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545-06-2

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545-06-2 Usage

Chemical Properties

colourless to slightly yellow liquid

Uses

Different sources of media describe the Uses of 545-06-2 differently. You can refer to the following data:
1. Insecticide.
2. Trichloroacetonitrile is involved as a reagent in Overman rearrangement, which is used to prepare alylic amines from allylic alcohols. It is also used to prepare bistrichloroacetimidates from diols leading to dihyrooxazines through acid catalyzed cyclization. Further, it is utilized in the synthesis of trichloroacetimidates by 1,8-Diazobicyclo[5.4.0]undec-7-ene (DBU) catalyzed addition of allylic alcohols. It finds application in the study of the methoxy methyl (MOM) catalyzed aza-Claisen rearrangement.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

May be sensitive to light and heat. Trichloroacetonitrile may react with water, steam, acid or acid fumes. Trichloroacetonitrile may hydrolyze under acidic or alkaline conditions. . The reaction of benzene and Trichloroacetonitrile evolves toxic chloroform and HCl gasses. (Hagedorn, F., H.-P. Gelbke, and Federal Republic of Germany. 2002. Nitriles. In Ullman Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA.).

Hazard

Strong irritant to tissue. Questionable carcinogen.

Fire Hazard

Trichloroacetonitrile is combustible.

Safety Profile

Poison by ingestion and intravenous routes. Moderately toxic by inhalation and skin contact. Human mutation data reported. A skin and severe eye irritant. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition or in reaction with water, steam, acid, or acid fumes it produces toxic fumes of CN-, Cl-, and NOx. Used as an insecticide. See also NITRILES and CYANIDE.

Check Digit Verification of cas no

The CAS Registry Mumber 545-06-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 545-06:
(5*5)+(4*4)+(3*5)+(2*0)+(1*6)=62
62 % 10 = 2
So 545-06-2 is a valid CAS Registry Number.

545-06-2 Well-known Company Product Price

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  • TCI America

  • (T0372)  Trichloroacetonitrile  >98.0%(GC)

  • 545-06-2

  • 25g

  • 85.00CNY

  • Detail
  • TCI America

  • (T0372)  Trichloroacetonitrile  >98.0%(GC)

  • 545-06-2

  • 100g

  • 245.00CNY

  • Detail
  • TCI America

  • (T0372)  Trichloroacetonitrile  >98.0%(GC)

  • 545-06-2

  • 500g

  • 750.00CNY

  • Detail
  • Supelco

  • (442821)  Trichloroacetonitrile  analytical standard

  • 545-06-2

  • 000000000000442821

  • 1,354.86CNY

  • Detail
  • Aldrich

  • (T53805)  Trichloroacetonitrile  98%

  • 545-06-2

  • T53805-5G

  • 439.92CNY

  • Detail
  • Aldrich

  • (T53805)  Trichloroacetonitrile  98%

  • 545-06-2

  • T53805-100G

  • 1,248.39CNY

  • Detail
  • Aldrich

  • (T53805)  Trichloroacetonitrile  98%

  • 545-06-2

  • T53805-500G

  • 3,850.47CNY

  • Detail

545-06-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Trichloroacetonitrile

1.2 Other means of identification

Product number -
Other names Acetonitrile, trichloro-

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:545-06-2 SDS

545-06-2Synthetic route

N-{2-[2,2,2-Trichloro-eth-(E)-ylidene-hydrazinocarbonyl]-phenyl}-benzamide
76716-10-4

N-{2-[2,2,2-Trichloro-eth-(E)-ylidene-hydrazinocarbonyl]-phenyl}-benzamide

A

2-phenyl-4(3H)-quinazolinone
1022-45-3

2-phenyl-4(3H)-quinazolinone

B

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 200 - 240℃; under 1 Torr;A n/a
B 64%
trichloroacetamide
594-65-0

trichloroacetamide

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
With trichlorophosphate
With phosphorus pentaoxide
With phosphorus pentaoxide
trichloroacetyl-triphenoxyphosphoranyliden-amine
94578-40-2

trichloroacetyl-triphenoxyphosphoranyliden-amine

A

phosphoric acid triphenyl ester
115-86-6

phosphoric acid triphenyl ester

B

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 300℃;
2,2,2-trichloro-acetimidic acid phenyl ester
409110-43-6

2,2,2-trichloro-acetimidic acid phenyl ester

A

trichloroacetonitrile
545-06-2

trichloroacetonitrile

B

phenol
108-95-2

phenol

Conditions
ConditionsYield
at 180℃;
(2,2,2-trichloro-1-phenoxy-ethyliden)-amidophosphoric acid diphenyl ester
111499-29-7

(2,2,2-trichloro-1-phenoxy-ethyliden)-amidophosphoric acid diphenyl ester

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 250 - 300℃;
chloroacetonitrile
107-14-2

chloroacetonitrile

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
With chlorine at 60℃;
With hydrogenchloride; chlorine
acetonitrile
75-05-8

acetonitrile

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
With sulfuryl dichloride; platinum at 200 - 500℃;
With chlorine; platinum at 200 - 500℃;
With hydrogenchloride; chlorine
<2,2,2-trichloro-1-<(pentachloroethyl)imino>ethyl>phosphorimidic trichloride
74067-78-0

<2,2,2-trichloro-1-<(pentachloroethyl)imino>ethyl>phosphorimidic trichloride

A

trichloroacetamide
594-65-0

trichloroacetamide

B

trichloroacetonitrile
545-06-2

trichloroacetonitrile

C

trichloroacetic acid
76-03-9

trichloroacetic acid

Conditions
ConditionsYield
With water for 0.25h; Heating;
acetonitrile
75-05-8

acetonitrile

A

chloroacetonitrile
107-14-2

chloroacetonitrile

B

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
With chlorine; iron(III) chloride at 24.9℃; for 168h; Product distribution; also in the presence of 2, various conc.;
acetonitrile
75-05-8

acetonitrile

A

dichloroacetonitrile
3018-12-0

dichloroacetonitrile

B

chloroacetonitrile
107-14-2

chloroacetonitrile

C

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
With chlorine at 22.9℃; under 700 Torr; Irradiation; Yield given. Title compound not separated from byproducts;
With chlorine at 22.9℃; under 700 Torr; Kinetics; Irradiation; different reaction temperature and pressure;
chlorine
7782-50-5

chlorine

acetonitrile
75-05-8

acetonitrile

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 60℃; Irradiation;
acetonitrile
75-05-8

acetonitrile

A

trichloroacetonitrile
545-06-2

trichloroacetonitrile

B

trimer(ic) and tetramer(ic) trichloroacetonitrile

trimer(ic) and tetramer(ic) trichloroacetonitrile

Conditions
ConditionsYield
With chlorine; pyrographite at 300℃;
trichloroacetamide
594-65-0

trichloroacetamide

phosphoric acid anhydride

phosphoric acid anhydride

trichloroacetonitrile
545-06-2

trichloroacetonitrile

trichloroacetamide
594-65-0

trichloroacetamide

POCl3 (0.5 mol)

POCl3 (0.5 mol)

trichloroacetonitrile
545-06-2

trichloroacetonitrile

dichloroacetonitrile
3018-12-0

dichloroacetonitrile

NOCl

NOCl

A

dichloroacethyl chloride
79-36-7

dichloroacethyl chloride

B

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 200℃;
trichlorophosphazotrichlorooxoethane
14335-48-9

trichlorophosphazotrichlorooxoethane

A

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 260℃;
tetrachloroethyliden-amidophosphoryl chloride
28460-70-0

tetrachloroethyliden-amidophosphoryl chloride

A

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
at 220℃;
(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate
849674-12-0

(1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate

C20H31FO7S2
920025-44-1

C20H31FO7S2

A

C30H37F7O7S2
920025-45-2

C30H37F7O7S2

B

C30H37F7O7S2
920025-46-3

C30H37F7O7S2

C

trichloroacetonitrile
545-06-2

trichloroacetonitrile

Conditions
ConditionsYield
Stage #1: (1S)-1-[3,5-bis(trifluoromethyl)phenyl]ethyl-2,2,2-trichloroethanimidoate; C20H31FO7S2 With tetrafluorohydroboric acid In dichloromethane; cyclohexane at -17 - 20℃; for 23.6667h;
Stage #2: With sodium hydroxide In dichloromethane; cyclohexane; water at 18 - 20℃; for 0.25h;
2-phenylethanol
60-12-8

2-phenylethanol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

β-phenylethyl trichloroacetimidate
99421-73-5

β-phenylethyl trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane100%
With sodium
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃;
trichloroacetonitrile
545-06-2

trichloroacetonitrile

benzyl alcohol
100-51-6

benzyl alcohol

O-benzyl 2,2,2-trichloroacetimidate
81927-55-1

O-benzyl 2,2,2-trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In n-heptane at 0℃; for 0.25h; Solvent;100%
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane; water at -15 - 20℃; for 1.5h;99%
With potassium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at -15 - 25℃; for 1h;97%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

trichloroacetamide
594-65-0

trichloroacetamide

Conditions
ConditionsYield
With sulfuric acid In nitrobenzene; chlorobenzene at 60℃; Rate constant; Thermodynamic data; Mechanism; various temperatures, ΔG (excit.), ΔH (excit.), ΔS (excit.);100%
With sulfuric acid at 25℃;100%
With C19H23Cl2N6PRuS3*3ClH; water at 100℃; for 1h; Inert atmosphere; Schlenk technique;86%
3,4-dihydro-isoquinoline 2-oxide
24423-87-8

3,4-dihydro-isoquinoline 2-oxide

trichloroacetonitrile
545-06-2

trichloroacetonitrile

2-Trichloromethyl-5,9b-dihydro-4H-3-oxa-1,3a-diaza-cyclopenta[a]naphthalene
121994-35-2

2-Trichloromethyl-5,9b-dihydro-4H-3-oxa-1,3a-diaza-cyclopenta[a]naphthalene

Conditions
ConditionsYield
In toluene at 100℃; for 0.0333333h;100%
2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose
33639-75-7

2,3,4-tri-O-benzyl-6-deoxy-α-L-galactopyranose

trichloroacetonitrile
545-06-2

trichloroacetonitrile

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate
120703-59-5

O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane at 20℃; for 2h; Molecular sieve;100%
With 4 A molecular sieve; sodium hydride; potassium carbonate 1.) dichloromethane, 6.5 h; 2.) dichloromethane, 5 h, r.t.; Yield given. Multistep reaction;
trichloroacetonitrile
545-06-2

trichloroacetonitrile

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate
74808-09-6

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 1h; Molecular sieve;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 2h;98%
With sodium hydride In dichloromethane for 2.5h; Ambient temperature;96%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate
74808-10-9

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1h;100%
polystyrene supported organic base (PS-DBU) In dichloromethane at 20℃; for 1.5h;99%
1,8-diazabicyclo[5.4.0]undec-7-ene at 0℃; for 1.5h; Addition;95%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate
86520-63-0

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1h;100%
With potassium carbonate In dichloromethane at 20℃;96.1%
1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 1.5h; Addition;95%
C-phenyl-N-methylnitrone
3376-23-6, 7372-59-0, 59862-60-1

C-phenyl-N-methylnitrone

trichloroacetonitrile
545-06-2

trichloroacetonitrile

5-trichloromethyl-2-methyl-3-phenyl-2,3-dihydro-1,2,4-oxadiazole
121994-37-4

5-trichloromethyl-2-methyl-3-phenyl-2,3-dihydro-1,2,4-oxadiazole

Conditions
ConditionsYield
In toluene at 110℃; for 0.0333333h;100%
2,3,4-tri-O-benzyl-L-rhamnopyranose
210426-02-1

2,3,4-tri-O-benzyl-L-rhamnopyranose

trichloroacetonitrile
545-06-2

trichloroacetonitrile

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate
83866-10-8

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane for 3.5h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;86%
With sodium hydride In dichloromethane for 0.5h; Ambient temperature;85%
With sodium hydride In dichloromethane at 20℃; for 1.5h;81%
Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 18h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;92%
With sodium hydride In dichloromethane for 30h; Ambient temperature;86%
(2R,3S)-2,3-epoxynerol
62777-72-4

(2R,3S)-2,3-epoxynerol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

2,2,2-Trichloro-acetimidic acid (2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester
125414-25-7

2,2,2-Trichloro-acetimidic acid (2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 1h;100%
6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranoside
88567-49-1, 88567-50-4, 93361-01-4, 101802-94-2, 101802-97-5, 127875-38-1

6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranoside

trichloroacetonitrile
545-06-2

trichloroacetonitrile

6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranosyl trichloroacetimidate
125164-10-5, 125164-11-6, 143826-39-5, 143826-40-8

6-O-acetyl-2,3,4-tri-O-benzyl-α/β-D-galactopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane for 4.5h;100%
2-oxo-3-(ethoxycarbonyl)-3,4-dihydro-β-carboline
106544-20-1

2-oxo-3-(ethoxycarbonyl)-3,4-dihydro-β-carboline

trichloroacetonitrile
545-06-2

trichloroacetonitrile

(4R,10bR)-2-Trichloromethyl-4,5,10,10b-tetrahydro-3-oxa-1,3a,10-triaza-cyclopenta[a]fluorene-4-carboxylic acid ethyl ester
121994-30-7

(4R,10bR)-2-Trichloromethyl-4,5,10,10b-tetrahydro-3-oxa-1,3a,10-triaza-cyclopenta[a]fluorene-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene at 80℃; for 0.0333333h;100%
O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1-3)-O-(2,4-di-O-benzyl-α-D-xylopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-D-glucopyranose

O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1-3)-O-(2,4-di-O-benzyl-α-D-xylopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-D-glucopyranose

trichloroacetonitrile
545-06-2

trichloroacetonitrile

O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1-3)-O-(2,4-di-O-benzyl-α-D-xylopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-α,β-D-glucopyranosyl trichloroacetimidate
140420-64-0, 140420-75-3

O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1-3)-O-(2,4-di-O-benzyl-α-D-xylopyranosyl)-(1-3)-2,4,6-tri-O-acetyl-α,β-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With CsCO3 In dichloromethane for 2h; Ambient temperature;100%
3-O-<3-O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-6-O-acetyl-2,4-di-O-benzoyl-β-D-galactopyranosyl>-6-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-α/β-D-glucopyranose
143826-53-3, 143826-54-4

3-O-<3-O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-6-O-acetyl-2,4-di-O-benzoyl-β-D-galactopyranosyl>-6-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-α/β-D-glucopyranose

trichloroacetonitrile
545-06-2

trichloroacetonitrile

3-O-<3-O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-6-O-acetyl-2,4-di-O-benzoyl-β-D-galactopyranosyl>-6-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl trichloroacetimidate
143826-70-4, 143826-71-5

3-O-<3-O-(2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl)-6-O-acetyl-2,4-di-O-benzoyl-β-D-galactopyranosyl>-6-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane for 4.5h; Ambient temperature;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

O-(4-methoxybenzyl)-trichloroacetimidate
89238-99-3

O-(4-methoxybenzyl)-trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In hexane at 0℃; for 0.25h; Solvent;100%
Stage #1: 4-Methoxybenzyl alcohol With sodium hydride In diethyl ether at 20℃; for 0.25h; Inert atmosphere;
Stage #2: trichloroacetonitrile In diethyl ether at 0℃;
98%
Stage #1: 4-Methoxybenzyl alcohol With sodium hydride In diethyl ether at 20℃; for 0.5h;
Stage #2: trichloroacetonitrile In diethyl ether at 0 - 20℃; Further stages.;
96%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

1-(1-imino-2,2,2-trichloroethoxy)-3-phenyl-2(E)-propene
59874-81-6

1-(1-imino-2,2,2-trichloroethoxy)-3-phenyl-2(E)-propene

Conditions
ConditionsYield
With sodium hydride In diethyl ether at -10℃;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h;98%
Stage #1: (2E)-3-phenyl-2-propen-1-ol With sodium hydride In diethyl ether; mineral oil at 20℃;
Stage #2: trichloroacetonitrile In diethyl ether; mineral oil at -10 - 20℃;
97%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

O--(2<*>3)-O-2-acetamido-3,4,6-tri-O-acetyl-2...

O--(2<*>3)-O-2-acetamido-3,4,6-tri-O-acetyl-2...

O--(2<*>3)-O-2-acetamido-3,4,6-tri-O-acetyl-2...

O--(2<*>3)-O-2-acetamido-3,4,6-tri-O-acetyl-2...

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.5h;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

C115H116O33

C115H116O33

O-(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-α-D-glucopyranosyl trichloroacetimidate
187863-32-7

O-(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-α-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; Ambient temperature;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate
132201-75-3

2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 20℃; for 23h; Esterification;100%
With PTBD In dichloromethane at 20℃; for 2h;100%
With potassium carbonate In dichloromethane at 20℃; for 4h; Inert atmosphere;100%
biphenyl-4-yl methanol
3597-91-9

biphenyl-4-yl methanol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

4-phenylbenzyl trichloroacetimidate
200057-74-5

4-phenylbenzyl trichloroacetimidate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane; water at 0 - 25℃;100%
Stage #1: biphenyl-4-yl methanol With sodium hydride In diethyl ether; oil at 20℃; for 0.0833333h;
Stage #2: trichloroacetonitrile In diethyl ether; oil at 20℃; for 2h;
97%
With sodium hydride In diethyl ether 1.) 20 min, 2.) r.t., 1 h;69%
With sodium hydride In diethyl ether at 20℃; for 1h;
Stage #1: biphenyl-4-yl methanol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: trichloroacetonitrile In tetrahydrofuran at 20℃; for 2h;
trichloroacetonitrile
545-06-2

trichloroacetonitrile

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
148926-02-7

2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside

O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate
213681-58-4

O-(2-O-benzoyl-3,4,6-tri-O-benzyl-D-glucopyranosyl)trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -30℃; for 0.5h; Addition;90%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

methyl O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->2)-3,4-di-O-acetyl-α-D-glucopyranuronate

methyl O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->2)-3,4-di-O-acetyl-α-D-glucopyranuronate

methyl O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->2)-3,4-di-O-acetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate
208709-53-9

methyl O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->2)-3,4-di-O-acetyl-1-O-trichloroacetimidoyl-α-D-glucopyranuronate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -5℃; for 2h; Addition;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -5℃; for 2h; Yield given;
6-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-2-enitol
128318-79-6

6-O-acetyl-1,5-anhydro-2,3-dideoxy-D-erythro-hex-2-enitol

trichloroacetonitrile
545-06-2

trichloroacetonitrile

6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-D-erythro-hex-2-enitol
197449-41-5

6-O-acetyl-1,5-anhydro-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-D-erythro-hex-2-enitol

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane Addition;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
197449-37-9

p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranoside
197449-38-0

p-methoxyphenyl 6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranoside

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at -17℃; for 0.25h; Addition;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl 6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
197449-39-1

6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl 6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranosyl 6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranoside
197449-40-4

6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranosyl 6-O-acetyl-2,3-dideoxy-4-O-(1-imino-2,2,2-trichloroethyl)-α-D-erythro-hex-2-enopyranoside

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane Addition;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate
192444-70-5

6-O-benzyl-3-O-[(S)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane at 20℃; for 0.5h; Addition;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate
192196-09-1

6-O-benzyl-3-O-[(R)-3-(benzyloxy)tetradecanoyl]-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With caesium carbonate In dichloromethane at 20℃; for 1h; Addition;100%
trichloroacetonitrile
545-06-2

trichloroacetonitrile

3-O,4-S-Dibenzoyl-2,6-dideoxy-4-thio-D-ribo-hexopyranose

3-O,4-S-Dibenzoyl-2,6-dideoxy-4-thio-D-ribo-hexopyranose

3-O,4-S-Dibenzoyl-2,6-dideoxy-4-thio-D-ribo-hexopyranosyl trichloroacetimidate
330450-30-1

3-O,4-S-Dibenzoyl-2,6-dideoxy-4-thio-D-ribo-hexopyranosyl trichloroacetimidate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 1h;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 1h; Ambient temperature;

545-06-2Relevant articles and documents

Preparation method of N-methyl triazine

-

Paragraph 0012, (2017/01/26)

The invention discloses a preparation method of N-methyl triazine. The preparation method comprises eight operation processes including BTCT preparation, low-temperature reaction, reflux reaction, salt filtering, distillation, amination, filtering and drying. Compared with the conventional preparation method, the preparation method provided by the invention has the obvious advantages in the aspects of lowering the safety risk, improving the product quality, reducing the work intensity, reducing the environment harm and the like.

POLYMORPHS OF A HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONIST

-

Page/Page column 24-25, (2008/12/05)

This application is directed to a novel polymorph of a hydroisoindoline tachykinin receptor antagonist having the following structural formula A.

Kinetics of the reactions of acetonitrile with chlorine and fluorine atoms

Tyndall, Geoffrey S.,Orlando, John J.,Wallington, Timothy J.,Sehested, Jens,Nielsen, Ole J.

, p. 660 - 668 (2007/10/03)

The rate coefficients for the reactions of chlorine and fluorine atoms with acetonitrile have been measured using relative and direct methods. In the case of chlorine atoms the rate coefficient k1 was measured between 274 and 345 K using competitive chlorination and at 296 K using laser flash photolysis with atomic resonance fluorescence. The rate coefficient measured at ambient temperature (296 ± 2 K) is (1.15 ± 0.20) × 10-14 cm3 molecule-1 s-1, independent of pressure between 5 and 700 Torr (uncertainties are 2 standard deviations throughout). This result is a factor of 6 higher than the currently accepted value. The results from the three independent determinations reported here yield the Arrhenius expression k1 = (1.6 ± 0.2) × 10-11 exp[-(2140 ± 200)/T] cm3 molecule-1 s-1. Product studies show that the reaction of Cl atoms with CH3CN proceeds predominantly, if not exclusively, by hydrogen abstraction at 296 K. The rate coefficient for the reaction of fluorine atoms with acetonitrile was measured using both the relative rate technique and pulse radiolysis with time-resolved ultraviolet absorption spectroscopy. The rate coefficient for the reaction of F atoms with CH3-CN was found to be dependent on total pressure. The observed rate data could be fitted using the Troe expression with Fc = 0.6, k0 = (2.9 ± 2.1) × 10-28 cm6 molecule-2 s-1, and k∞ = (5.8 ± 0.8) × 10-11 cm3 molecule-1 s-1, with a zero pressure intercept of (0.9 ± 0.4) × 10-11 cm3 molecule-1 s-1. The kinetic data suggest that the reaction of F atoms with CH3CN proceeds via two channels: a pressure-independent H atom abstraction mechanism and a pressure-dependent addition mechanism. Consistent with this hypothesis, two products were observed using pulsed radiolysis with detection by UV absorption spectroscopy. As part of the product studies, relative rate techniques were used to measure k(Cl+CH2ClCN) = (2.8 ± 0.4) × 10-14 and k(F+CH2FCN) = (3.6 ± 0.2) × 10-11 cm3 molecule-1 s-1.

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