Basic information
- 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
Show more names
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
LogP
log Kow= 2.39
2.82
2.39
Density
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
0.0045 POISE @ 20 °C
0.45 mPa*s at 20 °C
Solubility
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
20 °F (NTP, 1992)
15 °F (-9 °C) (Closed Cup)
-12 °C
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
Safety & regulation
GHS classification
GHS Classification
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
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.)
Fire Hazards
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.
Health Hazards
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
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]
Safety & protection
Fire Fighting
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
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
· 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
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:
Fire Fighting Procedures
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.
Spillage Disposal
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
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
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Immediate precautionary measure
Toxicology
Environmental Fate
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.
Signs and Symptoms
Cough. Sore throat. Drowsiness.
Redness. Dry skin.
Redness.
See Inhalation.
Ongoing Test Status
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]
Human Toxicity Excerpts
TOXIC ON PROLONGED INHALATION.
WEAKER CENTRAL NERVOUS DEPRESSANT ACTIONS THAN ETHYL CHLORIDE.
Regulatory information
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)
Chemistry & industry
Uses & manufacturing
Uses
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
2023: 100,000 - <250,000 lb
(1977) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
Methods of Manufacturing
IRRADIATION OF ETHYLENE AND HYDROGEN CHLORIDE WITH COBALT 60
PREPD FROM N-BUTYL ALC BY HEATING WITH HYDROCHLORIC ACID & ANHYDROUS ZINC CHLORIDE.
General Manufacturing Information
All other Petroleum and Coal Products Manufacturing
Butane, 1-chloro-: ACTIVE
Applications
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℃.
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
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
Downstream products
Suppliers50 total
Related reactions
Linked notes
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