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Chloroformic Acid, Oxydiethylene Ester is a bifunctional chloroformate compound used as a reactive intermediate in specialty chemical synthesis.
Chloroformic Acid, Oxydiethylene Ester provides two reactive chloroformate groups that support the preparation of polymers, crosslinking agents, and functional derivatives.
Chloroformic Acid, Oxydiethylene Ester is valued in controlled synthesis processes where efficient functionalization and molecular modification are required.
CAS Number: 106-75-2
EC Number: 203-430-9
Molecular Formula: C₆H₈Cl₂O₅
Molecular Weight: 231.03 g/mol
Synonyms: Oxydiethylene bis(chloroformate), Diethylene glycol bischloroformate, Diglycol chloroformate, DEG bis(chloroformate), DECF, Oxydiethylene chloroformate, Diethylene glycol chloroformate, Formic acid chloro- diester with diethylene glycol, 1,5-Bis((chlorocarbonyl)oxy)-3-oxapentane, Carbonochloridic acid oxydi-2,1-ethanediyl ester, Oxybis(ethane-2,1-diyl) bis(carbonochloridate), Bis(2-chlorocarbonyloxyethyl) ether, C,C'-(Oxydi-2,1-ethanediyl) dicarbonochloridate, HSDB 5374, NSC 2346, AI3-26267, BRN 1812829, MFCD00018800, UNII-0O453X86MX, DTXSID2026739, CHEMBL3188675, SCCHEMBL1063406, Tox21_301037, EINECS 203-430-9, CAS 106-75-2
Chloroformic Acid, Oxydiethylene Ester contains two chloroformate functional groups connected through a flexible diethylene glycol-based structure.
Chloroformic Acid, Oxydiethylene Ester is commonly employed as a reactive intermediate for introducing carbonate, carbamate, and related functional groups into organic molecules.
Chloroformic Acid, Oxydiethylene Ester can be used in the synthesis of specialty polymers, pharmaceutical intermediates, and performance-oriented chemical derivatives.
Chloroformic Acid, Oxydiethylene Ester offers bifunctional reactivity, allowing it to participate in coupling and crosslinking reactions.
Chloroformic Acid, Oxydiethylene Ester supports controlled modification of molecules containing hydroxyl or amino functional groups.
Chloroformic Acid, Oxydiethylene Ester is suitable for applications requiring a flexible spacer between two reactive functional sites.
Chloroformic Acid, Oxydiethylene Ester can contribute to the preparation of tailored molecular structures with specific physical and chemical characteristics.
Chloroformic Acid, Oxydiethylene Ester is valued in research and industrial synthesis because of its versatility as a difunctional building block.
Chloroformic Acid, Oxydiethylene Ester may be incorporated into multi-step synthesis routes for the production of advanced intermediates and specialty materials.
Uses of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate) is the principal co-monomer in the manufacture of CR-39 (Columbia Resin #39, allyl diglycol carbonate, ADC) — the world's most widely used thermosetting plastic for ophthalmic lenses; DECF reacts with allyl alcohol in the presence of a base to form the diallyl ester, which is then free-radically polymerised into a crosslinked thermoset with exceptional optical clarity, high Abbe number (low chromatic dispersion, ~58), refractive index 1.50, high impact resistance, and excellent surface hardness-to-weight ratio; the diethylene glycol spacer is critical to achieving the target optical properties of CR-39 that cannot be replicated with shorter- or longer-chain glycol analogues.
Diethylene glycol bis(chloroformate) is used as a bifunctional monomer and chain extender in the synthesis of flexible aliphatic polycarbonates and copolycarbonates — reacting with diols or bisphenols under interfacial polymerisation conditions (aqueous NaOH / organic solvent) or in solution to give polycarbonates with ether linkages in the backbone; the oxydiethylene unit lowers the polymer's glass transition temperature (Tg) relative to rigid aromatic analogues, enabling flexible optical films, conformable coatings, and soft-segment components in segmented copolymers without leachable plasticisers.
Diethylene glycol bis(chloroformate) is used in the R&D and manufacture of solid polymer electrolytes (SPE) for next-generation solid-state lithium batteries; poly(diethylene glycol carbonate) backbones derived from DECF provide ether linkages that facilitate high ionic conductivity and a wide electrochemical stability window, addressing key performance challenges in all-solid-state battery design.
Diethylene glycol bis(chloroformate) is used as a phosgene-free liquid bis-chloroformate reagent in laboratory and industrial-scale synthesis of polycarbonates and polyurethanes, avoiding the significant safety, handling, and regulatory complexities associated with phosgene gas; it supports interfacial polymerisation at ambient temperature with water as one phase, enabling a clean and scalable carbonate formation process.
Diethylene glycol bis(chloroformate) is used as a difunctional crosslinking agent for hydroxyl- and amine-containing polymers, resins, and hydrogels; the flexible ether spacer improves impact strength and toughness of rigid thermosets, and controls the swelling ratio and mechanical properties of biomedical hydrogels; it is also used to prepare nonvolatile plasticisers with bis-carbonate thermal stability for high-temperature processing applications.
Diethylene glycol bis(chloroformate) is used as a pharmaceutical intermediate in the synthesis of drug molecules requiring a two-carbon hydrophilic ether spacer — including prodrug ester linking groups, peptidomimetic scaffolds, and bifunctional crosslinkers in antibody-drug conjugate (ADC) chemistry; it is also used in agrochemical synthesis and in specialty chemical research as a carbonylating and acylating reagent for bifunctional substrates.
Benefits and Advantages of Diethylene Glycol Bis(chloroformate):
The symmetrical bifunctionality and structural uniqueness of DECF — a diethylene glycol spacer flanked by two reactive chloroformate groups — is irreplaceable in CR-39 lens production; substituting with shorter-chain analogues (ethylene glycol bis(chloroformate)) reduces flexibility and raises Tg, while using rigid monomers (bisphenol A bis(chloroformate)) produces a fully different material with fundamentally different optical properties that cannot meet CR-39 specifications.
DECF provides a practical, liquid-phase, phosgene-free route to polycarbonate and polycarbonate-urethane synthesis; unlike phosgene or triphosgene approaches, DECF eliminates generation of highly toxic gas in the polymerisation environment, substantially improving plant EHS performance and enabling ambient-temperature interfacial polymerisation with straightforward HCl scavenging in aqueous base.
The oxydiethylene backbone of DECF confers uniquely defined flexibility and thermal profile distinct from both shorter glycol analogues (stiffer backbone, higher Tg) and longer glycol analogues (softer backbone, lower modulus); this spacer-length specificity provides precise control over polymer chain architecture, segment mobility, and ionic conductivity in solid electrolyte applications — characteristics that cannot be tuned post-synthesis.
DECF's two chloroformate groups react cleanly and rapidly with diols, diamines, and polyols under mild conditions (0–25°C, with a base to neutralise HCl), with predictable stoichiometry and minimal side reactions, providing clean reaction profiles in synthesis that simplify process development, purification, and scale-up.
Features of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate) is a colourless to pale yellow, clear liquid at room temperature with a strong, pungent, irritating acid chloride odour; it is symmetrical — the central diethylene glycol unit O(CH₂CH₂)₂O has both terminal hydroxyl groups esterified as chloroformate esters; it is highly moisture-sensitive and must be handled under anhydrous conditions; it is soluble in acetone, ethanol, diethyl ether, chloroform, benzene, dichloromethane, THF, and toluene; it is insoluble in water (decomposes violently with water evolving HCl).
Key physical-chemical parameters: molecular weight 231.03 g/mol; exact mass 229.974879 Da; XLogP3 2; boiling point 229–280°C (127°C at 5 mmHg); flash point 118–146°C (open cup); vapour pressure 0.004 mmHg at 25°C; heat of vaporisation 51.9 kJ/mol; estimated density ~1.39–1.59 g/cm³; RTECS LQ6700000; Poison Class 2.
The structural feature defining DECF's reactivity is its two chloroformate groups (−O-C(=O)-Cl); these groups are strongly electrophilic acyl chlorides that react rapidly with: (1) hydroxyl groups (→ carbonate ester, releasing HCl); (2) primary and secondary amines (→ carbamate/urethane, releasing HCl); (3) water (→ diethylene glycol carbonic acid → CO₂ + diethylene glycol + HCl); reaction with water is exothermic and generates corrosive HCl fumes and CO₂; moisture exclusion during handling and storage is critical.
DECF reacts violently with water, alcohols, bases, and any protic nucleophile; in the presence of tertiary amines or Schotten-Baumann conditions (aqueous NaOH), the HCl generated is immediately neutralised, enabling clean interfacial polymerisation; storage stability requires moisture-free sealed containers under inert atmosphere (N₂ or Ar) at 2–8°C or below 25°C.
Chemical Properties of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate) has IUPAC name 2-(2-carbonochloridoyloxyethoxy)ethyl carbonochloridate, molecular formula C₆H₈Cl₂O₅, molecular weight 231.03 g/mol, exact mass 229.974879 g/mol, SMILES C(COC(=O)Cl)OCCOC(=O)Cl, InChI=1S/C6H8Cl2O5/c7-5(9)12-3-1-11-2-4-13-6(8)10/h1-4H2, InChIKey XFSAZBKSWGOXRH-UHFFFAOYSA-N; CAS 106-75-2; EC 203-430-9; EC index 607-141-00-2; Beilstein 1812829; MDL MFCD00018800; RTECS LQ6700000; UNII 0O453X86MX; DTXSID2026739; NSC 2346.
The principal chemical reactions of DECF are: (1) polymerisation with diols → polycarbonate (interfacial or solution polymerisation, NaOH as HCl scavenger): HO-R-OH + ClC(O)O-[DEG]-OC(O)Cl → [-O-R-OC(O)O-[DEG]-OC(O)-]ₙ + 2HCl; (2) reaction with allyl alcohol → diallyl diethylene glycol bis(carbonate) (CR-39 precursor); (3) crosslinking of polyols and polyamines → carbonate and carbamate crosslinked networks; (4) pharmaceutical conjugation via carbamate bond to amine-containing drugs; (5) hydrolysis → diethylene glycol + 2HCl + CO₂.
DECF is produced by phosgenation of diethylene glycol: HO-CH₂CH₂-O-CH₂CH₂-OH + 2 COCl₂ → ClC(O)O-CH₂CH₂-O-CH₂CH₂-OC(O)Cl + 2 HCl; alternatively, it is produced by reaction of diethylene glycol with carbonyl chloride (phosgene) in an inert solvent at 0–20°C, or by reaction with triphosgene; commercial production routes are carefully controlled due to phosgene handling requirements; purification is by vacuum distillation (BP 127°C at 5 mmHg).
DECF is incompatible with water (violent reaction, HCl evolution), alcohols (rapid esterification), amines (carbamate formation), bases (rapid decomposition), and oxidising agents; it is stable in anhydrous organic solvents under inert atmosphere; thermal decomposition above ~200°C yields HCl, CO₂, and chlorinated organic decomposition products; it is corrosive to skin, eyes, and mucous membranes; assay ≥98% (commercial grade).
Production of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate) is produced industrially and in specialty chemical synthesis by phosgenation of diethylene glycol with excess phosgene (COCl₂) in an inert solvent (toluene, chlorobenzene, or dichloromethane) at 0–20°C, followed by removal of residual phosgene and HCl and purification by vacuum distillation; the reaction proceeds in two steps: first formation of the monochloro-formate, then the bis(chloroformate) at the second hydroxyl; a catalytic amount of DMF may be used to activate phosgene.
Commercial diethylene glycol bis(chloroformate) is available at ≥98% purity (assay) as a colourless to yellow liquid; specification limits: assay ≥98% (GC or titration); appearance: colourless to light yellow liquid; packaging: 250 kg drum; stored under nitrogen or argon blanket at 2–8°C or below 25°C, protected from moisture; shelf life is limited by moisture sensitivity — consume shortly after opening.
Diethylene Glycol Bis(chloroformate) Material Safety Data Sheet (MSDS):
Handling of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate) is a corrosive, toxic chemical that reacts violently with water releasing corrosive HCl and CO₂; handle strictly under anhydrous conditions in a well-ventilated fume hood; avoid all contact with moisture, skin, eyes, and clothing; wear full PPE: acid-resistant gloves, chemical splash goggles, face shield, and chemical-resistant protective clothing; use SCBA or full-face OV/acid gas respirator where vapour concentration may be significant.
Avoid breathing vapours — they are pungent, corrosive acid chloride fumes; all operations should be conducted at or below ambient temperature whenever possible; use only in well-ventilated areas or a well-functioning fume hood; never use near water, open steam lines, or protic solvents; react promptly if skin or eye contact occurs — flush with large amounts of water immediately.
Diethylene Glycol Bis(chloroformate) SDS:
Stability and Reactivity of Diethylene Glycol Bis(chloroformate):
Chemical stability:
Diethylene glycol bis(chloroformate) is stable in anhydrous organic solvents at ambient temperature under inert atmosphere (N₂, Ar).
Diethylene glycol bis(chloroformate) is highly moisture-sensitive; contact with water, alcohols, or any protic solvent causes rapid hydrolysis with evolution of corrosive HCl gas and CO₂.
Reactivity:
Diethylene glycol bis(chloroformate) reacts violently with water, alcohols, amines, and bases — these reactions are exothermic and evolve HCl gas.
Thermal decomposition above ~200°C yields HCl, CO₂, chlorinated hydrocarbons, and other toxic decomposition products.
Conditions to avoid:
Water and atmospheric moisture — violent hydrolysis with HCl evolution.
Protic solvents (alcohols, water, acids).
Strong bases and amines (rapid reaction; HCl generation).
Elevated temperatures (>200°C) — thermal decomposition.
Air/moisture ingress during storage.
Incompatible materials:
Water — violent, exothermic hydrolysis with HCl and CO₂ evolution.
Alcohols, phenols, diols — rapid esterification.
Primary and secondary amines — rapid carbamate formation.
Strong bases (NaOH, KOH, pyridine) — rapid decomposition; in controlled Schotten-Baumann conditions, useful for polymerisation.
Strong oxidising agents.
Hazardous decomposition products:
Hydrogen chloride (HCl) gas — corrosive, pungent, toxic respiratory hazard.
Carbon dioxide (CO₂) — asphyxiant in confined spaces.
Chlorinated organic compounds — possible at elevated temperatures.
Phosgene (COCl₂) — possible trace formation upon thermal decomposition; extremely toxic.
Handling and Storage of Diethylene Glycol Bis(chloroformate):
Handling:
Handle exclusively in a dry, well-ventilated fume hood; never open containers in air without appropriate moisture exclusion techniques.
Wear acid-resistant gloves (nitrile heavy-duty or neoprene), chemical splash goggles, face shield, and chemical-resistant protective clothing.
Use N₂ or Ar blanket when transferring or measuring out product; pre-dry all glassware and solvents.
Avoid inhalation of vapours — use full-face respirator (OV+P100+Acid Gas) or SCBA where vapour levels may exceed acceptable limits.
Do NOT allow contact with water, steam, wet surfaces, alcohols, or amines.
Storage:
Store in tightly sealed, dry containers under inert atmosphere (N₂ or Ar) at 2–8°C or below 25°C in a cool, dry, well-ventilated area.
Keep away from water, moisture, bases, alcohols, amines, and protic reagents.
Packaging: 250 kg drum; smaller quantities in amber glass or stainless-steel containers with inert gas blanket.
Shelf life is limited by moisture sensitivity; consume promptly after opening; re-seal immediately under N₂.
First Aid Measures for Diethylene Glycol Bis(chloroformate):
Inhalation:
Immediately move the affected person to fresh air; monitor for respiratory distress; if cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis.
Administer oxygen and assist ventilation as required; treat bronchospasm with inhaled beta₂ agonist and oral or parenteral corticosteroids; seek immediate medical attention.
Skin contact:
Immediately remove all contaminated clothing; flush exposed areas thoroughly with large amounts of water for at least 15 minutes; wash with soap and water.
Seek medical examination — DECF is corrosive and causes skin burns on prolonged contact; burns may be delayed in appearance.
Eye contact:
Irrigate exposed eyes immediately with copious amounts of room-temperature water for at least 15 minutes; remove contact lenses immediately.
Seek immediate ophthalmological attention — DECF causes serious eye damage.
Ingestion:
Consider gastric lavage after ingestion of a potentially life-threatening amount if it can be performed soon after ingestion (generally within 1 hour).
Administer activated charcoal slurry (240 mL water/30 g charcoal); usual dose: 25–100 g in adults/adolescents, 25–50 g in children (1–12 years), 1 g/kg in infants <1 year; dilution with milk or water may be of benefit in caustic ingestion; seek immediate medical attention.
Firefighting Measures for Diethylene Glycol Bis(chloroformate):
Suitable extinguishing media:
CO₂, dry chemical, sand; water or foam may cause frothing and violent HCl evolution — use with extreme caution only to cool containers from distance.
Specific hazards:
Diethylene glycol bis(chloroformate) is a combustible liquid (flash point 118–146°C); thermal decomposition releases toxic and corrosive HCl, CO₂, and possible phosgene traces; vapours are heavier than air.
Protective equipment for firefighters:
Full SCBA and full acid-resistant protective clothing; evacuate all non-essential personnel.
Accidental Release Measures for Diethylene Glycol Bis(chloroformate):
Personal precautions:
Immediately evacuate area; wear full SCBA and acid-resistant protective clothing; eliminate all moisture and ignition sources; prevent HCl cloud formation in confined spaces.
Environmental precautions:
Diethylene glycol bis(chloroformate) hydrolyses in environmental moisture releasing HCl; prevent entry into water courses; immediately notify environmental authorities for large spills.
Clean-up methods:
Cover spill with dry absorbent (dry vermiculite, dry sand — NOT water or wet materials); sweep into dry sealed containers; neutralise residue carefully with dry sodium carbonate or sodium bicarbonate; dispose as halogenated chemical waste per applicable regulations.
Exposure Controls / Personal Protective Equipment for Diethylene Glycol Bis(chloroformate):
Engineering controls:
Work exclusively in a well-functioning fume hood or closed system; local exhaust ventilation at all transfer and metering points; maintain inert atmosphere wherever DECF is handled.
Eye protection:
Chemical splash goggles AND face shield — both required simultaneously.
Hand protection:
Heavy-duty acid-resistant gloves (thick nitrile, neoprene, or butyl rubber; tested to EN 374 for acid chloride/chloroformate resistance); inspect before each use; discard after contamination.
Skin and body protection:
Full chemical-resistant protective clothing; acid-resistant apron; solvent-resistant boots.
Respiratory protection:
Full-face respirator with OV+acid gas+P100 combination cartridge for routine operations; SCBA for spill response or emergency.
Hygiene measures:
Strict hygiene — DECF is corrosive and releases HCl on contact with moisture; wash hands and all exposed skin immediately after any contact; never eat, drink, or smoke in work areas; decontaminate all equipment before cleaning.
Diethylene Glycol Bis(chloroformate) Identifiers:
CAS Number: 106-75-2
EC Number: 203-430-9
EC Index Number: 607-141-00-2
Beilstein: 1812829
MDL Number: MFCD00018800
RTECS: LQ6700000
UNII: 0O453X86MX
DTXSID: DTXSID2026739
CHEMBL: CHEMBL3188675
NSC: 2346 (NCI)
HSDB: 5374
IUPAC Name: 2-(2-carbonochloridoyloxyethoxy)ethyl carbonochloridate
Molecular Formula: C₆H₈Cl₂O₅
Molecular Weight: 231.03 g/mol
Exact Mass: 229.974879 g/mol
SMILES: C(COC(=O)Cl)OCCOC(=O)Cl
InChI: InChI=1S/C6H8Cl2O5/c7-5(9)12-3-1-11-2-4-13-6(8)10/h1-4H2
InChIKey: XFSAZBKSWGOXRH-UHFFFAOYSA-N
XLogP3: 2
Heat of vaporisation: 51.9 kJ/mol
Vapour pressure: 0.004 mmHg (25°C)
GHS Signal Word: Danger
GHS Hazard Classes: Corrosive; Irritant; Environmental Hazard
Poison Class: 2
Flash point: 118–146°C (open cup)
Boiling point: 229–280°C; 127°C at 5 mmHg
Solubility: Insoluble in water (reacts); soluble in acetone, alcohol, ether, chloroform, benzene, DCM, THF
Assay: Min 98%
Colour: Yellow / colourless to light yellow
Packing: 250 kg drum
Properties of Diethylene Glycol Bis(chloroformate):
Physical state: Liquid
Appearance: Colourless to light yellow clear liquid
Odour: Strong, pungent, irritating (acid chloride)
Molecular formula: C₆H₈Cl₂O₅
Molecular weight: 231.03 g/mol
Boiling point: 229–280°C (760 mmHg); 127°C (5 mmHg)
Flash point: 118–146°C (open cup)
Vapour pressure: 0.004 mmHg (25°C)
Heat of vaporisation: 51.9 kJ/mol
XLogP3: 2
Water solubility: Insoluble (reacts violently with evolution of HCl)
Organic solvent solubility: Soluble in acetone, alcohol, ether, chloroform, benzene, DCM, THF, toluene
Reactivity: Extremely moisture-sensitive; hydrolyses to release HCl + CO₂ + diethylene glycol
GHS Classification: Danger — Corrosive, Irritant, Environmental Hazard
Assay: ≥98%
Storage: 2–8°C or below 25°C; inert atmosphere (N₂/Ar); moisture-free sealed containers
Diethylene Glycol Bis(chloroformate) Properties — Specifications:
Product name: Diethylene glycol bis(chloroformate) (DECF)
CAS Number: 106-75-2
EC Number: 203-430-9
Molecular Formula: C₆H₈Cl₂O₅
Molecular Weight: 231.03 g/mol
Assay: ≥98% (GC or titration)
Appearance: Colourless to light yellow liquid
Boiling point: 229–280°C; 127°C (5 mmHg)
Flash point: 118–146°C
Solubility: Soluble in organic solvents; insoluble in water (reacts)
Sensitivity: Extremely moisture-sensitive; inert atmosphere required
Storage: 2–8°C or below 25°C; N₂/Ar blanket; moisture-free
Packaging: 250 kg drum; smaller quantities in amber glass or SS containers under inert gas
Documents: CoA (Certificate of Analysis), MSDS/SDS available
Names of Diethylene Glycol Bis(chloroformate):
Diethylene glycol bis(chloroformate)
Oxydiethylene bis(chloroformate)
DECF
DEG bis(chloroformate)
Diglycol chloroformate
Oxydiethylene chloroformate
1,5-Bis((chlorocarbonyl)oxy)-3-oxapentane
Carbonochloridic acid oxydi-2,1-ethanediyl ester
Oxybis(ethane-2,1-diyl) bis(carbonochloridate)
Bis(2-chlorocarbonyloxyethyl) ether
Formic acid chloro- diester with diethylene glycol
C,C'-(Oxydi-2,1-ethanediyl) dicarbonochloridate
BRN 1812829
MFCD00018800
NSC 2346
HSDB 5374
UNII 0O453X86MX
CAS 106-75-2
EINECS 203-430-9
