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Propyl chloroformate

HCID 7998
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
109-61-5
Standard SMILES
CCCOC(=O)Cl
InChIKey
QQKDTTWZXHEGAQ-UHFFFAOYSA-N
Molecular formula
C4H7ClO2
Average molar mass
122.55 g/mol
Monoisotopic mass
122.0134572

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

Propyl chloroformate109-61-5Propyl chlorocarbonateN-PROPYL CHLOROFORMATECarbonochloridic acid, propyl esterFormic acid, chloro-, propyl esterUN2740A5Y2T003JUDTXSID3042342UN-2740RefChem:176484DTXCID1022342
Show more names
NPCFchloro-formicacipropylesterPropyl chloroforMatProply chloroformateChloride propyl forMatePropyl chloridocarbonate
203-687-7propyl carbonochloridateChloroformic Acid Propyl Estern-PrOCOClchloroformic acid n-propyl ester1-propyl chloroformatePropyl chloridocarbonate #propylchloroformate

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 · 2 items

Toxic Gases & Vapors -> Acid Halides

Flammable agents - 3rd degree

SpringerMaterials PropertiesDielectric constant
LogP1.12
Density · 5 items

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

Viscosity0.80 cP @ 20 °C
Color/FormCOLORLESS LIQUID
Solubility · 3 items

MISCIBLE WITH BENZENE, CHLOROFORM, ETHER

Insoluble in water

Solubility in water: reaction

Flash Point · 3 items

-58 °F (EPA, 1998)

-50 °C (-58 °F)

26 °C c.c.

Boiling Point · 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, 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

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 3 items

REACH registered substance: Propyl chloroformate (EC: 203-687-7)

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.)

DOT LabelPoison Inhalation Hazard Flammable Liquid Corrosive
Fire Hazards · 3 items

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)

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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

ImpuritiesCarbon dioxide, hydrogen chloride, phosgene, and alkyl chlorides; main impurities are corresponding carbonates /chloroformic esters/
U.S. ProductionND (1992)
Methods of ManufacturingPrepared by the reaction of liquid anhydrous alcohol /n-propyl alcohol/ with molar excess of dry, chlorine-free phosgene at low temperature /low molecular weight alkyl chlorofomates/
Formulations/Preparations · 2 items

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 · 2 items

Carbonochloridic acid, propyl ester: ACTIVE

Most chloroformate production is used captively and production figures are not available.

Applications · 2 items

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.

Related reactions

104 records
New reaction record
HRID 15810 reaction equation
HRID 15810As reactantuspto-grants-2010_06
HRID 30125 reaction equation
HRID 30125As reactantuspto-grants-2008_09
HRID 36254 reaction equation
HRID 36254As reactantuspto-grants-1995_05
HRID 72130 reaction equation
HRID 72130As reactantuspto-grants-2014_09
HRID 88419 reaction equation
HRID 88419As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 114368 reaction equation
HRID 114368As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 141965 reaction equation
HRID 141965As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 144296 reaction equation
HRID 144296As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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237 to 241 °F at 760 mmHg (EPA, 1998)

112.4 °C

115 °C

Vapor Density · 3 items

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 · 3 items

20.0 [mmHg]

20 mm Hg @ 25.3 °C

Vapor pressure, kPa at 20 °C: 2.6

Refractive IndexINDEX OF REFRACTION: 1.4045 @ 20 °C

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

· 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 · 2 items

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.

Hazards SummaryA corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation can cause pulmonary edema; [ICSC] A strong eye and mucous membrane irritant; [HSDB] See CHLOROFORMATES.
DOT ID and Guide2740 155
Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates
EC ClassificationSymbol: T; R: 10-23-34; S: (1/2)-26-36-45
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 3 and 8; UN Pack Group: I
Reactivity AlertsHighly Flammable
Reactivity Profile · 1 item

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 · 2 items

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 · 4 items

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 · 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

Warning: Propyl chloroformate is strongly irritating to eyes and mucous membranes. Caution is advised.

General First Aid:

Safe StorageFireproof. Provision to contain effluent from fire extinguishing. Separated from acids, alcohols, amines, bases, oxidants and food and feedstuffs. Dry. Well closed. Store in an area without drain or sewer access.
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 · 1 item

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.

Storage ConditionsOWING TO THE FACT THAT THESE COMPOUNDS DECOMP EASILY, STORAGE CONTAINERS SHOULD BE VENTED. /CHLOROFORMATES/
Nonfire Spill ResponseExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Spillage Disposal · 1 item

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 · 1 item

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 · 4 items

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

Immediate precautionary measure

Small spill:

Small spill:

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour and by ingestion.
Signs and Symptoms · 4 items

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.

ICSC Environmental DataThe substance is toxic to aquatic organisms.
Human Toxicity ExcerptsTHE VAPORS ARE STRONGLY IRRITATING TO THE EYES & MUCOUS MEMBRANES.
Toxicity DataLC50 (mice) = 319 ppm/1h

Regulatory information

CERCLA Reportable Quantities · 1 item

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) · 4 items

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)
Preparation methods · 1 item

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

Flow CellHydrochloric acid