기본 정보
- 표준 SMILES
O=C(Cl)OCc1ccccc1- InChIKey
HSDAJNMJOMSNEV-UHFFFAOYSA-N- 분자식
- C8H7ClO2
- 평균 분자량
- 170.59 g/mol
- 단동위원소 질량
- 170.01345714
개요
Benzyl chloroformate appears as a colorless liquid with an acrid odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Long-term inhalation of low concentrations or short-term inhalation of high concentrations can result in adverse health effects.
이름 및 식별자
- 우선 이름
- Benzyl chloroformate
- IUPAC
- benzyl carbonochloridate
- 현지명
- 벤질 클로로탄소산
- 영어명
- Benzyl chloroformate
- 분자식
- C8H7ClO2
- 분자량
- 170.59
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
501-53-1- PubChem CID
- 10387
- DTXSID
DTXSID9027158- ChEMBL
CHEMBL1581748- UNII
- 170BP0DD31
- EC Number
- 207-925-0
- Nikkaji
- J6.192A
물성
구조 계산 물성
- XLogP
- 3
- 극성 표면적
- 26.3 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 2
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 11
- 형식 전하
- 0
- 복잡도
- 130
실험 및 물리화학적 성질
Chemical Classes
Toxic Gases & Vapors -> Acid Halides
Corrosives
Odor
ACRID ODOR
ODOR OF PHOSGENE
SHARP, PENETRATING ODOR
Density
1.22 at 68 °F (USCG, 1999) - Denser than water; will sink
1.2166 20 °C/4 °C
Relative density (water = 1): 1.20
1.2166 @ 20°C
Color/Form
OILY LIQUID
COLORLESS TO PALE YELLOW LIQUID
Solubility
SOL IN ETHER, ACETONE, BENZENE
Solubility in water: reaction
Flash Point
227 °F Vigorous decomposition occurs at these temperatures; thus these values are anomalous due to the effect of the decomp. products (benzyl chloride and CO2). (USCG, 1999)
[HSDB] 80 °C
176 °F OC; 227 °F CC
80.0 °C c.c.
Boiling Point
306 °F at 760 mmHg (decomposes) (USCG, 1999)
152 °C AT 760 MM HG
152 °C @760 [mm Hg]
Decomposition
EMITS HIGHLY TOXIC PHOSGENE FUMES WHEN HEATED TO 100 °C.
DANGEROUS; WHEN HEATED TO DECOMP ... THEY EVOLVE HIGHLY TOXIC /HYDROGEN/ CHLORIDE FUMES. /CHLORIDES/
>100 °C
물리화학적 성질
- 녹는점
- -20 °C · -20 °C
- 끓는 점
- 103 °C20 · 103 °C20 mm Hg(lit.)
- 밀도
- 1.212 g/mL · 1.212 g/mL at 20 °C
- 증기 밀도
- 1 · 1 (vs air)
- 증기압
- 1.39 psi · 1.39 psi ( 20 °C)
- 굴절률
- 20 · n20/D 1.519(lit.)
- 인화점
- 197 °F · 197 °F
- 저장 조건
- 2 °C · Store at +2°C to +8°C.
- 용해도
- 에테르, 아세톤, 벤젠과 혼합 가능.
- 물리적 상태
- 액체
- 색상
- 약간 노란색에서 약간 분홍색
- 냄새
- 화나게 하는; 날카로운, 관통하는.
- 수용성
- 물에서 분해되다
- Merck
- 14 · 14,1801
- 안정성
- 안정적인. 물, 산화제와 호환되지 않습니다. 타기 쉬운.
- InChI
- 1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2
- InChIKey
- HSDAJNMJOMSNEV-UHFFFAOYSA-N
- SMILES
- ClC(=O)OCc1ccccc1
- NIST
- Benzyl chloroformate(501-53-1)
- EPA
- Carbonochloridic acid, phenylmethyl ester (501-53-1)
화학적 성질
colorless or light yellow oily liquid with rancid odor. soluble in ether, acetone, benzene and other organic solvents. It is used to protect amino groups in peptide synthesis.
안전 및 규제
GHS 분류
GHS Classification
Danger
H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P273, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P363, P391, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.6% (1 of 173) of reports.
Danger
H314 (99.4%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
유해성 정보
Regulatory Information
Chemical: Carbonochloridic acid, phenylmethyl ester
Carbonochloridic acid, phenylmethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Carbonochloridic acid, phenylmethyl 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: 02-03-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/12078
Benzyl chloroformate: Does not have an individual approval but may be used under an appropriate group standard
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: Toxic phosgene, hydrogen chloride, and benzyl chloride vapors may form.
· EXCEPT FOR ACETIC ANHYDRIDE (UN1715), THAT IS FLAMMABLE, some of these materials may burn, but none ignite readily.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards
Inhalation causes mucous membrane irritation. Eyes are irritated by excessive exposure to vapor. Liquid causes severe irritation of eyes and irritates skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
· CORROSIVE and/or TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.
안전 및 보호
Fire Fighting
Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:
Use dry powder, foam, carbon dioxide.
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.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
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.
· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.
First Aid
INHALATION: remove from exposure; support respiration; call physician.
General First Aid:
Fire Fighting Procedures
EXTINGUISH WITH DRY CHEMICALS, FOAM OR CARBON DIOXIDE.
If material on fire or involved in fire: Use dry chemical, dry sand, or carbon dioxide. Do not use water on material itself. If large quantities of combustibles are involved, use water in flooding quantities as spray and fog. Use water spray to knock-down vapors. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible.
Spillage Disposal
Collect leaking and spilled liquid in sealable containers as far as possible. Carefully collect remainder. Then store and dispose of according to local regulations. Personal protection: complete protective clothing including self-contained breathing apparatus.
Preventive Measures
If material not on fire and not involved in 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. Use water spray to knock-down vapors. Do not use water on material itself. Neutralize spilled material with crushed limestone, soda ash, or lime.
Personnel protection: Avoid breathing vapors. Keep upwind. Wear positive pressure self-contained breathing apparatus. Avoid bodily contact with the material. Wear appropriate chemical protective gloves, boots and goggles. 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 contact with the material anticipated, wear appropriate chemical protective clothing.
Isolation and Evacuation
Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:
Immediate precautionary measure
독성 정보
Signs and Symptoms
Cough. Shortness of breath. Sore throat. Laboured breathing.
Skin burns.
Watering of the eyes. Severe deep burns.
Burning sensation. Abdominal pain. Shock or collapse.
Human Toxicity Excerpts
... LACRIMATOR.
INHALATION CAUSES MUCOUS MEMBRANE IRRITATION. EYES ARE IRRITATED BY EXCESSIVE EXPOSURE TO VAPOR. LIQ CAUSES IRRITATION OF EYES & IRRITATES SKIN. INGESTION CAUSES IRRITATION OF MOUTH & STOMACH.
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LQ5860000
- ridadr
- UN 1739
- 독성
- LD50 orally in Rabbit: 3000 mg/kg
- HS 번호
- 2915 90 70
- risk_code
- 45-20-34-48/22-50/53-67-65-63-48/20-11-43-37-23
- hazard_code
- T,C,N,F
- safety_code
- 53-26-36/37/39-45-60-61-62-46-36/37
- 포장분류
- I
- 위험 등급
- 8
- 기존화학 물질
- KE-02790
- F 고인화성물질
- 19
- 자연 발화 온도
- 590 °C
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Skin Corr. 1BSTOT SE 3
- 스토리지 클래스
- 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 유해 물질 데이터
- 501-53-1(Hazardous Substances Data)
화학 및 산업
용도 및 제조
Uses
Used to make pharmaceuticals and other chemicals; [HSDB]
In peptide synthesis to block the amino group.
Reactive intermediate to pharmaceuticals and other chemicals.
Formulations/Preparations
GRADE OR PURITY: 97+%
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/
97%; 50 wt% in toluene
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
Carbonochloridic acid, phenylmethyl ester: ACTIVE
Most chloroformate production is used captively and production figures are not available /Chloroformic esters/
응용 분야
개요Benzyl chloroformate, also known as benzyl chlorocarbonate or Z-chloride, is the benzyl ester of chloroformic acid. It can be also described as the chloride of the benzyloxycarbonyl (Cbz or Z) group. In its pure form it is a water-sensitive oily colorless liquid, although impure samples usually appear yellow. It possesses a characteristic pungent odor and degrades in contact with water. The compound was first prepared by Leonidas Zervas in the early 1930s who used it for the introduction of the benzyloxycarbonyl protecting group, which became the basis of the Bergmann-Zervas carboxybenzyl method of peptide synthesis he developed with Max Bergmann. This was the first successful method of controlled peptide chemical synthesis and for twenty years it was the dominant procedure used worldwide until the 1950s. To this day, benzyl chloroformate is often used for amine group protection.
용도Benzyl chloroformate is widely used as a reactive chemical intermediate in plastic, pharmaceutical, agricultural and organic chemicals. It is useful for the introduction of carboxybenzyl (cbz) protecting group for amines such as aniline in organic synthesis. It is also involved in the synthesis of 1,2,4-oxadiazoles.
일반 설명Benzyl chloroformate appears as a colorless liquid with an acrid odor. Vapors irritate eyes and mucous membranes. Corrosive to metals and tissue. Long-term inhalation of low concentrations or short-term inhalation of high concentrations can result in adverse health effects.
제조 방법
Benzyl chloroformate is prepared in the lab by treating benzyl alcohol with phosgene:PhCH2OH + COCl2→ PhCH2OC(O)Cl + HClPhosgene is used in excess to minimise the production of the carbonate (PhCH2O)2C=O.The use of phosgene gas in the lab preparation carries a very large health hazard, and has been implicated in the chronic pulmonary disease of pioneers in the usage of the compound such as Zervas.
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