Propyl chloroformate

HCID 7998CAS 109-61-5

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

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 Esterchloroformic acid n-propyl esterpropylchloroformateChloroformicacidpropylesterHSDB 5392carbonochloridic acid propyl ester

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

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

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

Safety & regulation

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

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.)

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)

· 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.

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].

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.

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.

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通润丰石油化工有限公司66017690 19952660367 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]

Related reactions

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Linked notes

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