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15879-93-3

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15879-93-3 Usage

Description

Chloralose, (R)-1,2-O-(2,2,2-trichloroethylidene)- α-D-glucofuranose, is a crystalline powder which is soluble in water, fairly soluble in alcohol, diethyl ether, glacial acetic acid, sparingly soluble in chloroform, practically insoluble in petroleum ether.Chloralose is produced by reaction of glucose with waterfree chloral under heating (21).

Chemical Properties

needle-like crystals or powder

Uses

Different sources of media describe the Uses of 15879-93-3 differently. You can refer to the following data:
1. Coating seeds to protect them from birds.
2. It has been employed widely as an animal anesthetic in the laboratory setting. alpha-chloralose is a true anesthetic or an immobilizing agent with sedative-hypnotic properties has important implications. Canada geese (Branta canadensis) and blue geese (Chen caerulescens) were caught with alpha-chloralose, an oral hypnotic administered on bait. Wild turkeys (Meleagris gallopavo) were captured with alpha-chloralose, an oral anesthetic.
3. Chloralose is used for the control of rodents, particularly mice, and as a bird repellent and a bird narcotic.

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).

Check Digit Verification of cas no

The CAS Registry Mumber 15879-93-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,8,7 and 9 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 15879-93:
(7*1)+(6*5)+(5*8)+(4*7)+(3*9)+(2*9)+(1*3)=153
153 % 10 = 3
So 15879-93-3 is a valid CAS Registry Number.
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

15879-93-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A11492)  alpha-Chloralose, 98+%, beta anomer ca 15%   

  • 15879-93-3

  • 25g

  • 218.0CNY

  • Detail
  • Alfa Aesar

  • (A11492)  alpha-Chloralose, 98+%, beta anomer ca 15%   

  • 15879-93-3

  • 100g

  • 500.0CNY

  • Detail

15879-93-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name chloralose

1.2 Other means of identification

Product number -
Other names 1,2-O-[(1R)-2,2,2-trichloroethylidene]-α-D-glucofuranose

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:15879-93-3 SDS

15879-93-3Synthetic route

sulfuric acid
7664-93-9

sulfuric acid

chloral
75-87-6

chloral

levoglucosan
498-07-7

levoglucosan

α-chloralose
15879-93-3

α-chloralose

chloral hydrate
302-17-0

chloral hydrate

D-glucose
50-99-7

D-glucose

A

α-chloralose
15879-93-3

α-chloralose

B

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

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
ConditionsYield
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

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

α-chloralose

Conditions
ConditionsYield
With methanol; sodium methylate
α-D-chloralose
39598-39-5

α-D-chloralose

α-chloralose
15879-93-3

α-chloralose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: MeONa; MeOH
View Scheme
D-glucose
50-99-7

D-glucose

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

chloral
75-87-6

chloral

α-chloralose
15879-93-3

α-chloralose

Conditions
ConditionsYield
In chloroform
α-chloralose
15879-93-3

α-chloralose

C8H9Cl3O5

C8H9Cl3O5

Conditions
ConditionsYield
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

2,2-dimethoxy-propane

α-chloralose
15879-93-3

α-chloralose

5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-α-D-glucofuranose

5,6-O-isopropylidene-1,2-O-(R)-trichloroethylidene-α-D-glucofuranose

Conditions
ConditionsYield
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

4,4-dimethyl-5-methylene-1,3-dioxolan-2-one

α-chloralose
15879-93-3

α-chloralose

C15H17Cl3O10

C15H17Cl3O10

Conditions
ConditionsYield
With dmap In N,N-dimethyl-formamide at 25℃; for 24h;80%
α-chloralose
15879-93-3

α-chloralose

(R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose
124595-32-0

(R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose

Conditions
ConditionsYield
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

α-chloralose

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

1,2-O-R-(2,2,2-trichloroethylidene)-α-D-glucofuranose 3,5,6-phosphite

Conditions
ConditionsYield
With hexaethylphosphorous triamide at 100 - 110℃; for 2h;74%
acetone
67-64-1

acetone

α-chloralose
15879-93-3

α-chloralose

5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose
88390-57-2

5,6-O-isopropylidene-1,2-O-trichloroethylidene-α-D-glucofuranose

Conditions
ConditionsYield
With hydrogenchloride In N,N-dimethyl-formamide for 24h; Ambient temperature;71%
2-(dichloromethylidene)-1,3-dioxolane
4362-56-5

2-(dichloromethylidene)-1,3-dioxolane

α-chloralose
15879-93-3

α-chloralose

A

6-O-[2-(dichloromethyl)-1,3-dioxolan-2-yl]-1,2-O-[(R)-2,2,2-trichloroethane-1,1-diyl]-α-D-glucofuranose

6-O-[2-(dichloromethyl)-1,3-dioxolan-2-yl]-1,2-O-[(R)-2,2,2-trichloroethane-1,1-diyl]-α-D-glucofuranose

B

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

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
ConditionsYield
In nitromethane at 40℃; for 0.333333h;A 22.2%
B 11%
benzaldehyde
100-52-7

benzaldehyde

α-chloralose
15879-93-3

α-chloralose

O3,O5-((Ξ)-benzylidene)-O1,O2-((R)-2,2,2-trichloro-ethylidene)-α-D-glucofuranose

O3,O5-((Ξ)-benzylidene)-O1,O2-((R)-2,2,2-trichloro-ethylidene)-α-D-glucofuranose

Conditions
ConditionsYield
With zinc(II) chloride
chloral
75-87-6

chloral

α-chloralose
15879-93-3

α-chloralose

O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose
4096-55-3

O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose

Conditions
ConditionsYield
With sulfuric acid
α-chloralose
15879-93-3

α-chloralose

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

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

Conditions
ConditionsYield
With dinitrogen tetraoxide
water
7732-18-5

water

periodic acid

periodic acid

α-chloralose
15879-93-3

α-chloralose

A

formaldehyd
50-00-0

formaldehyd

B

(R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose
124595-32-0

(R)-1,2-O-(2,2,2-trichloroethylidene)-α-D-xylo-1,4-furanodialdose

dinitrogen tetraoxide
10544-72-6

dinitrogen tetraoxide

α-chloralose
15879-93-3

α-chloralose

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

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

sulfuric acid
7664-93-9

sulfuric acid

chloral
75-87-6

chloral

α-chloralose
15879-93-3

α-chloralose

O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose
4096-55-3

O1,O2;O5,O6-[(R,S)-bis-(2,2,2-trichloro-ethylidene)]-α-D-glucofuranose

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

acetyl chloride
75-36-5

acetyl chloride

α-chloralose
15879-93-3

α-chloralose

both Dr-1tF,2ξ,3rF,4-tetraacetoxy-1catF-<(2R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butanes

both Dr-1tF,2ξ,3rF,4-tetraacetoxy-1catF-<(2R)-5ξ-acetoxy-2r-trichloromethyl-<1,3>dioxolan-4c-yl>-butanes

acetyl chloride
75-36-5

acetyl chloride

α-chloralose
15879-93-3

α-chloralose

A

1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane

1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane

B

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

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

Conditions
ConditionsYield
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

acetyl chloride

α-chloralose
15879-93-3

α-chloralose

A

1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane

1,2,3,4-tetraacetoxy-1-(5-acetoxy-2-trichloromethyl-[1,3]dioxolan-4-yl)-butane

B

lower-melting Dr-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<2(R)-5ξ-acetoxy-2-trichloromethyl-<1,3>dioxolan-4c-yl>-butane

lower-melting Dr-1tF,2ξF,3rF,4-tetraacetoxy-1catF-<2(R)-5ξ-acetoxy-2-trichloromethyl-<1,3>dioxolan-4c-yl>-butane

Conditions
ConditionsYield
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

α-chloralose

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

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

Conditions
ConditionsYield
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

α-chloralose

(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

(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
ConditionsYield
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

α-chloralose

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

3-O-acetyl-(R)-1,2-O-trichloroethylidene-5,6,8-trideoxy-α-D-xylo-oct-5(E)-eno-1,4-furano-7-ulose

Conditions
ConditionsYield
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

α-chloralose

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

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

Conditions
ConditionsYield
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

α-chloralose

((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

((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
ConditionsYield
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

α-chloralose

(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

(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

Conditions
ConditionsYield
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

α-chloralose

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

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
ConditionsYield
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

α-chloralose

((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

((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
ConditionsYield
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

15879-93-3Relevant articles and documents

-

White,Hixon

, p. 2438,2443 (1933)

-

-

Pictet,Reichel

, p. 621,623, 626 (1923)

-

Glucofuranose derivatives as a library for designing and investigating low molecular mass organogelators

Luboradzki, Roman,Pakulski, Zbigniew,Sartowska, Bozena

, p. 10122 - 10128 (2005)

We designed and synthesized a class of saccharide-based gelators having three free OH groups in the glucofuranose fragment. The gelating abilities of fourteen compounds were examined to systematically study the influence of the hydrophobic fragment connected to the C2′ carbon. Also the correlation between the saccharide crystal structure and its gelating properties was examined, showing limited usefulness in this particular case. SEM observations were carried out in order to investigate the hierarchical structure of xerogels and changes depending on different gel concentration.

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

-

, (2008/06/13)

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.

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