Basic information
- Standard SMILES
CCCOC(=O)Cl- InChIKey
QQKDTTWZXHEGAQ-UHFFFAOYSA-N- Molecular formula
- C4H7ClO2
- Average molar mass
- 122.55 g/mol
- Monoisotopic mass
- 122.01345714
Overview
N-propyl chloroformate appears as a colorless liquid. May be decomposed by water. Severely irritates skin and eyes. Very toxic by ingestion, inhalation or skin absorption. Denser than water and vapors heavier than air. Flash point 50 °F. Used to make other chemicals.
Names & identifiers
- Preferred name
- Propyl chloroformate
- IUPAC
- propyl carbonochloridate
- English name
- Propyl chloroformate
- Molecular formula
- C4H7ClO2
- Molecular weight
- 122.55
Names & synonyms
Show more names
Database identifiers
- CAS
109-61-5- PubChem CID
- 7998
- DTXSID
DTXSID3042342- UNII
- A5Y2T003JU
- EC Number
- 203-687-7
- Nikkaji
- J34.719A
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 62.7
Experimental & physicochemical properties
Chemical Classes
Toxic Gases & Vapors -> Acid Halides
Flammable agents - 3rd degree
Density
1.09 at 68 °F (EPA, 1998) - Denser than water; will sink
1.091 AT 20 °C/4 °C
1.09 g/cm³
Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.06
1.09 @25 °C
Solubility
MISCIBLE WITH BENZENE, CHLOROFORM, ETHER
Insoluble in water
Solubility in water: reaction
Flash Point
-58 °F (EPA, 1998)
-50 °C (-58 °F)
26 °C c.c.
Boiling Point
237 to 241 °F at 760 mmHg (EPA, 1998)
112.4 °C
115 °C
Vapor Density
4.2 (EPA, 1998) - Heavier than air; will sink (Relative to Air)
4.2 (AIR= 1)
Relative vapor density (air = 1): 4.23
Vapor Pressure
20.0 [mmHg]
20 mm Hg @ 25.3 °C
Vapor pressure, kPa at 20 °C: 2.6
Physicochemical properties
- Boiling point
- 105 · 105-106 °C(lit.)
- Density
- 1.09 g/mL · 1.09 g/mL at 25 °C(lit.)
- vapor pressure
- 0.87 psi · 0.87 psi ( 20 °C)
- refractive index
- 20 · n20/D 1.404(lit.)
- Flash point
- 84 °F · 84 °F
- storage temp.
- 2 · 2-8°C
- solubility
- benzene: miscible(lit.)
- form
- Oil
- color
- Colourless
- Specific Gravity
- 1.09 · 1.09
- Merck
- 13 · 13,7940
- Dielectric constant
- 11.2 · 11.2(20℃)
- Stability
- Volatile
- InChIKey
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N
- LogP
- 1.385 · 1.385 (est)
- CAS DataBase Reference
- 109 · 109-61-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 Y2T003JU · A5Y2T003JU
- NIST Chemistry Reference
- n-Propylchloroformate(109-61-5)
- EPA Substance Registry System
- Propyl chloroformate (109-61-5)
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06,GHS08
- Signal word
- Danger
- Hazard statements
- 330 · H330-H302-H314-H371-H401-H225
- Precautionary statements
- 501 · P501-P273-P270-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- Hazard Codes
- T,F
- Risk Statements
- 10 · 10-23-34-22-11
- Safety Statements
- 26 · 26-36-45-16
- RIDADR
- 2740 · UN 2740
- WGK Germany
- 1 · 1
- RTECS
- 6830000 · LQ6830000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- I
- HS Code
- 29151300 · 29151300
- Hazardous Substances Data
- 109 · 109-61-5(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LC50,inhalation,319ppm/1H (319ppm),"Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 4, Pg. 758, 1978.
- 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, P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P233, 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, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Status: Active Update: 05-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1891
Carbonochloridic acid, propyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
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
When heated to decomposition, it emits toxic fumes of chlorine containing compounds. Propyl chloroformate is a flammable/combustible material; it may be ignited by heat, sparks or flames. Vapors may travel to a source of ignition and flash back. Container may explode in heat or fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Runoff from fire control or dilution water may cause pollution. Gradually decomposed by water and alcohol. Unstable, decomposes spontaneously to form hydrochloric acid and other products. Avoid moist air. (EPA, 1998)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 26 °C explosive vapour/air mixtures may be formed.
Health Hazards
Strongly irritating to eyes and mucous membranes. Poisonous; may be fatal if inhaled, swallowed or absorbed through skin. (EPA, 1998)
· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
Reactivity Profile
Unstable, decomposes spontaneously to form hydrochloric acid and other products. Avoid moist air. [EPA, 1998]. 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 Fighting
Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear positive pressure breathing apparatus and special protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire.
NO water. Use dry powder, carbon dioxide, alcohol-resistant foam. In case of fire: keep drums, etc., cool by spraying with water. NO direct contact with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
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. Give one or two glasses of water to drink. 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
Warning: Propyl chloroformate is strongly irritating to eyes and mucous membranes. Caution is advised.
General First Aid:
Exposure Control and Personal Protection
· 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
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. Apply water from as far a distance as possible. Use "alcohol" foam, carbon dioxide or dry chemical. Keep run-off water out of sewers and water sources.
Spillage Disposal
Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable dry plastic containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.
Preventive Measures
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 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Immediate precautionary measure
Small spill:
Small spill:
Toxicology
Signs and Symptoms
Sore throat. Burning sensation. Cough. Laboured breathing. Shortness of breath. Symptoms may be delayed.
Redness. Pain. Skin burns.
Redness. Pain. Severe deep burns.
Abdominal pain. Burning sensation. Shock or collapse.
Regulatory information
CERCLA Reportable Quantities
Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Propyl chloroformate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 lbs.
DHS Chemicals of Interest (COI)
Propyl chloroformate
1.00
10,000
Flammable chemical that can be released at a facility.
Safety data
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- LQ6830000
- ridadr
- UN 2740
- hs_code
- 29151300
- Toxicity
- mouse,LC50,inhalation,319ppm/1H (319ppm),"Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds. New York, John Wiley & Sons, Inc., 1978Vol. 4, Pg. 758, 1978.
- risk_code
- 10-23-34-22-11
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06,GHS08
- hazard_code
- T,F
- safety_code
- 26-36-45-16
- hazard_class
- 6.1
- packing_group
- I
- Hazard statements
- H330-H302-H314-H371-H401-H225
- REACH Registrations
- Active
- Precautionary statements
- P501-P273-P270-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P308+P311-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 109-61-5(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used in organic synthesis; [CAMEO] Used as a military poison gas (lachrymator); [Hawley] Used as a reactive intermediate to polymerization initiators and other chemicals; [HSDB]
Reactive intermediate to polymerization initiators and other chemicals
Formulations/Preparations
Typical specifications of commercial chloroformates: purity, 98%; phosgene, <0.1%, iron, <10 ppm; acidity as HCl, <0.1%; alcohol or phenol, <2% /chloroformic esters/
Commercial products have concentrations of 97-99 wt% /chloroformic esters/
General Manufacturing Information
Carbonochloridic acid, propyl ester: ACTIVE
Most chloroformate production is used captively and production figures are not available.
Applications
UsesPropyl Chloroformate is used as a dramatizing agent for the determination of morphine, codeine and 6-acetyl morphine in urine and blood using direct aqueous derivatization.
General DescriptionN-propyl chloroformate appears as a colorless liquid. May be decomposed by water. Severely irritates skin and eyes. Very toxic by ingestion, inhalation or skin absorption. Denser than water and vapors heavier than air. Flash point 50°F. Used to make other chemicals.
Preparation methods
PreparationSynthesis of Propyl chloroformate: Add n-propanol to the phosgene-passing kettle, start stirring, and then pass phosgene through the phosgene flowmeter. The phosgene-passing temperature is about 30 °C, and continue to pass the phosgene for several hours. When the end point is approached, sample and analyze, and stop when the standard is reached. Pass phosgene, cool, and then pass nitrogen to drive away phosgene and hydrogen chloride, destroy phosgene, and sample and analyze it as a product. Reaction equation: CH3CH2CH2OH+COCl2→ClCOOCH2CH2CH3
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Related reactions
Linked notes
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