Butyl carbonochloridate

C5H9ClO2

butyl carbonochloridate

CAS592-34-7
GHS02 Gefahrensymbol: Entzündbar – Flamme
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS05 Gefahrensymbol: Ätzend – Ätzwirkung
Danger

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Identification

CAS Number
592-34-7
EC Number
209-750-5
UN Number
2743
Index Number
607-138-00-6
PubChem CID
61140

Physical-chemical properties

Molecular Formula
C5H9ClO2
Molar Mass
136.58 g/mol
IUPAC Name
butyl carbonochloridate

Chemical Identifiers

InChI
InChI=1S/C5H9ClO2/c1-2-3-4-8-5(6)7/h2-4H2,1H3
InChI Key
NRDQFWXVTPZZAZ-UHFFFAOYSA-N

Overview

Butyl carbonochloridate (CAS 592-34-7) is a chloroformate ester compound with reactive carbonyl chloride functionality and significant industrial utility. This organic chemical, with molecular formula C5H9ClO2 and molecular weight 136.58 g/mol, belongs to the family of alkyl chloroformates that serve as important intermediates in synthetic organic chemistry and industrial manufacturing processes. As a carbonochloridate derivative, this substance exhibits high reactivity due to its electrophilic carbon center, making it valuable for various chemical transformations including esterification, carbamation, and carbonylation reactions. The compound presents significant safety considerations, classified under multiple hazard categories including flammable liquid (Category 3), acute toxicity, and skin corrosion (Category 1B). The GHS pictograms GHS02, GHS06, and GHS05 indicate its flammable, toxic, and corrosive properties respectively, requiring careful handling protocols and appropriate safety measures during storage and use. Butyl carbonochloridate finds primary applications in pharmaceutical intermediate synthesis, where it serves as a protecting group reagent for amino acids and other sensitive functional groups. The chemical industry also utilizes this compound in the production of specialty polymers and as a reagent in pesticide manufacturing. Unlike more reactive electrophiles such as 2-(chloromethyl)oxirane, butyl carbonochloridate offers controlled reactivity that makes it suitable for selective synthetic transformations. The compound's ADR classification as Class 6.1 reflects its toxic nature and necessitates specialized transportation and handling procedures. Industrial users must implement comprehensive safety protocols including appropriate ventilation systems, personal protective equipment, and emergency response procedures. OYSI provides butyl carbonochloridate to qualified industrial customers across Europe, ensuring compliance with all relevant chemical regulations and safety standards.

Safety & Classification

Danger
Classification:

Flam. Liq. 3; Acute Tox. 3 *; Skin Corr. 1B

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H226

Flammable liquid and vapour.

H331

Toxic if inhaled.

H314

Causes severe skin burns and eye damage.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Toxic

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Harmful

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Eye Contact

Harmful

Measures if substance gets into the eyes

First Aid Actions

  • +P305IF IN EYES:
  • +P351Rinse cautiously with water for several minutes.
  • +P338Remove contact lenses, if present and easy to do. Continue rinsing.
  • +P313Get medical advice/attention.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number2743
ADR Class6.1
Packing GroupII
Tunnel CodeD/E
Proper Shipping Namen-Butylchlorformiat
Marine PollutantNo

Frequently Asked Questions

What is butyl carbonochloridate?

Butyl carbonochloridate is an organochlorine chemical compound with the molecular formula C5H9ClO2 and CAS number 592-34-7. This substance belongs to the family of chloroformate esters, characterized by its reactive carbonyl chloride functional group. With a molecular weight of 136.58 g/mol, it presents significant hazards including flammability, acute toxicity, and corrosive properties, requiring careful handling in industrial applications.

What are the physicochemical properties of butyl carbonochloridate?

Butyl carbonochloridate is typically a colorless to pale yellow liquid at room temperature with a pungent, acrid odor characteristic of chloroformates. The compound is moisture-sensitive and reacts readily with water, releasing hydrogen chloride gas. It has limited solubility in water due to hydrolysis reactions but is miscible with most organic solvents. Its flammable nature (Flam. Liq. 3) indicates a flash point between 23°C and 60°C.

What is butyl carbonochloridate used for?

Butyl carbonochloridate is primarily used as a chemical intermediate in organic synthesis and pharmaceutical manufacturing. It serves as an acylating agent for introducing butoxycarbonyl protecting groups in peptide synthesis and pharmaceutical research. The compound is also utilized in the production of carbamate pesticides, polymers, and specialty chemicals. Its reactive chloroformate functionality makes it valuable for creating carbamate linkages and protecting amino groups in complex organic molecules.

How to handle butyl carbonochloridate safely?

Butyl carbonochloridate requires strict safety measures due to its corrosive (Skin Corr. 1B) and acutely toxic (Acute Tox. 3) properties. Essential personal protective equipment includes chemical-resistant gloves, safety goggles, face shield, and protective clothing. Work must be conducted in well-ventilated areas or under fume hoods to avoid inhalation exposure. Emergency eyewash stations and safety showers should be readily accessible, and all personnel must be trained in proper handling procedures.

How to store butyl carbonochloridate correctly?

Butyl carbonochloridate must be stored in tightly sealed containers in a cool, dry, well-ventilated area away from heat sources and ignition points. The storage area should be separated from incompatible materials such as water, alcohols, amines, and strong bases, which can cause violent reactions. Containers should be made of compatible materials and regularly inspected for signs of corrosion or leakage. Temperature control is essential to prevent decomposition and vapor buildup.

What to do in case of contact with butyl carbonochloridate?

Immediate action is required for any contact with butyl carbonochloridate due to its corrosive nature. For skin contact, remove contaminated clothing and flush affected areas with copious amounts of water for at least 15 minutes. In case of eye contact, rinse immediately with water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air immediately. For ingestion, do not induce vomiting and seek immediate medical attention while providing safety data sheet information.

How to dispose of butyl carbonochloridate properly?

Butyl carbonochloridate disposal must comply with local, national, and EU waste regulations as it is classified as hazardous waste. The substance should never be discharged into drains, soil, or waterways. Proper disposal typically involves incineration at authorized high-temperature facilities equipped with appropriate emission controls. Small quantities may be neutralized carefully under controlled conditions by qualified personnel. Always consult with licensed waste disposal companies and provide complete safety data sheet information.

How to transport butyl carbonochloridate?

Butyl carbonochloridate is classified under ADR transport regulations as Class 6.1 (toxic substances), Packing Group II, indicating moderate to high toxicity. Transport must comply with all ADR requirements including proper packaging, labeling with appropriate hazard pictogramms (GHS02, GHS06, GHS05), and documentation. Vehicles must carry appropriate emergency equipment and drivers require hazardous materials training. Shipping containers must be compatible with the chemical and properly secured to prevent damage during transit.

Is butyl carbonochloridate subject to specific regulations?

Butyl carbonochloridate is subject to multiple European regulations including CLP (Classification, Labelling and Packaging) regulation requiring hazard classification as Flam. Liq. 3, Acute Tox. 3, and Skin Corr. 1B with 'Danger' signal word. Under REACH regulation, it requires registration for manufacture or import above specified tonnages. The substance is not currently listed as SVHC (Substance of Very High Concern), but users must comply with occupational exposure limits and safety requirements under relevant national legislation.

Where to buy butyl carbonochloridate in Europe?

Butyl carbonochloridate is available through OYSI, a specialized European distributor of technical chemicals serving industrial and research customers across Europe. As a professional chemical supplier, OYSI ensures proper packaging, documentation, and compliance with all relevant safety and transport regulations. Contact OYSI directly for availability, technical specifications, safety data sheets, and delivery options to your specific location within Europe. All purchases require appropriate business credentials and intended use documentation.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.