Benzyl chloroformate

Base Information

• Chemical Name: Benzyl chloroformate
• CAS No.: 501-53-1
• Deprecated CAS: 94274-21-2,728010-31-9,960053-05-8,728010-31-9
• Molecular Formula: C8H7ClO2
• Molecular Weight: 170.595
• Hs Code.: 2915 90 70
• European Community (EC) Number: 207-925-0
• ICSC Number: 0990
• NSC Number: 83466
• UN Number: 1739
• UNII: 170BP0DD31
• DSSTox Substance ID: DTXSID9027158
• Nikkaji Number: J6.192A
• Wikipedia: Benzyl_chloroformate
• Wikidata: Q419534
• ChEMBL ID: CHEMBL1581748
• Mol file: 501-53-1.mol

Synonyms:benzyl chloroformate;carbobenzoxy chloride

Chemical Property of Benzyl chloroformate

Chemical Property:

• Appearance/Colour: light yellow liquid
• Vapor Pressure: 1.39 psi ( 20 °C)
• Melting Point: -20 °C
• Refractive Index: n20/D 1.519(lit.)
• Boiling Point: 223.984 °C at 760 mmHg
• Flash Point: 73.488 °C
• PSA: 26.30000
• Density: 1.244 g/cm³
• LogP: 2.56200
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ether, acetone and benzene.
• Water Solubility.: decomposes
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 170.0134572
• Heavy Atom Count: 11
• Complexity: 130
• Transport DOT Label: Corrosive

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl Chloroformate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, C, N, F
• Hazard Codes: T,C,N,F
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: C1=CC=C(C=C1)COC(=O)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly on spraying.
• Effects of Short Term Exposure: Lachrymation. The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the aerosol may cause lung oedema. The effects may be delayed. Medical observation is indicated.
• 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.
• 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.

Technology Process of Benzyl chloroformate

There total 22 articles about Benzyl chloroformate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

S-methyl O-benzyl carbonothioate (22426-83-1) → benzyl chloroformate (501-53-1,94274-21-2)

Guidance literature:

With sulfuryl dichloride; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.06.114

Reference yield: 99.0%

bis(trichloromethyl) carbonate (32315-10-9) + benzyl alcohol (100-51-6,185532-71-2) → benzyl chloroformate (501-53-1,94274-21-2)

Guidance literature:

With pyridine; In dichloromethane; at -5 - 10 ℃; for 13h; Reagent/catalyst; Temperature; Solvent;

Reference yield: 81.0%

S-ethyl O-benzyl carbonothioate (110177-67-8) → benzyl chloroformate (501-53-1,94274-21-2)

Guidance literature:

With sulfuryl dichloride; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)01331-5

upstream raw materials:

phosgene

benzyl alcohol

benzyl carbonochloridate

trichloromethyl chloroformate

Downstream raw materials:

CbzGlyGly

(2-indol-3-yl-ethyl)-carbamic acid benzyl ester

4-(N-Benzyloxycarbonylamino)phenol

benzyl (3-methoxyphenyl)carbamate

Refernces

• 1、 Long, Huan,Hu, Xiaolong,Wang, Baolin,Wang, Quan,Wang, Rong,Liu, Shumeng,Xiong, Fei,Jiang, Zhenzhou,Zhang, Xiao-Qi,Ye, Wen-Cai,Wang, Hao. "Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer". . p. 12089 - 12108. Retrieved 2021/09/06.
• 2、 Chang, Sukbok,Jung, Hoimin,Kim, Dongwook,Lee, Jeonghyo,Lee, Jia,Park, Juhyeon. "Versatile Cp*Co(III)(LX) Catalyst System for Selective Intramolecular C-H Amidation Reactions". supporting information. p. 12324 - 12332. Retrieved 2020/08/06.