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Ethyl chloroformate

HCID 10928
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
541-41-3
표준 SMILES
CCOC(=O)Cl
InChIKey
RIFGWPKJUGCATF-UHFFFAOYSA-N
분자식
C3H5ClO2
평균 분자량
108.52 g/mol
단동위원소 질량
107.99780708

개요

Ethyl chloroformate appears as a colorless liquid with a pungent odor. Flash point 66 °F. Very toxic by inhalation. Corrosive to metals and tissue. Vapors are heavier than air. Prolonged exposure to low concentrations or short exposure to high concentrations may have adverse health effects from inhalation.

이름 및 식별자

우선 이름
Ethyl chloroformate
IUPAC
ethyl carbonochloridate
영어명
Ethyl chloroformate
분자식
C3H5ClO2
분자량
108.5236

이름 및 동의어

ETHYL CHLOROFORMATE541-41-3Ethyl carbonochloridateEthyl chlorocarbonateCathyl chlorideEthoxycarbonyl chlorideChloroformic acid ethyl esterCarbonochloridic acid, ethyl esterChlorocarbonic acid ethyl esterEtil cloroformiatoEthylchloorformiaatETHYLCHLOROFORMATE
이름 더 보기
Etil clorocarbonatoFormic acid, chloro-, ethyl esterEthyl chloromethanoateChlorocarbonate D'ethyleEthyle, chloroformiat D'ClhorameisensaeureaethylesterCloroformiato de etiloTL 423

데이터베이스 식별자

CAS
541-41-3
PubChem CID
10928
DTXSID
DTXSID1027186
ChEMBL
CHEMBL3183406
UNII
09601EZP9R
EC Number
208-778-5
Nikkaji
J53.980E

물성

구조 계산 물성보충 중

XLogP
1.5
극성 표면적
26.3 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
2
무거운 원자 수
6
형식 전하
0
복잡도
52.8

실험 및 물리화학적 성질

Chemical Classes · 2건

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesBoiling point
OdorSharp, like hydrochloric acid
Density · 4건

1.135 at 68 °F (USCG, 1999) - Denser than water; will sink

1.1403 @ 20 °C/4 °C

Relative density (water = 1): 1.1

1.1442 @ 15°C

Color/FormWATER-WHITE LIQUID
Solubility · 3건

PRACTICALLY INSOL & GRADUALLY DECOMP IN WATER

MISCIBLE WITH ALC, BENZENE, CHLOROFORM, ETHER

Solubility in water: reaction

CorrosivityCorrosive
Flash Point · 4건

61 °F (USCG, 1999)

16 °C

61 °F (16 °C) (CLOSED CUP)

16 °C c.c.

Boiling Point · 4건

201 °F at 760 mmHg (USCG, 1999)

95 °C @ 760 MM HG

95 °C

94 °C @760 [mm Hg]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P320, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 3.7% (11 of 299) of reports.

Danger

H225 (96.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 5건

Chemical: Carbonochloridic acid, ethyl ester

Carbonochloridic acid, ethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbonochloridic acid, ethyl ester 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: 19-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/13646

Ethoxycarbonyl chloride: HSNO Approval: HSR002989 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.)

Other Safety InformationIMAP assessments - Carbonochloridic acid, ethyl ester: Human health tier I assessment
DOT LabelPoison Inhalation Hazard Flammable Liquid Corrosive
Fire Hazards · 3건

Special Hazards of Combustion Products: Toxic chlorine and phosgene gases may be formed in fires. (USCG, 1999)

화학 및 산업

용도 및 제조

Uses · 6건

Used as solvent in the photographic industry and to make carbamates for the production of dyes, drugs, veterinary medicines, herbicides and insecticides; Used as a stabilizer for PVC; [HSDB]

Photographic Processing [Category: Other]

CHEM INT FOR ORE FLOTATION AGENTS; DIETHYL CARBONATE; ISOCYANATES; POLYMERS

Organic synthesis

In the manufacture of ore flotation agents by reaction with various alkyl xanthates.

Used as solvent in the photographic industry; also employed in the production of carbamates that are used to synthesis dyes, drugs, veterinary medicines, herbicides and insecticides...ethyl chloroformate is the most important commercial chloroformic ester...it reacts with ethyl xanthate to produce diethyl xanthogen formate and diethylxanthic anhydride which are used in the floatation of ores...also used as a stabilizer for PVC and in the production of modified penicillins, eg binotal...used to produce carboxylic acids anhydrides from carboxylic acids, secondary amines from tertiary amines, and nitriles from amides and to make heterocyclic compounds.

ImpuritiesCarbon dioxide, hydrogen chloride, phosgene, and alkyl chlorides; main impurities are corresponding carbonates
U.S. Production2020: <50,000 lb
Industry UsesIntermediate
Methods of ManufacturingREACTION OF CARBON MONOXIDE WITH GASEOUS CHLORINE, PRODUCING PHOSGENE (COCL2) WHICH IS THEN TREATED WITH ANHYDROUS ETHANOL GIVING ETHYL CHLOROCARBONATE & SPLITTING OFF HYDROGEN CHLORIDE.
Formulations/Preparations · 3건

GRADES: TECHNICAL

Typical specifications of commercial chloroformates: purity, 98%; phosgene, <0.1%, iron, <10 ppm; acidity as HCl, <0.1%; alcohol or phenol, <2%

Commercial products have concentrations of 97-99 wt% /chloroformic esters/

General Manufacturing Information · 5건

All Other Basic Organic Chemical Manufacturing

관련 반응

6,185건
반응 기록 만들기
HRID 910 반응식
HRID 910반응물로uspto-grants-1998_03
HRID 1299 반응식
HRID 1299반응물로uspto-grants-1998_03
HRID 1804 반응식
HRID 1804반응물로uspto-grants-1998_03
HRID 2341 반응식
HRID 2341반응물로uspto-grants-1998_03
HRID 2447 반응식
HRID 2447반응물로uspto-grants-1998_03
HRID 2507 반응식
HRID 2507반응물로uspto-grants-1998_03
HRID 2508 반응식
HRID 2508반응물로uspto-grants-1998_03
HRID 2760 반응식
HRID 2760반응물로uspto-grants-1998_03
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Decomposition
DANGEROUS; WHEN HEATED TO DECOMPOSITION, IT EMITS HIGHLY TOXIC FUMES OF /HYDROGEN CHLORIDE/.
Melting Point · 4건

-114 °F (USCG, 1999)

-80.6 °C

-80.6 °C

-80.6 °C

Vapor Density · 2건

3.7 (AIR= 1)

Relative vapor density (air = 1): 3.7

물리화학적 성질

녹는점
-81 °C · -81 °C
끓는 점
93 °C · 93 °C
밀도
1.135 · 1.135
증기 밀도
3.75 · 3.75 (vs air)
증기압
54 hPa · 54 hPa at 20 °C
인화점
10 °C · 10 °C
물리적 상태
액체
색상
무색의
폭발한계
3.7 · 3.70-12.60%
수용성
불용성

· 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 Potential · 2건

DANGEROUS; WHEN EXPOSED TO HEAT, FLAME, OXIDIZERS

FLAMMABLE, DANGEROUS FIRE RISK

Health Hazards · 2건

Inhalation causes mucous membrane irritation, coughing, and sneezing. Vapor causes severe lachrymation; liquid causes acid-type burns of eyes and skin, like those of hydrochloric acid. Ingestion causes severe burns of mouth and stomach. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Hazards Summary · 1건

Corrosive to skin; Highly toxic; [Quick CPC] A corrosive substance that causes lacrimation and may cause lung edema after inhalation of high concentrations; [ICSC] A strong irritant to skin, eyes, and respiratory tract; Capable of causing severe burns to the eyes and skin; [HSDB] Reacts with water; [MSDSonline] See CHLOROFORMATES.

DOT ID and Guide1182 155
Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates
EC ClassificationSymbol: F, T+; R: 11-22-26-34; S: (1/2)-9-16-26-28-33-36/37/39-45
UN ClassificationUN Hazard Class: 6.1; UN Subsidiary Risks: 3 and 8; UN Pack Group: I

안전 및 보호

Fire Fighting · 2건

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

Use alcohol-resistant foam, powder, carbon dioxide. NO water. In case of fire: keep cylinder cool by spraying with water. NO direct contact with water.

First Aid Measures · 4건

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. Refer for medical attention .

Accidental Release Measures · 2건

· 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 · 2건

INHALATION: remove to fresh air; use artificial respiration if breathing has stopped; call a doctor; keep victim quiet and administer oxygen if needed.

General First Aid:

Safe StorageFireproof. Separated from strong oxidants, food and feedstuffs and incompatible materials. See Chemical Dangers. Cool. Dry. Well closed.
Firefighting HazardsFlammable liquid. Vapors are heavier than air & may travel to a source of ignition & flash back. Combustion by-products include hydrogen chloride & other irritants & toxic gases.
Exposure Control and Personal Protection · 2건

· 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 · 2건

Use dry chemical, foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.

Storage Conditions · 2건

Store in a cool, dry, well-ventilated location. Separate from acids, alkalies, amines, alcohols, oxidizing materials, & water. Normally kept refrigerated.

Chloroformates should be stored in a cool, dry atmosphere. They should be transferred from containers to storage tanks or reactors through a closed system using stainless steel, or glass pump, lines and valves.

Nonfire Spill ResponseExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Disposal Methods · 1건

Releases may require isolation or evacuation. Eliminate all ignition sources. Stop or control the leak, if this can be done without undue risk. Use water spray to cool & disperse vapors & protect personnel. Absorb in noncombustible material for proper disposal.

Spillage Disposal · 1건

Evacuate danger area! Consult an expert! Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus. Ventilation. Remove all ignition sources. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Ethyl chloroformate hydrolyzes readily in water (half-life of 31.5 min at 25 °C)(1); therefore, aqueous hydrolysis will be the dominate fate process in moist soils(SRC). Ethyl chloroformate has a relatively high vapor pressure (22.4 mm Hg at 25 dec C(2)) which suggests that evaporation from dry surfaces can occur(SRC). Results of a single biodegradation study (using the Japanese MITI protocol) have classified ethyl chloroformate as biodegradable(3) but this is probably the hydrolysis product(SRC).

AQUATIC FATE: Ethyl chloroformate hydrolyzes readily in water (half-life of 31.5 min at 25 °C)(1); therefore, aqueous hydrolysis will be the dominate fate process in the aquatic environment(SRC). Aqueous volatilization, bioconcentration and adsorption to sediment are not expected to be important fate processes due to ethyl chloroformate's rapid hydrolysis(SRC).

ATMOSPHERIC FATE: Based upon a vapor pressure of 22.4 mm Hg at 25 °C(1), ethyl chloroformate is expected to exist primarily in the vapor phase in the ambient atmosphere(2,SRC). It will degrade in the ambient atmosphere by reaction with photochemically produced hydroxyl radicals with an estimated half-life of about 11 day(3,SRC). Since ethyl chloroformate hydrolyzes readily in water, atmospheric degradation may occur through dissolution into clouds or through contact with rain or other atmospheric water(SRC).

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

Burning sensation. Cough. Laboured breathing. Shortness of breath. Sore throat. Symptoms may be delayed.

Skin burns. Blisters. Pain. Redness.

Redness. Pain. Severe deep burns.

Abdominal pain. Burning sensation. Shock or collapse.

ICSC Environmental DataEnvironmental effects from the substance have not been investigated adequately.
Medical SurveillanceSPECIAL ATTENTION SHOULD BE GIVEN THE EYES & RESP TRACT IN MEDICAL EXAM. /CHLOROFORMATES/
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indexes, the Koc for ethyl chloroformate can be estimated to be approximately 10(1,SRC). According to a suggested classification scheme(2), this estimated Koc value suggests that ethyl chloroformate has high mobility in soil(SRC). However, ethyl chloroformate hydrolyzes readily in water (half- life of 31.5 min at 25 °C)(3); therefore, leaching in soil is not expected to be an important fate process(SRC).

Human Toxicity Excerpts · 5건

EYE IRRITATION, IRRITATION OF UPPER RESPIRATORY TRACT, & SURFACE BURNS HAVE BEEN PRINCIPAL FINDINGS IN EXPOSED HUMANS. ... EYE IRRITATION MAY PERSIST SOME TIME AFTER EXPOSURE CEASES. SKIN SENSITIZATION MAY OCCUR. /CHLOROFORMATES/

... ETHYL ... CHLOROFORMATE CAN PRODUCE DELAYED PULMONARY EDEMA SIMILAR TO THAT PRODUCED BY PHOSGENE.

... LACRIMATORY PROPERTIES ARE WELL-KNOWN. ... NO EFFECTS ON GENERAL HEALTH NOR IN THE LABORATORY FINDINGS (BLOOD STUDIES AND LIVER FUNCTION TESTS) OF PERSONS MANUFACTURING CHLOROFORMATES WERE NOTED. /CHLOROFORMATES/

Its toxic properties resemble those of the methyl homolog in the degree of corrosiveness, irritation, and lacrimatory qualities.

For more Human Toxicity Excerpts (Complete) data for ETHYL CHLOROFORMATE (7 total), please visit the HSDB record page.

Artificial Pollution SourcesEthyl chloroformate's use as a solvent in the photographic industry and as chemical intermediate(1) could result in the release of the compound to the environment through evaporation or various waste streams(SRC).
Environmental BiodegradationUsing the Japanese MITI protocol (4 week incubation period with activated sludge inoculum), ethyl chloroformate was found to be biodegradable with a theoretical BOD of 81-86%(1) but this is probably the hydrolysis product(SRC).
Environmental BioconcentrationEthyl chloroformate hydrolyzes readily in water (half-life of 31.5 min at 25 °C)(1); therefore, bioconcentration in aquatic organisms will not be an important process(SRC).
Volatilization from Water/Soil · 1건

The Henry's Law constant for ethyl chloroformate can be estimated to be 3.1X10-3 atm-cu m/mole using a structure estimation method(1,SRC); this value of Henry's Law constant indicates that volatilization from water is potentially an important fate process(2). However, ethyl chloroformate hydrolyzes readily in water (half-life of 31.5 min at 25 °C)(3); therefore, volatilization from water is not expected to be important(SRC).

안전 데이터

ridadr
UN 1182
포장분류
I
위험 등급
6.1

Carbonochloridic acid, ethyl ester: ACTIVE

NORMEPERIDINE ETHYLCARBAMATE MAY BE FORMED BY REACTION OF NORMEPERIDINE & ETHYL CHLOROFORMATE, & EVIDENCE IS PRESENTED TO SHOW THAT THIS SAME REACTION PRODUCED NORMEPERIDINE ARTIFACT WHEN THIS DRUG IS BOILED IN CHLOROFORM IN PROCESS OF SOLVENT REMOVAL.

...one of the agents used in biochemical carbobenzoxy group removal, without scission of the peptide bond.

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