Basic information
- Standard SMILES
O=C(Cl)CCCl- InChIKey
INUNLMUAPJVRME-UHFFFAOYSA-N- Molecular formula
- C3H4Cl2O
- Average molar mass
- 126.97 g/mol
- Monoisotopic mass
- 125.96392011
Names & identifiers
- Preferred name
- 3-Chloropropionyl chloride
- IUPAC
- 3-chloropropanoyl chloride
- English name
- 3-Chloropropionyl chloride
- Molecular formula
- C3H4Cl2O
- Molecular weight
- 126.97
Names & synonyms
3-Chloropropionyl chloride3-Chloropropanoyl chloridePropanoyl chloride, 3-chloro-3-Chloropropionic acid chlorideUNII-24PO18998IEINECS 210-890-4NSC-84180betachloropropionyl chloride24PO18998IDTXSID5060801beta-Chloropropionic acid chlorideEC 210-890-4
Show more names
Chloropropionyl chlorideoropropionyL3-Chloropropionyl ch3-Chlorpropionylchlorid-Chloropropanoylchloride3-Chloropropinyl chloride3-chloro-propanoylchlorid3'ChloropropionylChloride
(CHLOROMETHYL)ACETYL CHLORIDE.beta.-Chloropropionic acid chloride.OMEGA.-CHLOROPROPANOYL CHLORIDE.OMEGA.-CHLOROPROPIONYL CHLORIDEPROPANOIC ACID,3-CHLORO,CHLORIDEBETA.-CHLOROPROPIONIC ACID CHLORIDERefChem:935343Chloropropanoyl chloride
Database identifiers
- CAS
625-36-5- PubChem CID
- 69364
- DTXSID
DTXSID5060801- UNII
- 24PO18998I
- EC Number
- 210-890-4
- Nikkaji
- J501K
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 52.8
Experimental & physicochemical properties
Chemical ClassesToxic Gases & Vapors -> Acid Halides
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physical DescriptionClear light yellow liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -32 °C · -32 °C
- Boiling point
- 143 · 143-145 °C(lit.)
- Density
- 1.33 g/mL · 1.33 g/mL at 25 °C(lit.)
- vapor pressure
- 10 hPa · 10.0 hPa
- RTECS
- 3934000 · UC3934000
- refractive index
- 20 · n20/D 1.457(lit.)
- Flash point
- 146 °F · 146 °F
- storage temp.
- Flammables area
- solubility
- Chloroform, Ethyl Acetate
- form
- liquid
- color
- red-brown
- PH
- 7 · <7 (H2O)
- explosive limit
- 8.8 · 8.8-20.2%(V)
- Water Solubility
- reacts
- Sensitive
- Moisture Sensitive
- BRN
- 635814 · 635814
- Stability
- Moisture Sensitive
- InChI
- 1S/C3H4Cl2O/c4-2-1-3(5)6/h1-2H2
- InChIKey
- INUNLMUAPJVRME-UHFFFAOYSA-N
- CAS DataBase Reference
- 625 · 625-36-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 24 PO18998I · 24PO18998I
- NIST Chemistry Reference
- 3 · Propanoyl chloride, 3-chloro-(625-36-5)
- EPA Substance Registry System
- 3 · Propanoyl chloride, 3-chloro- (625-36-5)
- UNSPSC Code
- 12352106 · 12352106
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 302 · H302-H314-H330
- Precautionary statements
- 260 · P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
- Hazard Codes
- T+
- Risk Statements
- 14 · 14-22-26-34-35-10
- Safety Statements
- 23 · 23-26-36/37/39-45-38-16-8
- RIDADR
- 3390 · UN 3390 6.1/PG 1
- WGK Germany
- 1 · 1
- F
- 21 · 21
- Autoignition Temperature
- 460 °C · 460°C
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- I
- HS Code
- 29159080 · 29159080
- Storage Class
- 6.1 A · 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 InhalationAcute · Acute Tox. 2 InhalationAcute Tox. 4 OralSkin Corr. 1B
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Danger
H290 (68.9%): May be corrosive to metals [Warning Corrosive to Metals]
P234, P260, P264, P264+P265, P270, P271, P280, P284, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P363, P390, P403+P233, P405, P406, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 180 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Propanoyl chloride, 3-chloro-
Status: Active Update: 06-07-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/16338
3-Chloropropionyl chloride: HSNO Approval: HSR004261 Approved with controls
Hazards Summary
Reacts violently with water; Causes burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Highly toxic by inhalation; Harmful by ingestion; [Sigma-Aldrich MSDS] See Chloropivaloyl chloride and Trimethylacetyl chloride.
Hazard Classes and CategoriesMet. Corr. 1 (68.9%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Toxicity DataLC50 (rat) = 1,000 mg/m3/1hr
Safety data
- F
- 21
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 3390 6.1/PG 1
- hs_code
- 29159080
- risk_code
- 14-22-26-34-35-10
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- T+
- safety_code
- 23-26-36/37/39-45-38-16-8
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- I
- Hazard statements
- H302-H314-H330
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 2 InhalationAcute Tox. 4 OralSkin Corr. 1B
- Autoignition Temperature
- 460°C
- Precautionary statements
- P260-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationPropanoyl chloride, 3-chloro-: ACTIVE
Applications
Description3-Chloropropionyl chloride is an important bifunctional reagent. It is capable of acylation and possesses a 2-chloro-ethyl fragment (CH2CH2Cl), which can be subjected to nucleophilic substitution and serves as a masked vinyl group. It can be used as a starting material in many reactions to construct a variety of (hetero)cyclic compounds.
Uses3-Chloropropionyl chloride is a reagent used in the synthesis of Beclamide (B119400), which is a chlorinated benzylpropanamide used as an anticonvulsant drug. It is used in the treatment of tonic-clonic seizyres and has sedative properties.
Preparation methods
Preparation3-Chloropropionyl chloride (1) is commercially available and can be prepared from β-propiolactone (2) and thionyl chloride.1 Other standard methods available for the preparation of acyl chlorides can also be applied: the reaction of acrylic acid (3) or 3-chloropropionic acid (4) with thionyl chloride, phosphoryl chloride, phosgene, or phosphorus trichloride.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
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