実験および物理化学的性質

Chemical Classes · 2 件

Dyes -> Acridine Dyes

Flammable agents - 3rd degree

PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
pHA WEAK BASE, COLORS LITMUS PAPER BLUE
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP · 2 件

Log P= 3.40

3.32

Density · 3 件

1.2 at 68 °F (approx.) (USCG, 1999) - Denser than water; will sink

1.005 @ 20 °C/4 °C

1.2

Color/Form · 4 件

RHOMBOHEDRAL NEEDLES OR PRISMS FROM ALCOHOL; MONOCLINIC, ORTHORHOMBIC

SMALL COLORLESS NEEDLES

ORTHORHOMBIC PLATES, NEEDLES FROM DILUTED ALCOHOL

SMALL, COLORLESS OR FAINTLY YELLOW CRYSTALS

Solubility · 5 件

SLIGHTLY SOL IN HOT WATER; VERY SOL IN ALCOHOL, ETHER, BENZENE AND CARBON DISULFIDE

Freely sol in hydrocarbons; slightly soluble in boiling water, liquid ammonia, liguid sulfur dioxide; sparingly soluble in light petroleum

Very soluble in carbon disulfide; very soluble in ethanol, ether, benzene; slightly soluble in water

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (94%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 50 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 3 件

Chemical: Acridine

Acridine: HSNO Approval: HSR001561 Approved with controls

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.)

DOT LabelPoison
Fire Hazards · 2 件

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.

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

Health Hazards · 2 件

Inhalation irritates respiratory system and causes sneezing, crying, and vomiting. Contact with liquid irritates eyes, skin, and mucous membranes. At high temperature and during sun exposure, damage to the cornea, skin, and mucous membranes may occur following the liberation of acridine vapor. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 2 件

May be the cause of the photoirritant reactions seen after skin contact with pitch, tar, and creosote; A strong skin, eye, and mucous membrane irritant; [HSDB] An irritant; May cause serious eye injury; Can be absorbed through skin; Effects in high-dose animal studies include lacrimation; [MSDSonline]

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

YIELDS ACRIDONE IN RABBITS: OTAKA, H & HASHIMOTO, Y, NIPPON UNIV J MED, 2, 1, (1960). /FROM TABLE/

... Metabolism of acridine by guinea pig liver enzymes induced by polychlorinated biphenyls ... produced phenolic metabolites. ...

PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)

Absorption, Distribution and Excretion · 2 件

ACRIDINE WAS RAPIDILY ACCUM FROM WATER BY FATHEAD MINNOWS. EQUIL CONCN WITHIN 24 HR @ CONCN FACTOR ((ACRIDINE)FISH,WET WT/(ACRIDINE)WATER) OF 125 +/- 10. DEPURATION WAS RAPID. NET ELIMINATION RATE WAS 0.23/HR (ACRIDINE)FISH @ EQUILIBRIUM.

4 POSSIBLE PATHWAYS FOR UPTAKE ARE DISCUSSED: UPTAKE BY INTERACTION; BY INGESTION OF CONTAMINATED ZOOPLANKTON & INVERTEBRATES; DIRECT UPTAKE.

用途と製造

Uses · 5 件

Occurs in coal tar; [Merck Index] Used to make dyes, pharmaceuticals, intermediates, and derivatives (especially acriflavine and proflavine); [HSDB]

MFR DYES AND INTERMEDIATES

IN THE SYNTHESIS OF PHARMACEUTICALS

Manufacture of derivatives, especially acriflavine, proflavine; analytical reagent.

PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)

U.S. Exports · 2 件

(1972) No Data

(1975) No Data

U.S. Imports · 2 件

(1972) No Data

(1975) No Data

関連反応

32 件
反応記録を作成
HRID 36385 の反応式
HRID 36385生成物としてuspto-grants-1995_05
HRID 37029 の反応式
HRID 37029生成物としてuspto-grants-1995_05
HRID 324169 の反応式
HRID 324169生成物としてuspto-grants-2001_04
HRID 324170 の反応式
HRID 324170生成物としてuspto-grants-2001_04
HRID 369524 の反応式
HRID 369524生成物としてuspto-grants-2000_10
HRID 369525 の反応式
HRID 369525生成物としてuspto-grants-2000_10
HRID 371694 の反応式
HRID 371694反応物としてuspto-grants-1978_05
HRID 378755 の反応式
HRID 378755生成物としてuspto-grants-2001_10
1 / 4 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す

1 gm soluble in <1 ml boiling benzene or alcohol; 5 ml benzene (20 °C); 6 ml alcohol (20 °C); 16 ml of ether (20 °C); 1.8 ml boiling cyclohexane.

In water= 38.4 mg/L at 24 °C.

Boiling Point · 3 件

655 °F at 760 mmHg (NTP, 1992)

345.5 °C @ 760 mm Hg

655 °F

Decomposition · 2 件

WHEN HEATED TO DECOMPOSITION, ACRIDINE EMITS TOXIC FUMES.

When heated to decomp ... emits toxic fumes of /nitrogen oxides/.

Melting Point · 3 件

225 to 230 °F (NTP, 1992)

111 °C; 106 °C (form a); 110 °C (form b)

225-230 °F

Vapor Pressure · 4 件

1 mmHg at 255.9 °F (NTP, 1992)

Vapor pressure= 1.35X10-4 mm Hg at 25 °C /extrapolated from experimentally-derived coefficients/

1 MM HG @ 129 °C

varies depending upon the specific compound

物理化学的性質

融点
106 · 106-109 °C
沸点
346 °C · 346 °C(lit.)
比重(密度)
1 · 1,005 g/cm3
屈折率
1.727 · 1.7270 (estimate)
闪点
346 °C · 346°C
貯蔵温度
Refrigerator
溶解性
0.1 g/mL、透明 · ジオキサン: 0.1 g/mL、透明
酸解離定数(Pka)
5.58 · 5.58(at 20℃)
外見
結晶性粉末
色
黄色から黄褐色
水溶解度
57.35 mg/L · 57.35mg/L(24℃)
Merck
14 · 14,122
BRN
120200 · 120200
Henry's Law Constant
3.3 · 3.3×101 mol/(m3Pa) at 25℃, Mackay et al. (2006)
安定性
安定。可燃性。強力な酸化剤とは相容れない。
主な用途
有機発光ダイオード、フォトレジスト、ナノセンサー、燃料電池、メモリデバイス、半導体、情報記憶装置、液晶ディスプレイ、製品偽造品の識別、インク、接着剤、繊維、毛髪染料、遺伝子検出アッセイ、細胞染色、バイオセンサー、核酸、タンパク質の検出、抗HCV抗体、抗菌剤、抗アミロイド剤、創傷被覆材、感染症、アレルギー、癌に対するワクチン
InChI
1S/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H
InChIKey
DZBUGLKDJFMEHC-UHFFFAOYSA-N
SMILES
c1ccc2nc3ccccc3cc2c1 || c1ccc2nc3ccccc3cc2c1
LogP
3.4 · 3.400
CAS データベース
260 · 260-94-6(CAS DataBase Reference)
EPAの化学物質情報
Acridine (260-94-6)

化学的性質

化学的特性colourless to light yellow crystals

See POLYCYCLIC AROMATIC HYDROCARBONS.

DOT ID and Guide2713 153
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsA REVIEW WITH 241 REFERENCES DICUSSING MUTAGENIC ACTIVITIES & BIOLOGICAL EFFECTS OF ACRIDINE & ITS DERIV.[NASIM A, BRYCHCY T; GENETIC EFFECTS OF ACRIDINE COMPOUNDS; MUTAT RES 65(4) 261 (1979)]
Reactivity Profile · 1 件

ACRIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Burns to give toxic oxides of nitrogen.

DOT Emergency Guidelines · 5 件

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: 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.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. 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. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.

For more DOT Emergency Guidelines (Complete) data for ACRIDINE (8 total), please visit the HSDB record page.

DOT Hazard Classification · 4 件

Acridine

UN2713

Div 6.1 Poisonous materials (49 eCFR § 173.132)

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

Air and Water ReactionsSlightly soluble in hot water.

安全と保護具

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Accidental Release Measures · 2 件

· 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.

First Aid · 2 件

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.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 1 件

If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

Storage Conditions · 1 件

...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 2 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Incineration: Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the solvent into a furnace with afterburner and scrubber. Pour into a mixture of sand and Na2CO3 /sodium carbonate/ (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in a furnace.

Preventive Measures · 5 件

WORKERS SHOULD FOLLOW A CONSCIENTIOUS PERSONAL HYGIENE ROUTINE AND SHOULD WASH THOROUGHLY AT THE END OF EACH WORKING PERIOD; ADEQUATE SANITARY FACILITIES SHOULD BE PROVIDED.

WHEN THE TEMPERATURE OF THE PROCESS OR THE CONDITIONS OF WORK ARE SUCH AS TO GIVE RISE TO SIGNIFICANT CONCENTRATIONS OF ACRIDINE VAPOR, LOCAL EXHAUST VENTILATION SHOULD BE PROVIDED TO PREVENT CONTAMINATION OF THE ATMOSPHERE IN THE VICINITY OF THE PROCESS.

SRP: 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.

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.

Personnel protection: Keep upwind. Avoid breathing dusts, and fumes from burning material. ... Do not handle broken packages unless wearing appropriate personal protective equipment.

Isolation and Evacuation · 2 件

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Threshold Limit Values (TLV)0.2 mg/m³ [1984]
Permissible Exposure Limit (PEL)0.2 mg/m³ as Coal tar pitch volatiles (benzene soluble fraction)

毒性情報

TreatmentThere is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
Health EffectsPAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
Environmental Fate · 4 件

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured Koc values of 14 soil and sediment samples, ranging from 5500 to 30,909 with an average value of 12,910(2), indicate that acridine will be immobile in soil(SRC). Higher sorption was reported for acidic subsoils compared with more neutral subsoils, consistent with compound ionization (pKa of acridine= 5.45(3)) and preferential retention of the organic cation over the neutral compound(4). Volatilization of acridine should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Volatilization of acridine from dry soil surfaces should not be a major fate process for this compound(SRC) based on an extrapolated vapor pressure of 1.35X10-4 mm Hg(SRC), calculated from experimentally-derived coefficients(6). Acridine is expected to be resistant to aerobic biodegradation and to readily biodegrade under anaerobic conditions(SRC). Acridine, at 500 mg/kg, was completely biodegraded within 83 days in soil samples(7). Norman aquifer materials, taken from two strictly anaerobic zones, also supported extensive degradation of acridine with 92, 96, and 97% degradation reported after 3 weeks for fermentative, denitrifying, and sulfate-reducing incubations, respectively(8). 2-Methylquinoline, phenyl-2-pentenoic acid, hexylbenzene, and benzoic acid were reported as products of the initial ring cleavage of acridine under anaerobic conditions(8).

AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values of 14 soil and sediment samples, ranging from 5500 to 30,909 with an average value of 12,910(2), indicate that acridine should adsorb to suspended solids and sediment in water(SRC). Acridine is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 4.0X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), BCF values of 30, 125-126, and 1300, measured in daphnia(5), fathead minnows(6,7), and guppies(8) suggest that bioconcentration in aquatic organisms ranges from low to very high, depending on the aquatic organism(SRC); depuration of this compound has been reported to occur(5,7,8).

AQUATIC FATE: Acridine is expected to be resistant to aerobic biodegradation and to readily biodegrade under anaerobic conditions(SRC). No significant biodegradation of acridine at concentrations from 0.1 to 20 mg/l in river die-away tests, using Green River water, was seen over 11 days(1). Norman aquifer materials, taken from two strictly anaerobic zones, also supported extensive degradation of acridine with 92, 96, and 97% degradation reported after 3 weeks for fermentative, denitrifying, and sulfate-reducing incubations, respectively(2). 2-Methylquinoline, phenyl-2-pentenoic acid, hexylbenzene, and benzoic acid were reported as products of the initial ring cleavage of acridine under anaerobic conditions(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acridine, which has an extrapolated vapor pressure of 1.35X10-4 mm Hg at 25 °C(SRC), determined from experimentally-derived coefficients(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acridine 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 about 14 hours(3,SRC). Particulate-phase acridine may be physically removed from the air by dry deposition(SRC).

Food Survey Values · 1 件

Acridine was measured in Finnish butter, 2 of 8 table margarines, cold pressed sunflower oil, corn oil, and coconut fat at 0.43, 0.18-0.32, 0.89, 0.05, and 0.25 ug/kg, respectively(1). Four of fifteen Finnish leaf lettuce samples, which had been grown in the open air in September 1984, contained acridine at concentrations of 0.05-0.13 ug/kg fresh weight(2).

Adverse EffectsDermatotoxin - PICD (photoirritant contact dermatitis).
Exposure RoutesOral (L10) ; inhalation (L10)
Toxicity Summary · 1 件

The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32)

Plant ConcentrationsTwo of twelve vegetation samples collected from areas surrounding the Urx chemical factory, Valasske Mezirici, Czechoslovakia in 1989 contained acridine at concentrations of 789.5 and 2319.4 ng/g(1).
Signs and SymptomsAcute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
Effluent Concentrations · 1 件

Acridine was detected in creosote-PCP wood preservative wastewater at a concentration of 55 mg/kg(1). Acridine was identified in a commercial coal tar leachate sample at unreported concentrations(2). Diesel exhaust collected from a 1979 Caterpillar Model 3208 contained acridine at unreported concentrations(3). Acridine was measured in coal-burning effluent from a residential furnace, in catalyst regeneration flue gas from a gas-oil stock of an oil refinery, and in air polluted with coal-tar pitch at 111, 3.3-65, and 0.870 ug/cu m, respectively(4). Coal tar emissions, and coke-oven emissions samples contained acridine at concentrations of 297 ug/cu m and 0.032-0.172 mg/g, respectively(4). A maltuned convective kerosene space heater emitted 0.2 ng/kJ acridine(5). Fine particle emissions from the combined exhaust of a vented natural gas-fired residential space heater plus a water heater contained acridine at 7.4 pg/kJ(6).

Soil Adsorption/Mobility · 1 件

Fourteen soil and sediment samples, collected from the Ohio, Missouri, Mississippi, and Illinois rivers and their watersheds had a wide range in pH (4.54-8.34), total clay (6.8 to 69.1%), organic carbon (0.11 to 2.38%), and expanding clay (2.0 to 60.0%). Koc values for acridine added to these soils/sediments ranged from 5500 to 30,909 with an average value of 12,910(1). According to a recommended classification scheme(2), these measured Koc values suggest that acridine will be immobile in soil(SRC). Adsorption of acridine to silica was measured in a continuous-flow column. The extent of adsorption was greater when the solution pH was below the pKa of acridine(pKa= 5.68(3)) than when it was above(4). Therefore, mobility should be greater in a sand soil when the pH is above the pKa of acridine and adsorption is greatest when the solution pH equals acridine's pKa(4). Sorption of acridine to two low organic carbon subsurface materials with similar properties but different equilibrium pH values when saturated with water was measured(5). Higher sorption was reported for the Loring subsoil (0.24% organic carbon, pH 4.85) than the Anvil Points subsoil (0.58% organic carbon, pH 8.15), consistent with compound ionization and preferential retention of the organic cation over the neutral compound(5).

Atmospheric Concentrations · 3 件

SOURCE DOMINATED: Ambient air samples collected near a Horizontal Stud Soderberg plant in Jonquiere, Quebec, Canada in 1982, contained acridine at unreported concentrations(1). 7 of 8 air samples collected in the surroundings of the Urx chemical factory, Valasske Mezirici, Czechoslovakia in 1989, contained acridine at concentrations of 42.5 to 467.7 ng/cu m(2).

URBAN/SUBURBAN: Acridine was measured in New York City and Antwerp, Belgium air at concentrations from 0.040-0.041 to 1.0 ng/cu m, respectively(1). Airborne particulate matter from the Upper Silesia region contained acridine(2). The average concentration of acridine in atmospheric particulate matter collected above an urban street in Tokyo, Japan was 3.5 ug/g particulates(3). Acridine was detected on aerosols collected over the southern North Atlantic Ocean at 0.02 ng/cu m(4). Particulate samples obtained from the urban atmospheric environment of several cities in Southern Ontario contained acridine at unreported concentrations(5). Acridine was detected in airborne particulate matter collected in Duisburg, Germany at unreported concentrations(6).

URBAN/SUBURBAN: Ambient air samples collected from Kokkola, Finland contained acridine in the vapor phase at concentrations from <0.1 to 1.5 ng/cu m; this compound was also detected in particulate matter samples at concentrations from 0.4 to 0.6 ng/cu m(1).

安全データ

wgk
3
tsca
TSCA listed
rtecs
AR7175000
ridadr
UN 2713
毒性
LD50 s.c. in mice: 0.40 g/kg (Rubbo)
hs_code
29333990
risk_code
22-68-36/37/38
hazard_code
Xn
safety_code
22-36-45-36/37/39-26
hazard_class
6.1
packing_group
III
Hazard Classifications
Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
有毒物質データの
260-94-6(Hazardous Substances Data)
U.S. Production · 2 件

(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS

(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS

Methods of Manufacturing · 5 件

EXTRACTION FROM ANTHRACENE FRACTION OF COAL TAR WITH SULFURIC ACID, ADDITION OF POTASSIUM DICHROMATE TO PRECIPITATE ACRIDINE CHROMATE, FOLLOWED BY TREATMENT WITH AMMONIA

...FROM N-PHENYLANTHRANILIC ACID: PERKIN, CLEMO, BRITISH PATENT 214,756 (1923); FROM CA-ANTHRANILATE: KOLLER, KRAKAUER, MONATSH 50, 51 (1928); BY PASSING BENZYLANILINE VAPOR OVER RED-HOT PLATINUM WIRE: MEYER, HOFMANN, MONATSH 37, 698 (1916)...

ACRIDINE IS PRESENT IN THE CRUDE ANTHRACENE OF COAL TAR, FROM WHICH IT CAN BE EXTRACTED WITH DILUTE SULFURIC ACID IN WHICH THE CHROMATE IS PRECIPITATED BY POTASSIUM DICHROMATE AND RECRYSTALLIZED FROM HOT WATER. IT CAN ALSO BE OBTAINED BY THE REDUCTION OF ACRIDONE.

OCCURS IN COAL TAR. ISOLATION: GRAEBE, CARO, ANN, 158, 265 (1871); FROM HIGH BOILING TAR OILS: WIRTH, GERMAN PATENT 440,771 (1926).

For more Methods of Manufacturing (Complete) data for ACRIDINE (6 total), please visit the HSDB record page.

General Manufacturing InformationAcridine: ACTIVE
応用分野 · 4 件

解説アクリジン.コールタールから得られるアントラセン油に少量含まれる.ジフェニルアミンとギ酸を塩化亜鉛とともに加熱するか,ジフェニルアミン-2-カルボン酸に硫酸または塩化ホスホリルを作用させたのち,還元すると得られる.無色の針状結晶.融点109~110 ℃,沸点346 ℃.pKa 5.6(20 ℃).100 ℃ で昇華しはじめる.水蒸気蒸留ができる.熱水にわずかに溶け,アルカリ性を示す.アルコール類,エーテル,炭化水素に易溶.希薄溶液は紫色の蛍光を出すが,アクリジンと酸から得られる黄色の塩は緑色の蛍光を出す.ハロゲン化アルキルまたはハロゲン化アリールと反応して,アクリジニウム塩をつくる.光の照射により二量化する.硫酸または水酸化カリウムと処理しても変化しない.二クロム酸カリウムで酸化するとアクリドンとなる.ニッケル触媒で還元するとアクリダン(9,10-ジヒドロアクリジン)となる.合成染料·殺菌剤(トリパフラピン)の原料,金属分析試薬として用いられる.皮膚や粘膜を強く刺激する性質がある.

用途アントラセンの1つの炭素が窒素に置換した構造を持っている。色素や他の化合物の原料となる。プロフラビンなどアクリジン誘導体の多くは殺菌作用を持っている。アクリジンやその誘導体はDNAやRNAにインターカレートし、結合することができる。アクリジンオレンジ(N,N,N',N'-テトラメチルアクリジン-3.6-ジアミン)は核酸を選択的に染色する。

使用manufacture of dyes and intermediates; some dyes derived from it are used as antiseptics, e.g. 9-aminoacridine, acriflavine and proflavine. The hydrochloride has been used as reagent for cobalt, iron and zinc.

一般的な説明Small colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion.

調製方法 · 1 件

純化方法Acridine has been crystallised twice from *benzene/cyclohexane, or from aqueous EtOH, then sublimed, removing and discarding the first 25% of the sublimate. The remainder is again crystallised and sublimed, discarding the first 10-15% [Wolf & Anderson J Am Chem Soc 77 1608 1955]. Acridine can also be purified by crystallisation from n-heptane and then from ethanol/water after pre-treatment with activated charcoal, or by chromatography on alumina with pet ether in a darkened room. Alternatively, acridine can be precipitated as the hydrochloride from *benzene solution by adding HCl, after which the base is regenerated, dried at 110o/50mm, and recrystallised to constant melting point from pet ether [Cumper et al. J Chem Soc 4518 1962]. The regenerated free base may be recrystallised, chromatographed on basic alumina, then vacuum-sublimed and zone-refined. [Williams & Clarke, J Chem Soc, Faraday Trans 1 73 514 1977, Albert, The Acridines Arnold Press 1966.] It can exist in five crystalline forms and is steam volatile. It is a strong IRRITANT to skin and mucous membranes and can become a chronic irritant— handle it with CARE. [Beilstein 20/8 V 199.]

上流・下流製品情報

上流原料

亜鉛 (粉末)N-フェニルアントラニル酸9(10H)-アクリドンBenzaldehyde, 2-(phenylamino)-2-アジドベンズアルデヒドアクリジン10-オキシド9,10-ジヒドロアクリジン9-アクリジンカルボン酸 水和物2-エチルフェノール2,2'-メチレンジアニリンジフェニルヨードニウム トリフルオロメタンスルホン酸2-ニトロベンズアルデヒドフェニルボロン酸

下流製品

カルバゾール9-クロロアクリジン9-フェニルアクリジン9-ブロモアクリジン

補足説明

定義A colorless crystalline heterocyclic compound with three fused rings. Derivatives of acridine are used as dyes and biological stains.