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Benzyl chloroformate501-53-1

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$33-34/MT FOB

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CAS No.:

501-53-1

Grade:

Pharmaceutical Grade

Content:

99.5%

Port:

上海

Brand:

OORENT

Packaging:

Vial/Bottle/Bag/Carton

Price valid (until):

2026-07-17

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Qingdao Orient Chemical Co.,LTD

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Trader

Location:

China

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Main Products:

pharmaceutical intermediates,peptides,electronic chemicals

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Product Description
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Description

Product Detail

Benzyl chloroformate Basic information

Product Name:	Benzyl chloroformate
Synonyms:	Benzyl Chlorofomate;Phenylmethyl chloroformate;BENZYL CHLOROFORMATE SOLUTION, 50% IN TO LUENE;BENZYL CHLOROFORMATE, TECH. 95%;Z-Cl (Cbz-Cl);Benzyl chloroformate, pract., 95%;Cbz-Cl (Carboobenzoxy Chloride);CBZ-Cl (Z-Cl)
CAS:	501-53-1
MF:	C8H7ClO2
MW:	170.59
EINECS:	207-925-0
Product Categories:	N-Protecting Reagents;Aromatic Esters;Amino Acid Derivatives;CHLOROFORMATES;Biochemistry;Cbz-Amino acid series;Pharmaceutical Intermediates;Benzene derivatives;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Synthetic Organic Chemistry;API Intermediate;bc0001;K00001
Mol File:	501-53-1.mol

Benzyl chloroformate Chemical Properties

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.)
Fp	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.
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 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)

Safety Information

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 1739
WGK Germany	3
RTECS	LQ5860000
F	19
Autoignition Temperature	590 °C
TSCA	TSCA listed
HS Code	2915 90 70
HazardClass	8
PackingGroup	I
Storage Class	6.1C - Combustible, acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Carc. 1B Eye Dam. 1 Skin Corr. 1B STOT SE 3
Hazardous Substances Data	501-53-1(Hazardous Substances Data)
Toxicity	LD50 orally in Rabbit: 3000 mg/kg

MSDS Information

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Benzyl chloroformate Usage And Synthesis

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.
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.
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.
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

Diphosgene-->PHOSGENE-->Benzyl alcohol

Preparation Products

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

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Basic Info

Product Name:

Benzyl chloroformate

Other Name:

Carbonochloridic acid,phenylmethyl ester;Formic acid,chloro-,benzyl ester;Benzyl chloroformate;(Benzyloxy)carbonyl chloride;Carbobenzoxy chloride;Carbobenzyloxy chloride;Chloroformic acid benzyl ester;Benzyl carbonochloridate;Benzyl chlorocarbonate;Phenylmethyl chloroformate;NSC 83466;Benzyl chloridocarbonate;Benzyloxyformyl chloride;94274-21-2;728010-31-9;960053-05-8

CAS No.:

501-53-1

Molecular Formula:

C8H7ClO2

InChIKeys:

InChIKey=HSDAJNMJOMSNEV-UHFFFAOYSA-N

Molecular Weight:

170.59

Exact Mass:

170.59

EC Number:

207-925-0

UNII:

170BP0DD31

ICSC Number:

0990

NSC Number:

83466

UN Number:

1739

DSSTox ID:

DTXSID9027158

Color/Form:

OILY LIQUID|COLORLESS TO PALE YELLOW LIQUID

HScode:

2915900090

Categories:

Bulk Drug Intermediates

Characteristics

PSA:

26.3

XLogP3:

2.68

Appearance:

Clear slightly yellow to slightly pink Solution

Density:

1.2166 g/cm³ @ Temp: 20 °C

Melting Point:

-20 °C

Boiling Point:

152 °C @ Press: 760 Torr

Flash Point:

197 °F

Refractive Index:

1.531

Water Solubility:

Decomposes in water.Miscible with ether, acetone and benzene.

Storage Conditions:

2-8°C

Vapor Pressure:

1.39 psi ( 20 °C)

Vapor Density:

1 (vs air)

Toxicity:

Oral-Rat LD50: 3000 mg/kg; Inhalation-Rat LC50: 590 mg/m3/4 hours

Flammability characteristics:

Decomposes carbon dioxide and toxic chlorides and phosgene vapors when exposed to heat; emits toxic and corrosive hydrogen chloride gas when exposed to water

Explosive limit:

CONTAINERS MAY EXPLODE /DURING FIRE/.

Odor:

ACRID ODOR

Experimental Properties:

DECOMP TO CO2 & BENZYL CHLORIDE UPON HEATING AT 100-155 °C|DECOMP IN HOT ETHANOL & WATER|CONVERSION FACTORS: 6.96 MG/CU M= 1 PPM|Reacts with water to form hydrochloric acid|Flash point: 80.0 °C (Tag open cup), 107.9 °C (Tag closed cup)

Air and Water Reactions:

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

Reactive Group:

Acyl Halides, Sulfonyl Halides, and Chloroformates

Reactivity Alerts:

Water-Reactive

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].

Heat of Combustion:

-10.000 BTU/LB= -5,700 CALORIES/G= -240X10+5 JOULES/KG (ESTIMATED)

Corrosivity:

Corrosive

Heat of Vaporization:

90 BTU/LB= 50 CALORIES/G= 2.1X10+5 JOULES/KG (ESTIMATED)

See More Benzyl chloroformate Properties 

Hazard Identification

Classification of the substance or mixture

Skin corrosion, Sub-category 1B

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

GHS label elements, including precautionary statements

Precautionary statement(s)
Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage H410 Very toxic to aquatic life with long lasting effects
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection/hearing protection/... P273 Avoid release to the environment.
Response	P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P316 Get emergency medical help immediately. P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to an appropriate treatment and disposal facility in accordance with applicable laws and regulations, and product characteristics at time of disposal.

Other hazards which do not result in classification

no data available

Handling and Storage

Precautions for safe handling

NO open flames. NO contact with water. Handling in a well ventilated place. Wear suitable protective clothing. Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Use non-sparking tools. Prevent fire caused by electrostatic discharge steam.

Conditions for safe storage, including any incompatibilities

Separated from food and feedstuffs. Dry. Well closed.

See More Benzyl chloroformate Safety Data Sheet 

Seller Information

Business Type:
Trader

Main Products:
pharmaceutical intermediates,peptides,electronic chemicals

Location:
Room 102, 1st Floor, East Office Building, No. 45 Pengwan Road, Qianwan Bonded Port Area, Qingdao Zone, China (Shandong) Pilot Free Trade Zone

Payment Terms:
100% TT in advance

Average lead Time:
10

Total Annual Revenue:
$10 million-$25 million

Total Employees:
51-100

Year of Establishment:
2024

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Website: orientchem.cc
Email: scarlett@orientchem.cc
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Benzyl chloroformate501-53-1

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