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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

CorrosionSkull and crossbones
GHS05,GHS06

Signal Word

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

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)

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J. Mol. Catal., 80, 269-269 (1993)
Xue Jiang et al.
Bioresource technology, 104, 473-479 (2011-11-25)
The influence of introduction of cyanuric chloride on glucose's yield (Y) in acid-catalyzed hydrolysis of microcrystalline cellulose (MCC) has been studied. The content of cyanuric chloride (C) in modified MCCs was determined by X-ray photoelectric spectroscopy. The chemical structures of
Chao Gao et al.
Chemical communications (Cambridge, England), 49(11), 1127-1129 (2013-01-04)
A series of novel triazinonide-bridged bisimidazolium pincers were easily synthesized by quaternization of functionalized N-phenylimidazoles with highly reactive cyanuric chloride under mild conditions. The pincer was proven to be a very efficient ligand for in situ Pd-catalyzed Suzuki-Miyaura reaction with
Ravi Bhushan et al.
Amino acids, 42(4), 1371-1378 (2011-01-20)
Six dichloro-s-triazine (DCT) reagents having L-Leu, D-Phg, L-Val, L-Met, L-Ala and L-Met-NH(2) as chiral auxiliaries in cyanuric chloride were introduced for enantioseparation of 13 proteinogenic amino acids. Four other DCTs and six monochloro-s-triazine (MCT) reagents having amino acid amides as
Ravi Bhushan et al.
Journal of chromatography. A, 1217(41), 6382-6387 (2010-09-08)
Four dichloro-s-triazine (DCT) and five monochloro-s-triazine (MCT) chiral derivatizing reagents (CDRs) were synthesized by incorporating amino acid amide moieties as chiral auxiliaries in trichloro-s-triazine and its 6-methoxy derivative, respectively. Another MCT reagent was synthesized by substitution of two chlorine atoms
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