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140465

Sigma-Aldrich

Di-tert-butyl hydrazodiformate

97%

Synonym(s):

tert-Butyl hydrazodiformate

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About This Item

Linear Formula:
[NHCO2C(CH3)3]2
CAS Number:
16466-61-8
Molecular Weight:
232.28
EC Number:
240-512-3
MDL number:
MFCD00015000
UNSPSC Code:
12352100
PubChem Substance ID:
24848470
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

123-126 °C (dec.) (lit.)

SMILES string

CC(C)(C)OC(=O)NNC(=O)OC(C)(C)C

InChI

1S/C10H20N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3,(H,11,13)(H,12,14)

InChI key

TYSZETYVESRFNT-UHFFFAOYSA-N

General description

Di-tert-butyl hydrazodiformate acts as hydrazine substrate during the preparation of protected pyridylhydrazine derivatives.

Application

Di-tert-butyl hydrazodiformate was used as starting reagent during the four-step synthesis of the aminobicyclopyrazolone hydrochloride. It was used as reagent during Pd-catalyzed amination reactions of halo-pyridine substrates.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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 B Arterburn et al.
Organic letters, 3(9), 1351-1354 (2001-05-12)
[reaction in text] Protected pyridylhydrazine derivatives were prepared in a one-step palladium-catalyzed amination reaction using chelating phosphine ligands. 2-Pyridyl chlorides, bromides, and triflates were effective electrophiles in these reactions. Di-tert-butyl hydrazodiformate was an excellent hydrazine substrate, and the resulting products
Jeffrey B Arterburn et al.
The Journal of organic chemistry, 68(18), 7063-7070 (2003-08-30)
The development of (99m)Tc-estradiol radiopharmaceuticals would be advantageous for the detection of estrogen receptor-positive breast tumors. Estradiol derivatives conjugated to organometallic tricarbonyl-Tc(I) and related Re(I) complexes are capable of achieving high receptor binding affinity, but effective methods for synthesizing radiolabeled
A Convenient Synthesis of Pyrazolidine and 3-Amino-6, 7-dihydro-1H, 5H-pyrazolo [1, 2-a] pyrazol-1-one.
Boros EE, et al.
Journal of Heterocyclic Chemistry, 38(3), 613-616 (2001)
Daniel T Cohen et al.
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