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Butyl Chloride

HCID 8005
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Basic information

CAS
109-69-3
Standard SMILES
CCCCCl
InChIKey
VFWCMGCRMGJXDK-UHFFFAOYSA-N
Molecular formula
C4H9Cl
Average molar mass
92.57 g/mol
Monoisotopic mass
92.03927797

Overview

Butyl chloride appears as a water white liquid with a sharp odor. Flash point 20 °F. Boiling point 77-78 °C (173 °F). Density 7.5 lb / gal. Slightly soluble in water. Vapors are heavier than air. Used in the manufacture of a variety of organic chemicals.

Names & identifiers

Preferred name
Butyl Chloride
IUPAC
1-chlorobutane
English name
1-Chlorobutane
Molecular formula
C4H9Cl
Molecular weight
92.57

Names & synonyms

1-Chlorobutane109-69-3Butyl chlorideN-BUTYL CHLORIDEChlorure de butyleButane, 1-chloro-NBC wormerN-Propylcarbinyl chlorideSure ShotNCI-C06155DTXSID8020206NSC-8419
Show more names
n-Chlorobutane1-butyl chloride1-CHLOROBUTANE, 99%1-CHLOROBUTANE, 99%1-CHLOROBUTANE, 99%1-CHLOROBUTANE, 99%n-C4H9Clorobutane
ZP7R667SGDDTXCID00206NBC Kaps WormerRefChem:57812Happy Jack Worm Capsules203-696-6chlorobutane1-CHLORO-BUTANE

Database identifiers

CAS
109-69-3、25154-42-1
PubChem CID
8005
DTXSID
DTXSID8020206
ChEMBL
CHEMBL47259
UNII
ZP7R667SGD
EC Number
203-696-6
Nikkaji
J2.435J

Properties

Computed structural properties

XLogP
2.6
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
2
Heavy atoms
5
Formal charge
0
Complexity
13.1

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Chlorinated Aliphatics
SpringerMaterials PropertiesSchoenflies notation
PesticidesPesticide -> EPA IRIS
LogP · 3 items

log Kow= 2.39

2.82

2.39

OdorUnpleasant
Density · 4 items

0.8862 at 68 °F (USCG, 1999) - Less dense than water; will float

0.88098 @ 25 °C/4 °C; 0.89197 @ 15 °C/4 °C; 0.88648 @ 20 °C/4 °C

Relative density (water = 1): 0.89 (20 °C)

0.892 @ 15°C

Viscosity · 2 items

0.0045 POISE @ 20 °C

0.45 mPa*s at 20 °C

Color/FormCOLORLESS LIQ
Solubility · 3 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, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

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)

Hazard information

Regulatory Information · 5 items

Chemical: Butane, 1-chloro-

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

Status: Active Update: 16-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13696

Butane, 1-chloro-: HSNO Approval: HSR001101 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 · 3 items

Special Hazards of Combustion Products: May produce phosgene gas in fire (USCG, 1999)

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

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.

Fire PotentialFLAMMABLE, DANGEROUS FIRE RISK.
Health Hazards · 2 items

Chemistry & industry

Uses & manufacturing

Uses · 6 items

Used as a solvent, intermediate, and veterinary anthelmintic; [HSDB]

SOLVENT; INT IN SYNTHESIS OF ALKYLATED ANILINES

Key intermediate for organotin stabilizer

Reacts with lithium metal in hydrocarbon media, eg, hexane and cyclohexane, to yield n-butyl lithium /the most important organolithium compound/

Reacts with magnesium metal in a hydrocarbon solvent to produce di-n-butylmagnesium (DNBM)

For more Uses (Complete) data for N-BUTYL CHLORIDE (7 total), please visit the HSDB record page.

U.S. Production · 3 items

2023: 100,000 - <250,000 lb

(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS

(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS

Consumer UsesIntermediate
Industry UsesCatalyst
Methods of Manufacturing · 2 items

IRRADIATION OF ETHYLENE AND HYDROGEN CHLORIDE WITH COBALT 60

PREPD FROM N-BUTYL ALC BY HEATING WITH HYDROCHLORIC ACID & ANHYDROUS ZINC CHLORIDE.

Formulations/PreparationsGRADES: NF; TECHNICAL.
Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
General Manufacturing Information · 2 items

All other Petroleum and Coal Products Manufacturing

Butane, 1-chloro-: ACTIVE

Applications · 5 items

DescriptionButyl chloride is a highly flammable, clear,colorless liquid. Molecular weight = 92.6 (n- and sec-isomers); Boiling point = 77℃; 69℃ (sec-isomer); Specificgravity (H2O:1) = 0.89; Freezing/Melting point =-123℃; Flash point = 9℃; - 10℃ (sec-isomer);Relative vapor density (air =1) = 3.2 (n- and sec-isomers);Vapor pressure = 81 mmHg at 20℃; Autoignitiontemperature = 240℃. Explosive limits: LEL = 1.8%;UEL = 10.1%. Insoluble in water. Hazard Identification(based on NFPA-704 M Rating System): Health 2,Flammability 3, Reactivity 0; (sec-) Health 2, Flammability4, Reactivity 0. Practically insoluble in water;solubility = 0.7% at 12℃.

Related reactions

152 records
New reaction record
HRID 3904 reaction equation
HRID 3904As reactantuspto-grants-1988_02
HRID 19678 reaction equation
HRID 19678As solventuspto-grants-2010_06
HRID 47944 reaction equation
HRID 47944As reactantuspto-grants-2004_03
HRID 64577 reaction equation
HRID 64577As solventuspto-grants-1986_09
HRID 66444 reaction equation
HRID 66444As solventuspto-grants-1982_08
HRID 76243 reaction equation
HRID 76243As solventuspto-grants-2014_09
HRID 90185 reaction equation
HRID 90185As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 90670 reaction equation
HRID 90670As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
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Compound notes

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less than 1 mg/mL at 59 °F (NTP, 1992)

PRACTICALLY INSOL IN WATER (0.066% @ 12 °C); MISCIBLE WITH ALC, ETHER

Solubility in water, g/l at 25 °C: 0.87 (practically insoluble)

Flash Point · 3 items

20 °F (NTP, 1992)

15 °F (-9 °C) (Closed Cup)

-12 °C

Animal DrugsActive Ingredients (N-butyl Chloride) -> FDA Greenbook

Physicochemical properties

Melting point
-123 °C · -123 °C (lit.)
Boiling point
77 · 77-78 °C (lit.)
Density
0.886 g/mL · 0.886 g/mL at 25 °C (lit.)
vapor density
3.2 · 3.2 (vs air)
vapor pressure
80.1 mm · 80.1 mm Hg ( 78.4 °C)
refractive index
20 · n20/D 1.402(lit.)
Flash point
-12 °F · -12 °F
storage temp.
2 · 2-8°C
solubility
0.11 g/L · water: soluble0.11g/L at 20°C
form
Viscous Liquid
color
White to pink to light brown
Odor
Unpleasant odor
Viscosity
0.45 mPa.s · 0.45 mPa.s (20°C)
explosive limit
1.8 · 1.8-10.1%(V)
Water Solubility
0.5 g/L · 0.5 g/L (20 ºC)
Merck
14 · 14,1560
BRN
1730909 · 1730909
Henry's Law Constant
5.6 · 5.6×10-4 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
9.6 · 9.6(20℃)
Stability
Stable. Highly flammable. Note low flash point and wide explosion limit range. Incompatible with strong oxidizing agents, strong bases.
InChI
1S/C4H9Cl/c1-2-3-4-5/h2-4H2,1H3
InChIKey
VFWCMGCRMGJXDK-UHFFFAOYSA-N
SMILES
CCCCCl
LogP
2.66 at · 2.66 at 20℃
Surface tension
23.74 mN/m · 23.74mN/m at 293.15K
Toxicology and Carcinogenesis
Toxicology and Carcinogenesis Studies of n-Butyl Chloride (CASRN 109-69-3) in F344/N Rats and B6C3F1 Mice (Gavage Studies)
CAS DataBase Reference
109 · 109-69-3(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
7 R667SGD · ZP7R667SGD
NIST Chemistry Reference
1 · Butane, 1-chloro-(109-69-3)
EPA Substance Registry System
1 · 1-Chlorobutane (109-69-3)
UNSPSC Code
41116105 · 41116105
NACRES
22 · NA.22
Symbol(GHS)
2 · GHS02,GHS08
Signal word
Danger
Hazard statements
303 · H303-H361-H304-H225
Precautionary statements
501 · P501-P202-P240-P210-P233-P201-P243-P241-P242-P280-P370+P378-P312-P331-P303+P361+P353-P301+P310-P403+P235-P405
Hazard Codes
F
Risk Statements
11 · 11
Safety Statements
9 · 9-16-29
RIDADR
1127 · UN 1127 (CHLOROBUTANES)
WGK Germany
2 · 2
RTECS
6300000 · EJ6300000
F
1 · 1-10
Autoignition Temperature
860 °F · 860 °F
TSCA
TSCA listed
HazardClass
3 · 3
PackingGroup
II
HS Code
29031990 · 29031990
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
3 Asp · Aquatic Chronic 3Asp. Tox. 1Flam. Liq. 2
Hazardous Substances Data
109 · 109-69-3(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: 2.67 g/kg (Smyth)
REACH Registrations
Active

Mildly irritating to the skin and eyes, liquid may cause rash due to removal of skin oils. Ingestion or skin absorbtion may cause intestinal upset, cramping, and central nervous system depression. (USCG, 1999)

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

Hazards Summary · 1 item

Dangerous fire risk; [Hawley] Reacts slowly with water evolving hydrochloric acid; A skin, eye, and respiratory tract irritant; The substance may cause effects on the nervous system. [ICSC] A skin and eye irritant; [HSDB] A mild skin and eye irritant based on animal studies; [CHEMINFO] An irritant; Effects in high-dose animal studies (subacute and chronic) include convulsions or effect on seizure threshold; [MSDSonline]

DOT ID and Guide1127 130
FDA RequirementsSpecification and dosage requirements for n-butyl chloride are given in detail for the removal of ascarids and hookworms in dogs, puppies, cats, and kittens.
Reactive GroupHalogenated Organic Compounds
UN ClassificationUN Hazard Class: 3; UN Pack Group: II
Special ReportsDHHS/NTP; Toxicology & Carcinogenesis Studies of n-Butyl Chloride in F344/N Rats and B6C3F1 Mice Technical Report Series No. 312 (1986) NIH Publication No. 86-2568
Reactivity AlertsHighly Flammable

Safety & protection

Fire Fighting · 2 items

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

Use powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

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:

Safe StorageFireproof. Separated from incompatible materials. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access. See Chemical Dangers.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting Procedures · 3 items

To fight fire: Foam, carbon dioxide, dry chemical.

If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemial or carbon dioxide.

If fire becomes uncontrollable or container is exposed to direct flame-consider evacuation of one-third (1/3) mile radius.

Nonfire Spill ResponseExcerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. Do NOT let this chemical enter the environment.

Preventive Measures · 4 items

If material /is/ not on fire and not involved in /a/ 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.

Avoid breathing vapors. Keep upwind. 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 material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and Evacuation · 2 items

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

Immediate precautionary measure

Eye PreventionWear safety spectacles or eye protection in combination with breathing protection.

Toxicology

Ecotoxicity ValuesLC50 Poecilia reticulata (guppy) 97 ppm/7 days /Conditions of bioassay not specified/
Environmental Fate · 4 items

TERRESTRIAL FATE: n-Butyl chloride has a very high vapor pressure, 100 mm Hg at 25 °C(1), indicating that volatilization from soil will be rapid and a primary removal process. It has an estimated low adsorptivity to soil (Koc = 93-102)(1-2) and therefore would be mobile in soil. Biodegradation in soil is unknown(SRC).

AQUATIC FATE: If released in water, n-butyl chloride will be lost rapidly by volatilization. Its estimated volatilization half-life in a model river and pond are 2.9 hr(1-2) and 34 hr(3), respectively. In groundwater, where volatilization may not occur, n-butyl chloride may be lost by hydrolysis. Based upon hydrolysis rates for alkyl chlorides, the half-life is estimated to be between 6 hr and 38 days at neutral pH(4). The half-life at higher pHs will be shorter. Photodegradation, adsorption to sediment, and bioconcentration in fish are not important aquatic fate processes(SRC).

ATMOSPHERIC FATE: n-Butyl chloride will degrade via reaction with photochemically produced hydroxyl radicals in the atmosphere. The half-life of n-butyl chloride in the atmosphere is estimated to be 7.0 days(1). n-Butyl chloride does not absorb radiation >290 nm and therefore it will not directly photolyze(2). Due to its water solubility, 1100 mg/l(3), washout by rain should occur. However, n-butyl chloride removed in this manner will revolatilize into the atmosphere(SRC).

Maximum permissible concentrations in open waters are 0.004 mg/l.

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Signs and Symptoms · 4 items

Cough. Sore throat. Drowsiness.

Redness. Dry skin.

Redness.

See Inhalation.

Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=109-69-3]

Effluent ConcentrationsIn a study of 63 industrial effluents that discharge into surface waters, chlorobutane was found in one effluent at a concentration of <10 ug/l(1).
ICSC Environmental DataBioaccumulation of this chemical may occur along the food chain.
EPA IRIS Information1-Chlorobutane
Soil Adsorption/MobilityUsing the water solubility for n-butyl chloride, 1100 mg/l(1), the Koc can be estimated to be 93 and 102 using two recommended regression equations(2,SRC). These estimates indicate that n-butyl chloride will have high mobility in soil(3).
Atmospheric ConcentrationsSOURCE DOMINATED: n-Butyl chloride was identified, but not quantified, in one of 10 samples of ambient air in the Kanawna Valley, WV(1). Various locations were sampled during three trips.
Human Toxicity Excerpts · 2 items

TOXIC ON PROLONGED INHALATION.

WEAKER CENTRAL NERVOUS DEPRESSANT ACTIONS THAN ETHYL CHLORIDE.

Regulatory information

FDA RequirementsSpecification and dosage requirements for n-butyl chloride are given in detail for the removal of ascarids and hookworms in dogs, puppies, cats, and kittens.
State Drinking Water Guidelines(FL) FLORIDA 2,800 ug/l

Safety data

F
1-10
wgk
2
tsca
TSCA listed
rtecs
EJ6300000
ridadr
UN 1127 (CHLOROBUTANES)
hs_code
29031990
Toxicity
LD50 orally in rats: 2.67 g/kg (Smyth)
risk_code
11
Signal word
Danger
Symbol(GHS)
GHS02,GHS08
hazard_code
F
safety_code
9-16-29
hazard_class
3
Storage Class
3 - Flammable liquids
packing_group
II
Hazard statements
H303-H361-H304-H225
REACH Registrations
Active
Hazard Classifications
Aquatic Chronic 3Asp. Tox. 1Flam. Liq. 2
Autoignition Temperature
860 °F
Precautionary statements
P501-P202-P240-P210-P233-P201-P243-P241-P242-P280-P370+P378-P312-P331-P303+P361+P353-P301+P310-P403+P235-P405
Hazardous Substances Data
109-69-3(Hazardous Substances Data)

Uses1-Chlorobutane is used as intermediates and solvents. It is used for HPLC, spectrophotometry and environmental testing. It is used as alkylating reagent in organic and organometallic compound synthesis. It is also employed as an antihelmintic in veterinary medicine.

Uses1-Chlorobutane may be used in the synthesis of ionic liquids, 1-butyl-3-methylimidazolium hydrogen sulfate ([Bmim]+[HSO4]-) and 1-butyl-3-methylimidazolium dihydrogen phosphate ([Bmim]+[H2PO4]-).

Uses1-Chlorobutane is used as an intermediate for the production of other chemicals in the chemical industry. 1-chlorobutane is a common extraction solvent in the forensic toxicology arena. A benefit of 1-chlorobutane is that it is less dense than water and therefore settles above the aqueous layer. As butylating agent in organic synthesis, e.g., in the manufacture of butyl cellulose. 1-chlorobutane will be halogenated to produce dichlorobutane using sulfuryl chloride via a free-radical chain reaction mechanism.

General DescriptionA water white liquid with a sharp odor. Flash point 20°F. Boiling point 77-78°C (173°F). Density 7.5 lb / gal. Slightly soluble in water. Vapors are heavier than air. Used in the manufacture of a variety of organic chemicals.

Preparation methods · 1 item

Preparation1-Chlorobutane is obtained by esterification of n-butanol with hydrogen chloride or hydrochloric acid at 100℃ either without a catalyst or utilizing the accelerating effect of zinc chloride, tripentylamine hydrochloride, or phosphorus pentachloride. n-Butyl chloride is also obtained, along with 2-chlorobutane, by the chlorination of butane over aluminum oxide at 200℃.

Upstream & downstream products

Upstream raw materials

Zinc chlorideHydrochloric acid1-Butanol

Downstream products

AZIMILIDEVanadyl acetylacetonateDibutyltin oxide3,6,9,12-tetraoxahexadecan-1-olBis(tributyltin) oxide1-Butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide4-(4-Fluorophenyl)pyrimidine-2-thiol2-(4-Chlorophenyl)-hexanenitrileDiethyl butylmalonate1,4-Dichlorobutanealpha-butyl-alpha-phenyl-1H-imidazole-1-propiononitrileMyclobutanil6-Bromopyridine-2-carbaldehydetert-ButylbenzeneButylamine2 -phenyl-HexanenitrileSisthsneMetsulfuron methylDibutyl sulfiden-Butyllithium