Many reagents need special handling or storage to maintain their purity and reactivity.

Detailed procedures for a large number of organic syntheses can be downloaded free from OrganicSyntheses.

Air- and Moisture-Sensitive Compounds

For a general overview of handling air- and moisture-sensitive compounds (by far the most common things to worry about), I strongly recommend reading the Sigma-Aldrich Technical Bulletin AL-134 (Handling and Storage of Air-Sensitive Reagents)Δ. This describes basics of using syringes and purge gases to transfer liquids without allowing contact with atmospheric water and oxygen.

Also see papers and guides to handling air-sensitive materials.

Dr. Schilke’s lab has a fume hood that has been plumbed to supply argon (Ar), a convenient gas for purging vessels because of its high density (it fills a container bottom-first, sort of like a liquid).

Reagents in our lab that need to be handled and stored under argon or nitrogen include:

• Silanes (aminopropyltriethoxysilane, trichlorovinylsilane, octadecyltrimethoxysilane, etc.)
• Organic bases (triethylamine, octylamine, diisopropylethylamine)
• Anhydrous or oxidation-prone solvents
• Any hygroscopic, air- or water-sensitive compound (e.g. EDC, FITC, fluorescamine, dansyl chloride, etc.)
• Any reagent bottle fitted with a septum cap
• Any alkyl ethers such as diethyl ether or tetrahydrofuran (THF). These compounds react with atmospheric oxygen to form explosive organic peroxides. The friction generated by twisting the cap off the bottle is sufficient to cause these organic peroxides to explode.
• PEO/mPEO and derivatives should be stored at temperatures < -15°C and covered with inert gas (N₂ or Ar) to prevent oxidation [Nektar catalog].

Also note, to prevent contamination with silicone and other compounds, use only glass syringes for reagent transfer. An acceptable alternative, especially for < 1 mL volumes, are all-polypropylene Norm-Ject® syringes (we usually have 1, 5 and 20 mL sizes on hand). Never use a standard syringe; the rubber plunger often swells and locks up the syringe.

Amine-Containing Organic Compounds

Amines, such as triethylamine (Et₃N/TEA) and diisopropylethylamine (DIPEA) should be stored under argon because they react with atmospheric water (hydrolysis) and carbon dioxide (forming carbamates). Always flush with argon after use.

Notes on specific reagents:

Some reagents have specific information that is difficult to find, or otherwise useful to record. The following (alphabetical) list contains links to pages for each of the compounds:

Acetic anhydride

This carboxylic acid anhydride is very commonly used to acetylate primary and secondary amines, hydroxyl groups, and other nucleophilic groups.

Amino Acids

Here is a very nice chart of the standard amino acids from Berk Zafer at UNC

bis(aminopropyl)-polydimethylsiloxane (H₂N-PDMS-NH₂)

Commercial telechelic PDMS polymer with terminal propylamino (-CH₂CH₂CH₂NH₂) groups.

Blood and plasma

Admittedly not a reagent, but something we use. Information on where to buy blood, plasma and serum for research purposes.

Chromosulfuric Acid

A nasty, toxic and carcinogenic acid that we use to clean OWLS sensor chips.

Epoxy (glycidyl) compounds

Epoxy-functional (glycidyl) compounds react spontaneously with a variety of nucleophiles. They are used to make epoxy glues and resins, and are useful synthetic and immobilization reagents.

Fluorescamine (fluram)

Fluram is a dye that reacts spontaneously with amines. It forms fluorescent products with primary amines only (secondary amine products are not fluors). It is hydrolyzed in seconds in water, so stock solutions are made in organic solvent (acetone, etc).

Fibrinogen

A large (340 kDa) heterohexameric blood protein which is necessary for blood clotting.

Fluorescein isothiocyanate (FITC)

FITC is an amine-reactive dye that is commonly used to label proteins and other amine-functional molecules. It is subject to photobleaching, so care should be taken to avoid strong light when handling it.

Jeffamine™ bisamino-PEO/PPO (H₂N-PEO/PPO-NH₂)

Commercially available telechelic (10 pts!) PEO/PPO polymers with -NH₂ terminal groups.

Nisin (lantibiotic)

A natural 34-residue polypeptide with unusual lanthionine (R-S-R) ring structures. Strong antimicrobial activity against Gram-positive bacteria.

Pluronic™ F108 and PEO, L61, L101, P65, P105, and End-Group-Activated Pluronic (EGAP)

These surface-active molecules are widely used to coat hydrophobic surfaces. They form a cell- and protein-repellent PEO brush by simple adsorption, with EGAP having reactive end-groups for further conjugation.

Polylysine and polyglutamic acid

Synthetic homopolymers of amino acids, which are used in structure-function studies because of their well-defined and pH-responsive 2° structure.

Poly(butadiene) and PEO-PBD-PEO block copolymers (“Hillmyer triblocks”)

The incorporation of a polymer rich in double-bonds (e.g. polybutadiene) into block copolymers can offer a means to immobilize them on many surfaces.

Trifluoroacetic anhydride (TFAA)

This compound, a relative of acetic anhydride, can be used to introduce a CF₃ group on primary and secondary amines, hydroxyl groups and possibly carboxylic acids. This is attractive for XPS and other analytical techniques sensitive to fluorine.

WLBU2 (RRWVRRVRRWVRRVVRVVRRWVRR)

A potent synthetic cationic antimicrobial peptide (CAP) based on host-derived antimicrobial peptides. The new nisin.

WR12 (RWWRWWRRWWRR)

Another (more) potent synthetic CAP. The new WLBU2.