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
Show more names
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
- Formal charge
- 0
- Complexity
- 66.9
Experimental & physicochemical properties
Solubility
MISCIBLE WITH ALCOHOL, CHLOROFORM, ETHER
Water solubility of 200 mg/l
Very soluble in acetone, chloroform, ethyl ether
Vapor Pressure
1.4 [mmHg]
1.4 mm Hg at 25 °C
Physical Description
Liquid
Colorless liquid with a fruity odor; [Merck Index]
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
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- alcohol: miscible(lit.)
- form
- clear liquid
- color
- Colorless to Almost colorless
- Water Solubility
- insoluble
- Specific Heat Capacity
- 2.39 J/ · Cp(liquid): 2.39 J/(g·K), at 25℃
- Merck
- 14 · 14,5118
- BRN
- 1698014 · 1698014
- Henry's Law Constant
- 6.8 · 6.8×10-3 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 2.8 · 2.8(20℃)
- InChI
- 1S/C10H22O/c1-9(2)5-7-11-8-6-10(3)4/h9-10H,5-8H2,1-4H3
- InChIKey
- AQZGPSLYZOOYQP-UHFFFAOYSA-N
- SMILES
- CC(C)CCOCCC(C)C
- LogP
- 5.078 at · 5.078 at 25℃
- CAS DataBase Reference
- 544 · 544-01-4(CAS DataBase Reference)
- FDA UNII
- 5 X9P91566R · 5X9P91566R
- NIST Chemistry Reference
- 1 · Butane, 1,1'-oxybis[3-methyl-(544-01-4)
- EPA Substance Registry System
- 1 · Butane, 1,1'-oxybis[3-methyl- (544-01-4)
- UNSPSC Code
- 12352112 · 12352112
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS09
- Signal word
- Warning
- Hazard statements
- 411 · H411-H226
- Precautionary statements
- 501 · P501-P273-P240-P210-P233-P243-P241-P242-P280-P370+P378-P391-P303+P361+P353-P403+P235
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,N
- Risk Statements
- 10 · 10-51/53-43-20
- Safety Statements
- 16 · 16-61-36/37-33-24/25
- RIDADR
- 3271 · UN 3271 3/PG 3
- WGK Germany
- 2 · 2
- RTECS
- 5433750 · EK5433750
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29091900 · 29091900
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 InhalationAquatic · Acute Tox. 3 InhalationAquatic Chronic 2Flam. Liq. 3Skin Sens. 1
- Hazardous Substances Data
- 544 · 544-01-4(Hazardous Substances Data)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Other Hazardous Reactions
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
Isoamyl ether
D: Other compounds that may form peroxides
Kelly
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flammable liquids - Category 3
Hazardous Reactivities and Incompatibilities
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
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
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).
Soil Adsorption/Mobility
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).
Environmental Biodegradation
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
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.
Volatilization from Water/Soil
The Henry's Law constant for di-iso-amyl ether is estimated as 1.5X10-3 atm-cu m/mole(SRC) from its vapor pressure, 1.4 mm Hg, and water solubility, 200 mg/l(1). This Henry's Law constant indicates that di-iso-amyl ether is expected to volatilize from water surfaces(2,SRC). Based on this Henry's Law constant, the estimated volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec) is approximately 4.4 hours(2,SRC). The estimated volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is approximately 5.2 days(2,SRC). Di-iso-amyl ether's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). Volatilization of di-iso-amyl ether from dry soil surfaces is expected(SRC) based on a vapor pressure of 1.4 mm Hg at 25 °C(1).
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of di-iso-amyl ether with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum(2). Di-iso-amyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3).
Environmental Fate/Exposure Summary
Di-iso-amyl ether's use as a solvent, in the manufacture of lacquers, and in regenerating rubber may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1.4 mm Hg at 25 °C indicates that di-iso-amyl ether will exist solely as a vapor in the ambient atmosphere. Vapor-phase di-iso-amyl ether 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 14 hours. Direct photolysis is not expected to be an important removal process since aliphatic ethers do not absorb light in the environmental spectrum. If released to soil, di-iso-amyl ether is expected to have high mobility based upon an estimated Koc of 120. Volatilization from moist soil surfaces may be an important fate process based upon an estimated Henry's Law constant of 1.5X10-3 atm-cu m/mole. Di-iso-amyl ether is expected to volatilize from dry soil surfaces based upon its vapor pressure. Di-iso-amyl ether reached 8% of its theoretical BOD over 2 weeks using an activated sludge seed, indicating biodegradation may be an important fate process in both soil and water. If released into water, di-iso-amyl ether is not expected to adsorb to suspended solids and sediment in water based upon the estimated Koc. Volatilization from water surfaces may be an important fate process based on this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4.4 hours and 5.2 days, respectively. BCFs ranging from 84 to 313 in carp suggest bioconcentration in aquatic organisms is moderate to high. Di-iso-amyl ether is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups. Occupational exposure to di-iso-amyl ether may occur through handling and use of consumer lacquer producats, inhalation and dermal contact with this compound at workplaces where di-iso-amyl ether is used. (SRC)
Antidote and Emergency Treatment
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Provide a low-stimulus environment. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Treat frostbite by rapid rewarming ... . /Ethers and related compounds/
Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W TKO /SRP: To keep open, "minimal flow rate"/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors for hypotension with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Ethers and related compounds/
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
- risk_code
- 10-51/53-43-20
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS09
- hazard_code
- Xn,N
- safety_code
- 16-61-36/37-33-24/25
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H411-H226
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 InhalationAquatic Chronic 2Flam. Liq. 3Skin Sens. 1
- Precautionary statements
- P501-P273-P240-P210-P233-P243-P241-P242-P280-P370+P378-P391-P303+P361+P353-P403+P235
- Hazardous Substances Data
- 544-01-4(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
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.
General Manufacturing Information
All Other Chemical Product and Preparation Manufacturing
Butane, 1,1'-oxybis[3-methyl-: ACTIVE
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Diisoamyl ether is an ether.
Related reactions
Linked notes
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