クロロぎ酸ベンジル

Benzyl chloroformate

HCID 10387CAS 501-53-1

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

BENZYL CHLOROFORMATE501-53-1Benzyl carbonochloridateCarbobenzoxy chlorideBenzyl chlorocarbonateBenzylcarbonyl chlorideBenzyloxycarbonyl chlorideCarbobenzyloxy chlorideCarbonochloridic acid, phenylmethyl esterChloroformic Acid Benzyl EsterChloroformic acid, benzyl esterBenzylcarbonochloridate
名称をさらに表示
クロロぎ酸ベンジル (30-35%トルエン溶液)カルボベンゾキシクロリドベンジルカルボニルクロリドクロロ炭酸ベンジル(ベンジルオキシ)ぎ酸クロリドCbzクロリドクロリド炭酸ベンジルベンジルオキシぎ酸クロリドクロロ酸ベンジルエステルベンジルクロロホルメートクロロギ酸ベンジル 塩化物クロロ炭酸ベンジルエステルベンジルクロロホルメトCbzクロリド (30-35%トルエン溶液)カルボベンゾキシクロリド (30-35%トルエン溶液)クロロ蟻酸ベンジルクロロ蟻酸ベンジル (30-35%トルエン溶液)クロル炭酸ベンジルカルボベンゾキシクロリド 50%トルエン溶液クロロぎ酸ベンジル 50%トルエン溶液CBZBCFZ-CLBenzyl ChlorofomateCBZCIZ-CHLORIDE
Formic acid, chloro-, benzyl esterDTXSID9027158170BP0DD31NSC-83466DTXCID607158RefChem:118863207-925-0Cbz chloride

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

実験および物理化学的性質

Chemical Classes · 2 件

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesChemical shift
Odor · 3 件

ACRID ODOR

ODOR OF PHOSGENE

SHARP, PENETRATING ODOR

Density · 4 件

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

Viscosity2.57 mPa-s (cP) @ 20 °C
Color/Form · 2 件

OILY LIQUID

COLORLESS TO PALE YELLOW LIQUID

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.)

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 · 6 件

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 · 5 件

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.)

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
DOT LabelCorrosive
Fire Hazards · 3 件

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.

Fire PotentialCOMBUSTIBLE
Health Hazards · 2 件

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 · 2 件

Excerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:

Use dry powder, foam, carbon dioxide.

First Aid Measures · 4 件

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 · 2 件

· 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 · 2 件

INHALATION: remove from exposure; support respiration; call physician.

General First Aid:

Safe StorageSeparated from food and feedstuffs. Dry. Well closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

毒性情報

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

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 · 2 件

... 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.

Toxicity DataLC50 (rat) = 590 mg/m3/4h

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

化学と産業

用途と製造

Uses · 3 件

Used to make pharmaceuticals and other chemicals; [HSDB]

In peptide synthesis to block the amino group.

Reactive intermediate to pharmaceuticals and other chemicals.

ImpuritiesMay contain 3% or less benzyl chloride
U.S. Production2023: 631,297 lb
Consumption PatternsAPPROX 100% AS A REAGENT IN /PRC: ORGANIC/ SYNTHESIS
Consumer UsesTerminator/Blocker
Industry UsesTerminator/Blocker
応用分野 · 5 件

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 · 2 件

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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