Diisopentyl ether

HCID 10989CAS 544-01-4

Basic information

Standard SMILES
CC(C)CCOCCC(C)C
InChIKey
AQZGPSLYZOOYQP-UHFFFAOYSA-N
Molecular formula
C10H22O
Average molar mass
158.28 g/mol
Monoisotopic mass
158.16706532

Overview

Diisoamyl ether is an ether.

Names & identifiers

Preferred name
Diisopentyl ether
IUPAC
3-methyl-1-(3-methylbutoxy)butane
English name
Isopentyl ether
Molecular formula
C10H22O
Molecular weight
158.28

Names & synonyms

Diisopentyl etherIsoamyl etherDiisoamyl etherIsopentyl ether544-01-4Isoamyl oxideDI-ISO-AMYL ETHER3-methyl-1-(3-methylbutoxy)butaneDi-3-methylbutyl etherButane, 1,1'-oxybis[3-methyl-1,1'-Oxybis(3-methylbutane)NSC 9281
Show more names
isoamyloxideIsoaMyl etheDiisoaMy etherlsopentyl ether
1,1'-Oxylbis(3-methylbutane)HSDB 2773Butane, 1,1'-oxybis(3-methyl-EINECS 208-857-4DTXSID8052198UNII-5X9P91566RAI3-02268Butane, 1,1'-oxylbis(3-methyl-

Database identifiers

CAS
544-01-4
PubChem CID
10989
DTXSID
DTXSID8052198
ChEBI
CHEBI:183294
UNII
5X9P91566R
EC Number
208-857-4
Nikkaji
J6.409B

Properties

Computed structural properties

XLogP
3.5
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
6
Heavy atoms
11

Experimental & physicochemical properties

SolventsSolvents -> Ethers (<C12)
SpringerMaterials PropertiesBoiling point
LogPLog Kow = 4.25
OdorPLEASANT, FRUITY ODOR
Density0.7777 @ 12 °C/4 °C
Color/FormCOLORLESS LIQUID

Physicochemical properties

Melting point
-28.46 °C · -28.46°C (estimate)
Boiling point
173 °C · 173 °C (lit.)
Density
0.778 g/mL · 0.778 g/mL at 25 °C (lit.)
vapor pressure
2.5 hPa · 2.5 hPa (20 °C)
refractive index
20 · n20/D 1.407
Flash point
46 °C · 46 °C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P210, P233, P240, P241, P242, P243, P261, P271, P272, P273, P280, P302+P352, P303+P361+P353, P304+P340, P316, P321, P333+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 293 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

Hazard information

Regulatory Information · 4 items

Chemical: Butane, 1,1'-oxybis[3-methyl-

Butane, 1,1'-oxybis[3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butane, 1,1'-oxybis[3-methyl- 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: 29-10-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/11852

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

Hazards SummaryOral LD50 (mouse) >10 gm/kg; [RTECS] An irritant; [MSDSonline]
Other Hazardous Reactions · 1 item

All ethers should be tested and separated from peroxidic products before distillation or evaporation. Many ethers autoxidize so readily that peroxidic compounds form, sometimes to dangerous levels, on storage in nonairtight containers. /Short alkyl-chain ethers/

Peroxide Forming Chemical · 3 items

Isoamyl ether

D: Other compounds that may form peroxides

Kelly

Hazard Classes and Categories · 2 items

Flam. Liq. 3 (100%)

Flammable liquids - Category 3

Hazardous Reactivities and Incompatibilities · 1 item

alpha-Hydroperoxy ethers are obtained readily from the autoxidation of most ethers /including di-isoamyl ether/ containing alpha-hydrogens. From certain ethers ... the initially formed alpha-hydroperoxy ethers can ... with acid treatment, form dangerously sensitive and explosive polymeric peroxides.

Safety & protection

Disposal Methods · 3 items

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.

Used ether containers, which are suspected of containing ether crystals or solids, are especially hazardous and may require bomb-squad assistance for their disposal. /Short alkyl-chain ethers/

This compound should be susceptible to removal from waste water by air stripping. /Bis(2-chloroethyl)ether/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC),determined from a structure estimation method(2), indicates that di-iso-amyl ether is expected to have high mobility in soil(SRC). Volatilization of di-iso-amyl ether from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(4). Volatilization of di-iso-amyl ether from dry soil surfaces is expected(SRC) based on this compound's vapor pressure(4). Biodegradation of di-iso-amyl ether in soil may be important(SRC), based upon its biodegradation in an aqueous screening study(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that di-iso-amyl ether is not expected to adsorb to suspended solids and sediment in water(SRC). Di-iso-amyl ether may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.5X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(4). Estimated volatilization half-lives for a model river and model lake are 4.4 hours and 5.2 days, respectively(3,SRC). According to a classification scheme(5), BCFs ranging from 84 to 313 in carp(6), suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC). Di-iso-amyl ether reached 8% of its theoretical BOD over 2 weeks using an activated sludge inoculum(6); 0% BOD was reached in a 5-day BOD study using a sewage inoculum(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), di-iso-amyl ether, which has a vapor pressure of 1.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase di-iso-amyl ether 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 14 hours(3,SRC). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(4).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for di-iso-amyl ether can be estimated to be about 120(SRC). According to a classification scheme(2), this estimated Koc value suggests that di-iso-amyl ether is expected to have high mobility in soil(SRC).

Artificial Pollution SourcesDi-iso-amyl ether's production and use as a solvent, in the manufacture of lacquers, and in regenerating rubber(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

Many ethers are known to be resistant to biodegradation(1). 0% biological oxygen demand was measured for di-iso-amyl ether in aqueous screening tests which used sewage inocula for 5 days(2). Di-iso-amyl ether reached 8% of its theoretical BOD over 2 weeks using an activated sludge inoculum(3).

Environmental Bioconcentration · 1 item

BCFs of 117 to 313 and 84 to 260 were measured for di-iso-amyl ether in carp at chemical concentrations of 60 and 6 ug/l, respectively(1). According to a classification scheme(2), these BCFs suggest bioconcentration in aquatic organisms is moderate to high.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
EK5433750
ridadr
UN 3271 3/PG 3
hs_code
29091900

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as a solvent in fats, oils, waxes, resins, Grignard reaction, lacquers, and regenerating rubber; [HSDB]

SOLVENT IN GRIGNARD REACTION; ALSO AS SOLVENT OF ODOROUS PRINCIPLES; MFR LACQUERS; REGENERATING RUBBER

General solvent for fats, oils, waxes, resins, etc.

U.S. Production2023: <50,000 lb
Consumer UsesSolvent
Industry UsesSolvent
General Manufacturing Information · 2 items

All Other Chemical Product and Preparation Manufacturing

Butane, 1,1'-oxybis[3-methyl-: ACTIVE

Applications · 3 items

UsesIsoamyl ether has been used in the synthesis of:silver nanoparticles in a continuous flow tubular microreactorsingle-crystal Ag nanocubes (with slight truncation) of around 13.5nm in edge length

UsesIsopentyl ether is used in the synthesis of silver nanoparticles in a continuous flow tubular microreactor,single-crystal Ag nanocubes (with slight truncation) of around 13.5nm in edge length.

UsesSolvent in Grignard reaction; also as solvent of odorous principles; manufacture of lacquers; regenerating rubber.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
江西益众化工有限公司15307925109 15350027073 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

DefinitionChEBI: Diisoamyl ether is an ether.

Related reactions

7 records

Linked notes

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