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Cyclobutane

HCID 9250
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
287-23-0
Standard SMILES
C1CCC1
InChIKey
PMPVIKIVABFJJI-UHFFFAOYSA-N
Molecular formula
C4H8
Average molar mass
56.11 g/mol
Monoisotopic mass
56.06260026

Overview

Gas that condenses to a liquid at 55 °F. Insoluble in water. Soluble in alcohol, acetone and ether. Under prolonged exposure to fire or intense heat the containers may rupture violently and rocket.

Names & identifiers

Preferred name
Cyclobutane
IUPAC
cyclobutane
English name
Cyclobutane
Molecular formula
C4H8
Molecular weight
56.11

Names & synonyms

CYCLOBUTANE287-23-0TetramethyleneUNII-5X619RB2CYHSDB 585X619RB2CYEINECS 206-014-5DTXSID2059772CHEBI:30377RefChem:5716DTXCID6037853206-014-5
Show more names
Cyclobutan
UN2601Cyclobutane [UN2601] [Flammable gas]CYCLOBUTANE [MI]cyclobutane, tetramethyleneSCHEMBL893CYCLOBUTANE [HSDB]SCHEMBL1997SCHEMBL2088

Database identifiers

CAS
287-23-0
PubChem CID
9250
DTXSID
DTXSID2059772
ChEBI
CHEBI:30377
UNII
5X619RB2CY
EC Number
206-014-5
Nikkaji
J2.562C

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
4
Formal charge
0
Complexity
8

Experimental & physicochemical properties

Chemical Classes · 2 items

Toxic Gases & Vapors -> Simple Asphyxiants

Flammable agents - 4th degree

SpringerMaterials PropertiesCoriolis coupling
Density0.7038 AT 0 °C; 0.7125 @ 5 °C
Color/FormColorless gas
Solubility · 2 items

INSOL IN WATER; FREELY SOL IN ALCOHOL, ACETONE

Sol in ethanol, ether, and acetone

Flash PointBELOW 50 °F Closed Cup
Boiling Point13.08 °C @ 741 MM HG
DecompositionWhen heated to decomposition it emits acrid smoke and fumes.
Melting Point-80 °C
Vapor Density1.93 (AIR= 1)

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 71 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationThe 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 Hazards · 2 items

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

· EXTREMELY FLAMMABLE.

Fire PotentialVERY DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Health Hazards · 2 items

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

· Vapors may cause dizziness or asphyxiation without warning, especially when in closed or confined areas.

Hazards Summary · 1 item

Fire hazard; [Hawley] In confined space spill, may displace air and act as simple asphyxiant; [HSDB] Evaporating liquid can cause frostbite; May cause asphyxiation without warning; [CAMEO] May cause difficulty breathing and suffocation; Evaporating liquid can cause frostbite; [MSDSonline] See n-Butane.

DOT ID and Guide2601 115
Reactive GroupHydrocarbons, Aliphatic Saturated

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Used as intermediate in organic synthesis; [HSDB]

INT IN ORGANIC SYNTHESIS

Methods of Manufacturing · 3 items

DISTILLATION OF PETROLEUM

PREPD BY HYDROGENATION OF CYCLOBUTENE IN PRESENCE OF NICKEL @ 100 °C. BY PYROLYSIS OF ETHER, ALONG WITH OTHER PRODUCTS. IN 39% YIELD FROM CYCLOBUTANECARBOXYLIC ACID.

Catalytic hydrogenation of cyclobutene

General Manufacturing Information · 2 items

Cyclobutane: ACTIVE

THE GAS.../SRP: HAS BEEN/ USED AS AN ANESTHETIC, BUT IT IS A WEAK CARDIAC SENSITIZER, AND A SIMPLE ASPHYXIANT.

Applications

General DescriptionGas that condenses to a liquid at 55°F. Density of liquid 0.7 g / cm3. Insoluble in water. Soluble in alcohol, acetone and ether. Under prolonged exposure to fire or intense heat the containers may rupture violently and rocket.

Upstream & downstream products

Upstream raw materials

Cyclobutene

Downstream products

Cyclobutyl chloride1-Butene

Suppliers7 total

温州共赢化学有限公司+86-0086-577-64498589 +86-15355981851 · [email protected]
Syntechem Co.,Ltd[email protected]

Related reactions

10 records
New reaction record
HRID 211322 reaction equation
HRID 211322As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 494009 reaction equation
HRID 494009As reactantuspto-grants-2009_05
HRID 851560 reaction equation
HRID 851560As reactantuspto-grants-1983_05
HRID 851561 reaction equation
HRID 851561As reactantuspto-grants-1983_05
HRID 953230 reaction equation
HRID 953230As reactantValidation data from https://doi.org/10.1039/C8SC04228D
HRID 953579 reaction equation
HRID 953579As reactantValidation data from https://doi.org/10.1039/C8SC04228D
HRID 1223460 reaction equation
HRID 1223460As reactantTraining data from https://doi.org/10.1039/C8SC04228D (5/10)
HRID 1548267 reaction equation
HRID 1548267As reactantTraining data from https://doi.org/10.1039/C8SC04228D (1/10)
Page 1 of 2

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Vapor Pressure
1.18X10+3 mm Hg @ 25 °C
Refractive IndexINDEX OF REFRACTION: 1.3625 @ 290 °C/D

Physicochemical properties

Melting point
-80 ° · -80°
Boiling point
741 · bp741 13.08°
Density
0 · d0 0.7038; d-5 0.7185
refractive index
0 · nD0 1.37520
Henry's Law Constant
1.3 · 1.3×10-6 mol/(m3Pa) at 25℃, Hayer et al. (2022)
FDA UNII
5 X619RB2CY · 5X619RB2CY
EPA Substance Registry System
Cyclobutane (287-23-0)
Symbol(GHS)
2 · GHS02,GHS04
Signal word
Danger
Hazard statements
220 · H220-H280
Precautionary statements
210 · P210-P377-P381-P403
RIDADR
2601 · UN 2601
TSCA
TSCA listed
HazardClass
2.1 · 2.1
Hazardous Substances Data
287 · 287-23-0(Hazardous Substances Data)
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

CYCLOBUTANE may be incompatible with strong oxidizing agents like nitric acid. Charring may occur followed by ignition of unreacted material and other nearby combustibles. In other settings, mostly unreactive. Not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents.

DOT Emergency Guidelines · 5 items

/GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Fire or Explosion: EXTREMELY FLAMMABLE. Will be easily ignited by heat, sparks or flames. Will form explosive mixtures with air. Vapors from liquefied gas are initially heavier than air and spread along ground. CAUTION: Hydrogen (UN1049), Deuterium (UN1957), Hydrogen, refrigerated liquid (UN1966) and Methane (UN1971) are lighter than air and will rise. Hydrogen and Deuterium fires are difficult to detect since they burn with an invisible flame. Use an alternate method of detection (thermal camera, broom handle, etc.) Vapors may travel to source of ignition and flash back. Cylinders exposed to fire may vent and release flammable gas through pressure relief devices. Containers may explode when heated. Ruptured cylinders may rocket.

/GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Health: Vapors may cause dizziness or asphyxiation without warning. Some may be irritating if inhaled at high concentrations. Contact with gas or liquefied gas may cause burns, severe injury and/or frostbite. Fire may produce irritating and/or toxic gases.

/GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Many gases are heavier than air and will spread along ground and collect in low or confined areas (sewers, basements, tanks). Keep out of low areas.

/GUIDE 115: GASES - FLAMMABLE (Including Refrigerated Liquids)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. Always wear thermal protective clothing when handling refrigerated/cryogenic liquids.

For more DOT Emergency Guidelines (Complete) data for CYCLOBUTANE (8 total), please visit the HSDB record page.

DOT Hazard Classification · 3 items

Cyclobutane

UN2601

Div 2.1 Flammable gas (49 eCFR § 173.115)

Safety & protection

Fire FightingExcerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Accidental Release Measures · 2 items

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 items

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresSTOP FLOW OF GAS; CARBON DIOXIDE, DRY CHEMICAL, OR WATER SPRAY.
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 Evacuation · 2 items

Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:

Immediate precautionary measure

Threshold Limit Values (TLV)1000.0 [ppm]
Personal Protective Equipment (PPE)Excerpt from ERG Guide 115 [Gases - Flammable (Including Refrigerated Liquids)]:
Emergency Response Planning Guidelines· DO NOT EXTINGUISH A LEAKING GAS FIRE UNLESS LEAK CAN BE STOPPED.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that cyclobutane is expected to have very high mobility in soil(SRC). Volatilization of cyclobutane from moist soil surfaces is expected to be important(SRC) given an estimated Henry's Law constant of 0.14 atm-cu m/mole(3). The potential for volatilization of cyclobutane from dry soil surfaces may exist(SRC) based on a vapor pressure of 1.18X10+3 mm Hg(4). Activated sludge tests suggest that biodegradation of cyclobutane is expected to be slow in soil(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 49(SRC), determined from a structure estimation method(2), indicates that cyclobutane is not expected to adsorb to suspended solids and sediment in water(SRC). Cyclobutane is expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 0.14 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 2 hrs and 3 days, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 10(3,SRC), from an estimated log Kow(2,SRC), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyclobutane is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Activated sludge tests suggest that biodegradation of cyclobutane is expected to be slow in water(6).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclobutane, which has a vapor pressure of 1.18X10+3 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclobutane 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 days(3,SRC). Cyclobutane is not expected to undergo direct photolysis due to the lack of absorption in the environmental spectrum(4).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Effluent ConcentrationsCyclobutane was found to be an emission from commercial natural gas, but not from gasoline or vehicle exhausts(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for cyclobutane can be estimated to be about 49(SRC). According to a classification scheme(2), this estimated Koc value suggests that cyclobutane is expected to have very high mobility in soil(SRC).

Human Toxicity ExcerptsMAY BE SIMPLE ASPHYXIANT.
Artificial Pollution SourcesCyclobutane's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

When incubated with either adapted or nonadapted activated sludge, cyclobutane underwent <25% of the theoretical BOD in 24 hrs(1). Pure culture studies showed various isolated species of bacteria were unable to utilize cyclobutane as the sole carbon source in soil(2).

Environmental Bioconcentration · 1 item

An estimated BCF of 10 was calculated for cyclobutane(1,SRC), using an estimated log Kow of 2.19(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Volatilization from Water/Soil · 1 item

The Henry's Law constant for cyclobutane is estimated as 0.14 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that cyclobutane is expected to volatilize rapidly 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 2 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 3 days(2,SRC). Cyclobutane's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of cyclobutane from dry soil surfaces may exist(SRC) based on a vapor pressure of 1.18X10+3 mm Hg(3).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of cyclobutane with photochemically-produced hydroxyl radicals of 1.20X10-12 cu cm/molecule-sec at 25 °C(1) corresponds to an atmospheric half-life of about 10 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(2,SRC). Cyclobutane is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3) nor to directly photolyze due to the lack of absorption in the environmental spectrum.

Probable Routes of Human Exposure · 2 items

INDUSTRIALLY...NOT EXPECTED TO BE HEALTH HAZARD.

Occupational exposure to cyclobutane may occur through inhalation and dermal contact with this compound at workplaces where cyclobutane is produced or used. (SRC)

Environmental Water ConcentrationsSURFACE WATER: Cyclobutane was detected in 1 of 8 Rhine River water samples, 1989, at a concn of 0.027 ug/l(1).

Safety data

tsca
TSCA listed
ridadr
UN 2601
Signal word
Danger
Symbol(GHS)
GHS02,GHS04
hazard_class
2.1
Hazard statements
H220-H280
Precautionary statements
P210-P377-P381-P403
Hazardous Substances Data
287-23-0(Hazardous Substances Data)
南通合润生物科技有限公司18362409333 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
Capot Chemical Co.,Ltd.+86-(0)57185586718 +86-13336195806 · [email protected]
Changzhou Ansciep Chemical Co., Ltd.+86 519 86305871 · [email protected]
上海宝杨宝欣生物科技有限公司021-56698539 19921169802 · [email protected]

Additional notes

DefinitionChEBI: Cyclobutane is a cycloalkane and a member of cyclobutanes.