2-Bromobutane

HCID 6554CAS 78-76-2

Basic information

Standard SMILES
CCC(C)Br
InChIKey
UPSXAPQYNGXVBF-UHFFFAOYSA-N
Molecular formula
C4H9Br
Average molar mass
137.02 g/mol
Monoisotopic mass
135.98876239

Overview

2-bromobutane appears as a colorless to pale-yellow colored liquid with a pleasant odor. Flash point 65 °F. Insoluble in water and denser than water. Vapors are heavier than air and may be narcotic in high concentrations. Used to make other chemicals.

Names & identifiers

Preferred name
2-Bromobutane
IUPAC
2-bromobutane
English name
2-Bromobutane
Molecular formula
C4H9Br
Molecular weight
137.02

Names & synonyms

2-Bromobutane78-76-2SEC-BUTYL BROMIDEButane, 2-bromo-2-Butyl bromideMethylethylbromomethaneSecondary butyl bromideDTXSID7021499SSI829JO4WNSC-8417DTXCID201499(+-)-2-Bromobutane
Show more names
S-BUTYL BROMIDEBROMOBUTANE, 2-(SG)2-Bromobutane sec-Butylbromidesec-C4H9Br2-Brombutan2-bromo-butanbromo-2butane
RefChem:85855201-140-71-Bromo-1-methylpropane2-Bromo-butaneMFCD00000156sec-ButylbromideCCRIS 106HSDB 2197

Database identifiers

CAS
78-76-2
PubChem CID
6554
DTXSID
DTXSID7021499
ChEMBL
CHEMBL156276
UNII
SSI829JO4W
EC Number
201-140-7
Nikkaji
J1.481H、J8.062D

Properties

Computed structural properties

XLogP
2.3
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
SolventsSolvents -> Brominated Solvents
OdorPleasant odor
Density · 2 items

1.258 at 68 °F (USCG, 1999) - Denser than water; will sink

1.2425 at 25 °C/25 °C

Color/FormClear, colorless liquid
SolubilitySoluble in alcohol and ether; insoluble in water.

Physicochemical properties

Melting point
-112 °C · -112 °C
Boiling point
91 °C · 91 °C(lit.)
Density
1.255 g/mL · 1.255 g/mL at 25 °C(lit.)
vapor pressure
70 hPa · 70 hPa (20 °C)
refractive index
20 · n20/D 1.4369(lit.)
Flash point
70 °F · 70 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 4 items

Chemical: Butane, 2-bromo-

Status: Active Update: 27-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23187

Butane, 2-bromo-: HSNO Approval: HSR001244 Approved with controls

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 Liquid
Fire Hazards · 2 items

Special Hazards of Combustion Products: Toxic fumes of Br

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire PotentialDangerous, when exposed to heat or flame.
Health Hazards · 2 items

Irritating to eyes, nose, throat, upper respiratory tract, and skin. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Hazards Summary · 1 item

Flammable liquid that is a dangerous fire risk; [Hawley] High concentrations may cause CNS depression; [HSDB] A skin, eye, nose, throat, and upper respiratory tract irritant; [CAMEO] An irritant; High concentrations may cause CNS depression; [MSDSonline]

Safety & protection

Fire FightingExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
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

Call a physician.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 2 items

To fight fire use water, spray or mist, foam, carbon dioxide, or dry chemical.

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. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

Nonfire Spill ResponseExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:

Toxicology

Treatment · 1 item

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 item

Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627)

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that sec-butyl bromide is expected to have high mobility in soil(SRC). Volatilization of sec-butyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). sec-Butyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 57 mm Hg(4). Biodegradation data were not available(SRC, 2005).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that sec-butyl bromide 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 1.6X10-2 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 3.5 hours and 4.7 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 19(SRC), from an estimated log Kow of 2.58(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sec-butyl bromide, which has a vapor pressure of 57 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase sec-butyl bromide 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 12 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). sec-Butyl bromide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1 item

Bromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (L626, L627, A543)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
EJ6228000
ridadr
UN 2339
hs_code
29033036

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626)

Uses & manufacturing

Uses · 2 items

Used for synthesis and as an alkylating agent; [Hawley]

Synthesis; alkylating agent

Methods of ManufacturingThe reaction of hydrogen bromide with 1-butene under ionic conditions and in the absence of a peroxides.
General Manufacturing InformationButane, 2-bromo-: ACTIVE
Applications · 3 items

Uses2-Bromobutane is utilized in the synthesis of non-nucleosides. It is used as a solvent as well as an intermediate in organic synthesis. It is an important raw material used to prepare Grignard reagent by reacting with magnesium. Further, it reacts with hydrocyanic acid to prepare sodium salt to get (+-)-sec-butyl cyanide. It is an important raw material used to prepare Grignard reagent by reacting with magnesium.

Uses2-Bromobutane is used in the various organic synthesis, existing as a grignard reagent.

General DescriptionA colorless to pale-yellow colored liquid with a pleasant odor. Flash point 65°F. Insoluble in water and denser than water. Vapors are heavier than air and may be narcotic in high concentrations. Used to make other chemicals.

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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
聊城信立新材料有限公司18963527911 18006357927 · [email protected]

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