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88185

Sigma-Aldrich

Tetrazole solution

suitable for DNA synthesis, filtered through a 1 μm filter, ~0.45 M in acetonitrile

Synonym(s):

1H-Tetrazole

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About This Item

Empirical Formula (Hill Notation):
CH2N4
CAS Number:
288-94-8
Molecular Weight:
70.05
Beilstein/REAXYS Number:
105799
MDL number:
MFCD00005247
UNSPSC Code:
12352100
PubChem Substance ID:
57653295
NACRES:
NA.21

form

liquid

Quality Level

300

quality

filtered through a 1 μm filter

concentration

~0.45 M in acetonitrile

technique(s)

DNA synthesis: suitable

impurities

≤0.003% water

bp

84 °C (lit.)

mp

156-158 °C (lit.)

density

0.798 g/mL at 20 °C

SMILES string

c1nnn[nH]1

InChI

1S/CH2N4/c1-2-4-5-3-1/h1H,(H,2,3,4,5)

Inchi Key

KJUGUADJHNHALS-UHFFFAOYSA-N

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General description

The product is ~0.45M solution of tetrazole in acetonitrile. Tetrazole ring plays significant role in various synthetic and industrial processes.

Application

Tetrazole solution is useful for DNA synthesis. It may be employed as a catalyst for the in situ synthesis of deoxyribonucleoside phosphoramidites. It may be used in the preparation of following anionic nucleotide-lipids:
  • thymidine 3′-(1,2-dilauroyl-sn-glycero-3-phosphate) , diC12-3′-dT
  • thymidine 3′-(1,2-dimyristoyl-sn-glycero-3-phosphate) diC14- 3′-dT
  • thymidine-3′-(1,2-dipalmitoyl-sn-glycero-3-phosphate) diC16- 3′-dT

Caution

Saturated solution at room temperature; storage below room temperature causes precipitation.

Other Notes

Catalyst used in the phosphite triester method of oligonucleotide synthesis for the coupling of (dialkylamino)phosphines

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Pricing

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

41.0 °F - closed cup

flash_point_c

5 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Azidoazomethine-tetrazole isomerism in solution: A thermochemical study.
Cubero E, et al.
The Journal of Organic Chemistry, 63(7), 2354-2356 (1998)
Salim Khiati et al.
Bioconjugate chemistry, 20(9), 1765-1772 (2009-08-29)
A family of new anionic nucleotide based lipids featuring thymidine-3'-monophosphate as nucleotide and 1,2-diacyl-sn-glycerol as lipid moiety for in vitro delivery of nucleic acids is described. The nucleotide lipids were prepared in three steps starting from 1,2-diacyl-sn-glycerols and 2'-deoxythymidine-3'-phosphoramidite. Gel
A D Barone et al.
Nucleic acids research, 12(10), 4051-4061 (1984-05-25)
Deoxynucleoside phosphoramidites can be prepared in good yield from deoxynucleosides, bis- dialkylaminophosphines , and the corresponding dialkylamine hydrotetrazolide or tetrazole as catalysts. These phosphoramidites generated in situ lead to the direct synthesis of deoxyoligonucleotides on polymer supports.
J Nielsen et al.
Nucleic acids research, 14(18), 7391-7403 (1986-09-25)
Deoxyribonucleoside phosphoramidites are prepared in situ from 5'-O,N-protected deoxyribonucleosides and 2-cyanoethyl N,N,N',N'-tetraisopropylphosphorodiamidite with tetrazole as catalyst, and the solutions applied directly on an automatic solid-phase DNA synthesizer. Using LCAA-CPG support and a cycle time of 12.5 min, oligonucleotides of 16-25
Falgun Shah et al.
Journal of chemical information and modeling, 52(3), 696-710 (2012-02-16)
Falcipains (FPs) are hemoglobinases of Plasmodium falciparum that are validated targets for the development of antimalarial chemotherapy. A combined ligand- and structure-based virtual screening of commercial databases was performed to identify structural analogs of virtual screening hits previously discovered in
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