基本情報
- 標準SMILES
OC1CCCC1- InChIKey
XCIXKGXIYUWCLL-UHFFFAOYSA-N- 分子式
- C5H10O
- 平均分子量
- 86.13 g/mol
- 単同位体質量
- 86.07316494
概要
Cyclopentanol appears as a colorless viscous liquid with a pleasant odor. Slightly less dense than water. Vapors heavier than air. Used to make perfumes and pharmaceuticals.
名称と識別子
- 優先名称
- Cyclopentanol
- IUPAC
- cyclopentanol
- 現地名
- シクロペンタノール
- 英語名
- Cyclopentanol
- 分子式
- C5H10O
- 分子量
- 86.13
名称と別名
名称をさらに表示
データベース識別子
- CAS
96-41-3- PubChem CID
- 7298
- DTXSID
DTXSID1033371- ChEMBL
CHEMBL288998- ChEBI
CHEBI:16133- UNII
- 1L43Q07TBU
- EC Number
- 202-504-8
- Nikkaji
- J43.298I
物性
構造計算による物性
- XLogP
- 0.8
- 極性表面積
- 20.2 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 6
- 形式電荷
- 0
- 複雑度
- 37.2
実験および物理化学的性質
Odor
Odor of amyl alcohol, somewhat like peppermint
Pleasant odor
Solubility
SOL IN ALCOHOL, ETHER, ACETONE; SLIGHTLY SOL IN WATER
Sparingly soluble in water. Soluble in ethanol.
Flash Point
124 °F (NFPA, 2010)
124 °F (51 °C) (CLOSED CUP)
物理化学的性質
- 融点
- -19 °C · -19 °C (lit.)
- 沸点
- 139 · 139-140 °C (lit.)
- 比重(密度)
- 0.948 g/mL · 0.948 g/mL at 20 °C 0.949 g/mL at 25 °C (lit.)
- 屈折率
- 20 · n20/D 1.453(lit.)
- 闪点
- 124 °F · 124 °F
- 貯蔵温度
- Flammables area
- 溶解性
- Chloroform (Soluble), Methanol (Sparingly)
- 酸解離定数(Pka)
- 15.31 · 15.31±0.20(Predicted)
- 外見
- 液体
- 色
- 無色透明~微黄色透明
- 水溶解度
- わずかに溶ける
- 比熱容量
- 2.12 J/ · Cp(liquid): 2.12 J/(g·K), at 25℃
- Merck
- 14 · 14,2742
- BRN
- 1900556 · 1900556
- Henry's Law Constant
- 4.2 · 4.2×100 mol/(m3Pa) at 25℃, Plyasunov and Shock (2000)
- Dielectric constant
- 18 · 18.0(20℃)
- 安定性
- 安定。可燃性。強力な酸化剤、酸塩化物、酸無水物とは相容れない。
- InChI
- 1S/C5H10O/c6-5-3-1-2-4-5/h5-6H,1-4H2
- InChIKey
- XCIXKGXIYUWCLL-UHFFFAOYSA-N
- SMILES
- OC1CCCC1
- LogP
- 0.71 · 0.710
- 表面張力
- 32.7 mN/m · 32.7mN/m at 20°C
- CAS データベース
- 96 · 96-41-3(CAS DataBase Reference)
- NISTの化学物質情報
- Cyclopentanol(96-41-3)
- EPAの化学物質情報
- Cyclopentanol (96-41-3)
化学的性質
化学的特性シクロペンタノールは化学式C5H10Oで表される有機化合物ですこの化合物は五メンバーリングのシクロアルカンであるシクロペンタンにヒドロキシル基OHが結合した構造を持っていますシクロペンタノールはアルコールの一種であり特に二級アルコールに分類されますその特徴として水とも有機溶剤とも混和可能であることが挙げられます
安全と法規制
GHS分類
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 57 reports by companies from 3 notifications to the ECHA C&L Inventory.
Danger
H226: Flammable liquid and vapor [Warning Flammable liquids]
危険有害性情報
Regulatory Information
Chemical: Cyclopentanol
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 30-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/15902
Cyclopentanol: HSNO Approval: HSR001247 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.)
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
Reactivity Profile
CYCLOPENTANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
DOT Emergency Guidelines
/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.
/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.
/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ 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 for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.
/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.
For more DOT Emergency Guidelines (Complete) data for CYCLOPENTANOL (8 total), please visit the HSDB record page.
DOT Hazard Classification
Cyclopentanol
UN2244
Class 3 Flammable and combustible liquid (49 eCFR § 173.120)
PG III: the degree of danger presented by the material is minor
安全と保護具
Accidental Release Measures
· 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
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
General First Aid:
Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. 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
IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED.
Disposal Methods
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.
Preventive Measures
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. Attempt to stop leak if without undue personnel hazard.
Personnel protection: Keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment.
Isolation and Evacuation
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Immediate precautionary measure
Personal Protective Equipment (PPE)
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
... Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus. ...
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 58(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that cyclopentanol will have high mobility in soil(SRC); leaching of this compound may be important under some environmental conditions(SRC). In soil, cyclopentanol is expected to readily biodegrade(SRC). In tests using activated sludge inocula, 95% of the inital COD (cyclopentanol at 200 mg/L COD), was removed over 120 hours(4); 97%(5) of the theoretical BOD was obtained within 5 days (cyclopentanol at 100 mg/L). Volatilization of cyclopentanol should be important from dry soil surfaces(SRC) given a measured vapor pressure of 1892 mm Hg at 25 °C(6). Volatilization from moist soil surfaces will be very slow(SRC) based on an estimated Henry's Law constant of 2.6X10-6 atm-cu m/mole(7,SRC).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 58(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that cyclopentanol will not adsorb to suspended solids and sediment(SRC) in the water. Cyclopentanol is expected to readily biodegrade in water(SRC). In tests using activated sludge inocula, 95% of the inital COD (cyclopentanol at 200 mg/L COD), was removed over 120 hours(4); 97%(5) of the theoretical BOD was obtained within 5 days (cyclopentanol at 100 mg/L). Cyclopentanol will volatilize from water surfaces based on an estimated Henry's Law constant of 2.6X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Estimated half-lives for a model river and model lake are 13 and 98 days, respectively(3,SRC). An estimated BCF value of 2(3,SRC), from a measured log Kow(2), suggests that cyclopentanol will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(7).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), a measured vapor pressure of 1892 mm Hg at 25 °C(2) indicates that cyclopentanol will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase cyclopentanol 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 1.5 days(3,SRC).
Soil Adsorption/Mobility
The Koc of cyclopentanol is estimated as approximately 58(SRC), using a measured log Kow of 0.71(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that cyclopentanol has high mobility in soil(SRC).
TSCA Test Submissions
Cyclopentanol (CAS # 96-41-3) was evaluated for acute oral toxicity. The test substance was administered by gavage to Wistar-derived male rats. Dosage and mortality data are as follows: 2.5 ml/kg (5/5); 1.25 ml/kg (5/5); and 0.625 ml/kg (5/6). Toxic signs included sluggish; unsteady gait; red fluid around eyes and mouth; and convulsions at 1.25 and 0.625 ml/kg. Gross pathology revealed mottled red and tan livers; distended and gas-filled stomachs; and pale kidneys.
Cyclopentanol (CAS # 96-41-3) was evaluated for acute dermal toxicity. The test substance was applied once to the clipped-intact skin of male New Zealand white rabbits for 24 hours. Dosages and mortality data are as follows: 1.60 ml/kg (2/2); 0.20 ml/kg (4/4); 0.10 ml/kg (0/4); and 0.05 ml/kg (0/2). The LD50 was determined to be 0.141 ml/kg. Toxic signs at 0.20 ml/kg and above, include erythema, edema, vocalization, hyperactivity, lacrimation and convulsions. Gross pathology revealed mottled red and light tan livers, and tan kidneys.
Cyclopentanol (CAS # 96-41-3) was evaluated for acute inhalation toxicity. The test substance was administered to 6 rats (strain and sex not indicated) per single exposure for 136 minutes (100% mortality) or 68 minutes (no mortalities) as a substantially saturated atmosphere at room temperature. LT50 was determined to be 96 minutes. Mortality resulted after a few hours. Toxic signs included lacrimation, hypoactivity, severe tremors, ataxia, salivation, dilated pupils, and coordination loss. Gross pathology revealed dark red lungs, and gas-filled stomach and intestines.
Cyclopentanol (CAS # 96-41-3) was evaluated for primary dermal irritation. The test substance was applied in 0.01 ml amounts to the clipped, uncovered intact skin of 5 rabbits (sex and strain not indicated), either undiluted or in dilutions of 10%, 1.0%, 0.1%, or 0.01% solvent. No irritation was noted on 4 rabbits, and moderate capillary injection was noted on one rabbit (Grade 2) at an unspecified concentration.
Cyclopentanol (CAS # 96-41-3) was evaluated for primary eye irritation. The test substance was applied to the conjunctival sac of 5 rabbits (sex and strain not indicated) at 0.005 ml, 0.02 ml, 0.10 ml, or 0.5 ml of undiluted or 0.5 ml of 40%, 15%, 5%, or 1% dilutions of test material. Moderate to severe corneal injury with iritis resulted from 0.005 ml of undiluted and 0.5 ml of 40% dilution of test material. No injury to minor corneal injury, with iritis in one rabbit, resulted from 15% dilution.
Atmospheric Concentrations
Cyclopentanol was detected in 10% of expired air samples taken from an urban population of humans(28 subjects, 224 expired air samples); the average concentration was 0.9 ng cyclopentanol/L expired air(1). 8.5% of 387 expired air samples from 54 human subjects contained cyclopentanol at an average concentration of 0.329 ng/L expired air(2).
Human Toxicity Excerpts
LIQUID ALICYCLIC HYDROCARBONS WILL DEHYDRATE & DELIPIDIZE SKIN ON REPEATED OR PROLONGED CONTACT & CAUSE DERMATITIS. DIRECT CONTACT...WITH LUNG TISSUE (ASPIRATION) WILL CAUSE PULMONARY EDEMA, PNEUMONITIS & HEMORRHAGE. VAPORS IN SUFFICIENT CONCN WILL CAUSE IRRITATION OF MUCOUS MEMBRANES. /ALICYCLIC HYDROCARBONS/
TOXICOLOGICALLY, THE ALICYCLIC HYDROCARBONS RESEMBLE THEIR OPEN CHAIN RELATIVES, THE ALIPHATIC HYDROCARBONS. IN GENERAL, THEY ARE ANESTHETICS & CNS DEPRESSANTS WITH A RELATIVLY LOW ORDER OF ACUTE TOXICITY. ...CUMULATIVE TOXICITY FROM REPEATED EXPOSURE TO LOW ATMOSPHERIC CONCN IS IMPROBABLE. /ALICYCLIC HYDROCARBONS/
Environmental Biodegradation
Cyclopentanol, present at a COD of 200 mg/L, was readily biodegraded with 97% COD removal in 5 days using an adapted, activated sludge inoculum(1). A 5 day BOD test using a non-adapted sewage culture resulted in a BOD nearly 95% of the theoretical for cyclopentanol(2). Cyclopentanol at 100 mg/L had a BOD 53% of the theoretical after 24 hours, using a Warburg respirometer(2). Trichosporon cutaneum KUY-6A, a yeast strain isolated from a soil enrichment culture, was able to grow using cyclopentanol(3).
Environmental Bioconcentration
An estimated BCF value of 2 was calculated for cyclopentanol(SRC), using a measured log Kow of 0.71(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for cyclopentanol is estimated as 2.6X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that cyclopentanol will volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is estimated as approximately 13 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 98 days(2,SRC). Cyclopentanol's high vapor pressure, 1892 mm Hg(3) indicates that volatilization from dry soil surfaces should occur(SRC); based on this compound's Henry's Law constant(1,SRC), significant volatilization from moist soil surfaces is not expected(SRC).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of cyclopentanol with photochemically produced hydroxyl radicals has been measured as 10.7X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 1.5 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
安全データ
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 2244
- hs_code
- 29061990
- risk_code
- 10-36/37/38
- 化審法
- (3)-2306
- 消防法
- 危-4-2-III
- hazard_code
- Xi
- safety_code
- 16-36-26
- hazard_class
- 3
- packing_group
- III
- Hazard Classifications
- Flam. Liq. 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 96-41-3(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used as a solvent (perfumes and pharmaceuticals) and for organic synthesis; [Hawley]
Perfume and pharmaceutical solvent, intermediate for dyes, pharmaceuticals, and other organics.
In the preparation of quingestanol acetate.
Methods of Manufacturing
BY REDUCTION OF CYCLOPENTANONE WITH LIALH4 IN ETHER @ ROOM TEMP.
...BY MODIFIED MEERWEIN-PONDORF-VERLEY REDUCTION OF CYCLOPENTANONE IN PRESENCE OF ALUMINUM ISOPROPOXIDE & SODIUM HYDROXIDE. BY CATALYTIC HYDROGENATION OF PURE CYCLOPENTANONE WITH COPPER CHROMITE @ 150 °C & 150 ATM.
BY CATALYTIC HYDROGENATION OF CYCLOPENTANONE WITH PLATINUM OXIDE & PLATINUM BLACK @ 2-3 ATM: NOLLER, ADAMS, J AM CHEM SOC 48, 1084 (1926); BY HYDRATION OF CYCLOPENTENE IN AQ H2SO4: HEPP, US PATENT 2,414,646 (1947 TO PHILLIPS PETR)...
応用分野
解説シクロペンタノール (Cyclopentanol) とは、の水素が一つヒドロキシ基で置換された構造をしている有機化合物です。 環状アルコールの1種にあたります。CAS登録番号は96-41-3です。分子式C5H10O、分子量86.13、融点-19℃、沸点139-140℃です。常温では無色からわずかにうすい黄色の液体となっており、 不快臭を放つとされています。密度は0.949g/mLです。 他の名称には、「シクロペンチルアルコール (Cyclopentyl alcohol) 」「ヒドロキシシクロペンタン (Hydroxycyclopentane) 」などがあります。水には難溶ですが、アルコール、エーテルおよびには極めて容易に溶けます。
用途香水や医薬品の中間体溶剤、染料、医薬品などの有機物
使用Cyclopentanol is a versatile compound used as a building block, intermediate and solvent.
一般的な説明A colorless viscous liquid with a pleasant odor. Slightly less dense than water. Flash point 124°F. Vapors heavier than air. Used to make perfumes and pharmaceuticals.
使用用途図2. シクロペンタノールの酸化によるシクロペンタノンの合成の例 シクロペンタノールの主な用途は、一般的な溶剤、香料調剤用の溶剤、医薬・農薬原料などです。また、シクロペンタノールは、のであり、TEMPOなどの安価な触媒で極めて高選択的にシクロペンタノンを製造することができます。 シクロペンタノンは各種産業用途で利用価値が高い化合物であるため、この変換反応は非常に重要です。例えば、特定フロンや1,1,1-は、金属材料に付着する油の洗浄液として有益ですが、環境に影響があるため、新しい代替洗浄液が必要となっています。 そこで、生分解性が良好であるシクロペンタノンが、近年代替洗浄液として注目を集めています。また、シクロペンタノン (及びその前駆体のシクロペンタノール) は、各種医薬品の合成中間体であるため、合成化学的にも重要な化合物と言えます。
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義ChEBI: Cyclopentanol is the simplest member of the class of cyclopentanols bearing a single hydroxy substituent. The parent of the class of cyclopentanols.
関連反応
関連ノート
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