基本情報
- 標準SMILES
C1COC1- InChIKey
AHHWIHXENZJRFG-UHFFFAOYSA-N- 分子式
- C3H6O
- 平均分子量
- 58.08 g/mol
- 単同位体質量
- 58.04186481
概要
1,3-propylene oxide is a clear, colorless liquid with an agreeable aromatic odor. (NTP, 1992)
名称と識別子
- 優先名称
- Oxetane
- IUPAC
- oxetane
- 現地名
- トリメチレンオキシド
- 英語名
- TRIMETHYLENE OXIDE
- 分子式
- C3H6O
- 分子量
- 58.08
名称と別名
名称をさらに表示
データベース識別子
- CAS
503-30-0- PubChem CID
- 10423
- DTXSID
DTXSID8025969- ChEMBL
CHEMBL1538076- ChEBI
CHEBI:30965- UNII
- I279Q16FU6
- EC Number
- 207-964-3
- Nikkaji
- J6.210C
物性
構造計算による物性
- XLogP
- -0.1
- 極性表面積
- 9.2 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
- 4
- 形式電荷
- 0
- 複雑度
- 17.2
実験および物理化学的性質
Density
0.893 at 77 °F (NTP, 1992) - Less dense than water; will float
0.8930 @ 25 °C/4 °C
Solubility
10 to 50 mg/mL at 68 °F (NTP, 1992)
SOL IN ALL PROPORTIONS OF WATER, ALCOHOL; SOL IN ETHER; VERY SOL IN ACETONE, ORGANIC SOLVENTS
In water, miscible.
Flash Point
-19 °F (NTP, 1992)
-28 °C
Boiling Point
122 °F at 760 mmHg (NTP, 1992)
48 °C @ 750 mm Hg
Vapor Pressure
324.0 [mmHg]
324 mm Hg @ 25 °C
物理化学的性質
- 融点
- -97 °C · -97°C
- 沸点
- 50 °C · 50 °C(lit.)
- 比重(密度)
- 0.893 g/mL · 0.893 g/mL at 25 °C(lit.)
- 蒸気圧
- 5.09 psi · 5.09 psi ( 20 °C)
- 屈折率
- 20 · n20/D 1.392(lit.)
- 闪点
- 19 °F · −19 °F
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 1000 g/リットル · 1000g/リットル
- 外見
- 液体
- 色
- 無色透明
- 臭い (Odor)
- 心地よい匂い
- 爆発限界(explosive limit)
- 2.4 % · 2.4%(V)
- 水溶解度
- 水に溶ける。
- Merck
- 14 · 14,9715
- BRN
- 102382 · 102382
- Henry's Law Constant
- 4 · 4.0×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- InChI
- 1S/C3H6O/c1-2-4-3-1/h1-3H2
- InChIKey
- AHHWIHXENZJRFG-UHFFFAOYSA-N
- SMILES
- C1COC1
- CAS データベース
- 503 · 503-30-0(CAS DataBase Reference)
- EPAの化学物質情報
- Oxetane (503-30-0)
化学的性質
化学的特性CLEAR COLOURLESS LIQUID
安全と法規制
GHS分類
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P321, P330, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P321, P330, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
危険有害性情報
Reactivity Profile
1,3-PROPYLENE OXIDE reacts with Grignard reagents and organolithium compounds. It is also incompatible with oxidizing agents and strong acids. (NTP, 1992). An explosion occurred when propylene oxide was added to epoxy resin. Polymerization was catalyzed by amine accelerator in the resin [Bretherick 1995]. Propylene oxide and sodium hydroxide base-catalyzed the polymerization of the former, causing ignition and explosion of a drum of the crude product. [Combust Sci. Technol., 1983].
Hazard Classes and Categories
Flam. Liq. 2 (100%)
Flammable liquid - category 2
Flam. Liq. 2
安全と保護具
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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 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.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a measured log Kow of -0.14(2) and a regression-derived equation(3), indicates that 1,3-epoxypropane is expected to have very high mobility in soil(SRC). Volatilization of 1,3-epoxypropane from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole(SRC), calculated from its vapor pressure of 324 mm Hg(4) and water solubility of 1,000,000 mg/l(5). The potential for volatilization of 1,3-epoxypropane from dry soil surfaces may exist(SRC) based upon its vapor pressure(4).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a measured log Kow of -0.14(2) and a regression-derived equation(3), indicates that 1,3-epoxypropane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of 1,3-epoxypropane from water surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole(SRC), calculated from its vapor pressure of 324 mm Hg(4) and water solubility of 1,000,000 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 29 and 269 hours, respectively(SRC). According to a classification scheme(6), an estimated BCF of 0.5(SRC), calculated from a log Kow of -0.14(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-epoxypropane, which has a vapor pressure of 3.24X10+002 mm Hg at 25 °C(2), is expected to exist solely in the vapor-phase. Vapor-phase 1,3-epoxypropane 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 1.6 days(SRC), calculated from its rate constant of 1.03X10-11 cu cm/molecule-sec at 25 °C(3).
Soil Adsorption/Mobility
The Koc of 1,3-epoxypropane is estimated as 20(SRC), using a log Kow of -0.14(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-epoxypropane is expected to have very high mobility in soil.
Environmental Bioconcentration
An estimated BCF of 0.5 was calculated for 1,3-epoxypropane(SRC), using a log Kow of -0.14(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for 1,3-epoxypropane is estimated as 2.5X10-5 atm-cu m/mole(SRC) based upon its vapor pressure, 324 mm Hg(1), and water solubility, 1,000,000 mg/l(2). This Henry's Law constant indicates that 1,3-epoxypropane is expected to volatilize from water surfaces(3). 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)(3) is estimated as 29 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 269 hours(SRC). 1,3-Epoxypropane's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,3-epoxypropane from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 1,3-epoxypropane with photochemically-produced hydroxyl radicals is 1.3X10-11 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 1.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1,3-Epoxypropane may undergo hydrolysis in the environment because it contains hydrolyzable functional groups(2) but is not expected to directly photolyze due to a lack of absorption in the environmental UV spectrum (>290 nm)(2).
Environmental Fate/Exposure Summary
1,3-Epoxypropane's production and use as a chemical intermediate may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 324 mm Hg at 25 °C indicates 1,3-epoxypropane will exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-epoxypropane will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 1.6 days. If released to soil, 1,3-epoxypropane is expected to have very high mobility based upon an estimated Koc of 20. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 2.5X10-5 atm-cu m/mole. 1,3-Epoxypropane may volatilize from dry soil surfaces based upon its vapor pressure. If released into water, 1,3-epoxypropane is not expected to adsorb to suspended solids and sediment based upon its estimated Koc. Volatilization from water surfaces may be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 29 and 269 hours, respectively. An estimated BCF of 0.5 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis may be an important environmental fate process since this compound contains hydrolyzable functional groups, however information regarding the kinetics of this reaction are not available. Occupational exposure to 1,3-epoxypropane may occur through inhalation and dermal contact with this compound at workplaces where 1,3-epoxypropane is produced or used. (SRC)
安全データ
- F
- 3-10-23
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- RQ6825000
- ridadr
- UN 1993 3/PG 2
- 毒性
- mmo-sat 3333 mg/plate EMMUEG 11(Suppl 12),1,88
- hs_code
- 29329990
- risk_code
- 11-20/21/22
- 消防法
- 危-4-1-II
- hazard_code
- F,Xn
- safety_code
- 9-16-26-29
- hazard_class
- 3
- packing_group
- II
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralFlam. Liq. 2
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 503-30-0(Hazardous Substances Data)
化学と産業
用途と製造
Uses
Used as a chemical intermediate for epoxy resins and 3-substituted propanols; [HSDB]
CHEM INT, EG, FOR EPOXY RESINS & 3-SUBSTITUTED PROPANOLS
Photoreactions leading to carefully selected oxetanes are impressive tools in the construction of complex molecules ... such as drugs, crop protection agents, and fragrants. /Oxetanes/
/Chemical intermediate/
Methods of Manufacturing
Prepd by dropwise addition of 3-chloropropyl acetate to hot potassium hydroxide soln: Noller, Org Syn 29, 92 (1949); modified procedure: Searles, J Am Chem Soc, 73, 124 (1951).
REACTION OF 3-BROMOPROPANOL WITH POTASSIUM HYDROXIDE
応用分野
解説オキセタン.1-アセトキシ-3-クロロプロパンのアルカリ処理により分子内環化させると得られる.沸点48 ℃.d25 0.8930.n20D 1.3929.有機溶媒に易溶.水と混和する.アミン,アルコール類のほか,フリーデル-クラフツ触媒の存在下に,ベンゼンをヒドロキシプロピル化するのに用いられる.有機リチウム化合物やグリニャール試薬と反応して,第一級アルコールを与える.
使用Trimethylene oxide useful for the synthesis of 3-substituted propanols by reaction with Grignards or organolithiums in the presence of CuBr.
一般的な説明Clear, colorless liquid with an agreeable aromatic odor.
使用用途オキセタンは、医薬品原料、染料原料、防腐剤原料に用いられます。有機合成では、アミン、アルコール、ベンゼンのヒドロキシプロピル化に利用可能です。 オキセタンを含む各種誘導体は、エポキシ樹脂の高速硬化やプラスチック材料に対する優れた密着性のような特徴を持つため、エポキシ樹脂用添加剤に使用され、塗料、、各種コーティング剤などの用途があります。柔軟性や密着性に優れるほか、環境にやさしい材料として注目を浴びています。 オキセタン環を有する化合物の中には、抗ウイルス剤や血小板凝集に関わる物質、抗がん剤などの生化学的特徴を持つものも多いです。
調製方法
純化方法Distil oxetane twice from sodium metal and then fractionate it through a small column at atmospheric pressure, b 47.0-47.2o. It can also be purified by preparative gas chromatography using a 2m silica gel column. Alternatively, add KOH pellets (50g for 100g of oxetane) and distil it through an efficient column or a column packed with 1/4in Berl Saddles with the main portion boiling at 45-50o being collected and redistilled over fused KOH. [Noller Org Synth Coll Vol III 835 1955, Dittmer et al. J Am Chem Soc 79 4431 1957, Beilstein 17 H 6, 17 I 3, 17 II 12, 17 III/IV 13, 17/1 V 11.]
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: A saturated organic heteromonocyclic parent that is a four-membered ring comprising of three carbon atoms and an oxygen atom.
関連反応
関連ノート
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