920-68-3

Basic information

• Product Name: Heptamethyldisilazane
• Synonyms: BIS(TRIMETHYLSILYL)METHYLAMINE;n,1,1,1-tetramethyl-n-(trimethylsilyl)-silanamin;N-1,1,1-tetramethyl-N-(trimethylsilyl)-Silanamine;N,1,1,1-tetramethyl-N-(trimethylsilyl)silylamine;1,1,1,2,3,3,3-Heptamethyldisilazane;HEPTAMETHYLDISILAZANE 97%;HEPTAMETHYLDISILAZANE 97+%;N N-BIS(TRIMETHYLSILYL)METHYLAMINE 99%
• CAS NO: 920-68-3
• Molecular Formula: C₇H₂₁NSi₂
• Molecular Weight: 175.42
• EINECS: 213-061-5
• Product Categories: Organics;Si (Classes of Silicon Compounds);Silazanes;Si-N Compounds
• Mol File: 920-68-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 144-147 °C(lit.)
• Flash Point: 27 °C
• Appearance: Clear and colorless liquid
• Density: 0.799 g/mL at 20 °C(lit.)
• Vapor Pressure: 6.216mmHg at 25°C
• Refractive Index: n20/D 1.421(lit.)
• Storage Temp.: Flammables area
• PKA: 14.41±0.70(Predicted)
• Water Solubility: Decomposes
• Sensitive: Moisture Sensitive
• BRN: 1737290
• CAS DataBase Reference: Heptamethyldisilazane(CAS DataBase Reference)
• NIST Chemistry Reference: Heptamethyldisilazane(920-68-3)
• EPA Substance Registry System: Heptamethyldisilazane(920-68-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• F: 10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 920-68-3(Hazardous Substances Data)

Usage

Chemical Properties

Clear liquid with amine odor

InChI:InChI=1/C7H21NSi2/c1-9(2,3)7(8)10(4,5)6/h7H,8H2,1-6H3

Upstream product

• 134644-75-0 B₂F₄(N(CH₃){Si(CH₃)3}2) 
• 16029-98-4 trimethylsilyl iodide 
• 127-19-5 N,N-dimethyl acetamide 
• 75-77-4 chloro-trimethyl-silane 
• 1070-89-9 sodium hexamethyldisilazane 
• 74-88-4 methyl iodide 
• 80-48-8 methyl p-toluene sulfonate 
• 75-79-6 Methyltrichlorosilane 
• 7651-91-4 N,N-dichloromethylamine 
• 2344-80-1 Chloromethyltrimethylsilane 
• 74-89-5 methylamine 
• 16513-17-0 methyltrimethylsilylamine 

Downstream Products

• 59466-99-8 2--3-phenyl-1,3,2-oxazaphospholidine 
• 59466-98-7 methyl-bis-(3-phenyl-[1,3,2]oxazaphospholidin-2-yl)-amine 
• 6222-22-6 hexane-1,6-diol bis(trimethylsilyl) ether 
• 18023-53-5 rac-2-ethyl-1-trimethylsilyoxy-hexane 
• 18023-52-4 trimethyl-(1-methyl-heptyloxy)-silane 
• 331432-75-8 1-aza-2,5-diduryl-3,4-diisopropylidene-1-methyl-2,5-diborolane 
• 27151-92-4 C₆H₅B{NCH₃Si(CH₃)3}2 
• 27190-81-4 methyl-bis{(methyl(trimethylsilyl)amino)phenylboryl}amine 
• 137728-89-3 ReNI₂(P(CH₃)2(C₆H₆))3 
• 56527-19-6 2,2,4,4-Tetrafluoro-1,3-dimethyl-2,4-bis-pentafluorophenyl-2λ⁵,4λ⁵-[1,3,2,4]diazadiphosphetidine 
• 2857-97-8 trimethylsilyl bromide 
• 877-07-6 hexamethylborazine 
• 88070-48-8 N-methylbenzamide 
• 107-46-0 Hexamethyldisiloxane 

Relevant articles and documents

Reaction of iodo(trimethyl)silane with N,N-dimethyl carboxylic acid amides

The reactions of iodo(trimethyl)silane with N,N-dimethylformamide and N,N-dimethylacetamide Me2NCOR (R = H, Me) at a molar ratio of 1: 2 involved mainly cleavage of the N-C(=O) bond with formation of up to 80% of N,N-dimethyltrimethylsilylamine Me3SiNMe2 and the corresponding acyl iodide RCOI. In the reaction with N,N-dimethylformamide, formyl iodide HCOI was detected for the first time by gas chromatography-mass spectrometry. The contribution of Me-N bond cleavage, leading to N-methyl-N-trimethylsilyl derivative Me(Me3Si)NCOR and methyl iodide was considerably smaller. Another by-product was the corresponding N-methyl imide MeN(COR)2 formed by reaction of the initial amide with acyl iodide. The primary intermediate in the reaction of iodo(trimethyl)silane with DMF and DMA is quaternary ammonium salt [Me2(Me3Si)N +COR] I- which decomposes via dissociation of the N-CO and N-Me bonds.

A Simple Synthesis pf Primary Amines via their N,N-Bis(trimethylsilyl) Derivatives

Primary halogen compounds 1 or the corresponding tosylates react with sodium bis(trimethylsilyl)amide (2) in hexamethyldisilazane to form N,N-bis(trimethylsilyl)amines 3, which are converted into the amine hydrochlorides 5 by treatment with aqueous HCl.