Myristoyl chloride

Base Information

• Chemical Name: Myristoyl chloride
• CAS No.: 112-64-1
• Deprecated CAS: 902459-01-2,1246204-30-7
• Molecular Formula: C14H27ClO
• Molecular Weight: 246.821
• Hs Code.: 29159000
• European Community (EC) Number: 203-994-6
• NSC Number: 9417
• UNII: B9J09WN7SU
• DSSTox Substance ID: DTXSID3059422
• Nikkaji Number: J94.930B
• Wikidata: Q72493391
• Mol file: 112-64-1.mol

Synonyms:Myristoyl chloride;Tetradecanoyl chloride;112-64-1;myristic acid chloride;tetradecanoic acid chloride;B9J09WN7SU;NSC 9417;NSC-9417;EINECS 203-994-6;EC 203-994-6;tetradecanoylchloride;MFCD00000741;Myristoyl chloride, 97%;UNII-B9J09WN7SU;C14H27ClO;Myristoyl chloride, >=99%;SCHEMBL179747;C14-H27-Cl-O;DTXSID3059422;NSC9417;AKOS015900627;BS-43799;FT-0629057;T0086;D97669;Q-201419

Chemical Property of Myristoyl chloride

Chemical Property:

• Appearance/Colour: Clear colorless to light yellowish-brown liquid
• Vapor Pressure: 0.00143mmHg at 25°C
• Melting Point: -1 °C
• Refractive Index: n20/D 1.449(lit.)
• Boiling Point: 296.5 °C at 760 mmHg
• Flash Point: 139.6 °C
• PSA: 17.07000
• Density: 0.92 g/cm³
• LogP: 5.45290
• Storage Temp.: −20°C
• Water Solubility.: MAY DECOMPOSE
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 246.1750432
• Heavy Atom Count: 16
• Complexity: 157

Purity/Quality:

99.9% ^*data from raw suppliers

Myristoyl Chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37-22
• Safety Statements: 26-36/37/39-45-28B

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)Cl
• General Description: Myristoyl chloride (tetradecanoyl chloride) is utilized in the synthesis of amphiphilic chitoheptaose derivatives as a key reagent for introducing hydrophobic tetradecanoyl groups via acylation. This modification enhances Myristoyl chloride's amphiphilic properties, enabling micelle formation in aqueous solutions, which is critical for improving biological activity through clustering effects. The process highlights its role in facilitating the hydrophobic functionalization of carbohydrate-based structures.

Technology Process of Myristoyl chloride

There total 5 articles about Myristoyl chloride 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: 98.1%

n-tetradecanoic acid (544-63-8) → tetradecanoyl chloride (112-64-1)

Guidance literature:

With thionyl chloride; In N,N-dimethyl-formamide; at -5 - 70 ℃; for 4.33333h;

Reference yield:

→ n-dodecanoyl chloride (112-16-3) + tetradecanoyl chloride (112-64-1)

Guidance literature:

Reference yield:

sodium myristoate (822-12-8) → tetradecanoyl chloride (112-64-1)

Guidance literature:

With thionyl chloride; at 20 ℃;

DOI:10.1016/S0968-0896(01)00023-2

upstream raw materials:

oxalyl dichloride

n-tetradecanoic acid

sodium myristoate

Downstream raw materials:

palmitic acid

1-(2-methyl-piperidino)-3-myristoyloxy-propane; hydrochloride

myristic anhydride

N-(4-hydroxyphenyl)tetradecanamide

Refernces

Synthesis of amphiphilic chitoheptaose derivative

10.1016/S0040-4039(97)10104-6

The study focuses on the synthesis of an amphiphilic chitoheptaose derivative, tetradecyl-4-O-chitohexaosyl-2-deoxy-2-tetradecanamido-?-D-glucopyranoside hexahydrochloride, which is expected to enhance biological activities through clustering. The synthesis involves multiple steps, starting with the preparation of a heptasaccharide skeleton using a disaccharide synthon for chain elongation. Key chemicals include NJV-diacetylchitobiose, which is converted into a pentenyl glycoside and then benzylidenated to form an elongation synthon. The 1,6-anhydro precursor of the reducing end is glycosylated using N-iodosuccinimide (NIS) and triethylsilyltriflate (TESOTf) as promoters. The introduction of hydrophobic groups involves acylation with tetradecanoyl chloride and a subsequent one-pot synthesis of tetradecyl glycoside. The final product is obtained after deprotection and purification, resulting in a compound that forms micelles in water, as indicated by its solubility in a 3% aqueous solution.