Isomer	CAS No.	Configuration	Chirality	Key Application
trans-DACH (racemic, ±)	1121-22-8	trans (R,R + S,S mixture)	Achiral (racemate)	Epoxy curing, industrial synthesis
(1R,2R)-DACH	20439-47-8	trans (R,R)	Chiral (ee ≥99%)	Oxaliplatin ligand, asymmetric catalysis
(1S,2S)-DACH	21436-03-3	trans (S,S)	Chiral (ee ≥99%)	Asymmetric synthesis, chiral ligands
cis-DACH	1436-59-5	cis	Achiral (meso)	Research, specialty chelation

Key Property Q&A What is the 1,2-diaminocyclohexane structure? DACH has a six-membered cyclohexane ring with two –NH₂ groups at the 1- and 2-positions. The trans isomer adopts a diequatorial conformation, making it more stable and less sterically strained than the cis (diaxial or equatorial/axial) form.  |  Is cis-1,2-diaminocyclohexane chiral? No - cis-1,2-diaminocyclohexane is a meso compound (achiral despite stereocenters). The trans isomers, however, are chiral: (1R,2R)- and (1S,2S)-DACH are non-superimposable mirror images (enantiomers).  |  What is 1,2-diaminocyclohexane used for? The two primary industrial uses are: (1) epoxy curing agent (racemic trans-DACH) and (2) chiral ligand/building block in pharmaceutical synthesis and asymmetric catalysis (enantiopure R,R or S,S isomers).

Specification	Industrial Grade Epoxy Curing / Synthesis	Pharmaceutical Grade API Intermediates / GMP	Chiral Grade (R,R / S,S) Asymmetric Synthesis
Purity (GC)	≥ 99.0%	≥ 99.5%	≥ 99.9%
Chiral Purity (ee%)	N/A (racemic)	≥ 98% (if chiral)	≥ 99.0% ee
Water Content	≤ 0.1%	≤ 0.05%	≤ 0.05%
Color (Pt-Co)	≤ 10	≤ 5	≤ 5
Boiling Point	104–110 °C (40 mmHg); ~80 °C (10 mmHg)
Density (20 °C)	0.931–0.935 g/cm³
Shelf Life	12 months (N₂-sealed)	12 months (N₂-sealed)	12 months (N₂-sealed, 2–8°C)
Packaging	180 kg steel drum 1000 kg IBC tote / tank truck	180 kg N₂-sealed drum	1 kg / 5 kg / 25 kg sealed container (chiral QC report included)

1. Pharmaceutical Industry - Oxaliplatin & Chiral API Synthesis

The most high-profile pharmaceutical application of 1,2-diaminocyclohexane is as the chiral diamine ligand in oxaliplatin (Eloxatin®) - a third-generation platinum-based anticancer drug used globally for colorectal cancer chemotherapy. Oxaliplatin is formed by coordination of (1R,2R)-DACH with platinum, and the specific R,R configuration is essential for its anticancer mechanism and toxicity profile. The compound dichloro(1,2-diaminocyclohexane)platinum(II) is a key synthesis intermediate in oxaliplatin manufacture.

Beyond oxaliplatin, enantiopure (R,R)- and (S,S)-DACH serve as chiral building blocks in the synthesis of antiviral agents, antibiotics, and other chiral APIs requiring a conformationally rigid diamine scaffold. Chiral-grade DACH (ee ≥99.0%) complies with GMP and ICH Q6A guidelines, with full chiral HPLC documentation.

Reference: PubChem - 1,2-Diaminocyclohexane (NIH) ↗

2. Epoxy & Polymer Industry - High-Performance Curing Agent

DACH is a premium cycloaliphatic epoxy curing agent that delivers outstanding performance compared to aliphatic amines: the rigid cyclohexane ring reduces chain mobility in the cured network, yielding coatings and composites with superior chemical resistance, hardness, UV stability, and thermal performance (Tg up to 150°C). It cures epoxy resins at ambient or moderately elevated temperatures with manageable pot life.

Key application sectors for DACH-cured epoxy systems include aerospace composite structures, electronic encapsulants, industrial protective coatings, and structural adhesives where the combination of mechanical strength, adhesion, and chemical resistance is critical. Industrial racemic trans-DACH (CAS 1121-22-8) is the standard grade for epoxy applications.

3. Asymmetric Catalysis - Chiral Ligand & Jacobsen's Catalyst

(R,R)-DACH is a cornerstone of asymmetric synthesis. It is the chiral backbone of Jacobsen's Mn-salen catalyst - one of the most widely used catalysts for asymmetric epoxidation of olefins - and of numerous chiral bis(oxazoline), salen, and diamine ligands used in metal-catalyzed hydrogenation, aldol reactions, and C–C bond-forming reactions.

Its rigid trans-diaxial coordination geometry locks the metal center in a defined chiral environment, enabling high enantiomeric excess (typically 90–99% ee) in complex target molecule synthesis. Both (R,R) and (S,S) enantiomers are supplied, allowing access to either product enantiomer on demand.

Reference: ECHA REACH - 1,2-Diaminocyclohexane Registration ↗

4. Chelating Agents - CDTA / DCTA & Water Treatment

1,2-Diaminocyclohexane tetraacetic acid (CDTA or DCTA), synthesized from DACH, is a highly effective hexadentate chelating agent that forms more stable metal complexes than EDTA for divalent and trivalent metal ions (Ca²⁺, Mg²⁺, Fe³⁺, Cu²⁺). CDTA is used in industrial water treatment, boiler descaling, analytical chemistry (as a titration agent for metal ions), and biochemical research as a phosphatase inhibitor.

DACH also serves directly as a corrosion inhibitor in water treatment formulations and metal surface passivation applications, leveraging its strong metal-binding amino groups to form protective complexes on metal surfaces.

5. Other Applications - Surfactants, Lubricants & Specialty Additives

DACH is an intermediate for synthesizing specialty surfactants, corrosion inhibitors, and lubricant additives where its cyclic diamine structure imparts thermal stability and metal-binding activity. It is also used in plastics modification to improve thermal stability and compatibility, and as a precursor to N,N-dimethyl-1,2-diaminocyclohexane - a methylated derivative used in palladium-catalyzed cross-coupling reactions (Buchwald-Hartwig amination).

⚠️ SAFETY NOTE: 1,2-Diaminocyclohexane is corrosive (skin/eye burns), combustible (flash point 80°C), and strongly basic - it reacts exothermically with acids. Vapors are irritating to the respiratory tract. Handle with full PPE in well-ventilated areas.

Note: Chiral grade (R,R)/(S,S)-DACH pricing is highly dependent on order volume, required ee specification, and delivery timeline. Long-term agreements for oxaliplatin intermediate supply offer the most competitive pricing. Request a custom DACH price quote →

Q: What is the CAS number for 1,2-diaminocyclohexane?

The CAS number depends on the stereoisomer: trans-racemic (±) mixture: CAS 1121-22-8; (1R,2R)-enantiomer: CAS 20439-47-8; (1S,2S)-enantiomer: CAS 21436-03-3; cis-isomer: CAS 1436-59-5. When purchasing, always specify which stereoisomeric form is required, as they have very different applications and prices. The racemic trans form (CAS 1121-22-8) is the most commercially available and lowest-cost form.

Q: What are the stereoisomers of 1,2-diaminocyclohexane, and which is chiral?

1,2-Diaminocyclohexane has three stereoisomeric forms: (1R,2R)-trans, (1S,2S)-trans, and cis. The two trans enantiomers are chiral (non-superimposable mirror images). The cis form is a meso compound - it has two stereocenters but is achiral due to an internal mirror plane. The racemic trans mixture contains equal amounts of (R,R) and (S,S). For asymmetric synthesis or pharmaceutical use, the pure enantiomers must be resolved from the racemate.

Q: How is enantiopure (R,R)-DACH obtained - what is chiral resolution with tartrate?

The classical method for resolution of 1,2-diaminocyclohexane uses L-tartaric acid as the resolving agent. The racemic trans-DACH is treated with L-tartaric acid, forming two diastereomeric 1,2-diaminocyclohexane tartrate salts - specifically the (1R,2R)-DACH·L-tartrate and (1S,2S)-DACH·L-tartrate - which have different solubilities and can be separated by selective crystallization. The desired enantiomer is then released by treatment with strong base. The 1,2-diaminocyclohexane mono-tartrate salt intermediate is commercially available as an alternative to the free base for certain synthetic applications.

Q: What is the connection between 1,2-diaminocyclohexane and oxaliplatin?

Oxaliplatin (INN), the third-generation platinum anticancer drug used in FOLFOX chemotherapy for colorectal cancer, has the chemical structure [(1R,2R)-DACH]Pt(oxalate). The (1R,2R)-1,2-diaminocyclohexane provides the chiral bidentate nitrogen ligand that coordinates to platinum, while the oxalate acts as the leaving group. The compound dichloro(1,2-diaminocyclohexane)platinum(II) - [Pt(DACH)Cl₂] - is the key synthesis intermediate. The R,R configuration is not interchangeable; the S,S isomer has different biological activity. This makes enantiopure (1R,2R)-DACH a strategically important pharmaceutical raw material.

Q: What is 1,2-diaminocyclohexane tetraacetic acid (CDTA)?

1,2-Diaminocyclohexane tetraacetic acid (CDTA), also called DCTA or cyclohexanediaminetetraacetic acid, is synthesized by tetraacetylation of DACH. It is a hexadentate chelating agent stronger than EDTA for most divalent metal ions, owing to the rigid cyclohexyl backbone which pre-organizes the binding groups. CDTA is used in: analytical chemistry (complexometric titrations, metal ion masking), industrial water treatment and boiler scale control, biochemical research as a phosphatase inhibitor and metal chelator, and as a component in electroless plating and photographic developer solutions.

Q: What is N,N-dimethyl-1,2-diaminocyclohexane used for?

N,N-dimethyl-1,2-diaminocyclohexane (Me₂N-DACH) is a methylated derivative of DACH used primarily as a ligand in palladium-catalyzed cross-coupling reactions, most notably the Buchwald-Hartwig amination (C–N bond formation) and copper-catalyzed Ullmann-type reactions. The dimethylamino group modifies the electronic and steric environment of the metal center, improving catalyst activity and selectivity for challenging substrates. It is also an intermediate in the synthesis of specialty surfactants and corrosion inhibitors. We supply this derivative on request alongside standard DACH grades.