Butyl carbonochloridate
C5H9ClO2
butyl carbonochloridate
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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 an organic chloroformate compound with reactive carbonyl chloride functionality and corrosive properties. This chemical intermediate belongs to the chloroformate family and serves as a versatile reagent in organic synthesis and industrial applications. With the molecular formula C5H9ClO2 and a molecular weight of 136.58 g/mol, butyl carbonochloridate exhibits significant reactivity due to its electrophilic carbonyl carbon, making it valuable for various chemical transformations including esterification and carbamate formation reactions. The compound presents considerable safety considerations, classified under multiple hazard categories including flammable liquid (Category 3), acute toxicity, and skin corrosion (Category 1B). Its corrosive nature requires strict handling protocols and appropriate personal protective equipment. The ADR classification of 6.1 indicates its toxic properties during transport, necessitating specialized packaging and labeling requirements. Like other reactive chloroformates such as 2-(chloromethyl)oxirane, butyl carbonochloridate demands careful storage conditions to prevent hydrolysis and maintain product integrity. Primary industrial applications include its use as a protecting group reagent in pharmaceutical synthesis, where it temporarily masks reactive amine functionalities during multi-step synthetic processes. The compound also finds application in polymer chemistry for surface modification and in the production of specialty esters and carbamates. Additionally, it serves as an intermediate in agrochemical manufacturing, particularly in the synthesis of herbicides and pesticides where selective reactivity is crucial. OYSI provides butyl carbonochloridate to European customers with comprehensive technical support and regulatory documentation, ensuring compliance with REACH regulations and industry quality standards for demanding industrial applications.
Safety & Classification
Flam. Liq. 3; Acute Tox. 3 *; Skin Corr. 1B
GHS Pictograms
HHazard Statements (H-Statements)
Describe the nature and severity of the hazard
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
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
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
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 Number | 2743 |
| ADR Class | 6.1 |
| Packing Group | II |
| Tunnel Code | D/E |
| Proper Shipping Name | n-Butylchlorformiat |
| Marine Pollutant | No |
Frequently Asked Questions
What is butyl carbonochloridate?
Butyl carbonochloridate is an organic chemical compound with the molecular formula C5H9ClO2 and CAS number 592-34-7. This chloroformate ester has a molecular weight of 136.58 g/mol and belongs to the family of carbonyl chlorides. It appears as a reactive liquid that is classified as hazardous due to its flammable, toxic, and corrosive properties, requiring careful handling in industrial applications.
What are the physicochemical properties of butyl carbonochloridate?
Butyl carbonochloridate is a clear, colorless to pale yellow liquid with a pungent, irritating odor characteristic of chloroformates. It has a molecular weight of 136.58 g/mol and is moisture-sensitive, readily hydrolyzing in the presence of water to form butanol, carbon dioxide, and hydrogen chloride. The compound is soluble in organic solvents but reacts vigorously with water and alcohols.
What is butyl carbonochloridate used for?
Butyl carbonochloridate is primarily used as an intermediate in organic synthesis and pharmaceutical manufacturing. It serves as a protecting group reagent for amino acids and peptides, and as a carbonylating agent in chemical reactions. The compound is also employed in the production of carbamates, urethanes, and various pharmaceutical intermediates where selective acylation or protection of functional groups is required.
How to handle butyl carbonochloridate safely?
Butyl carbonochloridate requires strict safety measures including wearing chemical-resistant gloves, safety goggles, and protective clothing in well-ventilated areas or under fume hoods. Due to its corrosive nature (Skin Corr. 1B) and acute toxicity (Acute Tox. 3), avoid skin contact, inhalation, and ingestion. Use only non-sparking tools due to its flammable properties (Flam. Liq. 3) and ensure emergency shower and eyewash stations are accessible.
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. Keep containers away from moisture, water, alcohols, and basic materials to prevent hydrolysis reactions. Store in secondary containment due to its corrosive nature and separate from incompatible materials including oxidizing agents, reducing agents, and reactive metals.
What to do in case of contact with butyl carbonochloridate?
Butyl carbonochloridate contact requires immediate action: for skin contact, immediately remove contaminated clothing and flush with plenty of water for at least 15 minutes. For eye contact, rinse immediately with water for at least 15 minutes and seek medical attention. If inhaled, move to fresh air immediately. In case of ingestion, do not induce vomiting and seek immediate medical attention. Always consult emergency services for serious exposures.
How to dispose of butyl carbonochloridate properly?
Butyl carbonochloridate disposal must comply with local and national hazardous waste regulations as it cannot be disposed of with regular waste. The material should be collected by licensed hazardous waste disposal companies and typically requires incineration at high temperatures in specialized facilities. Small quantities can be neutralized carefully under controlled conditions by trained personnel, but professional disposal is recommended for safety and regulatory compliance.
How to transport butyl carbonochloridate?
Butyl carbonochloridate is classified under ADR as Class 6.1 (toxic substances), Packing Group II, requiring specialized transport procedures. Packages must bear appropriate hazard labels including GHS02 (flame), GHS05 (corrosion), and GHS06 (skull and crossbones) pictograms with 'Danger' signal word. Transport must comply with dangerous goods regulations, using approved packaging and documentation, and drivers require ADR certification for toxic substances.
Is butyl carbonochloridate subject to specific regulations?
Butyl carbonochloridate is subject to REACH regulation requiring registration for manufacture or import above one tonne per year in the EU. It falls under CLP regulation with mandatory classification as Flam. Liq. 3, Acute Tox. 3, and Skin Corr. 1B. The substance is not currently listed as SVHC but users must comply with occupational exposure limits, safety data sheet requirements, and dangerous goods transport regulations.
Where to buy butyl carbonochloridate in Europe?
Butyl carbonochloridate is available through specialized chemical distributors in Europe, including OYSI, which supplies high-quality chemical products to industrial customers across European markets. Due to its hazardous classification and regulatory requirements, purchase typically requires proper licensing, safety documentation, and compliance with local regulations. Professional buyers should contact established distributors who can ensure proper handling, documentation, and regulatory compliance throughout the supply chain.
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Data Sources
Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.