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C95501

Sigma-Aldrich

Cyanuric chloride

99%

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Synonym(s):
2,4,6-Trichloro-1,3,5-triazine
Empirical Formula (Hill Notation):
C3Cl3N3
CAS Number:
108-77-0
Molecular Weight:
184.41
Beilstein/REAXYS Number:
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

signalword

Danger

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

supp_hazards

EUH014

wgk_germany

WGK 1

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Mild reduction of carboxylic acids to alcohols using cyanuric chloride and sodium borohydride
Falorni M, et al.
Tetrahedron Letters, 40(23), 4395-4396 (1999)
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
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)
Sanjay K Singh et al.
Frontiers in immunology, 11, 1812-1812 (2020-09-10)
C-reactive protein (CRP), a component of the innate immune system, is an antipneumococcal plasma protein. Human CRP has been shown to protect mice against infection with lethal doses of Streptococcus pneumoniae by decreasing bacteremia. in vitro, CRP binds to phosphocholine-containing
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