Benzylchlorformiat

Benzyl chloroformate

HCID 10387CAS 501-53-1

Grundinformationen

Standard-SMILES
O=C(Cl)OCc1ccccc1
InChIKey
HSDAJNMJOMSNEV-UHFFFAOYSA-N
Summenformel
C8H7ClO2
Durchschnittliche Molmasse
170,59 g/mol
Monoisotopische Masse
170,01345714

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Benzyl chloroformate
IUPAC
benzyl carbonochloridate
Lokaler Name
Benzylchlorformiat
Englischer Name
Benzyl chloroformate
Summenformel
C8H7ClO2
Molmasse
170.59

Namen und Synonyme

BENZYL CHLOROFORMATE501-53-1Benzyl carbonochloridateCarbobenzoxy chlorideBenzyl chlorocarbonateBenzylcarbonyl chlorideBenzyloxycarbonyl chlorideCarbobenzyloxy chlorideCarbonochloridic acid, phenylmethyl esterChloroformic Acid Benzyl EsterChloroformic acid, benzyl esterBenzylcarbonochloridate
Weitere Namen anzeigen
CBZBCFZ-CLBenzyl ChlorofomateCBZCIZ-CHLORIDE
Formic acid, chloro-, benzyl esterDTXSID9027158170BP0DD31NSC-83466DTXCID607158RefChem:118863207-925-0Cbz chloride

Datenbank-Bezeichner

CAS
501-53-1
PubChem CID
10387
DTXSID
DTXSID9027158
ChEMBL
CHEMBL1581748
UNII
170BP0DD31
EC Number
207-925-0
Nikkaji
J6.192A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Acid Halides

Corrosives

SpringerMaterials PropertiesChemical shift
Odor · 3 Einträge

ACRID ODOR

ODOR OF PHOSGENE

SHARP, PENETRATING ODOR

Density · 4 Einträge

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 Einträge

OILY LIQUID

COLORLESS TO PALE YELLOW LIQUID

Physikochemische Eigenschaften

Schmelzpunkt
-20 °C · -20 °C
Siedepunkt
103 °C20 · 103 °C20 mm Hg(lit.)
Dichte
1.212 g/mL · 1.212 g/mL at 20 °C
Dampfdichte
1 · 1 (vs air)
Dampfdruck
1.39 psi · 1.39 psi ( 20 °C)
Brechungsindex
20 · n20/D 1.519(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

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]

Gefahrenhinweise

Regulatory Information · 5 Einträge

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 Einträge

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 Einträge

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.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

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

Use dry powder, foam, carbon dioxide.

First Aid Measures · 4 Einträge

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 Einträge

· 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 Einträge

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).

Toxikologische Informationen

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

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 Einträge

... 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

Sicherheitsdaten

F
19
wgk
3
tsca
TSCA listed
ridadr
UN 1739
hs_code
2915 90 70
RTECS-Nr.
LQ5860000

Chemie und Industrie

Verwendung und Herstellung

Uses · 3 Einträge

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
Anwendungen · 2 Einträge

BeschreibungBenzyl 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.

VerwendenBenzyl 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.

Darstellung · 1 Eintrag

synthetischeBenzyl 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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