2-Ethylhexan-1,3-diol (Gemisch derDL- und meso-Form)

2-Ethyl-1,3-Hexanediol

HCID 7211CAS 94-96-2

Grundinformationen

Standard-SMILES
CCCC(O)C(CC)CO
InChIKey
RWLALWYNXFYRGW-UHFFFAOYSA-N
Summenformel
C8H18O2
Durchschnittliche Molmasse
146,23 g/mol
Monoisotopische Masse
146,13067982

Überblick

2-Ethyl-1,3-hexanediol is an aliphatic alcohol.

Namen und Bezeichner

Bevorzugter Name
2-Ethyl-1,3-Hexanediol
IUPAC
2-ethylhexane-1,3-diol
Lokaler Name
2-Ethylhexan-1,3-diol (Gemisch derDL- und meso-Form)
Englischer Name
2-Ethyl-1,3-hexanediol
Summenformel
C8H18O2
Molmasse
146.23

Namen und Synonyme

2-ETHYL-1,3-HEXANEDIOL94-96-2Ethohexadiol1,3-Hexanediol, 2-ethyl-Repellent 612Rutgers 612Carbide 6-126-12 insect repellent2-Ethyl-1,3-hexylene glycol2-Ethyl-3-propyl-1,3-propanediol3-Hydroxymethyl-n-heptan-4-olENT 375
Weitere Namen anzeigen
EHDETHYL HEXANEDIOL6-12Etohexadiol2-ethyl-3-hexanediol2-ETHYL-1,3-HEXANDIOL2-ETHYLHEXANE-1,3-DIOLent375
DTXSID4025292Latka 612NSC-3881M9JGK7U88VEPA Pesticide Chemical Code 041001DTXCID405292NSC3881RefChem:138417

Datenbank-Bezeichner

CAS
94-96-2
PubChem CID
7211
DTXSID
DTXSID4025292
ChEMBL
CHEMBL1451179
ChEBI
CHEBI:34273
UNII
M9JGK7U88V
EC Number
202-377-9
Nikkaji
J4.705H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,3
Polarare Oberfläche (TPSA)
40,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
5
Schwere Atome
10

Experimentelle und physikochemische Eigenschaften

PolymersOther Classes -> Alcohols and Polyols, Other
Cosmetics · 2 Einträge

Cosmetic ingredients (Ethyl Hexanediol) -> CIR (Cosmetic Ingredient Review)

Solvent

SpringerMaterials PropertiesBoiling point
OdorODORLESS
Density · 3 Einträge

0.9325 @ 22 °C/4 °C

FAINT ODOR OF WITCH HAZEL; DISTILLATION RANGE 241-249 °C; DENSITY: 0.939-0.943 @ 20 °C/20 °C /CRUDE/

0.9422 @ 20°C

Viscosity323 CENTIPOISES @ 20 °C

Physikochemische Eigenschaften

Schmelzpunkt
-40 °C · -40 °C (lit.)
Siedepunkt
241 · 241-249 °C (lit.)
Dichte
0.933 g/mL · 0.933 g/mL at 25 °C (lit.)
Dampfdichte
5 · 5 (vs air)
Dampfdruck
0.01 hPa · <0.01 hPa (20 °C)
Brechungsindex
20 · n20/D 1.451(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Danger

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: 1,3-Hexanediol, 2-ethyl-

1,3-Hexanediol, 2-ethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Hexanediol, 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: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13598

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

Other Safety InformationIMAP assessments - 1,3-Hexanediol, 2-ethyl-: Environment tier I assessment
Hazards Summary · 1 Eintrag

A moderate eye and mucous membrane irritant; Skin absorption may cause CNS depression; [HSDB] Produces birth defects when given to rats in high doses; No data on human exposure; [REPROTOX] Effects in high-dose animal studies include ataxia, somnolence, and liver changes; [RTECS] An irritant; May cause serious injury to eyes; May be absorbed through skin; [MSDSonline]

NFPA Hazard Classification · 3 Einträge

1 - Materials that, under emergency conditions, can cause significant irritation.

1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.

0 - Materials that in themselves are normally stable, even under fire conditions.

Hazard Classes and Categories · 4 Einträge

Eye Dam. 1 (100%)

Eye damage - category 1

Serious eye damage/eye irritation - Category 2A

Eye Dam. 1

Skin, Eye, and Respiratory Irritations... MODERATELY IRRITATING TO EYES, MUCOUS MEMBRANES, BUT NOT TO SKIN.

Sicherheit und Schutzausrüstung

Fire Fighting ProceduresWATER OR FOAM MAY CAUSE FROTHING. "ALCOHOL" FOAM.
Preventive Measures · 1 Eintrag

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.

Protective Action Criteria (PAC) · 3 Einträge

4.2 [mg/m3]

46 [mg/m3]

280 [mg/m3]

Toxikologische Informationen

InteractionsSUCKER CONTROL IN TOBACCO WAS EXHIBITED BY 5% 2-ETHYL-1,3-HEXANEDIOL BY ITSELF, & ESPECIALLY WHEN COMBINED WITH MALEIC HYDRAZIDE.
Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Human Toxicity Excerpts · 5 Einträge

... MODERATELY IRRITATING TO EYES, MUCOUS MEMBRANES, BUT NOT TO SKIN. INGESTION CAUSES CNS DEPRESSION.

ONCE ABSORBED /THROUGH SKIN/ IT CAUSES /CNS DEPRESSION/ BUT LITTLE ORGANIC INJURY.

TWO HUNDRED TWENTY-THREE HUMAN VOLUNTEERS WERE PATCH TESTED FOR SENSITIZATION WITH THE UNDILUTED PRODUCT. THREE ... DEVELOPED MILD SKIN REDDENING; OTHERWISE NO SIGNIFICANT SIGNS OF SENSITIZATION OCCURRED.

WHEN TESTED AS A REPELLENT IN STICK FORMULATIONS CONTAINING SODIUM STEARATE, NONE SHOWED SIGNS OF IRRITATION, SENSITIZATION, OR FATIGUING OF THE SKIN. /REPELLENT FORMULATION CONTAINING SODIUM STEARATE/

ITS WIDESPREAD USE CONFIRMS ITS LACK OF HAZARD & IRRITANT PROPERTIES IN MAN.

Non-Human Toxicity Excerpts · 5 Einträge

... WHEN RABBITS WERE INUNCTED DAILY FOR 90 DAYS, 2 ML/KG (1.88 G/KG) CAUSED ABOUT 50% MORTALITY, & SOMEWHAT GREATER MORTALITY RESULTED @ ... 4 ML/KG (3.76 G/KG). CONTINUED CONTACT CAUSED...IRRITATION TO SKIN ... & ANIMALS THAT DIED EXHIBITED MODERATE LIVER & KIDNEY INJURY. LEUKOCYTOSIS WAS OBSERVED IN ONLY 1 ANIMAL TREATED AT THE 4 ML/KG ... LEVEL.

... RATS WERE FED UP TO 2 YR ON DIETS CONTAINING 2.0, 4.0, & 8.0% OF 2-ETHYL-1,3-HEXANEDIOL. GROWTH WAS DEPRESSED @ ALL LEVELS. AT 8% LEVEL, ALL ANIMALS WERE DEAD WITHIN 18 WK ... DUE TO INANITION. THOSE @ 4.0 & 2.0% LEVELS SURVIVED, & AUTOPSY REVEALED NO ORGANIC INJURY ATTRIBUTABLE TO THE GLYCOL.

... RATS FED FOR 90 DAYS ON DIET THAT PROVIDED DAILY INTAKE OF 0.70 G/KG ... DID NOT GROW AS WELL AS CONTROLS, BUT ... SUFFERED NO ORGANIC INJURY. WHEN ... MAINTAINED ON ... DAILY INTAKE OF 0.48 G/KG, GROWTH WAS NORMAL & NO DETECTABLE ADVERSE EFFECTS ... NOTED.

RATS EXPOSED TO ESSENTIALLY SATURATED VAPORS GENERATED AT ROOM TEMPERATURE FOR 2 HR SURVIVED; THOSE EXPOSED FOR 8 HR DIED. THE RATS EXPOSED TO A MIST GENERATED @ 170 °C FOR 2 HR ALSO SURVIVED WHEREAS THOSE EXPOSED FOR 8 HR DIED. THOSE EXPOSED TO A FOG GENERATED AT 70 °C WITH A NEBULIZER AT A CONCN ESTIMATED TO BE 4800 PPM FOR 8 HR ALL SURVIVED.

For more Non-Human Toxicity Excerpts (Complete) data for 2-ETHYL-1,3-HEXANEDIOL (10 total), please visit the HSDB record page.

Toxicity DataLC (rat) > 4,800 ppm/8h

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29053980
RTECS-Nr.
MO2625000
risk_code
41
Toxizität
LD50 in male, female rats (ml/kg): 9.85, 4.92 orally (Ballantyne)

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

P - Antiparasitic products, insecticides and repellents

QP - Antiparasitic products, insecticides and repellents

Metabolism/Metabolites... UNABLE TO DETECT ANY METABOLITES ... WHEN ... FED TO RABBITS.
Absorption, Distribution and Excretion · 3 Einträge

TOPICAL & IV APPLICATIONS OF (14)C LABELED 2-ETHYL-1,3-HEXANEDIOL WERE MADE TO HAIRLESS DOGS. AFTER TOPICAL ADMIN, EXCRETION WAS NEARLY COMPLETE AFTER 4-5 DAYS. RADIOACTIVITY LEVELS IN BLOOD SAMPLES WERE TOO LOW TO BE ACCURATELY MEASURED. WITHIN 48-96 HR AFTER APPLICATION ONLY SMALL AMT OF RADIOACTIVITY WAS RECOVERED FROM SKIN. RATE OF URINARY EXCRETION AFTER IV ADMIN WAS COMPARABLE TO THAT RECORDED IN HUMANS. IT IS SUGGESTED THAT PERMEABILITY OF HAIRLESS DOG'S SKIN MAY BE QUITE SIMILAR TO THAT OF HUMAN SKIN.

AN IN VITRO APPARATUS WAS USED TO STUDY SKIN EVAPORATION & PENETRATION OF MOSQUITO REPELLENTS. IN VITRO REPELLENT DURATION, CALCULATED FROM REPELLENT EVAPORATION RATES, WAS COMPARED TO IN VIVO DURATION AT THE SAME DOSE (0.3 MG/SQ CM) TO ASSESS VALIDITY OF THE MODEL. IN VITRO DURATIONS FOR 2-ETHYL-1,3-HEXANEDIOL CORRELATED WITH IN VIVO DURATIONS, ALTHOUGH IN VITRO DURATION WAS LONGER THAN IN VIVO DURATION.

PERCENTAGE PENETRATION OF 2-ETHYL-1,3-HEXANEDIOL WAS DETERMINED ON HAIRLESS DOGS AT 4 UG/SQ CM. MEAN PERCENTAGE PENETRATION INCREASED SLIGHTLY WITH INCREASED DOSE OF 2-ETHYL-1,3-HEXANEDIOL, BUT NONE OF THESE CHANGES DIFFERED SIGNIFICANTLY AT THE 95% CONFIDENCE LEVEL.

Verwendung und Herstellung

Uses · 5 Einträge

CIR ingredient: Ethyl Hexanediol

Used as a solvent for resins; as a plasticizer; as a chemical intermediate in the production of polyurethane resins; as an insect repellent; in cosmetics; as a vehicle and solvent in printing inks; in medicines; as a chelating agent for boric acid; [HSDB]

Except for cosmetics, voluntarily removed from US and Canadian markets in 1991 after high-dose animal experiment showed poor lung expansion in offspring; [REPROTOX]

SOLVENT FOR RESINS & INKS; PLASTICIZER; CHEM INTERMEDIATE IN PRODN OF POLYURETHANE RESINS

INSECT REPELLENT, COSMETICS; VEHICLE AND SOLVENT IN PRINTING INKS, MEDICINE, CHELATING AGENT FOR BORIC ACID

U.S. Production2023: 75,000 - <500,000 lb
Industry UsesIntermediate
Methods of Manufacturing · 2 Einträge

PREPD BY CATALYTIC TRIMOLECULAR CONDENSATION OF BUTYRALDEHYDE WITH MAGNESIUM ALUMINUM ETHOXIDE YIELDING THE MONOBUTYRATE OF 2-ETHYL-1,3-HEXANEDIOL, FOLLOWED BY HYDROLYSIS OF THE ESTER.

... PRODUCED COMMERCIALLY BY HYDROGENATION OF BUTYRALDOL (2-ETHYL-3-HYDROXYCAPROALDEHYDE).

Formulations/Preparations · 2 Einträge

WIDELY USED IN MIXTURE (2 PARTS) WITH DIMETHYL PHTHALATE (6 PARTS) & INDALONE (2 PARTS).

GRADES: USP (AS ETHOHEXADIOL); INDUSTRIAL

Household ProductsInformation on 1 consumer products that contain Ethohexadiol in the following categories is provided:
Anwendungen · 1 Eintrag

Verwenden2-Ethyl-1,3-hexanediol is produced commercially by hydrogenating butyraldol (2-ethyl-3-hydroxycaproaldehyde). It is used largely as an insect repellent but also as a solvent for resins and inks, a plasticizer, and a chemical intermediate in the production of polyurethane resins .

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Vorgelagerte Rohstoffe

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