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Benzylchlorformiat

Benzyl chloroformate

HCID 10387
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Grundinformationen

CAS
501-53-1
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

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
3
Polarare Oberfläche (TPSA)
26,3 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
3
Schwere Atome
11
Formalladung
0
Komplexität
130

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

Solubility · 2 Einträge

SOL IN ETHER, ACETONE, BENZENE

Solubility in water: reaction

CorrosivityCorrosive
Flash Point

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

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.

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
Methods of Manufacturing/IT IS PREPARED/ ... BY ACTION OF PHOSGENE ABSORBED IN TOLUENE ON BENZYL ALCOHOL: CARTER ET AL, ORG SYN 23, 13 (1943); BY REACTING CARBONYL CHLORIDE & BENZYL ALCOHOL @ -20 TO -30 °C
Formulations/Preparations · 4 Einträge

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 · 3 Einträge

Pharmaceutical and Medicine Manufacturing

Carbonochloridic acid, phenylmethyl ester: ACTIVE

Most chloroformate production is used captively and production figures are not available /Chloroformic esters/

Anwendungen · 2 Einträge

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UNII
170BP0DD31
EC Number
207-925-0
Nikkaji
J6.192A
· 4 Einträge

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 · 3 Einträge

306 °F at 760 mmHg (decomposes) (USCG, 1999)

152 °C AT 760 MM HG

152 °C @760 [mm Hg]

Decomposition · 3 Einträge

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

Melting Point0 °C

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.)
Flammpunkt
197 °F · 197 °F
storage temp.
2 °C · Store at +2°C to +8°C.
Löslichkeit
Miscible with ether, acetone and benzene.
Aggregatzustand
Solution
Farbe
slightly yellow to slightly pink
Geruch (Odor)
Irritating; sharp, penetrating.
Wasserlöslichkeit
decomposes
Merck
14 · 14,1801
Stabilität
Stable. Incompatible with water, oxidizing agents. Combustible.
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 Datenbank
501 · 501-53-1(CAS DataBase Reference)
NIST chemische Informationen
Benzyl chloroformate(501-53-1)
EPA chemische Informationen
Carbonochloridic acid, phenylmethyl ester (501-53-1)

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.

Hazards SummaryCorrosive to skin; [Quick CPC] A skin, eye, and respiratory tract irritant; Lacrimator; [HSDB] A corrosive substance that causes lacrimation and may cause lung edema after inhalation of high concentrations; [ICSC] See CHLOROFORMATES.
DOT ID and Guide1739 137
Reactive GroupAcyl Halides, Sulfonyl Halides, and Chloroformates
EC ClassificationSymbol: C, N; R: 34-50/53; S: (1/2)-26-45-60-61
UN ClassificationUN Hazard Class: 8; UN Pack Group: I
Reactivity AlertsWater-Reactive

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).
Fire Fighting Procedures · 2 Einträge

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.

Nonfire Spill ResponseExcerpt from ERG Guide 137 [Substances - Water-Reactive - Corrosive]:
Spillage Disposal · 1 Eintrag

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 · 2 Einträge

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 · 2 Einträge

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

Immediate precautionary measure

Eye PreventionWear face shield or eye protection in combination with breathing protection.

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
risk_code
45-20-34-48/22-50/53-67-65-63-48/20-11-43-37-23
Toxizität
LD50 orally in Rabbit: 3000 mg/kg
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
Speicherklasse
6.1C - Combustible, acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
501-53-1(Hazardous Substances Data)
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Carc. 1BEye Dam. 1Skin Corr. 1BSTOT SE 3
Selbstentzündungstemperatur
590 °C

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.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

TrichlormethylchlorformiatCarbonylchloridBenzylalkohol

Nachgelagerte Produkte

2-(Boc-aminomethyl)-piperidineBENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATEAztreonam1-METHYL-[4,4']BIPIPERIDINYLH-BETA-ALA-OTBU HCLClarithromycinLisinopril DihydrateN-Benzyloxycarbonylglycin4-(Boc-Aminomethyl)piperidineGLY-7-AMINO-4-METHYLCOUMARIN1-Methylpiperazin-2-oneBenzylcarbamatCARUMONAM1H-Azepine-3-carboxylicacid,hexahydro-,methylester(9CI)Captopril(R)-(+)-1-Boc-3-aminopyrrolidineN-(1-Methylethyl)-4-((2-methyl-hydrazino)methyl)benzamid-monohydrochlorid2-PIPERAZIN-1-YL-ACETAMIDEHYDROCHLORIDE(R)-4-Boc-Piperazine-3-carboxylic acidN-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER1-(N-METHYLPIPERIDIN-3-YL-METHYL)PIPERAZINE3-[(Benzyloxycarbonyl)amino]propionaldehydeBenzyl 1-homopiperazine carboxylate1-[(Benzyloxy)carbonyl]piperidine-4-carboxylic acidBENZYL 1-PIPERAZINECARBOXYLATE5-(2-Aminoethyl)guajakolhydrochlorid