1,3-Pentadiene

HCID 62204

Basic information

CAS
2004-70-8
Standard SMILES
C=C/C=C/C
InChIKey
PMJHHCWVYXUKFD-SNAWJCMRSA-N
Molecular formula
C5H8
Average molar mass
68.12 g/mol
Monoisotopic mass
68.06260026

Overview

1,3-pentadiene appears as a clear colorless liquid with an acrid odor. A dangerous fire risk. Vapors are irritating to the eyes and respiratory system. Subject to polymerization if heated or contaminated. If the polymerization takes place inside a container, the container may violently rupture. Insoluble in water. Used to make intermediates and polymers.

Names & identifiers

Preferred name
1,3-Pentadiene
IUPAC
(3E)-penta-1,3-diene
English name
trans-1,3-Pentadiene
Molecular formula
C5H8
Molecular weight
68.12

Names & synonyms

1,3-PENTADIENEPiperylene504-60-91-MethylbutadieneFW963NF88B1-methyl-1,3-butadieneDTXSID3027160RefChem:906913DTXCID00809454207-995-2trans-1,3-Pentadienetrans-Piperylene
Show more names
(e)-3-pentadiene(E)-CH2=CHCH=CHCH31,trans-3-Pentadiene
2004-70-8(3E)-penta-1,3-diene(E)-1,3-Pentadiene1,3-Pentadiene, (3E)-trans-1-Methylbutadiene(3E)-1,3-Pentadienetrans-Penta-1,3-dieneRCRA waste number U186

Database identifiers

CAS
2004-70-8、41050-31-1、504-60-9、68308-15-6
PubChem CID
62204
DTXSID
DTXSID50858710
ChEBI
CHEBI:74165
UNII
00OA1GPF8R
EC Number
207-995-2、217-909-5
Nikkaji
J43.494I、J6.219G

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
Polymers · 2 items

Plastics & Rubber -> Other Monomers

Plastics & Rubber -> Other Monomers

SpringerMaterials PropertiesBoiling point
LogP · 4 items

log Kow= 2.44

log Kow= 2.44

1.5 (estimated)

2.44

Density · 5 items

0.6834 at 68 °F (average value for cis and trans isomers) (USCG, 1999) - Less dense than water; will float

0.6760 @ 20 °C/4 °C

0.6710 g/ml @ 25 °C

0.7 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.7

Color/Form · 2 items

Colorless liquid

Colorless liquid

Physicochemical properties

Melting point
-87 °C · -87 °C (lit.)
Boiling point
42 °C · 42 °C (lit.)
Density
0.678 g/mL · 0.678 g/mL at 20 °C 0.683 g/mL at 25 °C (lit.)
vapor density
2.4 · 2.4 (vs air)
vapor pressure
6.56 psi · 6.56 psi ( 20 °C)
refractive index
20 · n20/D 1.433(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 5.1% (13 of 256) of reports.

Danger

H225 (94.9%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P301+P316, P303+P361+P353, P331, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 256 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 6 items

Chemical: 1,3-Pentadiene

Chemical: 1,3-Pentadiene, (E)-

1,3-Pentadiene is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Pentadiene 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)

1,3-Pentadiene, (3E)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Pentadiene, (3E)- 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: No longer Valid Update: 30-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/1772

1,3-Pentadiene: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

DOT LabelFlammable Liquid
Fire Hazards · 2 items

Special Hazards of Combustion Products: Fire produces irritating and poisonous gases.

Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting.

Fire Potential · 2 items

HIGHLY FLAMMABLE, DANGEROUS FIRE RISK.

A very dangerous fire and explosion hazard when exposed to heat or flame; can react vigorously with oxidizing materials.

Health HazardsVapors may cause dizziness or suffocation; contact may irritate skin and eyes. (USCG, 1999)
Hazards Summary · 2 items

A skin and eye irritant; Inhaled at high concentrations, it may act as a simple asphyxiant; [NJ-HSFS] Causes somnolence and ataxia in lethal-dose inhalation studies of rodents; [RTECS] See trans-1,3-Pentadiene.

In lethal concentration studies, rats have somnolence, ataxia, and dyspnea; [RTECS] May cause moderate skin irritation on prolonged contact, based on animal studies; [CHEMINFO] An irritant; [MSDSonline]

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

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

First Aid Measures · 4 items

Fresh air, rest. Seek medical attention if you feel unwell.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention if skin irritation occurs.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Do NOT induce vomiting. Seek medical attention if you feel unwell.

First AidINHALATION: Move victim to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Safe StorageSeparated from strong oxidants. Fireproof. Store in an area without drain or sewer access. Ventilation along the floor.
Fire Fighting ProceduresWATER MAY BE EFFECTIVE.
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Toxicology

Environmental Fate · 6 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a log Kow of 2.44(2) and a regression-derived equation(3), indicates that 1,3-pentadiene is expected to have low mobility in soil(SRC). Volatilization of 1,3-pentadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.069 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of 1,3-pentadiene from dry soil surfaces may exist based upon a vapor pressure of 405 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a log Kow of 2.44(2) and a regression-derived equation(3), indicates that 1,3-pentadiene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected to be an important fate process(3) based upon an estimated Henry's Law constant of 0.069 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 and 78 hrs, respectively(SRC). According to a classification scheme(5), an estimated BCF of 15(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. No biodegradation data were located for 1,3-pentadiene(SRC), but the biodegradation half-life of 1,3-butadiene has been reported as 7 days in aerobic water and 28 days in anaerobic water(7). These data suggest that 1,3-pentadiene will also be biodegraded in aquatic systems(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-pentadiene, which has a vapor pressure of 405 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-pentadiene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules(SRC). The half-life for the reaction in air with hydroxyl radicals is estimated to be 3.7 hours(SRC), calculated from its rate constant of 1.01X10-10 cu cm/molecule-sec at 24 °C(3). The half-life for the reaction in air with ozone is estimated to be 5 hours(SRC), calculated from its rate constant of 5.26X10-17 cu cm/molecule-sec(SRC), estimated with a structure estimation method(4). The vapor phase reaction of 1,3-pentadiene with nitrate radicals may be an important atmospheric removal process in urban areas at night(5), but the rate of this reaction is not known.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a measured log Kow of 2.44(2) and a regression-derived equation(3), indicates that trans-1,3-pentadiene is expected to have low mobility in soil(SRC). Volatilization of trans-1,3-pentadiene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). The potential for volatilization of trans-1,3-pentadiene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 411 mm Hg(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 500(SRC), determined from a measured log Kow of 2.44(2) and a regression-derived equation(3), indicates that trans-1,3-pentadiene is 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 0.12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 51 min and 78 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 15(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-1,3-pentadiene, which has a vapor pressure of 411 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase trans-1,3-pentadiene 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 3.7 hours(SRC), calculated from its rate constant of 1.05X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Vapor-phase trans-1,3-pentadiene is also degraded in the atmosphere by reaction with photochemically-produced ozone(SRC); the half-life for this reaction in air is estimated to be 5.2 hours(SRC), calculated from its rate constant of 5.26X10-17 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). In general, the night time degradation of conjugated diolefins by the gas-phase reaction with nitrate radicals may be important in urban areas or in heavily polluted atmospheres(4), and this may be an important removal process for trans-1,3-pentadiene(SRC).

Adverse Effects · 2 items

Neurotoxin - Acute solvent syndrome

Neurotoxin - Acute solvent syndrome

Exposure RoutesThe substance can be absorbed into the body by inhalation.
Signs and Symptoms · 3 items

Redness.

Redness.

Nausea. Vomiting. Aspiration hazard!

Effluent Concentrations · 2 items

1,3-Pentadiene was identified, not quantified, as a stack emission from waste incinerators(1). 1,3-Pentadiene has been identified, not quantified, in the exhaust of gasoline and diesel engines(2). 1,3-Pentadiene was detected in the exhaust of a single component fuel at a concn of 0.66 ppm(3). 1,3-Pentadiene was identified, not quantified, in the volatile emissions of garden waste(4).

trans-1,3-Pentadiene has been qualitatively detected in the exhaust of gasoline and diesel engines(1).

Soil Adsorption/Mobility · 2 items

The Koc of 1,3-pentadiene is estimated as 500(SRC), using a log Kow of 2.44(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-pentadiene is expected to have low mobility in soil(SRC).

The Koc of trans-1,3-pentadiene is estimated as 500(SRC), using a measured log Kow of 2.44(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that trans-1,3-pentadiene is expected to have low mobility in soil(SRC).

Regulatory information

RCRA Requirements · 1 item

U186; As stipulated in 40 CFR 261.33, when 1,3-pentadiene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

DHS Chemicals of Interest (COI) · 4 items

1,3-Pentadiene

1

10000

Flammable chemical that can be released at a facility.

Safety data

PPE
Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
RZ2465000
ridadr
UN 3295 3/PG 2
hs_code
2901.29.5000

Chemistry & industry

Uses & manufacturing

Uses · 4 items

Used as an intermediate and co-monomer in production of polymers and other organic chemicals; [Hawley]

A product of combustion; Used to make polymers and other chemicals; [HSDB]

/co-monomer in production of/ polymers, maleic anhydride adducts; intermediate.

Polymers, maleic anhydride adducts; intermediate

ImpuritiesCyclopentene
U.S. Production · 3 items

2023: 2,500,000 - <4,000,000 lb

2023: 54,196,074 lb

(1988) 123 million lb

Consumer Uses · 2 items

Not Known or Reasonably Ascertainable

Other

Industry Uses · 2 items

Fuel

Other

Methods of Manufacturing · 2 items

The methylation of butadiene with dimethyl sulfoxide in the presence of a base, such as potassium t-butoxide, produces 1,3-pentadiene (80% trans, 20% cis)

The methylation of butadiene with dimethyl sulfoxide in the presence of a base such as potassium t-butoxide.

Applications · 3 items

Uses1,3-Pentadiene (PD) is a major component of the C5 fraction, a byproduct of the ethylene industry, and also a key component in the cationic polymerization synthesis of aliphatic hydrocarbon petroleum resins. The application of homopolymers of PD is limited by their performance defects; therefore, copolymerization with other olefins has become a primary method for resin modification. For example, the copolymerization of PD with isobutylene and the copolymerization of PD with styrene (St) in dichloromethane have been studied. Trans-1,3-Pentadiene is the trans isomer of 1,3-Pentadiene.

UsesHydroxyl radical reactions with diolefins in atmospheric and combustion environments: This study provides insights into the reactions of hydroxyl radicals with diolefins such as trans-1,3-Pentadiene, highlighting their significance in both atmospheric chemistry and combustion processes. This research helps in understanding the reactive pathways and kinetics that could inform both environmental and industrial applications of trans-1,3-Pentadiene (Khaled et al., 2019).

General DescriptionTrans-1,3-Pentadiene spectra is recorded in the 5000-17500 cm(-1) region with conventional and intracavity laser photoacoustic spectroscopy. It can be determined by the spectrophotometric method based on the Diels-Alder reaction. In this reaction, cisoid 1,3-dienes and tetracyanoethylene (TCNE) react with an aromatic-TCNE pi-complex.

Suppliers41 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
江苏艾康生物医药研发有限公司025-66061636 19370895928 · [email protected]
上海仲因实业有限公司2537653158 16621191650 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes

DefinitionChEBI: An alkadiene consisting of pentane with the two double bonds located at positions 1 and 3.

Related reactions

6 records

Compound notes

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