15879-93-3

Basic information

• Product Name: alpha-Chloralose
• Synonyms: (r)-1,2-o-(2,2,2-trichloroethylidene)-alpha-d-glucofuranose;2-o-(2,2,2-trichloroethylidene)-(r)-alpha-d-glucofuranos;2-o-(2,2,2-trichloroethylidene)-(theta)-alpha-d-glucofuranos;alfamat;alpha-chloralos;alphakil;aphosal;chloralosane
• CAS NO: 15879-93-3
• Molecular Formula: C₈H₁₁Cl₃O₆
• Molecular Weight: 309.53
• EINECS: 240-016-7
• Product Categories: Biochemistry;Glucose;O-Substituted Sugars;Sugars;Dextrins、Sugar & Carbohydrates
• Mol File: 15879-93-3.mol

Chemical Properties

• Melting Point: 178-182 °C
• Boiling Point: 424.33°C (rough estimate)
• Flash Point: 258.9 °C
• Appearance: needle-like crystals or powder
• Density: 1.6066 (rough estimate)
• Vapor Pressure: 2.75E-12mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Solubility: ethanol: 10 mg/mL or yellow-brown, clear to slightly hazy,
• PKA: 12.89±0.60(Predicted)
• Water Solubility: 0.44 g/100 mL (15 ºC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2072
• BRN: 85418
• CAS DataBase Reference: alpha-Chloralose(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Chloralose(15879-93-3)
• EPA Substance Registry System: alpha-Chloralose(15879-93-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22-20/21/22
• Safety Statements: 16-24/25-28-28A-36
• RIDADR: 3249
• WGK Germany: 1
• RTECS: FM9450000
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 15879-93-3(Hazardous Substances Data)

Usage

Uses

Used in Animal Anesthesia:
alpha-Chloralose is used as an animal anesthetic in laboratory settings, acting as a true anesthetic or an immobilizing agent with sedative-hypnotic properties. It has important implications for the capture and handling of various bird species, such as Canada geese (Branta canadensis), blue geese (Chen caerulescens), and wild turkeys (Meleagris gallopavo), which are caught using alpha-chloralose as an oral hypnotic administered on bait.
Used in Rodent Control:
alpha-Chloralose is used for the control of rodents, particularly mice, due to its effectiveness as a bird repellent and a bird narcotic.
Used in Seed Protection:
alpha-Chloralose is also employed as a coating for seeds to protect them from birds, ensuring the successful growth of crops and reducing damage caused by avian species.

Hazard

May cause addiction, highly toxic.

Safety Profile

Poison by ingestion, subcutaneous, and intraperitoneal routes. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits toxic fumes of Cl-.

Metabolic pathway

Chloralose is effectively a chloral generator which, in turn, affords trichloroethanol by metabolism. This is the narcotic agent. Sleep is induced in mice before death and therefore the compound is regarded as a humane mouse killer. It is particularly effective when a quick clearout is required but there is evidence that mice can become tolerant.

Degradation

Chloralose is hydrolysed by acid and base to glucose and chloral (2, trichloroacetaldehyde).

InChI:InChI=1/C8H11Cl3O6/c9-8(10,11)7-16-5-3(14)4(2(13)1-12)15-6(5)17-7/h2-7,12-14H,1H2/t2-,3+,4-,5-,6-,7-/m1/s1

Synthetic route

sulfuric acid (7664-93-9) + chloral (75-87-6) + levoglucosan (498-07-7) → α-chloralose (15879-93-3)

chloral hydrate (302-17-0) + D-glucose (50-99-7) → α-chloralose (15879-93-3) + O1,O2-<(S)-2,2,2-trichloro-ethylidene>-α-D-glucofuranose; 4 O1,O2;O5,O6-bis-<2,2,2-trichloro-ethylidene>-α-D-glucofuranoses

Conditions	Yield
With sulfuric acid

Acetic acid (2R,3aR,5R,6S,6aR)-5-((R)-1,2-diacetoxy-ethyl)-2-trichloromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester → α-chloralose (15879-93-3)

Conditions	Yield
With methanol; sodium methylate

α-D-chloralose (39598-39-5) → α-chloralose (15879-93-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: MeONa; MeOH View Scheme

D-glucose (50-99-7) + toluene-4-sulfonic acid (104-15-4) + chloral (75-87-6) → α-chloralose (15879-93-3)

Conditions	Yield
In chloroform

α-chloralose (15879-93-3) → C8H9Cl3O5

Conditions	Yield
With 4,4-dimethyl-5-methylene-1,3-dioxolan-2-one; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 24h;	90%

2,2-dimethoxy-propane (77-76-9) + α-chloralose (15879-93-3) → 5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-α-D-glucofuranose

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 24h;	84%

4,4-dimethyl-5-methylene-1,3-dioxolan-2-one (4437-80-3) + α-chloralose (15879-93-3) → C15H17Cl3O10

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 25℃; for 24h;	80%

α-chloralose (15879-93-3) → (R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose (124595-32-0)

Conditions	Yield
With sodium periodate In methanol; water at 20℃; for 2h;	78%
With sodium periodate In methanol; water at 20℃; for 4h;	76%
With periodic acid
With sodium periodate In methanol; water

α-chloralose (15879-93-3) → 1,2-O-R-(2,2,2-trichloroethylidene)-α-D-glucofuranose 3,5,6-phosphite (187029-11-4)

Conditions	Yield
With hexaethylphosphorous triamide at 100 - 110℃; for 2h;	74%

acetone (67-64-1) + α-chloralose (15879-93-3) → 5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose (88390-57-2)

Conditions	Yield
With hydrogenchloride In N,N-dimethyl-formamide for 24h; Ambient temperature;	71%

2-(dichloromethylidene)-1,3-dioxolane (4362-56-5) + α-chloralose (15879-93-3) → 6-O-[2-(dichloromethyl)-1,3-dioxolan-2-yl]-1,2-O-[(R)-2,2,2-trichloroethane-1,1-diyl]-α-D-glucofuranose + 3,6-di-O-[2-(dichloromethyl)-1,3-dioxolan-2-yl]-1,2-O-[(R)-2,2,2-trichloroethane-1,1-diyl]-α-D-glucofuranose

Conditions	Yield
In nitromethane at 40℃; for 0.333333h;	A 22.2% B 11%

benzaldehyde (100-52-7) + α-chloralose (15879-93-3) → O3,O5-((Ξ)-benzylidene)-O1,O2-((R)-2,2,2-trichloro-ethylidene)-α-D-glucofuranose

Conditions	Yield
With zinc(II) chloride

chloral (75-87-6) + α-chloralose (15879-93-3) → O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose (4096-55-3)

Conditions	Yield
With sulfuric acid

α-chloralose (15879-93-3) → O1,O2-((R)-2,2,2-trichloro-ethylidene)-α-D-glucofuranuronic acid-3-lactone

Conditions	Yield
With dinitrogen tetraoxide

water (7732-18-5) + periodic acid + α-chloralose (15879-93-3) → formaldehyd (50-00-0) + (R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose (124595-32-0)

dinitrogen tetraoxide (10544-72-6) + α-chloralose (15879-93-3) → O1,O2-((R)-2,2,2-trichloro-ethylidene)-α-D-glucofuranuronic acid-3-lactone

sulfuric acid (7664-93-9) + chloral (75-87-6) + α-chloralose (15879-93-3) → O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose (4096-55-3)

(E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) + acetyl chloride (75-36-5) + α-chloralose (15879-93-3) → both Dr-1tF,2ξ,3rF,4-tetraacetoxy-1catF-<(2R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butanes

acetyl chloride (75-36-5) + α-chloralose (15879-93-3) → 1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane + higher-melting Dr-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<2(R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butane

Conditions	Yield
With zinc(II) chloride D&r-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<(2R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butane of mp: 151.5 degree;

acetyl chloride (75-36-5) + α-chloralose (15879-93-3) → 1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane + lower-melting Dr-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<2(R)-5ξ-acetoxy-2-trichloromethyl-<1,3>dioxolan-4c-yl>-butane

Conditions	Yield
With zinc(II) chloride higher-melting-Dr-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<(2R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butane;

α-chloralose (15879-93-3) → 5-(E)-eno-3-hydroxy-1,2-O-(R)-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-1,4-furano-7-ulose

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaIO4 / H2O; methanol / 2 h / 20 °C 2: dimethylformamide / 2 h / 100 °C View Scheme

α-chloralose (15879-93-3) → (E)-3-((2R,3aR,5R,6S,6aR)-6-Hydroxy-2-trichloromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-acrylic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaIO4 / H2O; methanol / 2 h / 20 °C 2: dimethylformamide / 2 h / 100 °C View Scheme

α-chloralose (15879-93-3) → 3-O-acetyl-(R)-1,2-O-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-oct-5(E)-eno-1,4-furano-7-ulose (620593-16-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / NaIO4 / H2O; methanol / 2 h / 20 °C 2: dimethylformamide / 2 h / 100 °C 3: 0.99 g / pyridine / 20 °C View Scheme

α-chloralose (15879-93-3) → methyl 3-O-acetyl-5,6-dideoxy-(R)-1,2-O-trichloroethylidene-α-D-xylo-hept-5(E)-eno-1,4-furanouronate

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / NaIO4 / H2O; methanol / 2 h / 20 °C 2: dimethylformamide / 2 h / 100 °C 3: 0.98 g / pyridine / 20 °C View Scheme

α-chloralose (15879-93-3) → ((2R,4S,4aS,5aR,7R,8aR,8bS)-4-Chloromethyl-2-oxo-7-trichloromethyl-tetrahydro-2λ5-[1,3]dioxolo[4,5]furo[3,2-d][1,3,2]dioxaphosphinin-2-yl)-diethyl-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / hexaethyl phosphoroustriamide / 2 h / 100 - 110 °C 2: 83 percent / Cl2 / CH2Cl2 / -25 °C 3: 58 percent / acetonitrile / 0.33 h / Ambient temperature View Scheme

α-chloralose (15879-93-3) → (2R,4S,4aS,5aR,7R,8aR,8bS)-2-Chloro-4-chloromethyl-7-trichloromethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3,2]dioxaphosphinine 2-oxide (187029-12-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / hexaethyl phosphoroustriamide / 2 h / 100 - 110 °C 2: 83 percent / Cl2 / CH2Cl2 / -25 °C View Scheme

α-chloralose (15879-93-3) → Dibutyl-((2R,4S,4aS,5aR,7R,8aR,8bS)-4-chloromethyl-2-oxo-7-trichloromethyl-tetrahydro-2λ5-[1,3]dioxolo[4,5]furo[3,2-d][1,3,2]dioxaphosphinin-2-yl)-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 74 percent / hexaethyl phosphoroustriamide / 2 h / 100 - 110 °C 2: 83 percent / Cl2 / CH2Cl2 / -25 °C 3: 61 percent / acetonitrile / 1 h / Ambient temperature View Scheme

α-chloralose (15879-93-3) → ((2S,4S,4aS,5aR,7R,8aR,8bS)-4-Chloromethyl-2-oxo-7-trichloromethyl-tetrahydro-2λ5-[1,3]dioxolo[4,5]furo[3,2-d][1,3,2]dioxaphosphinin-2-yl)-diethyl-amine

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / hexaethyl phosphoroustriamide / 2 h / 100 - 110 °C 2: 72 percent / CH2Cl2 / 24 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 74 percent / hexaethyl phosphoroustriamide / 2 h / 100 - 110 °C 2: 83 percent / Cl2 / CH2Cl2 / -25 °C 3: acetonitrile / 0.33 h / Ambient temperature View Scheme

Upstream product

• 7664-93-9 sulfuric acid 
• 75-87-6 chloral 
• 498-07-7 levoglucosan 
• 302-17-0 chloral hydrate 
• 50-99-7 D-glucose 
• 104-15-4 toluene-4-sulfonic acid 
• 10257-28-0 D-Galactose 
• 59-23-4 D-Galactose 
• 39598-39-5 α-D-chloralose 

Downstream Products

• 115-22-0 3-Hydroxy-3-methyl-2-butanone 
• 174314-34-2 3,5,6-tri-O-tosyl-1,2-O-trichloroethylidene-α-D-galactofuranose 
• 87987-63-1 Acetic acid (3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trichloromethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 112047-81-1 O³-methyl-D-lyxo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 88390-60-7 5,6-O-isopropylidene-3-O-tosyl-1,2-O-trichloroethylidene-α-D-glucofuranose 

Relevant articles and documents

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Herbicidal composition containing dioxolane, dioxane, or dioxepane derivatives as antidote

The invention relates to a herbicidal composition which contains, besides binding, wetting, dispersing, emulsifying agents, solvents and/or surface-active substances, herbicides as active agent of thiocarbamate, carbamate, acid amide or urea type alone or in a combination, furthermore as antidote a compound of the general formula I STR1 wherein R1 and R2, independently of each other, are hydrogen, C1-6 alkyl, C2-6 alkenyl, C1-4 cyanoalkyl, C1-6 haloalkyl, phenyl-C1-4 -haloalkyl, phenyl, halogenphenyl, C1-4 -alkyl-phenyl, C1-4 -alkoxyphenyl, furfuryl; R3 and R4, independently of each other, are hydrogen, C1-18 -alkyl, C2-4 -haloalkyl, C2-4 -cyanoalkyl, C1-4 -alkoxy-C2-4 -alkyl, C5-6 -cycloalkyl, phenyl-C1-4 -alkyl, C3-4 -alkenyl, phenyl-C3-4 -alkenyl, di-C1-4 -alkylamino-C2-4 -alkyl, hydroxy-C2-6 -alkyl, furfuryl, tetrahydrofurfuryl, C1-4 -alkoxy-C2-4 -alkoxy-C2-4 -alkyl; R3 and R4, together, are C2-4 -alkylene, C4 -alkenylene, glucofuranosylene, acetoxy-C3 -alkylene, C1-4 -alkoxy-C3 -alkylene, hydroxy-C3 -alkylene, halogen-C3 -alkylene; wherein the quantity of the antidote lies between 0.01 and 15 parts by weight referred to 1 part by weight of herbicidal agent, furthermore the composition contains altogether 0.1 to 95 percent by weight of the herbicidal agents and the antidote.