Isobutyl chloroformate

Base Information

• Chemical Name: Isobutyl chloroformate
• CAS No.: 543-27-1
• Molecular Formula: C5H9ClO2
• Molecular Weight: 136.578
• Hs Code.: 29159000
• European Community (EC) Number: 208-840-1
• ICSC Number: 1594
• NSC Number: 8429
• UN Number: 2742
• UNII: 6S785TC0OB
• DSSTox Substance ID: DTXSID8052194
• Nikkaji Number: J95.612K
• Wikidata: Q27265420
• Mol file: 543-27-1.mol

Synonyms:chloroformic acid isobutyl ester;isobutyl chloroformate

Chemical Property of Isobutyl chloroformate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 0.33 mm Hg ( 20 °C)
• Melting Point: -80 °C
• Refractive Index: n20/D 1.407(lit.)
• Boiling Point: 130 °C at 760 mmHg
• Flash Point: 27.8 °C
• PSA: 26.30000
• Density: 1.081 g/cm³
• LogP: 2.01780
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: benzene: miscible
• Water Solubility.: Immiscible with water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 136.0291072
• Heavy Atom Count: 8
• Complexity: 80.5
• Transport DOT Label: Poison Corrosive Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Isobutyl chloroformate, 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 10-22-23-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Acid Halides
• Canonical SMILES: CC(C)COC(=O)Cl
• Inhalation Risk: A harmful contamination of the air will be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of the vapour may cause lung oedema. The effects may be delayed.
• Uses: Isobutyl chloroformate is used as a peptide reagent. It is also used in the preparation of phenethyl-carbamic acid isobutyl ester by reaction with phenethylamine. Peptide reagent.

Technology Process of Isobutyl chloroformate

There total 13 articles about Isobutyl 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: 70.0%

(R)-N5-[amino-(nitroimino)-methyl]-N2-(diphenylacetyl)ornithine (159013-58-8) + N-dimethyl-N'-[4-(aminomethyl) phenyl]urea → (R)-N5-[amino(nitroimino)methyl]-N-[[4-[[(dimethylamino)carbonyl]amino]phenyl]methyl]-N2-(diphenylacetyl)-ornithinamide (164645-67-4) + isobutyl chloroformate (543-27-1)

Guidance literature:

ammonia;

Reference yield: 64.0%

→ 4-hydroxyphenyl-4'-isobutoxycarbonylaminophenyl sulfide + isobutyl chloroformate (543-27-1)

Guidance literature:

Reference yield:

carbonic acid monoisobutyl ester (57272-07-8) → isobutyl chloroformate (543-27-1)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.chempr.2021.07.005

upstream raw materials:

phosgene

2-methyl-propan-1-ol

(R)-N₅-[amino-(nitroimino)-methyl]-N₂-(diphenylacetyl)ornithine

bis(trichloromethyl) carbonate

Downstream raw materials:

1-piperazino-carboxylic acid isobutyl ester

isobutyl N-phenethylcarbamate

N-(N-benzyloxycarbonyl-glycyl)-DL-phenylalanine methyl ester

N-benzyloxycarbonyl-L-isoglutamine

Refernces

Design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors

10.1016/j.bmcl.2006.11.020

The research focuses on the design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors, aiming to develop new anti-tumor agents. The purpose of this study is to create compounds that can inhibit the activity of the 20S proteasome, a protein complex involved in the degradation of proteins, which is often dysregulated in pathological conditions such as cancer. The researchers synthesized a series of furan-based compounds, including nine peptide derivatives and six statine peptidomimetics, with the C-terminal furanyl moiety introduced as furan-based amino acids to target the proteasome. The synthesis involved the use of various chemicals such as Boc-protected α-amino acids, isobutyl chloroformate (IBCF), N-methylmorpholine (NMM), trifluoroacetic acid (TFA), and others in a series of reactions including methylation, coupling, and hydrolysis. The study concluded that compound 12 emerged as a selective and moderate potent proteasome peptidomimetic inhibitor, effectively inhibiting the proliferation of HepG2 (human hepatoma) and HL-60 (acute human myeloid leukemic) cell lines. The research provides insights into the potential of these furan-based inhibitors as anti-tumor agents by targeting the 20S proteasome and offers a detailed synthetic route for the development of these compounds.