4488-22-6

Basic information

• Product Name: (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE
• Synonyms: 1,1'-BINAPHTHYL-2,2'-DIAMINE;(+/-)-1,1'-BINAPHTHALENE-2,2'-DIAMINE;(+/-)-2,2'-DIAMINO-1,1'-BINAPHTHALENE;2,2-DIAMINO-1,1'-BINAPHTHALENE;RACEMIC-2,2'-DIAMINO-1,1'-BINAPHTHYL, MIN. 96%;1,1-BINAPHY1-2,2'-DIAMINE;(+/-)-2,2'-Diamino-1,1'-binaphthyl;racemic-2,2'-Diamino-1,1'-binaphthyl,min.96%
• CAS NO: 4488-22-6
• Molecular Formula: C₂₀H₁₆N₂
• Molecular Weight: 284.35
• Product Categories: Nitrogen Compounds;Organic Building Blocks;Polyamines;Achiral Nitrogen;BINAM Series
• Mol File: 4488-22-6.mol
• Article Data: 25

Chemical Properties

• Melting Point: 242-244 °C(lit.)
• Boiling Point: 416.85°C (rough estimate)
• Appearance: slightly beige/
• Density: 1.249
• Refractive Index: 1.6450 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.79±0.10(Predicted)
• Water Solubility: Insoluble in water
• CAS DataBase Reference: (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE(4488-22-6)
• EPA Substance Registry System: (S)-(-)-1,1'-BINAPHTHYL-2,2'-DIAMINE(4488-22-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-41-22
• Safety Statements: 26-39
• WGK Germany: 3
• RTECS: DU3090000
• F: 10
• Hazardous Substances Data: 4488-22-6(Hazardous Substances Data)

Usage

Description

1,1'-Binaphthalene]-2,2'-diamine is an axially asymmetric binaphthyl ligand mainly used in enantioselective catalysis.

Chemical Properties

off-white to beige-pink powder

Uses

Novel axially chiral Rh N-heterocyclic carbene complexes were prepared from axially dissymmetric 1,1'-Binaphthalene]-2,2'-diamine and applied in the Rh-catalyzed enantioselective hydrosilylation of methyl ketones. The enantioselective direct aldol reaction, organocatalyzed by recoverable BINAM- prolinamide derivatives can be highly accelerated by a catalytic amount of a carboxylic acid without a detrimental of the obtained enantioselectivities.

Safety Profile

Questionable carcinogen withexperimental tumorigenic data. When heated todecomposition it emits toxic fumes of NOx.

Upstream product

• 188-55-6 benzo[f]naphtho[2,1-c]cinnoline 
• 64-19-7 acetic acid 
• 7803-57-8 hydrazine hydrate 
• 135-19-3 β-naphthol 
• 100-63-0 phenylhydrazine 
• 582-08-1 2,2'-azonaphthalene 
• 2243-57-4 2-hydrazinonaphthalene 
• 110-86-1 pyridine 
• 91-59-8 naphthalen-2-ylamine 
• 7647-01-0 hydrogenchloride 
• 76905-82-3 2,2'-dinitro-[1,1']binaphthyl 
• 970-62-7 2,2'-hydrazonaphthalene 
• 602-09-5 1,1'-bi-2-naphthol 
• 1620543-69-2 2'-azido-[1,1'-binaphthalen]-2-amine 

Downstream Products

• 10147-27-0 4,5-diphenyl-dinaphtho[2,1-e;1',2'-g][1,4]diazocine 
• 18741-85-0 (R)-1,1'-binaphthyl-2,2'-diamine 
• 18531-95-8 (S)-2,2'-diamino-1,1'-binaphthalene 
• 902777-94-0 2-(tosylamino)-2'-(imidazol-1-yl)-1,1'-binaphthyl 
• 136568-67-7 N,N′-([1,1′-binaphthalene]-2,2′-diyl)bis(4-methylbenzenesulfonamide) 
• 185683-42-5 Cu(C₆H₂OCHN(SC₆H₅)(C(CH₃)3))2(C₂₀H₁₂) 
• 185683-45-8 Cu(C₆H₃OCHN(SC₆H₅))2(C₂₀H₁₂) 
• 1620543-70-5 2,2'-diazido-1,1'-binaphthyl 
• 224-56-6 dibenzophenazine 
• 194-59-2 7H-dibenzo[c,g]carbazole 
• 188-55-6 benzo[f]naphtho[2,1-c]cinnoline 

Relevant articles and documents

Synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene

The invention relates to a synthesis method of 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene, which is realized by the following steps: step 1, carrying out BUCHERER reaction on 1, 1 '-binaphthyl-2-naphthol to generate 1, 1'-binaphthyl-2, 2 '-diamine; 2, subjecting 1, 1 '-binaphthyl-2, 2'-diamine to a Sandmeyer reaction to generate binaphthyl dibromide; and 3, carrying out a Grignard reaction onthe binaphthyl dibromide and diphenyl phosphine chloride to generate 2, 2 '-bisdiphenylphosphino-1, 1'-binaphthalene (BINAP). Bulk chemical raw materials are used and are low in price and easy to obtain, and the production cost is effectively reduced; the method has the advantages of easily available raw materials, high reaction yield, simple post-treatment, facilitation of industrial amplification, and strong industrial application prospect.

Catalytic, Enantioselective Sulfenylation of Ketone-Derived Enoxysilanes

A catalytic, enantioselective, Lewis base-catalyzed α-sulfenylation of silyl enol ethers has been developed. To avoid acidic hydrolysis of the silyl enol ether substrates, a sulfenylating agent that did not require additional Br?nsted acid activation, namely N-phenylthiosaccharin, was developed. Three classes of Lewis bases - tertiary amines, sulfides, and selenophosphoramides - were identified as active catalysts for the α-sulfenylation reaction. Among a wide variety of chiral Lewis bases in all three classes, only chiral selenophosphoramides afforded α-phenylthio ketones in generally high yield and with good enantioselectivity. The selectivity of the reaction does not depend on the size of the silyl group but is highly sensitive to the double bond geometry and the bulk of the substituents on the double bond. The most selective substrates are those containing a geminal bulky substituent on the enoxysilane. Computational analysis revealed that the enantioselectivity arises from an intriguing interplay among sterically guided approach, distortion energy, and orbital interactions.

CuCl2 and FeCl3 as a new and efficient catalyst for the oxidative coupling of aryl amines into 1,1′-binaphthalene-2,2 /-diamines in the ionic liquid media

A practical synthesis of 1,1′-binaphthalene-1,1′-diamines (BINAM) from a-naphthylamine is described here. The facile purification procedure of the method makes it amenable to gram scale synthesis of 1,1′-binaphthalene-1,1′-diamines with fairly high optical purity and yield of product.