Sec-Butylbenzene

HCID 8680CAS 135-98-8

Basic information

Standard SMILES
CCC(C)c1ccccc1
InChIKey
ZJMWRROPUADPEA-UHFFFAOYSA-N
Molecular formula
C10H14
Average molar mass
134.22 g/mol
Monoisotopic mass
134.10955045

Overview

Sec-butylbenzene is an alkylbenzene that is benzene substituted by a butan-2-yl group.

Names & identifiers

Preferred name
Sec-Butylbenzene
IUPAC
butan-2-ylbenzene
English name
sec-Butylbenzene
Molecular formula
C10H14
Molecular weight
134.22

Names & synonyms

SEC-BUTYLBENZENE135-98-82-Phenylbutane(1-Methylpropyl)benzeneBenzene, (1-methylpropyl)-Secondary butylbenzeneDTXSID2022333B70I0RSX3JNSC-8466DTXCID902333CHEBI:35097RefChem:182125
Show more names
205-227-01-sec-butylbenzeneBenzene, sec-butyl-butan-2-ylbenzenes-Butylbenzene(Butan-2-yl)benzeneMFCD00009329(methylpropyl)benzene

Database identifiers

CAS
135-98-8、68411-44-9
PubChem CID
8680
DTXSID
DTXSID2022333
ChEMBL
CHEMBL27516
ChEBI
CHEBI:35097
UNII
B70I0RSX3J
EC Number
205-227-0
Nikkaji
J5.616B

Properties

Computed structural properties

XLogP
4.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
10

Experimental & physicochemical properties

Chemical ClassesVolatile Organic Compound (VOC)
SolventsSolvents -> Aromatic Solvents
LogPlog Kow = 4.57
Density · 2 items

0.8580 g/cu cm @ 25 °C

0.8580 @25 °C

Color/FormColorless liquid
Solubility · 2 items

In water, 17.6 mg/L @ 25 °C

Miscible with alcohol, ether, benzene

Physicochemical properties

Melting point
-82.7 °C · -82.7 °C
Boiling point
173.5 °C · 173.5 °C
Density
0.858 g/cm3 · 0.8580 g/cm3(Temp: 25 °C)
Symbol(GHS)
2 · GHS02,GHS07,GHS09
Signal word
Warning
Hazard statements
226 · H226-H302-H410

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 6.9% (6 of 87) of reports.

Danger

H226 (74.7%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P273, P280, P301+P316, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 87 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

Hazard information

Regulatory Information · 4 items

Chemical: Benzene, (1-methylpropyl)-

Hazard Traits - Nephrotoxicity and Other Toxicity to the Urinary System

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

s-Butylbenzene: Does not have an individual approval but may be used under an appropriate group standard

Fire PotentialFlammable
Hazards SummaryAn irritant; [MSDSonline]
TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. sec-Butylbenzene is included on this list.

Flammable LimitsLower flammable limit: 0.8% by volume; Upper flammable limit: 6.9% by volume
DOT Emergency Guidelines · 5 items

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substances may be transported hot. /Butylbenzenes/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Butylbenzenes/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Butylbenzenes/

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Butylbenzenes/

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

Safety & protection

Fire Fighting Procedures · 2 items

Personnel protection: ... Wear positive pressure self-container breathing apparatus when fighting fires involving this material. ... /Butyl benzenes/

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Butyl benzenes/

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 2 items

Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ... If contact with the material anticipated, wear appropriate chemical protective clothing. /Butyl benzenes/

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Butyl benzenes/

Protective Action Criteria (PAC) · 3 items

5.8 [ppm]

64 [ppm]

380 [ppm]

Personal Protective Equipment (PPE)Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. ... /Butyl benzenes/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7,200(SRC), determined from a log Kow of 4.57(2) and a regression-derived equation(3), indicates that sec-butylbenzene is expected to be immobile in soil(SRC). Volatilization of sec-butylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.018 atm-cu m/mole(SRC), derived from its vapor pressure, 1.75 mm Hg(4), and water solubility, 17.6 mg/L(5). However, adsorption to soil is expected to attenuate volatilization(SRC). The potential for volatilization of sec-butylbenzene from dry soil surfaces may exist(SRC), based upon its vapor pressure(4). Based on an aquatic biodegradation screening test, where sec-butylbenzene was found to degrade 56-67% after 5 days when incubated at 25 °C with activated sludge(6), sec-butylbenzene may biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7,200(SRC), determined from a log Kow of 4.57(2) and a regression-derived equation(3), indicates that sec-butylbenzene 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 0.018 atm-cu m/mole(SRC), derived from its vapor pressure, 1.75 mm Hg(4), and water solubility, 17.6 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.4 hours and 4.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 88 days if adsorption is considered (6). According to a classification scheme(7), an estimated BCF of 660(SRC), from its log Kow of 4.57(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Based on an aquatic biodegradation screening test, where sec-butylbenzene was found to degrade 56-67% after 5 days when incubated at 25 °C with activated sludge(9), sec-butylbenzene may biodegrade in aquatic environments(SRC). sec-Butylbenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sec-butylbenzene, which has a vapor pressure of 1.75 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase sec-butylbenzene 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 1.9 days(SRC), calculated from its rate constant of 8.5X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). sec-Butylbenzene is not expected to be susceptible to direct photolysis by sunlight(SRC), since it does not absorb light with wavelengths >290 nm(4).

Food Survey Values · 1 item

A total of 228 compounds, including sec-butylbenzene, were identified in the volatile flavor isolated from 540 pounds of baked potatoes(1). sec-Butylbenzene was detected in 5 foods of the 234 table-ready food items of the FDA Total Diet Study; the average concn was 5.67 ppb (range: 3.88-7.76 ppb), with the highest levels found in sauerkraut(2).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Effluent Concentrations · 1 item

sec-Butylbenzene was detected in 1978 and 1983 at 10.7 and 11 ug/L, respectively, in the basin floodwater from the sewage treatment plant that treats domestic wastewater from Fort Devens, a US Army installation approximately 52 km northwest of Boston, MA(1,2). Emission from various stove and fuel types were measured for non-methane hydrocarbons in China; sec-butylbenzene, in combination with 1,2,4-methylbenzene, was not detected in 12 of the 16 fuel/stove combinations(3). Emission factors for sec-butylbenzene and 1,2,4-trimethylbenzene were 1.77, 1.90, 1.47, and 0.030 mg of compound/kg dry fuel for honeycomb coal briquette with a metal coal stove with a flue and without a flue, coal powder with a metal coal stove with a flue, and coal gas with a traditional gas stove without a flue, respectively(3). sec-Butylbenzene was observed only at minor concns in the volatile organic compounds introduced in to the water by boats with combustion engines(4). sec-Butylbenzene was generally not detected effluent from 4 wastewater treatment plants in Milwaukee, WI, Akron, OH, Gary, IN, and Detroit, MI; a maximum concn of 74 ppb was detected in the effluent of 1 plant in Akron, OH(5). sec-butylbenzene was measured at a concn of 160 ug/L in the formation water (the water produced with oil and gas) from offshore oil production operations in the Gulf of Mexico(6). sec-Butylbenzene was detected in industry average gasoline, EPA certification gasoline and M-85 (85% methanol, 15% gasoline), respectively, but was not detected in either exhaust or evaporative auto emissions(7). sec-Butylbenzene was identified in the volatile organic compounds releases from textile floor coverings(8).

Soil Adsorption/Mobility · 1 item

The Koc of sec-butylbenzene is estimated as 7,200(SRC), using a log Kow of 4.57(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that sec-butylbenzene is expected to be immobile in soil.

Natural Pollution Sourcessec-Butylbenzene was detected in the air of the solfataric (volcanic area that gives off sulfurous gases and stems) fields of three active volcanoes on the Kunashir Islands off the coast of Russia in the Pacific Ocean(1).

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. sec-Butylbenzene is included on this list.

State Drinking Water Guidelines · 2 items

(FL) FLORIDA 280 ug/l

(NH) NEW HAMPSHIRE 260 ug/L

Safety data

Signal word
Warning
Symbol(GHS)
GHS02,GHS07,GHS09
Hazard statements
H226-H302-H410
Precautionary statements
P210-P273-P301+P312+P330

Chemistry & industry

Pharmacology

Metabolism/MetabolitesThey are metabolized by side-chain hydroxylation and conjugation for urinary excretion. /Butylbenzenes/

Uses & manufacturing

Uses · 3 items

Used as an intermediate, a plasticizer, and a solvent for coatings; [Hawley]

Painting (Solvents) [Category: Paint]

Solvent for coating compositions, organic synthesis, plasticizer, and surface active agents

U.S. Production2023: <50,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Methods of ManufacturingPrepared from benzene and n-butyl chloride in presence of AlCl3
General Manufacturing Information · 3 items

All Other Chemical Product and Preparation Manufacturing

Benzene, (1-methylpropyl)-: ACTIVE

The temperature range for smooth interaction of bromobenzene, 1-bromobutane, and sodium in ether to give butylbenzene is critical. Below 15 C reaction is delayed but later becomes vigorous , and above 30 C the reaction becomes violent.

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]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]

Related reactions

19 records

Linked notes

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