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インデン

Indene

HCID 7219
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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
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基本情報

CAS
71551-80-9
標準SMILES
C1=Cc2ccccc2C1
InChIKey
YBYIRNPNPLQARY-UHFFFAOYSA-N
分子式
C9H8
平均分子量
116.16 g/mol
単同位体質量
116.06260026

概要

Indene appears as a colorless liquid derived from coal tar. Fp: -2 °C; bp:182 °C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.

名称と識別子

優先名称
Indene
IUPAC
1H-indene
現地名
インデン
英語名
Indene
分子式
C9H8
分子量
116.16

名称と別名

INDENE1H-Indene95-13-6IndonaphtheneIndenDTXSID8042052NSC 927067H8Y6LB8ANSC-9270DTXCID6022052CHEBI:41921RefChem:790898
名称をさらに表示
インデン1H-インデンインドナフテンインデン標準品インデン ODOR STANDARDインデン, 50 µg/mL in TolueneTechnicalindenendene1-indeneIndene >Indene,90+%Indene techIndene Odor
CHEBI:37910202-393-6Indenyl radicalMFCD00003777indene, (1H-indene)INDENE, REAGWLN: L56 BHJCHEMBL192812

データベース識別子

CAS
71551-80-9、9003-64-9、95-13-6
PubChem CID
7219
DTXSID
DTXSID8042052
ChEMBL
CHEMBL192812、CHEMBL506735
ChEBI
CHEBI:41921
UNII
67H8Y6LB8A
EC Number
202-393-6
Nikkaji
J4.708B

物性

構造計算による物性補完中

XLogP
2.9
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
9
形式電荷
0
複雑度
124

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Aromatic Hydrocarbons

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
FragrancesFragrance Ingredient (1H-Indene) -> IFRA transparency List
LogP · 2 件

Log Kow = 2.92

2.92

Density · 5 件

0.997 (NIOSH, 2024) - Less dense than water; will float

0.9968 @ 20 °C/4 °C

0.997

0.996 @25 °C

0.997

Color/Form · 3 件

LIQUID

Colorless liquid

Colorless liquid [Note: A solid below 29 degrees F].

Solubility · 5 件

Insoluble (NIOSH, 2024)

INSOL IN WATER, MISCIBLE WITH MOST ORGANIC SOLVENTS

SOL IN ALL PROPORTIONS IN ALC, ETHER, N BENZENE, PYRIMIDENE, CARBON DISULFIDE

Soluble in ethanol; it is miscible with diethyl ether, naphtha, pyridine, carbon tetrachloride, chloroform, and carbon disulfide

Insoluble

Flash Point · 5 件

173 °F (NIOSH, 2024)

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 · 6 件

This chemical does not meet GHS hazard criteria for 0.5% (2 of 400) of reports.

Danger

H226 (99.2%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 400 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 5 件

Chemical: 1H-Indene

1H-Indene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1H-Indene 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)

REACH registered substance: Indene (EC: 202-393-6)

Indene: Does not have an individual approval but may be used under an appropriate group standard

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 LabelCombustible Liquid
Fire HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Fire PotentialDEFLAGRATES ON HEATING. /INDENE PICRATE/
Health HazardsExcerpt from NIOSH Pocket Guide for Indene:
Hazards SummaryAnimals exposed to 800-900 ppm for six 7-hour periods show evidence of liver and kidney injury. [ACGIH]

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

YIELDS CIS-1,2-DIHYDROXYINDANE & TRANS-1,2-DIHYDROXYINDANE IN RABBITS. /FROM TABLE/

RAT-LIVER MICROSOMES SUPPLEMENTED WITH NADPH CONVERTED INDENE INTO TRANS-INDANE-1,2-DIOL ...

THE OXIDATION OF INDENE TO TRANS-1,2-DIHYDROXYINDANE IN LIVER PREPN IN VITRO WAS DEMONSTRATED. THE REACTION WAS MEDIATED BY LIVER MICROSOMES OF RATS & RABBITS IN THE PRESENCE OF NADPH-GENERATING SYSTEMS.

用途と製造

Uses · 4 件

Used to prepare coumarone-indene resins; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

Used as a comonomer in coumarone and petroleum-derived aromatic hydrocarbon resins. Technical pure indene is used for the production of indan and its derivatives. Esters of indene-1-carboxylic acid, which are effective as acaricides, can be synthesized from indene for use in, eg, collars

It is composed of a benzene ring fused with a cyclopentene ring.

U.S. Production2023: 500,000 - <1,000,000 lb
Industry UsesMonomers
Methods of Manufacturing · 2 件

... FROM ACETYLENE OVER ACTIVATED CHARCOAL @ 625 °C ... MFR FROM TETRAHYDRONAPHTHALENE BY PASSING OVER SIO2-AL2O3 CATALYST @ 670 °C

Pyrolysis residual oils from olefin production contain varying amounts of indene, which can be separated by extractive distillation with N-methyl-2- pyrrolidone or by crystallization. Indene is recovered industrially from dephenolated and debased tar light oil by rectifying distillation followed by crystallization. When the phenol extraction is omitted a highly concentrated indene fraction can also be obtained by azeotropic distillation of an indene- phenol fraction with water, whereby the phenol is separated as a bottom product.

Use ClassificationFragrance Ingredients
General Manufacturing Information

関連反応

215 件
反応記録を作成
HRID 1306 の反応式
HRID 1306反応物としてuspto-grants-1998_03
HRID 22443 の反応式
HRID 22443反応物としてuspto-grants-1995_06
HRID 22444 の反応式
HRID 22444反応物としてuspto-grants-1995_06
HRID 36480 の反応式
HRID 36480生成物としてuspto-grants-1995_05
HRID 39114 の反応式
HRID 39114反応物としてuspto-grants-2013_09
HRID 47413 の反応式
HRID 47413反応物としてuspto-grants-2004_03
HRID 52676 の反応式
HRID 52676反応物としてuspto-grants-1997_04
HRID 52819 の反応式
HRID 52819生成物としてuspto-grants-1997_04
1 / 27 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

173 °F

173 °F

173 °F

173 °F

Boiling Point · 5 件

359 °F at 760 mmHg (NIOSH, 2024)

181.6 °C 760 MM HG

359 °F

182 °C @760 [mm Hg]

359 °F

Melting Point · 5 件

29 °F (NIOSH, 2024)

-1.8 °C

29 °F

-1.5 °C

29 °F

Odor ThresholdOdor Threshold Low: 0.0042 [ppm]
Vapor Pressure · 3 件

1.1 [mmHg]

1.1 mm Hg at 25 °C

0.75 [mm Hg] @12 °C

物理化学的性質

融点
-5 · -5--3 °C (lit.)
沸点
181 · 181-182 °C (lit.)
比重(密度)
0.996 g/mL · 0.996 g/mL at 25 °C (lit.)
蒸気圧
1.7 hPa · 1.7 hPa (20 °C)
屈折率
20 · n20/D 1.595(lit.)
闪点
138 °F · 138 °F
貯蔵温度
2 · 2-8°C
溶解性
有機溶剤: 混和性
酸解離定数(Pka)
20 · 20(at 25℃)
外見
結晶性粉末
色
白色~淡黄色
臭気閾値(Odor Threshold)
0.0038 ppm · 0.0038ppm
水溶解度
不溶性
比熱容量
1.61 J/ · Cp(liquid): 1.61 J/(g·K), at 25℃
Merck
14 · 14,4939
BRN
635873 · 635873
Henry's Law Constant
6.2 · 6.2×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
80 · 安定していますが、空気や光に敏感で、光の中で重合が起こることがあります。通常、約80~100ppmのp-tert-ブチルフェノールが抑制剤として含まれる。冷凍。可燃性。強力な酸化剤とは相容れない。
化粧品成分の機能
香料
InChI
1S/C9H8/c1-2-5-9-7-3-6-8(9)4-1/h1-6H,7H2
InChIKey
YBYIRNPNPLQARY-UHFFFAOYSA-N
SMILES
C1C=Cc2ccccc12
LogP
3.02 at · 3.02 at 25℃ and pH6.4
CAS データベース
95 · 95-13-6(CAS DataBase Reference)
NISTの化学物質情報
Indene(95-13-6)
EPAの化学物質情報
Indene (95-13-6)

化学的性質

化学的特性Yellow green clear liquid

化学性质インデンは二つの炭素環すなわち五員環と六員環が融合した構造を持っていますこの特異な構造はインデンに独特の化学的および物理的性質を与えます例えばインデンは高い熱安定性と良好な溶解性を持ち多くの有機溶剤に溶けやすいです

Reactive GroupHydrocarbons, Aromatic
Reactivity AlertsPolymerizable
Reactivity Profile · 1 件

INDENE is combustible (flash point between 140 °F and 200 °F). Polymerizes and oxidizes on standing in the air. This reaction is accelerated by heating, acids, and catalysts, including peroxides. Has exploded during nitration with a mixture of H2SO4 and HNO3.

Flammable LimitsClass IIIA Combustible Liquid: Fl.P. at or above 140 °F and below 200 °F.
Air and Water ReactionsPeroxide formation with air with initiation of polymerization
NIOSH RecommendationsRecommended Exposure Limit: 10 Hr Time-Weighted Avg: 10 ppm (45 mg/cu m).

安全と保護具

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First Aid · 2 件

Excerpt from NIOSH Pocket Guide for Indene:

(General first aid procedures)

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 1 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.

Preventive Measures · 2 件

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.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Respirator RecommendationsImportant additional information about respirator selection
Threshold Limit Values (TLV) · 4 件

5.0 [ppm]

8 hr Time Weighted Avg (TWA): 5 ppm.

Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.

5 ppm [2007]

Permissible Exposure Limit (PEL) · 2 件

10 ppm (45 mg/m³) OSHA Construction and Maritime industries only.

none See Appendix G

Protective Action Criteria (PAC) · 3 件

70 [mg/m3]

100 [mg/m3]

620 [mg/m3]

Recommended Exposure Limit (REL) · 2 件

10 ppm (45 mg/m³)

TWA 10 ppm (45 mg/m3)

Personal Protective Equipment (PPE) · 3 件

Excerpt from NIOSH Pocket Guide for Indene:

Wear appropriate personal protective clothing to prevent skin contact.

Wear appropriate eye protection to prevent eye contact.

毒性情報

Toxicological InformationRanking: 303 (total points: 714.72)
Body Burden · 1 件

Indene was detected in respiratory gas from 7 of 8 male volunteers (3 smokers) at a concn range of 0.14-83 ug/hr-expired air; according to this study, indene may result from or be related to normal human metabolism(1). Indene was found at an average concn of 0.138 ng/L in 59 of 387 expired air samples obtained from 54 nonsmoking-volunteers(2).

Target OrgansEyes, skin, respiratory system, liver, kidneys, spleen
Environmental Fate · 3 件

TERRESTRIAL FATE: The estimated Koc value of 540(1-2,SRC) suggests that indene will have low mobility in soil(3). If spilled on soil surfaces, some indene may photolyze(4,SRC) or volatilize into the air (estimated Henry's Law constant of 1.59X10-3 atm-cu m/mol at 25 °C(5)). However, adsorption may limit these processes(SRC). Limited data suggest indene is biodegradable in soil(6-7).

AQUATIC FATE: Based on the estimated Koc value of 540(1-2,SRC), indene may adsorb to sediment; indene was found in a river sediment(3). Oxidation via reaction with sunlight produced alkyl peroxy radicals is very slow (estimated half-life of 1,100 days(4)). Limited data suggest indene is biodegradable. Indene may be susceptible to some direct photolysis in sunlight(5); however, this is not expected to be an important removal process(SRC). Indene is not expected to hydrolyze in the aquatic environments(SRC). Volatilization from water is fast with estimated half-lives of 3.7 hrs and 4.4 days from a model river and model lake, respectively(1,SRC).

ATMOSPHERIC FATE: Based upon a measured vapor pressure of 1.1 mm Hg at 25 °C(1), indene is expected to exist almost entirely in the vapor phase in the ambient atmosphere(2,SRC). Vapor-phase indene will degrade rapidly in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 6.2 hours(3,SRC).

Food Survey ValuesIndene was qualitatively identified as a volatile component of roasted filberts(1).
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 Routesinhalation, ingestion, skin and/or eye contact
Signs and SymptomsIn Animals: irritation eyes, skin, mucous membrane; dermatitis, skin sensitization; chemical pneumonitis (aspiration liquid); liver, kidney, spleen injury
Effluent Concentrations · 2 件

Indene was qualitatively identified in effluents from a POTW facility in Sauget, Illinois(1). On October 24, 1974, indene was qualitatively found in advanced waste treatment concentrates from Lake Tahoe, CA(2). During August and September of 1979, indene was found at a concn range of 0.08-0.4 ug/cu-m in the Allegheny Mountain Tunnel in Pennsylvania(3). Indene was identified at a concn range of 10.3-137.6 ng/L in paper-mill effluents being discharged into the Rainy River(4). Indene was identified in a plume of contaminated water moving through sand away from creosote waste disposal lagoons(5). Indene was found at a concn of 1.28 in an air sample taken near an oil fire(6).

Indene was found in a groundwater sample prior to coal gasification (0.03 ppm), process water during gasification (272 and 72 ppm), and aqueous condensate from low-BTU coal gasification (363 ppm)(1). Indene was found at a concn of 15 ng/L in a canal to a harbor of a freshwater lake before any boat traffic was observed; after 1,293 boats passed through the canal, the concn of indene was 74 ng/L(2). Indene has been detected in wastewater effluents from the timber products industry at a concn of 8,252 ng/ul extract(3).

Soil Adsorption/MobilityBased on a measured log Kow of 2.92(2) and a regression derived equation(1), the Koc for indene can be estimated to be about 540(SRC). According to a suggested classification scheme(3), this Koc value suggests low mobility in soil.
Natural Pollution SourcesIndene is found in high-temperature coal tar at an average concn of 1 percent(1). It can be released to the environment in emissions from biomass combustion(2).
Atmospheric Concentrations · 1 件

In 1977, indene was qualitatively identified in the air of six industrial cities of the former USSR(1). Indene was qualitatively found in the air of three South African cities during the summer of 1975-winter of 1976(2). Indene was qualitatively identified in air taken at Homebush Bay, Australia on June 3, 1975(3). Indene was qualitatively identified in Paris air on October 24, 1972(4).

安全データ

F
8
OEB
A
OEL
TWA: 10 ppm (45 mg/m3)
wgk
1
tsca
TSCA listed
rtecs
NK8225000
ridadr
UN 3295 3/PG 3
hs_code
2902 90 00
risk_code
10-65-36/37/38-20
化審法
(4)-580
安衛法
57,57-2
消防法
危-4-2-III
hazard_code
Xn
safety_code
23-24/25-62-37/39-26
hazard_class
3
packing_group
III
Hazard Classifications
Asp. Tox. 1Flam. Liq. 3
ストレージクラス
3 - Flammable liquids
有毒物質データの
95-13-6(Hazardous Substances Data)
· 2 件

Petrochemical Manufacturing

1H-Indene: ACTIVE

応用分野 · 6 件

解説インデン,融点-2 ℃,沸点182 ℃.d20"0.9966.nD20"1.5763.多くの有機溶媒に可溶.きわめて不安定で,酸素を吸収して,過酸化物を与える.常温·暗所でもすみやかに重合する.クマロン-インデン樹脂をつくるのに用いられる.森北出版「化学辞典(第2版)

用途樹脂原料古くからクマロンーインデン樹脂としてSBRゴム製品の強化用にブレンドされている。

用途有機合成原料。

使用Preparation of coumarone-indene resins, intermediate.

一般的な説明A colorless liquid derived from coal tar. Fp: -2°C; bp:182°C. Density 0.997 g cm-3. Insoluble in water but soluble in organic solvents.

使用用途インデンは、光機能材料、機能性樹脂、医薬中間体などの有機合成原料に使われています。主に、塗料、ゴムの配合材、粘着剤、印刷用インク、などです。 クマロンやなどを重合する際に、樹脂改質剤として有用です。とくにクマロン-インデン樹脂 (英: coumarone-indene resin) は、石油樹脂とは異なる特性を持っています。接着性、機械物性、電気特性を持ち、ゴムの物性改善、塗料の密着性や防食性の向上、エポキシ樹脂の吸水性や誘電率の低減など、各種樹脂性能の改善に優れています。

調製方法 · 1 件

純化方法Shake indene with 6M HCl for 24hours (to remove basic nitrogenous material), then reflux it with 40% NaOH for 2hours (to remove benzonitrile). Fractionally distil, then fractionally crystallise it by partial freezing. The higher-melting portion is converted to its sodium salt by adding a quarter of its weight of sodamide under nitrogen and stirring for 3hours at 120o. Unreacted organic material is distilled off at 120o/1mm. The sodium salts are hydrolysed with water, and the organic fraction is separated by steam disillation, followed by fractional distillation. Before use, the distillate is passed, under nitrogen, through a column of activated silica gel. It turns yellow in air as it readily oxidizes and polymerises. [Russell J Am Chem Soc 78 1041 1956, Beilstein 5 IV 1532.]

上流・下流製品情報

上流原料

Motor benzolheavy benzolColumn plateコールタールナフサHeavy benzene2,3-ベンゾフラン

下流製品

1-インダノンインダン1-アミノインダンナフタレンアプリンジンINDANYL-1-CARBOXYLIC ACIDホモフタル酸スリンダク1-メチルナフタレンインデロキサジン·塩酸塩2,3-ベンゾフラン臭化トリフェニルホスホニウム2-アミノインダンジベンゾ[def,mno]クリセン2-ブロモインデン
補足説明 · 1 件

定義indene: A colourless flammable hydrocarbon,C9H8; r.d. 0.996; m.p.–1.8°C; b.p. 182.6°C. Indene is anaromatic hydrocarbon with a five-memberedring fused to a benzenering. It is present in coal tar and isused as a solvent and raw materialfor making other organic compounds.