ISO 9001:2008 Certified U.S. Based Manufacturing Since 1928

Leaders in Small Molecule Building Blocks Shipping/Receiving Columbus, OH Manufacturing Complex

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

Leaders in Small Molecule Building Blocks Equipment Capabilities and Scale (Organic Division) Kilo Lab Scale –Glassware up to 72 L scale –Distillation support up to 50L scale Short path –Bench Strip –Rotary Evaporators Long path –18” to 48” packed columns –Stainless, Hastelloy, Ceramic packing Pilot Scale –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 – gal Hastelloy – gal Glass – gal Stainless –Distillation support Short path –50 gal-500 gal glass lined Long path –4’ to 16’ column –Stainless, Hastelloy, Glass packing –Solids Handling Hastelloy and Stainless centrifugation 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

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

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

Leaders in Small Molecule Building Blocks Liquid Ammonia CC n Z n=2 to 7 R CCCN R NH 3

Leaders in Small Molecule Building Blocks Acetylene Reactions HC CR HC CC 2 OH HC CC n Cl HC CC n C CH RC CC CCOH HC CH

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

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

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

Leaders in Small Molecule Building Blocks Organometallics (Mg, Li, Na) R R’ Ar R (Ar) RC CR’ R(CH2) n OTHP RMgX RLi

Leaders in Small Molecule Building Blocks Organometallics (Mg, Li, Na) RCHO RCCOH Z E O R’ R’ CC CR RMgX RLi

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

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

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 ) 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 Lithium amide Lithium metal Magnesium Sodium amide Sodium hydride Sodium metal Trialkylsilanes Iodine Hydrogen Chloride