基本情報
- 標準SMILES
O=C(Cl)OCc1ccccc1- InChIKey
HSDAJNMJOMSNEV-UHFFFAOYSA-N- 分子式
- C8H7ClO2
- 平均分子量
- 170.59 g/mol
- 単同位体質量
- 170.01345714
概要
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.
名称と識別子
- 優先名称
- Benzyl chloroformate
- IUPAC
- benzyl carbonochloridate
- 現地名
- クロロぎ酸ベンジル
- 英語名
- Benzyl chloroformate
- 分子式
- C8H7ClO2
- 分子量
- 170.59
名称と別名
名称をさらに表示
データベース識別子
- CAS
501-53-1- PubChem CID
- 10387
- DTXSID
DTXSID9027158- ChEMBL
CHEMBL1581748- UNII
- 170BP0DD31
- EC Number
- 207-925-0
- Nikkaji
- J6.192A
物性
構造計算による物性
- XLogP
- 3
- 極性表面積
- 26.3 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 2
- 回転可能結合数
- 3
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 130
実験および物理化学的性質
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
物理化学的性質
- 融点
- -20 °C · -20 °C
- 沸点
- 103 °C20 · 103 °C20 mm Hg(lit.)
- 比重(密度)
- 1.212 g/mL · 1.212 g/mL at 20 °C
- 蒸気密度
- 1 · 1 (vs air)
- 蒸気圧
- 1.39 psi · 1.39 psi ( 20 °C)
- 屈折率
- 20 · n20/D 1.519(lit.)
- 闪点
- 197 °F · 197 °F
- 貯蔵温度
- 2 °C · Store at +2°C to +8°C.
- 溶解性
- エーテル、アセトン、ベンゼンと混和します。
- 外見
- 解決
- 色
- クリアー ほんのりイエロー~ほんのりピンク
- 臭い (Odor)
- イライラする;鋭い、貫く。
- 水溶解度
- 分解する
- Merck
- 14 · 14,1801
- 安定性
- 安定。水、酸化剤と相容れない。可燃性。
- 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
- CAS データベース
- 501 · 501-53-1(CAS DataBase Reference)
- NISTの化学物質情報
- Benzyl chloroformate(501-53-1)
- EPAの化学物質情報
- Carbonochloridic acid, phenylmethyl ester (501-53-1)
化学的性質
化学的特性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.
安全と法規制
GHS分類
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]
危険有害性情報
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.
安全と保護具
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
毒性情報
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.
安全データ
- F
- 19
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LQ5860000
- ridadr
- UN 1739
- 毒性
- LD50 orally in Rabbit: 3000 mg/kg
- PRTR法
- 第一種指定化学物質
- hs_code
- 2915 90 70
- risk_code
- 45-20-34-48/22-50/53-67-65-63-48/20-11-43-37-23
- 化審法
- (3)-1835, (3)-2885
- 安衛法
- 有機則 第二種有機溶剤等
- 消防法
- 危-4-3-III
- hazard_code
- T,C,N,F
- safety_code
- 53-26-36/37/39-45-60-61-62-46-36/37
- hazard_class
- 8
- packing_group
- I
- 自然発火温度
- 590 °C
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Skin Corr. 1BSTOT SE 3
- ストレージクラス
- 6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 501-53-1(Hazardous Substances Data)
化学と産業
用途と製造
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/
応用分野
用途ペプチド合成用
用途有機過酸化物(重合触媒)?樹脂改質剤?医薬?農薬原料 、ペプチド合成時のアミノ基ブロック剤
説明Benzyl 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.
使用Benzyl 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.
一般的な説明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.
調製方法
製造方法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.
純化方法The commercial material is usually better than 95% pure and may contain some toluene, benzyl alcohol, benzyl chloride and HCl. After long storage (e.g. two years at 4o, Greenstein and Winitz [The Chemistry of the Amino Acids Vol 2 p. 890, J Wiley and Sons NY, 1961] recommended that the liquid should be flushed with a stream of dry air, filtered and stored over sodium sulfate to remove CO2 and HCl which are formed by decomposition. It may further be distilled from an oil bath at a temperature below 85o because Thiel and Dent [Annalen 301 257 1898] stated that benzyloxycarbonyl chloride decarboxylates to benzyl chloride slowly at 100o and vigorously at 155o. Redistillation at higher vacuum below 85o yields material which shows no other peaks than those of benzyloxycarbonyl chloride by NMR spectroscopy. [Beilstein 6 IV 2278.] LACHRYMATORY and TOXIC.
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