Vinyl acetylene

HCID 12720CAS 689-97-4

Basic information

Standard SMILES
C#CC=C
InChIKey
WFYPICNXBKQZGB-UHFFFAOYSA-N
Molecular formula
C4H4
Average molar mass
52.07 g/mol
Monoisotopic mass
52.03130013

Overview

1-buten-3-yne appears as a colorless gas or liquid. Derived by the dimerization of acetylene. Used in the synthesis of neoprene and for other organic syntheses.

Names & identifiers

Preferred name
Vinyl acetylene
IUPAC
but-1-en-3-yne
English name
Vinylacetylene
Molecular formula
C4H4
Molecular weight
52.07

Names & synonyms

1-BUTEN-3-YNEVinylacetyleneBut-1-en-3-yneButenyneVinyl acetyleneMonovinylacetylene689-97-41-Butenyne3-Buten-1-yneEthene, ethynyl-1-Butyn-3-eneVinylethyne
Show more names
HSDB 5743EINECS 211-713-3VW72FM10OQ3-BUTYN-1-ENEDTXSID4029199CHEBI:480881-BUTEN-3-YNE [HSDB]1Butenyne

Database identifiers

CAS
689-97-4
PubChem CID
12720
DTXSID
DTXSID4029199
ChEBI
CHEBI:48088
UNII
VW72FM10OQ
EC Number
211-713-3
Nikkaji
J1.725F

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
4

Experimental & physicochemical properties

Chemical Classes · 2 items

Other Classes -> Aliphatics, Unsaturated

Flammable agents - 4th degree

SpringerMaterials PropertiesCoriolis coupling
Odoracetylene-like odor
Density0.7095 @ 0 °C/0 °C
Color/FormColorless gas or liquid
Solubility · 2 items

Sol in benzene

In water, 1.79X10+3 mg/l @ 30 °C

Physicochemical properties

Boiling point
5.1 °C · 5.1 °C
Density
0.7095 g/cm3 · 0.7095 g/cm3(Temp: 0 °C)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H220 (100%): Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P280, P377, P381, P403, and P410+P403 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

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

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 Gas
Fire HazardsExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Health HazardsExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Hazards SummaryGeneral anesthetic in mouse lethal inhalation studies; [RTECS] An irritant; Inhalation of high concentrations can cause CNS depression; [MSDSonline]
Reactive GroupHydrocarbons, Aliphatic Unsaturated

Safety & protection

Fire FightingExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
First AidExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Nonfire Spill ResponseExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Disposal Methods · 1 item

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.

Isolation and EvacuationExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a measured water solubility of 1,790 mg/l(2) and a regression-derived equation(3), indicates that 1-buten-3-yne is expected to have high mobility in soil(SRC). Volatilization of 1-buten-3-yne from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.029(SRC), calculated from its vapor pressure of 1,350 mm Hg(4) and water solubility(2). The potential for volatilization of 1-buten-3-yne from dry soil surfaces may exist(SRC) based upon its vapor pressure(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 70(SRC), determined from a measured water solubility of 1,790 mg/l(2) and a regression-derived equation(3), indicates that 1-buten-3-yne 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 0.029 atm-cu m/mole(SRC), calculated from its vapor pressure of 1,350 mm Hg(4) and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2 and 69 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 10(SRC), determined from an estimated log Kow of 1.4(6) and a regression-derived equation(7), 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), 1-buten-3-yne, which has a vapor pressure of 1,350 mm Hg at 25 °C(2), is expected to exist in the gas phase in the ambient atmosphere. Gas-phase 1-buten-3-yne 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 10 hours(SRC), calculated from its rate constant of 40X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

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

The Koc of 1-buten-3-yne is estimated as 70(SRC), using a measured water solubility of 1,790 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this Koc value suggests that 1-buten-3-yne is expected to have high mobility in soil.

Artificial Pollution Sources1-Buten-3-yne's production and use as a chemical intermediate(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 10 was calculated for 1-buten-3-yne(SRC), using an estimated log Kow of 1.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 1-buten-3-yne is estimated as 0.029 atm-cu m/mole(SRC) based upon its vapor pressure, 1,350 mm Hg(1), and water solubility, 1,790 mg/l(2). This Henry's Law constant indicates that 1-buten-3-yne is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 70 hours(SRC). 1-Buten-3-yne's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1-buten-3-yne from dry soil surfaces may exist(SRC) based upon its vapor pressure(1).

Regulatory information

DHS Chemicals of Interest (COI) · 4 items

Vinyl acetylene

1

10000

Flammable chemical that can be released at a facility.

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as an intermediate in the manufacture of neoprene and other organic compounds; [HSDB]

Intermediate in mfr of neoprene and for various organic syntheses

U.S. Production2023: 1,000,000 - <8,500,000 lb
Consumer UsesIntermediate
Industry UsesIntermediate
Methods of ManufacturingThe dimer of acetylene, formed by passing it into a soln of cuprous and ammonium chlorides in hydrochloric acid.
General Manufacturing Information · 2 items

Petroleum Refineries

1-Buten-3-yne: ACTIVE

Suppliers23 total

安徽旺山旺水特种气体有限公司15906197626 · [email protected]
江西核研院新材料有限公司18901398682 18901398682 · [email protected]
湖南省华中特种气体有限公司0734-8755555 15674722888 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
尚澜气体(上海)有限公司4001882517 13323475516 · [email protected]

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