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C95501

Sigma-Aldrich

Cyanuric chloride

99%

Synonym(s):

2,4,6-Trichloro-1,3,5-triazine

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About This Item

Empirical Formula (Hill Notation):
C3Cl3N3
CAS Number:
108-77-0
Molecular Weight:
184.41
Beilstein:
124246
EC Number:
203-614-9
MDL number:
MFCD00006046
UNSPSC Code:
12352101
PubChem Substance ID:
24893171
NACRES:
NA.22

vapor density

6.36 (vs air)

Quality Level

200

vapor pressure

0.8 mmHg ( 62.2 °C)

Assay

99%

form

powder

bp

190 °C (lit.)

mp

145-147 °C (lit.)

storage temp.

2-8°C

SMILES string

Clc1nc(Cl)nc(Cl)n1

InChI

1S/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1

InChI key

MGNCLNQXLYJVJD-UHFFFAOYSA-N

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Application

Cyanuric chloride can be used as a reagent:   
  • In the preparation of acyl azides from carboxylic acids and sodium azide.       
  • For the conversion of carboxylic acids, N-Boc, N-Cbz, and N-Fmoc amino acids into corresponding alcohols.      
  • For the conversion of alcohols into the corresponding carbonyl compounds by alternative Swern oxidation reaction.


It can also be employed as a catalyst in the Beckmann rearrangement of ketoximes into amides in the presence of ZnCl2.
Reagent for the conversion of alcohols to chlorides and for the immobilization of microorganisms and enzymes.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H302,H314,H317,H330,H335

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1A - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

>392.0 °F - closed cup

Flash Point(C)

> 200 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J. Mol. Catal., 80, 269-269 (1993)
Synthesis of acyl azides from carboxylic acids using cyanuric chloride
Bandgar BP and Pandit SS
Tetrahedron Letters, 43(18), 3413-3414 (2002)
A mild and efficient alternative to the classical Swern oxidation.
L De Luca et al.
The Journal of organic chemistry, 66(23), 7907-7909 (2001-11-10)
Yoshiro Furuya et al.
Journal of the American Chemical Society, 127(32), 11240-11241 (2005-08-11)
The first general organocatalytic Beckmann rearrangement of ketoximes into amides has been realized by the catalytic use of cyanuric chloride. Furthermore, acids such as HCl and ZnCl2 are effective as cocatalysts with cyanuric chloride. For example, azacyclotridecan-2-one, which is synthetically
Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride
Falorni M, et al.
Tetrahedron Letters, 40(23), 4395-4396 (1999)
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