Butyryl chloride

HCID 8855CAS 141-75-3

Basic information

Standard SMILES
CCCC(=O)Cl
InChIKey
DVECBJCOGJRVPX-UHFFFAOYSA-N
Molecular formula
C4H7ClO
Average molar mass
106.55 g/mol
Monoisotopic mass
106.01854252

Overview

Butyryl chloride appears as a clear colorless liquid with a sharp odor. Slightly denser than water. Flash point near 20 °F. Severely irritates skin, eyes, and mucous membranes. Used to make other chemicals.

Names & identifiers

Preferred name
Butyryl chloride
IUPAC
butanoyl chloride
English name
Butyryl chloride
Molecular formula
C4H7ClO
Molecular weight
106.55

Names & synonyms

Butyryl chlorideButanoyl chlorideN-BUTYRYL CHLORIDECCRIS 5989n-Butyric acid chlorideDTXSID5024710HSDB 6016UNII-2XVM8E16IREINECS 205-498-5UN2353N-BUTANOYL CHLORIDEDTXCID104710
Show more names
butyrylBUTYRIC ACID CHLORIDEN-BUTYLVINYLETHERBUTYROYL CHLORIDEN-ButyrylButyrylchloridbutyricchlorideBUTIRYL CHLORIDE
N-BUTYRYL CHLORIDE [MI]EC 205-498-5N-BUTYRYL CHLORIDE [HSDB]UN 2353BUTYROL CHLORIDERefChem:122378205-498-5DVECBJCOGJRVPX-UHFFFAOYSA-N

Database identifiers

CAS
141-75-3
PubChem CID
8855
DTXSID
DTXSID5024710
ChEMBL
CHEMBL1300263
UNII
2XVM8E16IR
EC Number
205-498-5
Nikkaji
J2.538K

Properties

Computed structural properties

XLogP
1.6
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 2 items

Toxic Gases & Vapors -> Other Toxic Gases & Vapors

Flammable agents - 3rd degree

SpringerMaterials PropertiesCoriolis coupling
Odor · 2 items

Pungent acid chloride odor

Sharp odor

Density · 2 items

1.0277 at 68 °F (USCG, 1999) - Denser than water; will sink

1.0263 at 20.6 °C/4 °C

Color/FormColorless liquid
Solubility · 3 items

Reaction (NTP, 1992)

Dissolves slowly with decomposition in water

Dissolves slowly with decomposition in alcohol; miscible with ether

Physicochemical properties

Melting point
89 °C · −89 °C(lit.)
Boiling point
102 °C · 102 °C(lit.)
Density
1.026 g/mL · 1.026 g/mL at 25 °C(lit.)
vapor density
3.7 · 3.7 (vs air)
vapor pressure
39 hPa · 39 hPa (20 °C)
refractive index
20 · n20/D 1.412(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

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

P210, P233, P234, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P370+P378, P390, P403+P233, P403+P235, P405, P406, and P501 (click each P-code to see the statement)

Hazard information

Hazards IdentificationWater-reactive material (WR)
Regulatory Information · 4 items

Chemical: Butanoyl chloride

Status: Active Update: 02-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5853

Butyryl chloride: Does not have an individual approval but may be used under an appropriate group standard

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.)

Other Safety InformationIMAP assessments - Butanoyl chloride: Human health tier I assessment
DOT LabelFlammable Liquid Corrosive
Fire Hazards · 2 items

Special Hazards of Combustion Products: Emits toxic fumes of chlorine gas (USCG, 1999)

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

Fire PotentialFlammable ... .

Safety & protection

Fire FightingExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
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

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

Firefighting Hazards · 2 items

Reacts with alcohol and water.

... Corrosive.

Exposure Control and Personal Protection · 2 items

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 3 items

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Use water spray to cool unopened containers.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: n-Butyryl chloride decomposes in water to yield hydrochloric acid and butyric acid(1), therefore, leaching in soil and volatilization from moist soil for the parent compound are not expected to be important fate processes(SRC). n-Butyryl chloride is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 41.7 mm Hg at 25 °C(1).

AQUATIC FATE: n-Butyryl chloride decomposes exothermically in water to yield hydrochloric acid(1). This decomposition reaction will be the dominant fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butyryl chloride, which has a vapor pressure of 41.7 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-butyryl chloride 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 4.1 days(SRC), calculated from its rate constant of 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). n-Butyryl chloride fumes in air and decomposes in water to yield hydrochloric acid and butyric acid(2); therefore, n-butyryl chloride vapor in air can react with moisture in air.

Adverse EffectsDermatotoxin - Skin burns.
Toxicity SummaryIDENTIFICATION AND USE: n-Butyryl chloride is a colorless liquid. It is used in organic synthesis. HUMAN STUDIES: The chemical is toxic by ingestion and inhalation, and also a strong irritant. ANIMAL STUDIES: There are no data available.
Ongoing Test Status · 1 item

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of May 1, 2017: http://actor.epa.gov/dashboard/]

Soil Adsorption/Mobilityn-Butyryl chloride decomposes in water to yield hydrochloric acid and butyric acid(1), therefore, leaching in soil is not expected to be an important fate process(SRC).
Human Toxicity Excerpts/OTHER TOXICITY INFORMATION/ Toxic by ingestion and inhalation. Strong irritant to tissue.

Safety data

F
13
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
1
tsca
TSCA listed
ridadr
UN 2353
hs_code
2915 90 70

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used for organic synthesis; [HSDB]

Toxic Gas from Spilling Chemical in Water [Category: Other]

Organic synthesis.

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production(1986) No Data
Methods of ManufacturingPreparation from butyric acid.
General Manufacturing InformationButanoyl chloride: ACTIVE
Applications · 2 items

UsesButyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone. It is also used as an acylation reagent. Further, it is used in the preparation of peroxides such as benzoyl peroxide, benzophenone and t-butyl perbenzoate. In addition to this, it is involved in the preparation of chromones and antiproliferative agents. Butyryl chloride has been used to esterify wood meal dissolved in the ionic liquid, 1-butyl-3-methylimidazolium chloride.

General DescriptionA clear colorless liquid with a sharp odor. Slightly denser than water. Flash point near 20°F. Severely irritates skin, eyes, and mucous membranes. Used to make other chemicals.

Preparation methods · 1 item

PreparationButyryl chloride is obtained by the reaction of butyric acid with thionyl chloride. Heat the thionyl chloride to reflux, add butyric acid dropwise over approximately 4 hours, reflux for another hour, then distill. Collect the fraction at 95–115°C, redistill once, and collect the fraction at 101–105°C to obtain the final product, with a yield of over 70%. Phosphorus trichloride can also be added to the reaction, yielding a 75% yield.

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]
常州市紫东联化进出口有限公司0519-85560282 13656141470 · [email protected]

Related reactions

913 records

Linked notes

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