25979-07-1

Basic information

• Product Name: tert-Butyldichlorophosphine
• Synonyms: DICHLORO-TERT-BUTYLPHOSPHINE;AURORA KA-1260;T-BUTYLDICHLOROPHOSPHINE;T-BUTYLPHOSPHONOUS DICHLORIDE;TERT-BUTYLDICHLOROPHOSPHINE;Phosphonous dichloride, (1,1-dimethylethyl)-;tert-Butylphosphonous dichloride;tert-C4H9PCl2
• CAS NO: 25979-07-1
• Molecular Formula: C₄H₉Cl₂P
• Molecular Weight: 158.99
• EINECS: 247-386-9
• Product Categories: Chlorophosphines;Ligand;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Phosphorus Precursors;organophosphine halide
• Mol File: 25979-07-1.mol
• Article Data: 22

Chemical Properties

• Melting Point: 44-49 °C(lit.)
• Boiling Point: 142-150 °C
• Flash Point: 43.045 °C
• Appearance: White to light yellow/Low Melting Crystalline Mass
• Density: 0.766 g/mL at 25 °C
• Vapor Pressure: 5.57mmHg at 25°C
• Storage Temp.: Flammables area
• Water Solubility: Reacts with water. Soluble in n-Pentane, n-Hexane, Ether, Toluene,THF. tert-Butyldichlorophosphine is infinitely soluble in hydr
• Sensitive: Air Sensitive
• CAS DataBase Reference: tert-Butyldichlorophosphine(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyldichlorophosphine(25979-07-1)
• EPA Substance Registry System: tert-Butyldichlorophosphine(25979-07-1)

Safety Data

• Hazard Codes: C,T,F
• Statements: 14-34-29-23/24/25-17-11-67-22-19
• Safety Statements: 26-27-28-36/37/39-45-8-16
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• TSCA: No
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 25979-07-1(Hazardous Substances Data)

Usage

Description

tert-Butyldichlorophosphine (TBDCP) is a white to light yellow crystalline powder that serves as a versatile reagent in the field of organic chemistry. It is primarily recognized for its role in the synthesis of alkali metal complexes and as an intermediate in various chemical reactions.

Uses

Used in Chemical Synthesis:
tert-Butyldichlorophosphine is used as a reactant for the synthesis of alkali metal complexes, playing a crucial role in the formation of these compounds.
Used as Intermediates:
In the chemical industry, TBDCP is utilized as an intermediate in a variety of chemical reactions, contributing to the synthesis of different products.
Used in Metal Complexes:
tert-Butyldichlorophosphine is employed as a key component in the preparation of monoand bidentate phosphine ligands in metal complexes. These ligands are essential for catalytic chiral asymmetric hydrogenations and other asymmetric reactions, as well as transition metal coupling reactions.
Used in Catalytic Polymerization:
TBDCP is also used in the preparation of other phosphines that are vital in catalytic polymerization reactions, which are significant in the production of various types of polymers.

InChI:InChI=1/C4H9Cl2P/c1-4(2,3)7(5)6/h1-3H3

Upstream product

• 507-20-0 tertiary butyl chloride 
• 21187-18-8 tert-butylphosphonothioic dichloride 
• 686-69-1 diethylchlorophosphine 
• 131551-82-1 tert-butylpivaloylphosphinic acid chloride 
• 79044-45-4 tert-Butylchlor(trimethylsilyl)phosphan 
• 105414-84-4 S-ethyl tert-butylthiophosphinite 
• 75-36-5 acetyl chloride 
• 811-51-8 sodium thioethylate 
• 42491-33-8 tert-butylbis(trimethylsilyl)phosphine 
• 80705-63-1 tert-Butyl<(tert-butylchlorphosphino)(trimethylsiloxy)methylen>phosphan 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 61695-12-3 tri-tert-butylcyclotriphosphane 
• 677-22-5 tert-butylmagnesium chloride 
• 2259-30-5 tert-butylmagnesium bromide 

Downstream Products

• 56522-07-7 Benzyl-tert-butylphosphinous Chloride 
• 39768-05-3 tert-Butylbis(phenylethynyl)phosphan 
• 78681-46-6 1-tert-Butyl-4-cyclohexyl-1-methoxy-λ⁵-phosphorin 
• 345618-69-1 trans-1-tert-Butyl-4-cyclohexyl-1,4-dihydro-4-methoxyphosphorin 
• 78681-48-8 1-tert-Butyl-1-methoxy-4-phenyl-λ⁵-phosphorin 
• 78681-23-9 trans-1-tert-Butyl-1,4-dihydro-4-methoxy-4-phenylphosphorin 
• 42491-33-8 tert-butylbis(trimethylsilyl)phosphine 
• 77013-87-7 tert-Butyl-bis-phosphin 
• 126516-60-7 C₁₆H₁₇Br₂O₂P 
• 75-77-4 chloro-trimethyl-silane 
• 91070-22-3 2,3-di-tert-butyltelluradiphosphirane 
• 87869-43-0 2,3,4-Tri-tert-butyl-[1,2,3,4]telluratriphosphetane 
• 92208-95-2 (2S,4S,5R)-2-tert-Butyl-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin 
• 92208-95-2 (2R,4S,5R)-2-tert-Butyl-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholidin 

Relevant articles and documents

Tetra-tert-butylcyclotetraphosphane, 4

C16H36P4, monoclinic, P21/c, a=9.391 (1), b=14.029 (2), c=16.854 (2) Angstroem, β=95.80 (1) deg, V=2196 Angstroem3, Z=4, Do (by flotation in ZnCl2 solution)=1.08, Dc=1.07 Mg m-3.The central P4 ring is non-planar with P-P distances of 2.212 (2) Angstroem and P-P-P-P torsion angles of 24.5 deg.The tert-butyl groups are on alternate sides of the ring such that the molecule very nearly possesses 42m symmetry.The final R was 0.037 for the 1981 observed reflections.

Novel Heterocycles Comprising Alternating Phosphorus Atoms and Alkyne Units

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A new and convenient approach for the synthesis of P-stereogenic intermediates bearing a tert-butyl(methyl)phosphino group

Chiral organophosphorus compounds possessing a P-stereogenic center have been widely used as agricultural chemicals, pharmaceuticals, organocatalysts, and ligands for transition-metal catalysis. P-Stereogenic intermediates bearing a tert-butyl(methyl)phosphino group are important for the preparation of several commonly used diphosphine ligands. However, previously reported synthetic methods used hazardous starting materials and are difficult to operate. In order to overcome these limitations, a new and convenient synthesis for a number of P-stereogenic intermediates possessing a tert-butyl(methyl)phosphino group has been developed. The reported route relies on an air- and moisture-stable secondary phosphine oxide prepared from a readily available starting material, trichlorophosphane.

Phosphorus chiral important intermediate preparation method

The invention discloses a phosphorus chiral important intermediate preparation method, which comprises: carrying out a substitution reaction on phosphorus trichloride and tert-butyl magnesium chlorideto obtain tert-butyl phosphine dichloride I; carrying out an esterification reaction on the tert-butyl phosphine dichloride I and ethanol to obtain tert-butyl ethyl phosphite II; carrying out a methylation reaction on the tert-butyl ethyl phosphite II under the action of a methyl Grignard reagent methyl magnesium iodide to generate methyl tert-butyl phosphine oxide III; and obtaining a methyl tert-butyl phosphine hydrogen compound VI protected with borane through a borane reduction one-pot method. According to the present invention, the method has advantages of low-cost and easily-available raw material, short route, simple operation and good atomic economy, and provides the simple and easy-performing route for the preparation of the borane methyl tert-butyl phosphine hydrogen.