1,2-Bis-(tert-butyldimethylsilyl)hydrazine

Base Information

• Chemical Name: 1,2-Bis-(tert-butyldimethylsilyl)hydrazine
• CAS No.: 10000-20-1
• Molecular Formula: C12H32N2Si2
• Molecular Weight: 260.57
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID20471430
• Nikkaji Number: J2.051.464G
• Wikidata: Q82299934
• Mol file: 10000-20-1.mol

Synonyms:1,2-Bis-(tert-butyldimethylsilyl)hydrazine;10000-20-1;1,2-bis[tert-butyl(dimethyl)silyl]hydrazine;Hydrazine, 1,2-bis[(1,1-dimethylethyl)dimethylsilyl]-;1,2-bis(tert-butyldimethylsilyl)hydrazine;N-t-butyldimethylsilylhydrazone;SCHEMBL1252958;DTXSID20471430;AKOS030255269;FT-0663217;J-000001

Chemical Property of 1,2-Bis-(tert-butyldimethylsilyl)hydrazine

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C
• Boiling Point: 256.157oC at 760 mmHg
• PKA: 10.62±0.70(Predicted)
• Flash Point: 108.72oC
• PSA: 24.06000
• Density: 0.825g/cm3
• LogP: 4.87280
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 260.21040210
• Heavy Atom Count: 16
• Complexity: 208

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2-Bis-(tert-butyldimethylsilyl)hydrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)NN[Si](C)(C)C(C)(C)C
• General Description: 1,2-Bis-(tert-butyldimethylsilyl)hydrazine (also known as bis-TBDMS hydrazine) is a reagent used in enantioselective synthesis to protect hydrazones with nearly full retention of stereochemical integrity, as demonstrated in the preparation of second-generation light-driven rotary molecular motors. Its application avoids racemization, enabling the production of enantiomerically pure compounds (>99% ee) critical for controlled unidirectional rotary processes.

Technology Process of 1,2-Bis-(tert-butyldimethylsilyl)hydrazine

There total 4 articles about 1,2-Bis-(tert-butyldimethylsilyl)hydrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

tert-butyldimethylsilyl chloride (18162-48-6) → 1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1)

Guidance literature:

With hydrazine; at 23 - 70 ℃; for 3h;

DOI:10.1021/ja049694s

Reference yield: 27.0%

hydrazine hydrochloride (2644-70-4,14011-37-1,5341-61-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1)

Guidance literature:

With triethylamine; at 110 ℃; for 4.5h;

DOI:10.1021/jo902348u

Reference yield:

2-(trimethylsilyl)propene (18163-07-0) → 1,2-bis(tert-butyldimethylsilyl)hydrazine (10000-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₄F*HF, H₂SO₄

2: ClSiMe₃, AlCl₃

3: N₂H₄ / diethyl ether

With ammonium fluoride; chloro-trimethyl-silane; aluminium trichloride; sulfuric acid; hydrogen fluoride; hydrazine; In diethyl ether;

DOI:10.1021/ja00972a022

upstream raw materials:

tert-butyldimethylsilyl chloride

2-(trimethylsilyl)propene

tert-butyldimethylfluorosilane

hydrazine hydrochloride

Downstream raw materials:

4'-bromoacetophenone N-tert-butyldimethylsilylhydrazone

5-[3-((1S,2S)-2-{4-[1-(4-methoxy-benzyloxy)-hexyl]-phenyl}-3-oxo-cyclopentyl)-propyl]-thiophene-2-carboxylic acid methyl ester TBS hydrazone

C₁₃H₂₂N₂Si