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2-エチルヘキサナール

2-Ethylhexanal

HCID 31241
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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
123-05-7
標準SMILES
CCCCC(C=O)CC
InChIKey
LGYNIFWIKSEESD-UHFFFAOYSA-N
分子式
C8H16O
平均分子量
128.21 g/mol
単同位体質量
128.12011513

概要

2-ethylhexaldehyde is a white liquid with a mild odor. Floats on water. (USCG, 1999)

名称と識別子

優先名称
2-Ethylhexanal
IUPAC
2-ethylhexanal
現地名
2-エチルヘキサナール
英語名
2-ETHYLHEXANAL
分子式
C8H16O
分子量
128.21

名称と別名

2-Ethylhexanal123-05-72-EthylhexaldehydeHexanal, 2-ethyl-3-Formylheptane2-Ethylcaproaldehyde2-EthylhexylaldehydeButylethylacetaldehydeEthylbutylacetaldehydeETHYLHEXALDEHYDEButyl ethyl acetaldehydealpha-Ethylcaproaldehyde
名称をさらに表示
2-エチルヘキサナールブチルエチルアセトアルデヒド2エチルヘサナール2-エチルヘキサンアルデヒド2-エチルヘキシルアルデヒドオクチルアルデヒド(2-エチルヘキシルアルデヒド)2-エチルヘキサアルデヒドオクチルアルヒド2‐エチルヘキサナールエチルヘキサナール, 2-α-EthylhexanalETHYLHEXANAL, 2-hexanal,2-ethyl-2-ETHYLHEXYL ALDEHYDE2-ETHYLHEXAL2-ethyl-hexana
beta-Propyl-alpha-ethylacroleinDTXSID9025291alpha-EthylhexanalSEN8S34O6UNSC-42871DTXCID005291CHEBI:87809EHALD

データベース識別子

CAS
123-05-7
PubChem CID
31241
DTXSID
DTXSID9025291
ChEMBL
CHEMBL1558074
ChEBI
CHEBI:87809
UNII
SEN8S34O6U
EC Number
204-596-5
Nikkaji
J24.149K

物性

構造計算による物性補完中

XLogP
2.6
極性表面積
17.1 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
5
重原子数
9
形式電荷
0
複雑度
69

実験および物理化学的性質

Chemical Classes · 2 件

Other Classes -> Aldehydes

Flammable agents - 2nd degree

LogPlog Kow = 3.07, measured OECD Method 107
OdorMild odor
Density · 4 件

0.82 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8540 g/cu cm at 20 °C

Bulk density = 6.8 lb/gal

Relative density (water = 1): 0.85

Flavoring AgentsEU Flavoring substances
Viscosity1.0527 cP at 25 °C
Color/FormColorless high-boiling liquid
Solubility · 6 件

less than 1 mg/mL at 70 °F (NTP, 1992)

Miscible with most organic solvents

Slightly soluble in carbon tetrachloride; soluble in ethanol and ether

In water, less than 0.5 g/100g at 25 °C

In water, 400 ppm at 25 °C

Solubility in water, g/100ml at 20 °C: 0.07

Flash Point · 4 件

125 °F (NTP, 1992)

46 °C

112 °F (44 °C) (Closed cup)

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

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P272, P280, P302+P352, P303+P361+P353, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1785 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 6 件

Chemical: Hexanal, 2-ethyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Hexanal, 2-ethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanal, 2-ethyl- 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)

Status: Active Update: 02-07-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/13822

Hexanal, 2-ethyl-: 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 LabelFlammable Liquid
Fire Hazards · 3 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 46 °C explosive vapour/air mixtures may be formed.

Fire PotentialDangerous fire hazard; spontaneously flammable in air.
Health Hazards

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

Aldehydes are readily oxidized to organic acids, which, in turn, can serve as substrates for fatty acid oxidation pathways and the Krebs cycle. ... Oxidation of aldehydes is catalyzed by aldehyde dehydrogenase, which has been found in the brain, erythrocytes, liver, kidney, heart, and placenta. /Aldehydes/

... The detoxification of aldehydes can be seen to proceed basically via two routes: (1) an oxidation to yield readily metabolized acids; (2) inactivation by reaction with sulfhydryl groups, particularly glutathione. Under conditions that either deplete glutathione levels, or that result in an inhibition of aldehyde dehydrogenase (for example, Antabuse treatment), the acute and chronic effects of aldehyde toxicity might be more fully expressed. /Aldehydes/

用途と製造

Uses · 6 件

Used as a disinfectant and chemical intermediate for perfumes and other chemicals; [HSDB]

Using Disinfectants or Biocides [Category: Clean]

Organic synthesis, perfumes

As a disinfectant

2-Ethylhexanal is used for the manufacture of 2-ethylhexanol and 2-ethylhexanoic acid. Aminating hydrogenation leads to 2-ethylhexylamines, which are important intermediates in organic syntheses. The condensation of 2-ethylhexanal with aromatic amines results in products that are used as vulcanizing agents and antioxidants for rubber.

CHEMICAL INTERMEDIATE IN PERFUMES,2-ETHYLHEXANOIC ACID;1-TETRADECANOL; 2-(2-CYANOETHYL)-2-ETHYLHEXANAL

U.S. Production · 6 件

2023: 50,000,000 - <100,000,000 lb

(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Hexanal, 2-ethyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5193]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Hexanal, 2-ethyl-. Aggregated National Production Volume: 50 to < 100 million pounds.

関連反応

38 件
反応記録を作成
HRID 53410 の反応式
HRID 53410生成物として反応物としてuspto-grants-1997_04
HRID 53411 の反応式
HRID 53411反応物としてuspto-grants-1997_04
HRID 64940 の反応式
HRID 64940反応物としてuspto-grants-1986_09
HRID 74133 の反応式
HRID 74133反応物としてuspto-grants-2014_09
HRID 170402 の反応式
HRID 170402反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 188546 の反応式
HRID 188546反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 256269 の反応式
HRID 256269生成物としてuspto-grants-1987_10
HRID 374861 の反応式
HRID 374861反応物としてuspto-grants-1996_01
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46 °C c.c., 52 °C o.c.

Boiling Point · 3 件

326.1 °F at 760 mmHg (NTP, 1992)

163 °C

163 °C

DecompositionWhen heated to decomposition it emits acrid and irritating fumes.
Melting Point · 2 件

less than -100 °C

-85 °C

物理化学的性質

融点
-76 °C · -76 °C
沸点
55 °C13.5 · 55 °C13.5 mm Hg(lit.)
比重(密度)
0.822 g/mL · 0.822 g/mL at 25 °C(lit.)
蒸気圧
2 · 2-2.8hPa at 18.5-23.4℃
屈折率
20 · n20/D 1.415(lit.)
闪点
108 °F · 108 °F
貯蔵温度
Flammables area
溶解性
0.01 g/l · 0.01g/l
外見
液体
色
無色透明
爆発限界(explosive limit)
1 · 1.0-6.6%(V)
水溶解度
水にわずかに溶ける。
BRN
1700556 · 1700556
Henry's Law Constant
1.2 · 1.2×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
安定性
Air Sensitive
化粧品成分の機能
香料
InChI
1S/C8H16O/c1-3-5-6-8(4-2)7-9/h7-8H,3-6H2,1-2H3
InChIKey
LGYNIFWIKSEESD-UHFFFAOYSA-N
SMILES
[H]C(=O)C(CC)CCCC
LogP
3.07 at · 3.07 at 25℃
表面張力
47.1 mN/m · 47.1mN/m at 730mg/L and 20.2℃
CAS データベース
123 · 123-05-7(CAS DataBase Reference)
EPAの化学物質情報
2 · 2-Ethylhexanal (123-05-7)

化学的性質

化学的特性clear liquid

· 2 件

Inhalation may be irritating to mucous membrane; overexposure may cause dizziness and collapse. Ingestion causes irritation of mouth and stomach. Contact with eyes or skin causes irritation. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards SummaryA skin, eye, and respiratory tract irritant; Flammable; Explosive mixtures with air may form above 46 deg C; [ICSC] An irritant; [MSDSonline]
DOT ID and Guide1191 129
Reactive GroupAldehydes
UN ClassificationUN Hazard Class: 3; UN Pack Group: III
TSCA Requirements · 2 件

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. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant 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. Hexanal, 2-ethyl- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

Reactivity AlertsHighly Flammable
Reactivity Profile · 1 件

2-ETHYLHEXALDEHYDE is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents Not to Be Used: Water may be ineffective

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Rest. Refer for medical attention .

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:

Safe StorageFireproof. Separated from acids, bases and oxidants. Cool. Well closed.
Firefighting HazardsVapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresUse dry chemical, carbon dioxide or foam extinguishers.
Storage ConditionsStore in tightly closed containers in a cool, well ventilated area away from oxidizers, strong bases and combustible materials.
Cleanup MethodsAbsorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep ethyl hexaldehyde out of a confined space, such as a sewer, because of the possibility of an explosion ...
Nonfire Spill ResponseExcerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

毒性情報

Body Burden2-Ethylhexaldehyde was qualitatively detected in the expired air from control and diabetic nonsmoking populations(1).
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 18(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexaldehyde is expected to have very high mobility in soil(SRC). Volatilization of 2-ethylhexaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-4 atm-cu m/mole(SRC), based upon its vapor pressure, 2 mm Hg(3), and water solubility, 400 mg/L(4). 2-Ethylhexaldehyde is expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure(SRC). Using OECD Method 301F (Ready Biodegradability, Manometric Respirometry Test) with a domestic activated sludge inoculum and a 28-day incubation period, 2-ethylhexaldehyde had a theoretical BOD of 71.8%(5) which classifies it as readily biodegradable(SRC). By analogy, isobutyraldehyde (a structurally similar branched saturated aldehyde to 2-ethylhexaldhyde), present at 30 mg/L, reached 81% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/L in the Japanese MITI test(6) which also classifies it as readily biodegradable(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 18(SRC), determined from a structure estimation method(2), indicates that 2-ethylhexaldhyde is not 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 8.4X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 2 mm Hg(4), and water solubility, 400 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 4.6 hours and 4.9 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 49(SRC), from its log Kow of 3.07(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). 2-Ethylhexaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Using OECD Method 301F (Ready Biodegradability, Manometric Respirometry Test) with a domestic activated sludge inoculum and a 28-day incubation period, 2-ethylhexaldehyde had a theoretical BOD of 71.8%(7) which classifies it as readily biodegradable(SRC). By analogy, isobutyraldehyde (a structurally similar branched saturated aldehyde to 2-ethylhexaldhyde), present at 30 mg/L, reached 81% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/L in the Japanese MITI test(8) which also classifies it as readily biodegradable(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-ethylhexaldehyde , which has a vapor pressure of 2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-ethylhexaldehyde 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Food Survey Values2-Ethylhexaldehyde has been qualitatively detected as a volatile compound of baked potatoes(1).
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Signs and Symptoms · 4 件

Cough. Sore throat.

Dry skin. Redness. See Inhalation.

Redness. Pain.

Abdominal pain. Nausea. Vomiting.

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2-ethylhexaldehyde can be estimated to be 18(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2-ethylhexaldehyde is expected to have very high mobility in soil(SRC).

Natural Pollution SourcesHas apparently not been reported to occur in nature. In public use since the 1950s.
Atmospheric ConcentrationsSOURCE DOMINATED: 2-Ethylhexaldehyde was qualitatively detected in ambient air samples collected in an industrial area in Mumbai, India in 2004(1).
Human Toxicity Excerpts · 1 件

/SIGNS AND SYMPTOMS/ The mucus membranes of the nasal and oral passages and the upper respiratory tract are affected, producing a burning sensation ... bronchial constriction, choking, and coughing. The eyes tear, and a burning sensation is noted on the skin of the face. /Aldehydes/

Artificial Pollution Sources · 2 件

2-Ethylhexaldehyde's production and use as an intermediate in organic syntheses and use in vulcanizing agents and antioxidants for rubber(1), and its use in perfumes(2) may result in its release to the environment through various waste streams(SRC).

2-Ethyhexaldehyde is a metabolite resulting from the biodegradation of bis(2-ethylhexyl) phthalate(1).

Environmental Biodegradation · 2 件

AEROBIC: Using OECD Method 301F (Ready Biodegradability, Manometric Respirometry Test) with a domestic activated sludge inoculum and a 28-day incubation period, 2-ethylhexaldehyde had a theoretical BODT of 71.8%(1) which classifies it as readily biodegradable(SRC). By analogy, isobutyraldehyde (a structurally similar branched saturated aldehyde to 2-ethylhexaldhyde), present at 30 mg/L, reached 81% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 100 mg/L in the Japanese MITI test(2).

PURE CULTURE: Uptake of oxygen by coccobacillus grown on di(2-ethylhexyl)phthalate using 2-ethylhexaldehyde as substrate was 66 uL/hour at 30 °C(1).

法規制情報

TSCA Requirements · 2 件

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. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant 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. Hexanal, 2-ethyl- is included on this list. Effective date: 9/30/91; Sunset date: 6/30/98.

安全データ

wgk
1
tsca
TSCA listed
rtecs
MN7525000
ridadr
UN 1191 3/PG 3
hs_code
29121990
risk_code
10-36/37/38-43-38-63
化審法
(2)-494
消防法
危-4-2-III
hazard_code
Xi,Xn
safety_code
26-36-36/37
hazard_class
3
packing_group
III
Hazard Classifications
Flam. Liq. 3Repr. 2Skin Sens. 1
ストレージクラス
3 - Flammable liquids
有毒物質データの
123-05-7(Hazardous Substances Data)
Consumer UsesSolvent
Industry UsesIntermediate
Methods of Manufacturing · 2 件

The base-catalyzed aldol condensation of butanal leads to 2-ethyl-2-hexenal, which is converted to 2-ethylhexanal by hydrogenation.

ALDOL CONDENSATION OF BUTYRALDEHYDE OR BUTYRALDEHYDE & ACETALDEHYDE IN BASE FOLLOWED BY HYDROGENATION

Formulations/PreparationsGrades: Technical
General Manufacturing Information · 3 件

All Other Basic Organic Chemical Manufacturing

Hexanal, 2-ethyl-: ACTIVE

In public use since the 1950s. Use in fragrances in the USA amounts to approximately 25,000 lb/yr.

応用分野

使用2-Ethylhexanal is used as an intermediate for chemical synthesisand in the production of pharmaceuticals and odorous substances.

一般的な説明White liquid with a mild odor. Floats on water.

上流・下流製品情報

上流原料

2-エチル-2-ヘキセナール2-エチル-1-ヘキサノールPiperidine, 1-(1E)-1-hexen-1-yl-2,2,6-trimethyl-1-Hexen-1-amine, N-(1,1-dimethylethyl)-N-(1-methylethyl)-, (1E)-2-ブチリデンシクロヘキサノン2-エチルヘキシルニトラートビス(2-エチルヘキシル)エーテル2-ブチルシクロヘキサノン2-エチル-2-ヘキセン-1-オール2-エチルヘキサン酸2-エチルヘキシル

下流製品

2-エチルヘキサン酸3-ヘプタノン3-ヘプタノールN,N-ジメチル-2-エチルヘキサン-1-アミン

補足説明

定義ChEBI: A fatty aldehyde that is heptane in which one of the hydrogens at position 3 has been replaced by a formyl group. It is a metabolite of the plasticisers di-2-ethylhexyl phthalate (DEHP) and di-2-ethylhexyl adipate (DEHA).