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Butyryl chloride

HCID 8855
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Basic information

CAS
141-75-3
Standard SMILES
CCCC(=O)Cl
InChIKey
DVECBJCOGJRVPX-UHFFFAOYSA-N
Molecular formula
C4H7ClO
Average molar mass
106.55 g/mol
Monoisotopic mass
106.0185425

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
Formal charge
0
Complexity
51.5

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

CorrosivityCorrosive to metals
Flash Point · 2 items

71 °F (NTP, 1992)

18 °C (64 °F) - closed cup

Boiling Point · 2 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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

REACH registered substance: Butyryl chloride (EC: 205-498-5)

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.

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.

Related reactions

913 records
New reaction record
HRID 1163 reaction equation
HRID 1163As reactantuspto-grants-1998_03
HRID 1165 reaction equation
HRID 1165As reactantuspto-grants-1998_03
HRID 5565 reaction equation
HRID 5565As reactantuspto-grants-1993_09
HRID 6090 reaction equation
HRID 6090As reactantuspto-grants-1993_09
HRID 9389 reaction equation
HRID 9389As reactantuspto-grants-2006_08
HRID 9465 reaction equation
HRID 9465As reactantuspto-grants-2006_08
HRID 10003 reaction equation
HRID 10003As reactantuspto-grants-2006_08
HRID 10015 reaction equation
HRID 10015As reactantuspto-grants-2006_08
Page 1 of 115

Compound notes

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216 °F at 760 mmHg (NTP, 1992)

101-102 °C

DecompositionDissolves slowly with decomposition in water, alcohol.
Melting Point · 2 items

-128 °F (NTP, 1992)

-89 °C

Vapor Density3.67 (vapor specific gravity)

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.)
RTECS
595000 · EM0595000
Flash point
71 °F · 71 °F
storage temp.
30 °C · Store below +30°C.
solubility
Miscible with ether.
form
Liquid
color
Clear slightly yellow
Odor
pungent odor
explosive limit
2.5 · 2.5-7.3%(V)
Water Solubility
decomposes
FreezingPoint
-89 ℃ · -89℃
Sensitive
Moisture Sensitive
Merck
14 · 14,1598
BRN
605395 · 605395
InChI
1S/C4H7ClO/c1-2-3-4(5)6/h2-3H2,1H3
InChIKey
DVECBJCOGJRVPX-UHFFFAOYSA-N
SMILES
CCCC(Cl)=O
LogP
0.51 at · 0.51 at 25℃
CAS DataBase Reference
141 · 141-75-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
2 XVM8E16IR · 2XVM8E16IR
NIST Chemistry Reference
Butanoyl chloride(141-75-3)
EPA Substance Registry System
Butanoyl chloride (141-75-3)
UNSPSC Code
12352106 · 12352106
NACRES
22 · NA.22
Symbol(GHS)
2 · GHS02,GHS05
Signal word
Danger
Hazard statements
314 · H314-H225-H290
Precautionary statements
501 · P501-P240-P210-P233-P234-P243-P241-P242-P264-P280-P370+P378-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes
F,C
Risk Statements
11 · 11-34
Safety Statements
16 · 16-23-26-36-45
RIDADR
2353 · UN 2353
WGK Germany
1 · 1
F
13 · 13
Autoignition Temperature
280 °C · 280 °C
TSCA
TSCA listed
HS Code
2915 · 2915 90 70
HazardClass
3 · 3
PackingGroup
II
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 InhalationAcute · Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2Eye Dam. 1Flam. Liq. 2Skin Corr. 1B
Hazardous Substances Data
141 · 141-75-3(Hazardous Substances Data)
REACH Registrations
Active
Limited Quantities
1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Fire Potential
Flammable ... .
Health Hazards · 2 items

Extremely destructive to the mucous membranes, upper respiratory tract, eyes, and skin. Inhalation may cause death as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1 item

Evolves HCl when spilled in water; [ERG 2016] A strong irritant; [HSDB] A severe skin, eye, and mucous membrane irritant; Inhalation may cause chemical pneumonitis and pulmonary edema; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause edema and chemical pneumonitis; [MSDSonline]

DOT ID and Guide2353 155
Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

BUTYRYL CHLORIDE slowly dissolves in water with decomposition and formation of a weakly acidic solution. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

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.

Storage ConditionsKeep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Storage class (TRGS 510): Flammable liquids.
Cleanup Methods · 1 item

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.

Nonfire Spill ResponseExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Disposal Methods · 2 items

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Preventive Measures · 4 items

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains.

Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Use explosion-proof equipment. Keep away from sources of ignition. No smoking. Take measures to prevent the build up of electrostatic charge.

Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Isolation and Evacuation · 4 items

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

Immediate precautionary measure

When spilled in water

When spilled in water

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.
Artificial Pollution Sources · 1 item

n-Butyryl chloride's production and use in organic synthesis(1) may result in its release to the environment through various waste streams(SRC). Butyryl chloride is used as an intermediate for the synthesis of active pharmaceutical ingredients benzoyl peroxide, t-butyl perbenzoate, and benzophenone(2). It is used as an acylation reagent and it is involved in the preparation of chromones and antiproliferative agents(2).

Environmental Bioconcentrationn-Butyryl chloride decomposes in water to yield hydrochloric acid(1), therefore, bioconcentration in aquatic organisms is not expected to be an important fate process(SRC).
Volatilization from Water/Soil · 1 item

n-Butyryl chloride decomposes in water to yield hydrochloric acid adn butyric acid(1), therefore, volatilization of n-butyryl chloride from water or moist soil is not expected to be an important fate process(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).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of n-butyryl chloride with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.1 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). n-Butyryl chloride fumes in air(2). It decomposes exothermically in water to yield corrosive hydrochloric acid. Based on a scenario where the chemical is spilled into an excess of water (at least 5 fold excess of water), half of the maximum theoretical yield of hydrogen chloride gas will be created in 0.47 minutes(2).

Probable Routes of Human Exposure · 1 item

Occupational exposure to n-butyryl chloride may occur through inhalation and dermal contact with this compound at workplaces where n-butyryl chloride is produced or used. Available use data indicate that the general population is not exposed to n-butyryl chloride. (SRC)

Environmental Fate/Exposure Summary · 1 item

n-Butyryl chloride's production and use in organic synthesis may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 41.7 mm Hg at 25 °C indicates n-butyryl chloride will exist solely as a vapor in the atmosphere. Vapor-phase n-butyryl chloride will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 4.1 days. n-Butyryl chloride fumes in air and can react with moisture in air. If released to soil, leaching in soil and volatilization from moist soil are not expected to be important fate processes because n-butyryl chloride reacts and decomposes in water. n-Butyryl chloride is expected to volatilize from dry soil surfaces based upon its vapor pressure. If released into water, n-butyryl chloride decomposes exothermically to yield hydrochloric acid and butyric acid. This decomposition reaction will be the dominant fate process in water. Occupational exposure to n-butyryl chloride may occur through inhalation and dermal contact with this compound at workplaces where n-butyryl chloride is produced or used. Available use data indicate that the general population is not exposed to n-butyryl chloride. (SRC)

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
risk_code
11-34
Signal word
Danger
Symbol(GHS)
GHS02,GHS05
hazard_code
F,C
safety_code
16-23-26-36-45
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
II
Hazard statements
H314-H225-H290
Limited Quantities
1.0 L (0.3 gallon) (liquid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 2Eye Dam. 1Flam. Liq. 2Skin Corr. 1B
Autoignition Temperature
280 °C
Precautionary statements
P501-P240-P210-P233-P234-P243-P241-P242-P264-P280-P370+P378-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P406-P405
Hazardous Substances Data
141-75-3(Hazardous Substances Data)

Upstream & downstream products

Upstream raw materials

AcetoneButyric Acid101Phosphorus trichlorideThionyl chloride

Downstream products

Esfenvalerate2-Benzyl-2-(dimethylamino)-4'-morpholinobutyrophenoneEthyl 2-acetyl-3-oxo-hexanoateButyric anhydrideHymexazol4-Methyl-2-n-propyl-1H-benzimidazole-6-carboxylic acid(R)-Glycidyl butyrate4-Chlorophenyl cyclopropyl ketoneButyrophenone1,1'-Di-n-butylferrocene1-(2,3-Dichloro-4-hydroxyphenyl)butan-1-one2-chloro-2-trichloroethyl-3,3-dimethyl cyclobutenonecycloxydimFlucycloxuronDeltamethrinGERANYL BUTYRATEButylferroceneADSEthyl(4-butyry-2,3-dichloro)phenoxyacetate7-Methyl-2-propyl-1H-benzoimidazole-5-carboxylic acid methyl esterFenvalerate1-TetraloneSethoxydimDiethyl butyrylmalonateLINALYL BUTYRATEEthacrynic acidS-Butyrylthiocholine IodideBunazosin hydrochloride