ChemicalBook > CAS DataBase List > Benzyl chloroformate

Benzyl chloroformate

Product Name
Benzyl chloroformate
CAS No.
501-53-1
Chemical Name
Benzyl chloroformate
Synonyms
CBZ;Benzyl carbonochloridate;BCF;Z-CL;BENZYLOXYCARBONYL CHLORIDE;Benzyl Chlorofomate;CBZ CHLORIDE;CARBOBENZOXY CHLORIDE;Z-CHLORIDE;CBZ-Cl (Z-Cl)
CBNumber
CB7853678
Molecular Formula
C8H7ClO2
Formula Weight
170.59
MOL File
501-53-1.mol
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Benzyl chloroformate Property

Melting point:
-20 °C
Boiling point:
103 °C20 mm Hg(lit.)
Density 
1.212 g/mL at 20 °C
vapor density 
1 (vs air)
vapor pressure 
1.39 psi ( 20 °C)
refractive index 
n20/D 1.519(lit.)
Flash point:
197 °F
storage temp. 
Store at +2°C to +8°C.
solubility 
Miscible with ether, acetone and benzene.
form 
Solution
color 
slightly yellow to slightly pink
Odor
Irritating; sharp, penetrating.
Water Solubility 
decomposes
Sensitive 
Moisture Sensitive
Merck 
14,1801
Exposure limits
ACGIH: TWA 1 ppm
OSHA: TWA 1 ppm(5 mg/m3)
NIOSH: IDLH 10 ppm; Ceiling 1 ppm(5 mg/m3)
Stability:
Stable. Incompatible with water, oxidizing agents. Combustible.
CAS DataBase Reference
501-53-1(CAS DataBase Reference)
NIST Chemistry Reference
Benzyl chloroformate(501-53-1)
EPA Substance Registry System
Carbonochloridic acid, phenylmethyl ester (501-53-1)
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Safety

Hazard Codes 
T,C,N,F
Risk Statements 
45-20-34-48/22-50/53-67-65-63-48/20-11-43-37-23
Safety Statements 
53-26-36/37/39-45-60-61-62-46-36/37
RIDADR 
UN 2924 3/PG 2
WGK Germany 
3
RTECS 
LQ5860000
F 
19
Autoignition Temperature
590 °C
TSCA 
Yes
HS Code 
2915 90 70
HazardClass 
8
PackingGroup 
I
Hazardous Substances Data
501-53-1(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 3000 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

H335May cause respiratory irritation

H350May cause cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.14688
Product name
Benzyl chloroformate
Purity
(stabilised) for synthesis
Packaging
250ML
Price
$199
Updated
2024/03/01
TCI Chemical
Product number
B3021
Product name
Benzyl Chloroformate
Purity
>96.0%(T)
Packaging
25g
Price
$27
Updated
2024/03/01
TCI Chemical
Product number
B3021
Product name
Benzyl Chloroformate
Purity
>96.0%(T)
Packaging
250g
Price
$71
Updated
2024/03/01
Alfa Aesar
Product number
A15682
Product name
Benzyl chloroformate, 95%, stab. with ca 0.1% sodium carbonate
Packaging
50g
Price
$54.4
Updated
2024/03/01
Alfa Aesar
Product number
A15682
Product name
Benzyl chloroformate, 95%, stab. with ca 0.1% sodium carbonate
Packaging
250g
Price
$216
Updated
2024/03/01
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Benzyl chloroformate Chemical Properties,Usage,Production

Description

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.

Chemical Properties

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.

Uses

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.

Preparation

Benzyl chloroformate is prepared in the lab by treating benzyl alcohol with phosgene:
PhCH2OH + COCl2→ PhCH2OC(O)Cl + HCl
Phosgene 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.

Application

Benzyl chloroformate is used as a reagent in peptide synthesis to protect the amine functionality as the benzyloxycarbonyl (Cbz or Z) derivative.
Cbz-protected anilines were prepared directly from aromatic carboxylic acids, sodium azide and Cbz-Cl.
Protecting reagent in peptide synthesis.

General Description

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.

Air & Water Reactions

Decomposes in moist air. Decomposes slowly in water to give corrosive hydrochloric acid and organic acids.

Reactivity Profile

Benzyl chloroformate decomposes slowly in water forming benzyl alcohol, HCl, and CO2. Gives off HCl fumes in moist air. Reacts with bases, both organic and inorganic. Attacks many metals especially in humid atmosphere [Handling Chemicals Safely 1980. p. 476]. Catalytic impurity incidents involving the iron catalyzed decomposition of benzoyl chloroformate have caused several explosions. The iron presumably comes from corrosion of steel storage tanks [Loss Prev. Bull., 1975, (003), 2]. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Hazard

Highly toxic, emits very toxic phosgene fumes at 100C. Irritant to eyes.

Health Hazard

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.

Safety Profile

Poison by ingestion andinhalation routes. A powerful corrosive irritant. Thermallyunstable. Will react with water or steam to produce toxic and corrosive fumes and heat. Iron salts catalyze theexplosive decomposition of the ester. When heated todecomp.

Synthesis

Benzyl chloroformate (CbzCl) was synthesized by combining the carbonylation of benzyl alcohol with carbon monoxide and sulfur (or carbonyl sulfide) in the presence of DBU, with the chlorination using sulfuryl chloride.
https://doi.org/10.1016/S0040-4039(02)01834-8

storage

Store at temperature at or below –15°C (5°F) in a dry, well‐ventilated location. All equipment and storage vessels must be constructed of Teflon or glass‐lined steel. Keep container tightly closed. Protect from sunlight and avoid any contact with iron.Product is stable when stored properly at recommended storage temperature. Storage in recommended temperatures and conditions will ensure product quality for minimum 12 months before retesting may be needed to determine assay. Storage in conditions between –15°C (5°F) and –5°C (23°F) may require retesting after 6 months to determine assay. Storage above 0°C (32°F) not recommended.

Purification Methods

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.

Benzyl chloroformate Preparation Products And Raw materials

Raw materials

101 Diphosgene

Preparation Products

2-(Boc-aminomethyl)-piperidine BENZYL 4-(BROMOMETHYL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE Aztreonam 1-METHYL-[4,4']BIPIPERIDINYL H-BETA-ALA-OTBU HCL Clarithromycin Lisinopril Dihydrate N-Carbobenzyloxyglycine 4-(Boc-Aminomethyl)piperidine GLY-7-AMINO-4-METHYLCOUMARIN 1-Methylpiperazin-2-one Benzyl carbamate CARUMONAM 1H-Azepine-3-carboxylicacid,hexahydro-,methylester(9CI) Captopril (R)-(+)-1-Boc-3-aminopyrrolidine Procarbazine hydrochloride 2-PIPERAZIN-1-YL-ACETAMIDEHYDROCHLORIDE (R)-4-Boc-Piperazine-3-carboxylic acid N-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER 1-(N-METHYLPIPERIDIN-3-YL-METHYL)PIPERAZINE 3-[(Benzyloxycarbonyl)amino]propionaldehyde Benzyl 1-homopiperazine carboxylate 1-[(Benzyloxy)carbonyl]piperidine-4-carboxylic acid BENZYL 1-PIPERAZINECARBOXYLATE 3-O-Methyldopamine hydrochloride
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View Lastest Price from Benzyl chloroformate manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Benzyl chloroformate 501-53-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
5tons
Release date
2021-11-24
Hebei Mojin Biotechnology Co., Ltd
Product
Benzyl chloroformate 501-53-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-15
Hebei Miaobian Biotechnology Co., Ltd
Product
Benzyl chloroformate 501-53-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99.99
Supply Ability
10Ton
Release date
2021-03-17

501-53-1, Benzyl chloroformateRelated Search:

Choline chloride Benzyl formate Citric acid Benzyl alcohol Benzyl benzoate Folic acid Sodium chloride Calcium chloride Ethyl 2-(Chlorosulfonyl)acetate Polyvinyl chloride Ammonium chloride Sulfuryl chloride Ferric chloride Carbobenzoxyhydrazide Hyaluronic acid Potassium chloride Phenyl chloroformate Ascoric Acid

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