Innovative Chemical Technology For Innovative Applications ISO 9001

Innovative Chemical Technology For Innovative Applications ISO 9001: 2008 Certified U. S. Based Manufacturing Since 1928

Shipping/Receiving Columbus, OH Manufacturing Complex www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Why Source from GFS? • Manufacturer, since 1928 – ISO certified; non-c. GMP • Depth and diversity of core product lines • Support for Research → Commercial volumes • Support for custom specifications and products www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Equipment Capabilities and Scale (Organic Division) Pilot Scale Kilo Lab Scale – Glassware up to 72 L scale – Distillation support up to 50 L scale • Short path – Bench Strip – Rotary Evaporators • Long path – 18” to 48” packed columns – Stainless, Hastelloy, Ceramic packing www. GFSChemicals. com – 10 gal – 100 gal glass lined steel – 10 gal – 200 gal Stainless – Distillation Support • Rotary Evaporator • 30 gal – 50 gal glass lined steel distillation pots – 4’ to 12’ columns – Glass & stainless packing Leaders in Small Molecule Building Blocks

Equipment Capabilities and Scale (Organic Division) Plant Scale – – 350 -500 gal Hastelloy 100 -1000 gal Glass 200 -1000 gal Stainless Distillation support • Short path – 50 gal-500 gal glass lined • Long path – 4’ to 16’ column – Stainless, Hastelloy, Glass packing Plant Scale Supports – Vacuum capabilities to < 10 Torr – Pressure handled to < 100 psi – Reaction conditions controlled from -40 o. C to +140 o. C – Distillation conditions controlled from 20 o. C to 250 o. C – Scrubbing supports for acid/base, ammonia and sulfide – Nitrogen used as inerting atmosphere – Solids Handling • Hastelloy and Stainless centrifugation www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Core Organic Technologies • Reactions in Liquid Ammonia • Acetylene Reactions • Alkyne Chemistry • Organometallic Chemistry (Mg, Li, Na) • Halogen Chemistry (Cl, Br, I) • Heteroaromatic Compounds www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Liquid Ammonia RC CH RC CR' NH 3 RC CCCOH www. GFSChemicals. com RNH 2 Leaders in Small Molecule Building Blocks

Liquid Ammonia CCn Z n=2 to 7 NH 3 R CCCN R www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Acetylene Reactions HC CR HC CC 2 OH HC HC CCn. C www. GFSChemicals. com CH HC CCn. Cl CH RC Leaders in Small Molecule Building Blocks CC CCOH

Alkyne Chemistry RC CCHO RC CC(O)R 1 RC CCO 2 R 1 RC CH RC CCO 2 H RC CCOH www. GFSChemicals. com RC Leaders in Small Molecule Building Blocks CC 2 OH

Alkyne Chemistry RC CC CR RC RC CC X n www. GFSChemicals. com RC CC CR’ CH RC CC C Leaders in Small Molecule Building Blocks n CC X m

Alkyne Chemistry Indoles Benzofurans Isocoumarins RC CH Pyrimidines Isoquinolines www. GFSChemicals. com Furopyridines Leaders in Small Molecule Building Blocks

Organometallics (Mg, Li, Na) R R’ Ar R (Ar) RMg. X RLi RC CR’ www. GFSChemicals. com R(CH 2)n. OTHP Leaders in Small Molecule Building Blocks

Organometallics (Mg, Li, Na) RCHO RCCOH RMg. X RLi Z E www. GFSChemicals. com O R’ R’ CC CR Leaders in Small Molecule Building Blocks

Halogen Chemistry (Cl, Br, I) RCC CCBr CH 3 CCH 2 I CH 3 Cl, Br, I I Br(CH 2)Cl www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Heteroaromatic Chemistry Phenanthrolines Quinolines Pyridines Phenylenediamines Acetylenes Bipyridines Terpyridines Pyrimidines www. GFSChemicals. com Leaders in Small Molecule Building Blocks

Core Organic Synthetic Methods Performed at GFS • • • Acetylene Chemistry Halogenation Dehydrohalogenation Alkylation(NH 3) Sonogashira Reactions Kumada Couplings Cadiot-Chodkiewicz Suzuki Coupling Trans Reductions(NH 3) www. GFSChemicals. com • • Diels-Alder Synthesis Ethynylation Barbier Reaction Skraup Synthesis Birch Reduction Heck Reaction Grignard/Alkyl Lithium Synthesis • Finklestein Reaction • Phase Transfer Leaders in Small Molecule Building Blocks

Reagents Handled Routinely at GFS in > 100 kg Quantities • • • Acetylene Ammonia, liq. Alkyllithium Carbon disulfide Chloroformates Chlorosulfonic acid Epichlorohydrin Ethylene oxide Bromine www. GFSChemicals. com • • • Lithium amide Lithium metal Magnesium Sodium amide Sodium hydride Sodium metal Trialkylsilanes Iodine Hydrogen Chloride Leaders in Small Molecule Building Blocks