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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:
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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Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

41.0 °F - closed cup

Flash Point(C)

5 °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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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.
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
An approach to the site-selective deoxygenation of hydroxy groups based on catalytic phosphoramidite transfer.
Peter A Jordan et al.
Angewandte Chemie (International ed. in English), 51(12), 2907-2911 (2012-02-10)
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