2-Chloro-1,3-propanediol (CAS 63393-96-4) 98% Colorless to Pale Yellow Viscous Liquid | α-Chlorohydrin / Halogenated Diol Building Block

1. Product Overview

2-Chloro-1,3-propanediol (CAS 63393-96-4), also referred to as α-chlorohydrin or 3-chloro-1,2-propanediol isomer (specifically the 2-chloro-1,3-diol form), has molecular formula C₃H₇ClO₂ and MW 110.54 g/mol. It bears a primary chloride flanked by two primary hydroxyl groups, allowing orthogonal O-functionalization (tosylation, silylation, ether/ester formation) and SN2 displacement of the chloride. This compound is used as a bifunctional linker precursor and in the synthesis of oxazolidines, morpholines, and chloro-substituted heterocycles.

2. Key Features and Benefits

• Bifunctional Halogenated Diol: Two primary OH groups for selective protection/derivatization; primary Cl for nucleophilic substitution.

• Small C₃ Scaffold: Introduces a three-carbon spacer with terminal OH and central Cl in molecular architecture studies.

• Oxazolidine Precursor: Condenses with aldehydes/ketones under acid catalysis to form 5-membered cyclic acetals (oxazolidines).

• High Purity Liquid: Supplied ≥98% (GC), convenient for syringe-based addition in anhydrous setups.

3. Major Applications

• Organic Synthesis: Used in the preparation of O-tosyl/silyl derivatives and subsequent SN2 displacement to introduce C₃ chains.

• Heterocycle Formation: Cyclocondensation with carbonyls → oxazolidines; with diamines → morpholine analogs under appropriate conditions.

• Linker / Spacer Research: Incorporated as a short chloro-diol tether in ligand or probe design.

• Protecting Group Studies: Diol can be differentially protected (e.g., one OH as TBDMS, the other as acetate) for stepwise elaboration.

• Analytical Reference: Standard for GC/HPLC method development in halogenated diol impurity profiling.

4. Technical Specifications

Item Description
Product Name 2-Chloro-1,3-propanediol (α-Chlorohydrin)
Synonyms 3-Chloro-1,2-propanediol (related isomer context); α-Chlorohydrin; 2-Chloro-propane-1,3-diol
CAS Number 63393-96-4
Molecular Formula C₃H₇ClO₂
Molecular Weight 110.54 g/mol
MDL Number MFCD00004671
PubChem CID 5285275
Assay (Purity) ≥98% (GC)
Appearance Colorless to pale yellow viscous liquid
Melting Point −11 to −8 °C
Boiling Point 115–118 °C / 15 mmHg (Literature)
Density 1.321–1.325 g/mL at 25 °C
Refractive Index n²⁰/D ≈ 1.480–1.483
Flash Point >110 °C (closed cup, estimated)
Calculated LogP ~−0.3 to 0.0
Polar Surface Area (PSA) 40.5 Ų
Hydrogen Bond Donors 2 (OH ×2)
Hydrogen Bond Acceptors 2 (O ×2)
Rotatable Bonds 2
Solubility Miscible with water, methanol, ethanol; soluble in DMSO, DMF, ethyl acetate, dichloromethane; slightly soluble in ether, insoluble in hexane.
SMILES OC(CO)C(CCl)O
InChI Key YPFBHNJYSBLAKO-UHFFFAOYSA-N — verify via database
Storage 2–8 °C, sealed, protect from moisture; hygroscopic. Stable ≥18–24 months.
HS Code 2905.49.90 / 3822.90.00

5. Storage and Handling

Store in a tightly sealed container at 2–8 °C, protected from moisture (hygroscopic). Allow vial to reach room temperature before opening to prevent condensation. Handle in a fume hood—chlorohydrins can be irritants. Dissolve in water, MeOH, EtOH, or anhydrous DCM/THF for reactions. For SN2 displacement, use K₂CO₃ or NaH in polar aprotic solvent. Avoid strong bases at elevated temperature with concurrent elimination risk.

6. Safety Summary

• GHS Classification: GHS05 (Corrosive / Irritant) + GHS07 – Warning

• Signal Word: Warning / Danger (per conc.)

• Hazard Statements: H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation)

Pls input...