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
• Mol file: 10000-20-1.mol

Synonyms:1,2-bis[tert-butyl(dimethyl)silyl]hydrazine;

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)

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:

• Physical properties: bp 118–119°C/9 Torr;55–65°C/0.05 Torr; n25 D 1.4456.
• Uses: 1,2-Bis(t-butyldimethylsilyl)hydrazine is a source of latent hydrazine used in the preparation of stable alkyl and aryl N-silyl hydrazones, gem-dihalides, vinyl halides, and room temperature Wolff–Kishner reductions.Wolff–Kishner Reduction.A particularly useful reaction of the N-silyl hydrazones is their use as substrates in the Wolff– Kishner reaction, where reduction of the corresponding carbonyl compound can be accomplished at relatively modest temperatures. This is in marked contrast to the more traditional Wolff– Kishner reaction, and its Huang–Minlon modification, which require high temperatures and the use of potassium hydroxide.Room temperature conditions for the Wolff–Kishner reaction, previously reported by Cram and co-workers, were adapted by Myers and Furrow to the current N-silyl hydrazone methodology (eq 4).

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

C₁₃H₂₂N₂Si

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

3-phenoxybenzaldehyde N-tert-butyldimethylsilylhydrazone

Refernces

• 1、 Pijper, Thomas C.,Pijper, Dirk,Pollard, Michael M.,Dumur, Frederic,Davey, Stephen G.,Meetsma, Auke,Feringa, Ben L.. "An enantioselective synthetic route toward second-generation light-driven rotary molecular motors". . p. 825 - 838. Retrieved 2010.
• 2、 Furrow, Michael E.,Myers, Andrew G.. "Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides". . p. 5436 - 5445. Retrieved 2007/10/03.