2937-50-0

Basic information

• Product Name: Allyl chloroformate
• Synonyms: 2-propenylchloroformate;ALLYLCHLOROFORMATE(ACF);allylesterkyselinychlormravenci;carbonochloridicacid,2-propenylester;chlorocarbonicacidallylester;chloro-formicaciallylester;CHLOROFORMIC ACID ALLYL ESTER;ALLYL CHLOROCARBONATE
• CAS NO: 2937-50-0
• Molecular Formula: C₄H₅ClO₂
• Molecular Weight: 120.53
• EINECS: 220-916-6
• Product Categories: Pharmaceutical Intermediates;CHLOROFORMATES;Amine ProtectionProtection and Derivatization;Others;Peptide Synthesis;Protecting and Derivatizing Reagents;Specialty Synthesis
• Mol File: 2937-50-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 106℃
• Boiling Point: 109 °C
• Flash Point: 88 °F
• Appearance: Clear slightly yellow to light orange to reddish brown/Liquid
• Density: 1.134 g/mL at 20 °C(lit.)
• Vapor Pressure: 3.67 psi ( 20 °C)
• Refractive Index: n20/D 1.422(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• Water Solubility: insoluble
• Stability: Moisture Sensitive
• BRN: 773915
• CAS DataBase Reference: Allyl chloroformate(CAS DataBase Reference)
• NIST Chemistry Reference: Allyl chloroformate(2937-50-0)
• EPA Substance Registry System: Allyl chloroformate(2937-50-0)

Safety Data

• Hazard Codes: T+
• Statements: 10-22-26-34
• Safety Statements: 26-28-36/37/39-45
• RIDADR: UN 1722 6.1/PG 1
• WGK Germany: 3
• RTECS: LQ5775000
• F: 19
• HazardClass: 6.1(b)
• PackingGroup: I
• Hazardous Substances Data: 2937-50-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Allyl Chloroformate is used in the synthesis of poly(ethylene oxide) hybrid systems for therapeutic applications and drug delivery. Also used in the synthesis of benzothiazole derivatives with potent anti-tumor properties.

General Description

A colorless liquid with a pungent odor. Flash point 88°F. Corrosive to metals and tissue. Very toxic by inhalation, ingestion and/or skin contact. Vapors are heavier than air.

Air & Water Reactions

Highly flammable. Water reaction produces heat and acidic HCl. In the presence of moist air, corrosive hydrogen chloride is produced.

Reactivity Profile

Acid halides, such as Allyl chloroformate, are water reactive; some are violently reactive. They are incompatible with strong oxidizing agents, alcohols, amines, alkali. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Health Hazard

Vapor irritates eyes and respiratory tract. Contact with liquid causes eye and skin irritation, and ingestion irritates mouth and stomach.

Chemical Reactivity

Reactivity with Water Reacts slowly generating hydrogen chloride; Reactivity with Common Materials: Corrosive metals; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water, rinse with sodium bicarbonate solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Poison by inhalation and ingestion. Corrosive. Dangerous when exposed to heat, open flame (or sparks), or powerful oxidizers. Can react with oxidizing materials. To fight fire, use alcohol foam, spray or mist, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also ALLYL COMPOUNDS and ESTERS.

InChI:InChI=1/C9H12FN3O5/c10-3-1-13(9(17)12-7(3)11)8-6(16)5(15)4(2-14)18-8/h1,4-6,8,14-16H,2H2,(H2,11,12,17)/t4-,5-,6+,8-/m1/s1

Upstream product

• 44605-74-5 allyl 1H-benzo[d][1,2,3]triazol-1-ylcarbonate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 107-18-6 allyl alcohol 
• 75-44-5 phosgene 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 104669-68-3 N,O-bis-allyloxycarbonyl-L-tyrosine 
• 90711-56-1 2-[{(allyloxy)carbonyl}amino]acetic acid 
• 89744-06-9 carbonic acid allyl ester-(2,4-dichloro-phenyl ester) 
• 84000-75-9 2,2-bis-(4-allyloxycarbonyloxy-phenyl)-propane 
• 7460-72-2 (1-carboallyloxy-ethyl)-allyl carbonate 
• 91871-27-1 N-allyloxycarbonyl-L-glutamic acid 
• 98572-84-0 2,2-bis-(4-allyloxycarbonyloxy-3,5-dibromo-phenyl)-propane 
• 6269-32-5 carbonic acid allyl ester-(2-chloro-phenyl ester) 
• 855422-85-4 bis-(4-allyloxycarbonyloxy-3-chloro-phenyl)-sulfone 
• 129080-27-9 bis-(4-allyloxycarbonyloxy-phenyl)-sulfone 
• 27961-25-7 2,2-bis-(4-allyloxycarbonyloxy-3,5-dichloro-phenyl)-propane 
• 40940-57-6 (S)-(N-Allyloxycarbonyl)phenylalanine 
• 90724-06-4 carbonic acid allyl ester-(2,4,5-trichloro-phenyl ester) 
• 93345-64-3 1,3-bis-allyloxycarbonyloxy-benzene 

Relevant articles and documents

Synthesis of N-trifluoromethyl amides from carboxylic acids

Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.

In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates

Novel selenocyanate and diselenide derivatives containing a carbamate moiety were synthesised and evaluated in vitro to determine their cytotoxic and radical scavenging properties. Cytotoxic activity was tested against a panel of human cell lines including CCRF-CEM (lymphoblastic leukaemia), HT-29 (colon carcinoma), HTB-54 (lung carcinoma), PC-3 (prostate carcinoma), MCF-7 (breast adenocarcinoma), 184B5 (non-malignant, mammary gland derived) and BEAS-2B (non-malignant, derived from bronchial epithelium). Most of the compounds displayed high antiproliferative activity with GI50 values below 10 μM in MCF-7, CCRF-CEM and PC-3 cells. Radical scavenging properties of the new selenocompounds were confirmed testing their ability to scavenge DPPH and ABTS radicals. Based on the activity of selenium-based glutathione peroxidases (GPxs), compounds 1a, 2e and 2h were further screened for their capacity to reduce hydrogen peroxide under thiol presence. Results suggest that compound 1a mimics GPxs activity. Cytotoxic parameters, radical scavenging activity and ADME profile point to 1a as promising drug candidate.

Heat-sensitive recording materials and phenol compounds

Heat-sensitive recording materials contain an electron-donating chromogenic compound and an electron-attracting compound. The recording materials also contain at least one compound represented by the following formula: STR1 wherein R1 and R3 mean a hydrogen atom or an alkyl, aralkyl or aryl group, R2 and R4 denote an alkyl, alkenyl, aralkyl or aryl group, X1, X2, Y1 and Y2 stand for an oxygen or a sulfur atom, and --Z1 -- and --Z2 -- are a specific aromatic group. Also provided are phenol compounds represented by the following formula: STR2 wherein R1, R2, X1 and Y1 have the same meanings as defined above; R5 and R6 are a hydrogen or halogen atom or an alkyl, alkoxy, aralkyl, aryl or hydroxyl group; p and q stand for an integer of 1-4; R5 and R6 may be either the same or different when p and q represent an integer of 2 or greater; and --Z3 -- means a specific divalent group.